Visible-light promoted catalyst-free (VLCF) multi-component synthesis of spiro indolo-quinazolinone-pyrrolo[3,4-a]pyrrolizine hybrids: evaluation of in vitro anticancer activity, molecular docking, MD simulation and DFT studies

References

• Acosta-Quiroga, K., Rojas-Peña, C., Nerio, L. S., Gutiérrez, M., & Polo-Cuadrado, E. (2021). Spirocyclic derivatives as antioxidants: A review. RSC Advances, 11(36), 21926–21954. https://doi.org/10.1039/d1ra01170g
   PubMed Web of Science ®Google Scholar
• Albini, A., & Fagnoni, M. (2004). Green Chemistry and Photochemistry were Born at the Same Time. Green Chem., 6, 1.
   Web of Science ®Google Scholar
• Albini, A., & Fagnoni, M. (2008) 1908: Giacomo Ciamician and the concept of green chemistry. ChemSusChem, 1, 63.
   PubMed Web of Science ®Google Scholar
• Allen, L. F., Eiseman, I. A., Fry, D. W., & Lenehan, P. F. (2003). CI-1033, an irreversible Pan-erbB receptor inhibitor and its potential application for the treatment of breast cancer. Seminars in Oncology, 30, 65–78.
   PubMed Web of Science ®Google Scholar
• Ansari, M. I., Hussain, M. K., Arun, A., Chakarvarti, B., Konwar, R., & Hajela, K. (2015). Synthesis of targeted dibenzo [b, f] thiepines and dibenzo[b,f]oxepines as potential lead molecules with promising anti-breast cancer activity. European Journal of Medicinal Chemistry, 99, 113.
   PubMed Web of Science ®Google Scholar
• Ansari, M. I.; Arun, A., Hussain, M. K., Konwar, R., & Hajela, K. (2016). Discovery of 3, 4, 6‐triaryl‐2‐pyridones as potential anticancer agents that promote ROS‐independent mitochondrial‐mediated apoptosis in human breast carcinoma cells. Chemistry Select, 1, 4255.
   Google Scholar
• Bach, T., & Hehn, J. P. (2011). Photochemical reactions as key steps in natural product synthesis. Angewandte Chemie International Edition, 50, 1000.
   PubMed Web of Science ®Google Scholar
• Baker., W.R., & Mitscher. (1995). L.A., U.S. Patent., 5, 441, 955.
   Google Scholar
• Bandekar, P. P., Roopnarine, K. A., Parekh, V. J., Mitchell, T. R., Novak, M. J., & Sinden, R. (2010). R. Antimicrobial activity of tryptanthrins in Escherichia coli. Journal of Medicinal Chemistry i., 53, 3558. https://doi.org/10.1016/j.bbrc.2007.04.107
   PubMed Web of Science ®Google Scholar
• Barker, A. J., Gibson, K. H., Grundy, W., Godfrey, A. A., Barlow, J. J., Healy, M. P., Woodburn, J. R., Ashton, S. E., Curry, B. J., & Scarlett, L. (2001). Studies leading to the identification of ZD1839 (Iressa™): An orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer. Bioorganic & Medicinal Chemistry Letters, 11(14), 1911–1914.
   PubMed Web of Science ®Google Scholar
• Bashir, M., Yousuf, I., & Prasad, C. P. (2022). Mixed Ni(II) and Co(II) complexes of nalidixic acid drug: synthesis, characterization, DNA/bsa binding profile and in vitro cytotoxic evaluation against MDA-MB-231 and HepG2 cancer cell lines. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 271, 120910. https://doi.org/10.1016/j.saa.2022.120910
   PubMed Web of Science ®Google Scholar
• Becke, A. D. (1988). Density-functional Exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38, 3098.
   PubMed Web of Science ®Google Scholar
• Becke, A. D. (1993). Density‐functional thermochemistry. III. the role of exact exchange. Journal of Chememical Physics, 98, 5648.
   Web of Science ®Google Scholar
• Bhattacharjee, A. K., Hartell, M. G., Nichols, D. A., Hicks, R. P., Stanton, B., Van Hamont, J. E., & Milhous, W. K. (2004). Eur. Structure–activity relationship study of antimalarial indolo[2,1-b]quinazoline-6,12-diones (ttryptanthrins). Three dimensional pharmacophore modeling and identification of new antimalarial candidates. J. Med. Chem, 39, 59.
   Web of Science ®Google Scholar
• Bhattacharjee, A. K., Skanchy, D. K., Jennings, B., Hudson, T. H., Brendle, J. J., & Werbovetz, K. A. (2002). Analysis of stereoelectronic properties, mechanism of action and pharmacophore of synthetic indolo[2,1-b]quinazoline-6,12-dione derivatives in relation to antileishmanial activity using quantum chemical, cyclic voltammetry and 3-D-QSAR CATALYST procedures. Bioorganic & Medicinal Chemistry, 10(6), 1979–1989. https://doi.org/10.1016/S0968-0896(02)00013-5
   PubMed Web of Science ®Google Scholar
• Bouali, N., Hammouda, M. B., Ahmad, I., Ghannay, S., Thouri, A., Dbeibia, A., Patel, H., Hamadou, W.S., Hosni, K., Snoussi, M., Adnan, M., Hassan, M. D., Noumi, E., Aouadi K., & Kadri, A. (2022). Multifunctional derivatives of spiropyrrolidine tethered indeno-quinoxaline heterocyclic hybrids as potent antimicrobial, antioxidant and antidiabetic agents: design, synthesis, in vitro and in silico approaches. Molecules, 27, 7248.
   PubMed Web of Science ®Google Scholar
• Bowman, W. R., Elsegood, M. R., Stein, T., & Weaver, G. W. (2007). Radical Reactions with 3Hquinazolin- 4-ones: Synthesis of Deoxyvasicinone, Mackinazolinone, Luotonin A, Rutaecarpine and Tryptanthrin. Organic & Biomolecular Chemistry, 5(1), 103, 113.
   PubMed Web of Science ®Google Scholar
• Brufani, M., Fedeli, W., Mazza, F., Gerhard, A., & Keller-Schierlein, W. (1971). The structure of tryptanthrin. Experientia, 27, 1249.
   PubMedGoogle Scholar
• Cai, S., Yang, K., & Wang, D. Z. (2014). Gold catalysis coupled with visible light stimulation: syntheses of functionalized indoles. Organic Letters, 16, 2606.
   PubMed Web of Science ®Google Scholar
• Calvo, E., Tolcher, A. W., Hammond, L. A., Patnaik, A., de Bono, J. S., Eiseman, I. A., Olson, S. C., Lenehan, P. F., McCreery, H., & LoRusso, P. (2004) Administration of CI-1033, An irreversible Pan-erbB tyrosine kinase inhibitor, is feasible on a 7-day on, 7-day off schedule a phase i pharmacokinetic and food effect study. Clinical Cancer Research, 10, 7112. https://doi.org/10.1053/j.seminoncol.2003.08.009
   PubMed Web of Science ®Google Scholar
• Carmi, C., Cavazzoni, A., Vezzosi, S., Bordi, F., Vacondio, F., Silva, C., Rivara, S., Lodola, A., Alfieri, R. R., Monica, S. L., Galetti, M., Ardizzoni, A., Petronini, P. G., & Mor, M. (2010). Novel irreversible epidermal growth factor receptor inhibitors by chemical modulation of the cysteine-trap portion. Journal of Medicinal Chemistry, 53(5), 2038–2050.
   PubMed Web of Science ®Google Scholar
• Chan, H. L., Yip, H. Y., Mak, N. K., & Leung, K. N. (2009). Modulatory effects and action mechanisms of tryptanthrin on murine myeloid leukemia cells. Cellular & Molecular Immunology, 6, 335. https://doi.org/10.1046/j.1440-1827.2001.01204.x
   PubMed Web of Science ®Google Scholar
• Coldham, I., & Hufton, R. (2005). Intramolecular dipolar cycloaddition reactions of azomethine ylides. Chemical Review, 105, 2765.
   Google Scholar
• Dai, W., Jiang, X.-L., Wu, Q., Shi, F., & Tu, S.-J. (2015). Diastereo- and enantioselective construction of 3,3′-pyrrolidinyldispirooxindole framework via catalytic asymmetric 1,3-dipolar cycloadditions. Journal of Organic Chemistry, 80, 5737.
   Google Scholar
• De Souza, M. V. (2006). Promising drugs against tuberculosis. Recent Patents on anti-Infect Drug Discovery, 1, 33.
   PubMedGoogle Scholar
• Ding, L., Meazza, M., Guo, H., Yang, J. W., & Rios, R., (2018). New development in the enantioselective synthesis of spiro compounds. Chemical Society Reviews, 47(15), 5946–5996. https://doi.org/10.1039/c6cs00825a
   PubMed Web of Science ®Google Scholar
• Douglas, J. J., Sevrin, M. J., & Stephenson, C. R. J. (2016). Visible light photocatalysis: applications and new disconnections in the synthesis of pharmaceutical agents. Organic Process Research & Development, 20(7), 1134–1147. https://doi.org/10.1021/acs.oprd.6b00125
   Web of Science ®Google Scholar
• Dreger, M., Stanisławska, M., Krajewska-Patan, A., Mielcarek, S., & Mikołajczak, P. L., Buchwald, W. (2009). Pyrrolizidine alkaloids–chemistry, biosynthesis, pathway, toxicity, safety and perspectives of medicinal usage. Herba Polonica, 55, 127.
   Google Scholar
• Eissa, I. H., Yousef, R. G., Elkady, H., Alsfouk, A. A., Alsfouk, B. A., Husein, D. Z., Ibrahim, I. M., Elkaeed, E. B., Metwaly, & A. M. (2023). A new anticancer semisynthetic theobromine derivative targeting egfr protein: CADDD study. Life, 13(1), 191. https://doi.org/10.3390/life13010191
   PubMedGoogle Scholar
• Eivazzadeh-Keihan, R., Radinekiyan, F., Maleki, A., Bani, M. S., & Azizi, M. (2020). A New Generation of star polymer: Magnetic aromatic polyamides with unique microscopic flower morphology and in vitro hyperthermia of cancer therapy. Journal of Material Science, 55, 319.
   Web of Science ®Google Scholar
• Eldehna, W. M., El Hassab, M. A., Elsayed, Z. M., Al-Warhi, T., Elkady, H., Abo-Ashour, M. F., Abourehab, M. A. S., Eissa, I. H., & Abdel-Aziz, H. A. (2022). Design, synthesis, in vitro biological assessment and molecular modeling insights for novel 3-(naphthalen-1-yl)-4,5-dihydropyrazoles as anticancer agents with potential EGFR inhibitory activity. Science Reports, 12, 12821. https://doi.org/10.1038/srep16750
   PubMed Web of Science ®Google Scholar
• Fagnoni, M., Dondi, D. Ravelli, & D., Albini. (2007). A photocatalysis for the formation of the C–C bond. Chemical Review, 107, 2725. https://doi.org/10.1021/cr00017a016
   PubMed Web of Science ®Google Scholar
• Fedeli, W., & Mazza, F. (1974). Crystal Structure of Tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione). J. Chem. Soc., Perkin Trans. 2, 2, 1621.
   Google Scholar
• Filatov, A., Knyazev, N., Shmakov, S., Bogdanov, A., Ryazantsev, M., Shtyrov, A., Starova, G., Molchanov, A., Larina, A., Boitsov, V., & Stepakov, A. (2019). Concise synthesis of tryptanthrin spiro analogues with in vitro antitumor activity based on one-pot, three-component 1,3-dipolar cycloaddition of azomethine ylides to cyclopropenes. Synthesis, 51(03), 713–729. https://doi.org/10.1055/s-0037-1611059
   Google Scholar
• Fox, M. A., & Dulay, M. T. (1993). Heterogeneous photocatalysis. Chemical Reviews, 93(1), 341–357.
   Web of Science ®Google Scholar
• Friedlànder., P., & Roschdestwensky., N. (1915). Chemische Berichte, 48, 1841.
   Google Scholar
• Gandin, V., Ferrarese, A., Dalla Via, M., Marzano, C., Chilin, A., & Marzaro, G. (2015). Targeting kinases with anilinopyrimidines: discovery of N-phenyl-N’-[4-(pyrimidin-4-ylamino) phenyl]urea derivatives as selective inhibitors of class III receptor tyrosine kinase subfamily. Scientific Reports, 5(1), 16750.
   PubMedGoogle Scholar
• Ganjoo, K. N., & Wakelee, H. (2007). Review of Erlotinib in the treatment of advanced non-small cell lung cancer. Biologics: Targets and Therapy, 1, 335.
   PubMedGoogle Scholar
• Gaster, L. M., Joiner, G. F., King. F. D., Wyman. P. A., Sutton. J. M., Bingham. S., Ellis. E. S., Sanger. G. J., & Wardle. K. A. (1995). N-[(1-Butyl-4-piperidinyl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide hydrochloride: the first potent and selective 5-HT4 receptor antagonist amide with oral activity. Journal of Medicinal Chemistry, 38, 4760.
   PubMed Web of Science ®Google Scholar
• Gothelf, A. S., Gothelf, K. V., Hazell, R. G., Jørgensen, K. A. Catalytic asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides—a simple approach to optically active highly functionalized proline derivatives. Angewandte Chemie International Edition, 2002, 41, 4236.
   Google Scholar
• Gothelf, K. V., Kobayashi, S., & Jørgensen, K. A. (2002). Cycloaddition reactions in organic synthesis. Wiley-VCH, Weinheim ed., 211.
   Google Scholar
• Grant, B. J., Rodrigues, A. P. D. C., Elsawy, K. M., Mccammon, A. J., & Caves, L. S. D. (2006). Bio3d: An R package for the comparative analysis of protein structures. Bioinformatics (Oxford, England), 22(21), 2695–2696. https://doi.org/10.1093/bioinformatics/btl461
   PubMed Web of Science ®Google Scholar
• Guda, R., Korra, R., Balaji, S., Palabindela, R., Eerla, R., Lingabathula, H., Yellu, N. R., Kumar, G., & Kasula, M. (2017). Design, synthesis and biological evaluation of 8-substituted-6-hydrazonoindolo[2,1-b]quinazolin- 12(6H)-one scaffolds as potential cytotoxic agents: IDO-1 targeting molecular docking studies. Bioorganic & Medicinal Chemistry Letters, 27, 4741.
   PubMed Web of Science ®Google Scholar
• Gupta, A., Iqbal, S., Roohi; Hussain, M. K., Zaheer, M. R., & Shankar, K. (2022). Visible Light-Promoted green and sustainable approach for one-pot synthesis of 4,4’-(arylmethylene)bis(1H-pyrazol-5-ols), in vitro anticancer activity, and molecular docking with Covid-19 Mpro. ACS Omega, 7, 34583. https://doi.org/10.1021/acsomega.2c04506
   PubMedGoogle Scholar
• Hartmann, T. (1999). Chemical ecology of pyrrolizidine alkaloids. Planta, 207, 483.
   Web of Science ®Google Scholar
• Hicks, R. P., Nichols, D. A., DiTusa, C. A., Sullivan, D. J., Hartell, M. G., Koser, B. W., Bhattacharjee, A. K. (2005) .Evaluation of 4–azaindolo[2,1–b]quinazoline–6,12–diones’ Interaction with hemin and hemozoin: a spectroscopic, X– ray crystallographic and molecular modeling study. Internet Electronic Journal of Molecular Design, 4, 751. https://doi.org/10.1039/B614075K
   Google Scholar
• Hiesinger, K., Dar’in, D., Proschak, E., & Krasavin, M. (2021). Spirocyclic scaffolds in medicinal chemistry. Journal of Medicinal Chemistry, 64(1), 150–183. https://doi.org/10.1021/acs.jmedchem.0c01473
   PubMed Web of Science ®Google Scholar
• Hirshfeld, F. (1977). Bonded-atom fragments for describing molecular charge densities. Theoretica Chimica Acta, 2, 44, 129, 138.
   Google Scholar
• Honda, G., Tabata, M., & Tsuda, M. (1979). The antimicrobial specificity of tryptanthrin. Planta Med., 37, 172.
   PubMed Web of Science ®Google Scholar
• Hou, H., Li, H., Han, Y., & Yan, C. (2018). Synthesis of visible-light mediated tryptanthrin derivatives from isatin and isatoic anhydride under transition metal-free conditions. Organic Chemistry Frontiers, 5(1), 51–54. https://doi.org/10.1039/C7QO00740J
   Web of Science ®Google Scholar
• Hussain, M. H., Ansari, M. I., Yadav, N., Gupta, P. K., Gupta, A. K., Saxena, R., Fatima, I., Manohar, M., Kushwaha, P., Khedgikar, V., Gautam, J., kant, R., Moulik, P. R., Trivedi, R., Dwivedi, A., Kumar, K. R., Saxena A. K., & Hajela, K. (2014). Design and synthesis of ERα/ERβ selective coumarin and chromene derivatives as potential anti-breast cancer and anti-osteoporotic agents. RSC Advances, 4, 8828.
   Google Scholar
• Imtiaz, S., & Syed Mashhood Ali, S. M. (2022). Atom accurate structure determination of alprazolam/cyclodextrin inclusion complexes by ROESY and computational approaches. Journal of the Indian Chemical Society, 99(1), 100299. https://doi.org/10.1016/j.jics.2021.100299
   Web of Science ®Google Scholar
• Imtiaz, S., Banoo, S., Muzaffar, S., & Ali, S. M. (2020). Structural determination of midazolam/beta-cyclodextrin inclusion complex by an already proposed protocol and molecular docking Studies by quantitative analysis. Structural Chemistry, 32, 128419.
   Web of Science ®Google Scholar
• Ishihara, T., Kohno, K., Ushio, S., Iwaki, K., Ikeda, M., Kurimoto, M. (2000). Tryptanthrin inhibits nitric oxide and prostaglandin E2 synthesis by murine macrophages. European Journal of Parmacology, 407(1-2), 197, 204.
   PubMed Web of Science ®Google Scholar
• Iwaki, K., Ohashi, E., Arai, N., Kohno, K., Ushio, S., Taniguchi, M., & Fukuda, S. (2011). Tryptanthrin inhibits Th2 development, and IgE-mediated degranulation and IL-4 production by rat bbasophilic leukemia RBL-2H3 cells. Journal of Ethno Pharmacology, 134, 450.
   PubMed Web of Science ®Google Scholar
• Ji, W., Tan, H., Wang, M., Li, P., & Wang, L. (2016). Photocatalyst-free hypervalent iodine reagent catalyzed decarboxylative acylarylation of acrylamides with α-oxocarboxylic acids driven by visible-light irradiation. Chemical Communication, 52, 1462.
   PubMed Web of Science ®Google Scholar
• Jun, K. Y., Park, S. E., Liang, J. L., Jahng, Y., & Kwon, Y. (2015). Benzo[b]tryptanthrin inhibits MDR1, topoisomerase activity, and reverses adriamycin resistance in breast cancer cells. ChemMedChem, 10(5), 827–835. https://doi.org/10.1002/cmdc.201500068
   PubMed Web of Science ®Google Scholar
• Kataoka, M., Hirata, K., Kunikata, T., Ushio, S., Iwaki, K., Ohashi, K., Ikeda, M., & Kurimoto, M. J. (2001). Antibacterial action of tryptanthrin and kaempferol, isolated from the indigo plant (Polygonum tinctorium Lour.), against helicobacter pylori-infected mongolian gerbils. Gastroenterology, 36, 5.
   Web of Science ®Google Scholar
• Kim, I., Park, S., & Hong, S. (2020). Functionalization of pyridinium derivatives with 1,4-dihydropyridines enabled by photoinduced charge transfer. Organic Letters, 22(21), 8730, 8734.
   PubMed Web of Science ®Google Scholar
• Kimoto, T., Hino, K., Koya-Miyata, S., Yamamoto, Y., Takeuchi, M., Nishizaki, Y., Micallef, M. J., Ushio, S., Iwaki, K., Ikeda, M., & Kurimoto, M. (2001). Cell Differentiation and apoptosis of monocytic and promyelocytic leukemia cells (U-937 and HL-60) by tryptanthrin, an active ingredient of polygonum tinctorium lour. Pathology International, 5, 51, 315, 325.
   PubMed Web of Science ®Google Scholar
• King, F. D., Gaster, L. M., Wyman, P. A., & Joiner, G. F. (1994). Worldwide patent 9407859. Chemistry Abstracts, 121, 157530.
   Google Scholar
• Krivogorsky, B., Grundt, P., Yolken, R., & Jones-Brando, L. (2008). Inhibition of Toxoplasma gondii by indirubin and tryptanthrin analogs. Antimicrobial Agents of Chemotheraphy, 52, 4466.
   PubMed Web of Science ®Google Scholar
• Kumar, A., Gupta, M. K., & Kumar, M. (2012). l-Proline catalysed multicomponent synthesis of 3-Amino alkylated indoles via a mannich-type reaction under solvent-free conditions. Green Chemistry, 2., 14, 290, 295.
   Web of Science ®Google Scholar
• Latypova, D. K., Shmakov, S. V., Pechkovskaya, S. A., Filatov, A. S., Stepakov, A. V., Knyazev, N. A., & Boitsov, V. M. (2021). Identification of spiro-fused pyrrolo[3,4-a]pyrrolizines and tryptanthrines as potential antitumor agents: synthesis and in vitro evaluation. International Journal of Molecular Sciences, 22(21), 11997. https://doi.org/10.3390/ijms222111997
   PubMed Web of Science ®Google Scholar
• Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785.
   PubMed Web of Science ®Google Scholar
• Lewis, N. S. (2007). Toward Cost-effective Solar Energy Use. Science, 315, 798. https://doi.org/10.1038/443019a
   PubMed Web of Science ®Google Scholar
• Li, Y., Zhang, J., Li, D., Chen, Y. (2018). Metal-Free C(sp3)–H allylation via aryl carboxyl radicals enabled by donor–acceptor complex. Organic Letters, , 20, 3296.
   PubMed Web of Science ®Google Scholar
• Liao, X., & Leung, K. N. (2013). Tryptanthrin induces growth inhibition and neuronal differentiation in the human neuroblastoma LA-N-1 cells. Chemico-Biological Interactions, 203, 512.
   PubMed Web of Science ®Google Scholar
• Liddel, J. R. (1996). Pyrrolizidine alkaloids. Natural Product Reports, 13, 187.
   Web of Science ®Google Scholar
• Liu, T.-L., He, Z.-L., Li, Q.-H., Tao, H.-Y., & Wang, C.-J. (2011). Catalytic asymmetric construction of spirocycles containing pyrrolidine motifs and spiro quaternary stereogenic centers via 1,3-dipolar cycloaddition of azomethine ylides with 2-alkylidene-cycloketones. Advanced Synthesis & Catalysis, 353, 1713.
   Web of Science ®Google Scholar
• Lown, J. W. (1984). 1,3-Dipolar cycloaddition chemistry. In: Padwa, A. ed. Vol. 1, Wiley, 2.
   Google Scholar
• Luque, F. J., Lopez, J. M., & Orozco, M. ( 2000). Perspective on “electrostatic interactions of a solute with a continuum. a direct utilization of ab initio molecular potentials for the prevision of solvent effects”. Theoretical Chemistry Accounts, 103, 343.
   Google Scholar
• Ma, F., Xie, X., Ding, L., Gao, J., & Zhang, Z. (2011). Palladium-catalyzed coupling reaction of amino acids (esters) with aryl bromides and chlorides. Tetrahedron, 67(48), 9405–9410. https://doi.org/10.1016/j.tet.2011.09.109
   Web of Science ®Google Scholar
• Maleki, A. (2012). Fe3O4/SiO2 Nanoparticles: An efficient and magnetically recoverable nanocatalyst for the one-pot multicomponent synthesis of diazepines. Tetrahedron, 68, 7827.
   Web of Science ®Google Scholar
• Maleki, A. (2013). One-pot multicomponent synthesis of diazepine derivatives using terminal alkynes in the presence of silica-supported superparamagnetic iron oxide nanoparticles. Tetrahedron Letters, 54, 2055.
   Web of Science ®Google Scholar
• Maleki, A. (2014). One-Pot three-component synthesis of pyrido[20, 10: 2, 3]imidazo [4, 5-c]isoquinolines using Fe3O4-SiO2–OSO3H as an efficient heterogeneous nanocatalyst. RSC Advances, 109, 64169.
   Google Scholar
• Maleki, A. (2018). An efficient magnetic heterogeneous nanocatalyst for the synthesis of pyrazinoporphyrazine macrocycles. Polycyclic Aromatic Compounds, 38, 402.
   Web of Science ®Google Scholar
• Micallef, M. J., Iwaki, K., Ishihara, T., Ushio, S., Aga, M., Kunikata, T., Koya-Miyata, S., Kimoto, T., Ikeda, M., & Kurimoto, M. (2002). The natural plant product tryptanthrin ameliorates dextran sodium sulfate-induced colitis in mice. International Immunopharmacology, 2(4), 565–578. https://doi.org/10.1016/s1567-5769(01)00206-5
   PubMed Web of Science ®Google Scholar
• Mitscher, L. A., & Baker, W. (1998). Tuberculosis: A search for novel therapy starting with natural products. Medicinal Research Reviews, , 18, 363.
   PubMed Web of Science ®Google Scholar
• Moon, S. Y., Lee, J.-H., Choi, H. Y., Cho, I. J., Kim, S. C., & Kim, Y. W. (2014). Tryptanthrin protects hepatocytes against oxidative stress via activation of the extracellular signal regulated kinase/NF-E2-related factor 2 pathway. Biological & Pharmaceutical Bulletin, 37(10), 1633–1640. https://doi.org/10.1248/bpb.b14-00363
   PubMed Web of Science ®Google Scholar
• Morton, O. (2006). Silicon Valley sunrise. Nature, 443(7107), 19–22.
   PubMed Web of Science ®Google Scholar
• Moteki, S. A., Usui, A., Selvakumar, S., Zhang, T., & Maruoka, K. (2014). Metal-free C-H Bond activation of branched aldehydes with a hypervalent iodine(III) catalyst under visible-light photolysis: successful trapping with electron-deficient olefins. Angewandte Chemie, International Edition, 53, 11060.
   PubMed Web of Science ®Google Scholar
• Motoki, T., Takami, Y., Yagi, Y., Tai, A., Yamamoto, I., & Gohda, E. (2005). Inhibition of hepatocyte growth factor induction in human dermal fibroblasts by tryptanthrin. Biological and Pharmaceutical Bulletin, 28(2), 260, 266.
   PubMed Web of Science ®Google Scholar
• Movassaghi, M., & Jacobsen, E. N. (2002). The simplest "enzyme”. Science (New York, N.Y.), 298(5600), 1904–1905. https://doi.org/10.1126/science.1076547
   PubMed Web of Science ®Google Scholar
• Mulliken, R. S. (1934). A new electroaffinity scale; together with data on valence states and on valence ionization potentials and electron affinities. Journal of Chemical Physics. 2(11), 782–793. https://doi.org/10.1063/1.1749394
   Google Scholar
• Mulliken, R. S. (1950). Structures of complexes formed by halogen molecules with aromatic and with oxygenated solvents. Journal of the American Chemical Society, 72, 600.
   Web of Science ®Google Scholar
• Mulliken, R. S. (1952). Molecular compounds and their spectra. III. The interaction of electron donors and acceptors. The Journal of Physical Chemistry, 7, 56, 801, 822.
   Web of Science ®Google Scholar
• Muzaffar, S., Imtiaz, S., & Ali, S. M. (2020). Demonstrating accuracy of the proposed protocol for structure elucidation of cyclodextrin inclusion complexes by validation using DFT studies. Journal of Molecular Structure, 1217, 128419. https://doi.org/10.1016/j.molstruc.2020.128419
   Web of Science ®Google Scholar
• Nájera, C., & Sansano, J. M. ( 2009). 1,3-dipolar cycloadditions: applications to the synthesis of antiviral agents. Organic Biomolecular Chemistry, 7, 4567.
   Google Scholar
• Nocera, D. G. (2006). On the future of global energy. Daedalus, 135, 112.
   Web of Science ®Google Scholar
• Nossier, E. S., Alasfoury, R. A., Hagras, M., El-Manawaty, M., Sayed, S. M., Ibrahim, I. M., Elkady, H., Eissa, I. H., & Elzahabi, H. S. A. (2022). Modified pyrido[2,3-d]pyrimidin-4(3h)-one derivatives as EGFRWT and EGFRT790M inhibitors: design, synthesis, and anti-cancer evaluation. Journal of Molecular Structure, 1270, 133971. https://doi.org/10.1016/j.molstruc.2022.133971
   Web of Science ®Google Scholar
• O’Hagan, D. (2000). Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids. Natural Product Reports, 17, 435.
   PubMed Web of Science ®Google Scholar
• O'Boyle, N. M., Banck, M., James, C. A., Morley, C., Vandermeersch, T., & Hutchison, G. R. (2011). Open babel: An open chemical toolbox. Journal of Chemical Information, 3, 33.
   Google Scholar
• Okulik, N., & Jubert, A. H. (2005). Theoretical analysis of the reactive sites of non–steroidal anti–inflammatory drugs. internet electron. Journal of Computer-Aided Molecular Design, 4, 17.
   Google Scholar
• Osyanin, V. A., Klimochkin, Y. N. (2009). Synthesis of the New Heterocyclic System, Indolo[2,1-b] benzoxazine. Chemistry of Heterocyclic Compounds, 45, 833.
   Google Scholar
• Panday, S. K. (2011). Advances in the chemistry of proline and its derivatives: an excellent amino acid with versatile applications in asymmetric synthesis. Tetrahedron: Asymmetry, 22, 1817.
   Google Scholar
• Pandey, G., Banerjee, P., & Gadre, S. R. (2006). Construction of enantiopure pyrrolidine ring system via asymmetric [3 + 2]-cycloaddition of azomethine ylides. Chemical Reviews, 106, 4484.
   Google Scholar
• Parr, R. G., & Pearson, R. G. (1983). Absolute hardness: companion parameter to absolute electronegativity. Journal of the American Chemical Society, 105, 7512. https://doi.org/10.1021/ed064p561
   Web of Science ®Google Scholar
• Parr, R. G., Szentpály, L. V., & Liu, S. (1999). Electrophilicity Index. Journal of the American Chemical Society, 121, 1992.
   Web of Science ®Google Scholar
• Parr, R.G., & Chattaraj, P. K. (1991). Principle of maximum hardness. Journal of the American Chemical Society, 113, 1854.
   Web of Science ®Google Scholar
• Pearson, R. G. (1987). Recent advances in the concept of hard and soft acids and bases. Journal of Chemical Education, 64(7), 561.
   Web of Science ®Google Scholar
• Pitzer, K. K., Scovill, J. P., Kyle, D. E., & Gerena, L. (2000). PCT Int. Appl. WO0018769A2
   Google Scholar
• Popczun, E. J., McKone, J. R., Read, C. G., Biacchi, A. J., Wiltrout, A. M., Lewis, N. S., & Schaak, R. E. (2013). Nanostructured nickel phosphide as an electrocatalyst for the hydrogen evolution reaction. Journal of the American Chemical Society, 135, 9267.
   PubMed Web of Science ®Google Scholar
• Protti, S., & Fagnoni, M. (2009). The Sunny Side of Chemistry: Green Synthesis by Solar Light. Photochemical & Photobiological Sciences: Official Journal of the European Photochemistry Association and the European Society for Photobiology, 8(11), 1499–1516. https://doi.org/10.1039/b909128a
   PubMed Web of Science ®Google Scholar
• Pu, X., Dang, Q.-D., Yang, L., Zhang, X., & Niu, D. (2022). Doubly stereoconvergent construction of vicinal all-carbon quaternary and tertiary stereocenters by cu/mg-catalyzed propargylic substitution. Nature Communications, 13(1), 2457. https://doi.org/10.1038/s41467-022-29986-y
   PubMed Web of Science ®Google Scholar
• Rajesh, S. M., Bala, B. D., Perumal, S., & Menendez, J. C. (2011). l-Proline-catalysed sequential four-component “on water” protocol for the synthesis of structurally complex heterocyclic Ortho-quinones. Green Chemistry, 13, 3248. https://doi.org/10.1039/C1GC16297G
   Web of Science ®Google Scholar
• Ramon, D. J., & Yus, M. (2005). Asymmetric Multicomponent Reactions (AMCRs): The New Frontier. Angewandte Chemie (International ed. in English), 44(11), 1602–1634. https://doi.org/10.1002/anie.200460548
   PubMed Web of Science ®Google Scholar
• Ravelli, D., Fagnoni, M., & Albini, A. (2013). Photoorganocatalysis. Chemical Society Reviews, 42(1), 97–113. https://doi.org/10.1039/c2cs35250h
   PubMed Web of Science ®Google Scholar
• Recio, M.-C., Cerdá-Nicolás, M., Potterat, O., Hamburger, M., Ríos, J.-L. Anti-inflammatory and antiallergic activity in vivo of lipophilic isatis tinctoria extracts and tryptanthrin. Planta Medica, 2006, 72, 539.
   PubMed Web of Science ®Google Scholar
• Rehman, M. T., Ahmed, S., & Khan, A. U. (2016). Interaction of meropenem with ‘n’ and ‘b’ isoforms of human serum albumin: a spectroscopic and molecular docking study. Journal of Biomolecular Structure & Dynamics, 34(9), 1849–1864. https://doi.org/10.1080/07391102.2015.1094411
   PubMed Web of Science ®Google Scholar
• Robertson, J., & Stevens, (2014). Pyrrolizidine alkaloids. Natural Product Reports, 31, 1721.
   Google Scholar
• Roth, H. D. (1989). The beginnings of organic photochemistry. Angewandte Chemie International Edition (English), 28, 1193.
   Web of Science ®Google Scholar
• Samanta, T., Dey, L., Dinda, J., Chattopadhyay, S. K., Seth., & S. K. (2014). Cooperativity of anion⋯π and π⋯π interactions regulates the self-assembly of a series of carbene proligands: towards quantitative analysis of intermolecular interactions with Hirshfeld Surface. Journal of Molecular Structure. 1068, 58–70. https://doi.org/10.1016/j.molstruc.2014.03.059
   Web of Science ®Google Scholar
• Saquib, M., Baig, M. H., Khan, M. F., Azmi, S., Khatoon, S., Rawat, A. K., Dong, J. J., Asad, M., Arshad, M., Hussain, & Design M. K. (2021). Synthesis of bioinspired benzocoumarin-chalcones chimeras as potential anti-breast cancer agents Chemistry Select, 6, 8754.
   Google Scholar
• Sarkar, T., Das, B. K., Talukdar, K., Shah, T. A., & Punniyamurthy, T. (2020). recent advances in stereoselective ring expansion of spirocyclopropanes: access to the spirocyclic compounds. ACS Omega. 5, 26316.
   PubMed Web of Science ®Google Scholar
• Schindler, F., & ZäHner, H. (1971). Stoffwechselprodukte von mikroorganismen. Archiv für Mikrobiologie, 79(3), 187–203. https://doi.org/10.1007/BF00408783
   PubMedGoogle Scholar
• Schmidt, V. A., Quinn, R. K., Brusoe, A. T., & Alexanian, E. J. (2014). Site-selective aliphatic c–h bromination using n-bromoamides and visible light. Journal of the American Chemical Society, 136, 14389.
   PubMed Web of Science ®Google Scholar
• Scovill, J., Blank, E., Konnick, M., Nenortas, E., & Shapiro T. (2002). Antitrypanosomal Activities of Tryptanthrins. Antimicrobial Agents and Chemotherapy, 46, 882. https://doi.org/10.18433/J3501W
   PubMed Web of Science ®Google Scholar
• Scrocco, E., & Tomasi, J. (1973). The electrostatic molecular potential as a tool for the interpretation of molecular properties. In: New concepts II. Topics in current chemistry Fortschritte der Chemischen Forschung (Vol. 42), Springer.
   Google Scholar
• Shankar G, M., Alex, V. V., Nisthul A, A., Bava, S. V., Sundaram, S., Retnakumari, A. P., Chittalakkottu, S., & Anto, R. J. (2020). Cancer pre‐clinical evidences for the efficacy of tryptanthrin as a potent suppressor of skin cancer. Cell Proliferation, 53(1), e12710. https://doi.org/10.1111/cpr.12710
   PubMed Web of Science ®Google Scholar
• Shi, F., Tao, Z.-L., Luo, S.-W., Tu, S.-J., & Gong, L.-Z. (2012). Scaffold-inspired enantioselective synthesis of biologically important spiro[pyrrolidin-3,2′-oxindoles] with structural diversity through catalytic isatin-derived 1,3-dipolar cycloadditions. Chemistry—A European Journal, 18, 6885.
   Google Scholar
• Shi, F., Zhu, R.-Y., Liang, X., & Tu, S.-J. (2013). Catalytic asymmetric 1,3-dipolar cycloadditions of alkynes with isatin-derived azomethine ylides: enantioselective synthesis of spiro[indoline-3,2′-pyrrole] derivatives. Advanced Synthesis and Catalysis, 355, 2447.
   Google Scholar
• Shi, Q., Li, P., Zhang, Y., & Wang, L. (2017). Visible light-induced tandem oxidative oyclization of 2-alkynylanilines with disulfides (diselenides) to 3-sulfenyl- and 3-selenylindoles under transition metal-free and photocatalyst-free conditions. Organic Chemistry Frontiers., 4, 1322.
   Web of Science ®Google Scholar
• Singh, K., Sharma, P., Kumar, A., Chaudhary, A., & Roy, R. (2013). 4-Aminoquinazoline analogs: A novel class of anticancer agents. Mini-Reviews in Medicinal Chemistry, 13, 1177. https://doi.org/10.1021/jm901558p
   PubMed Web of Science ®Google Scholar
• Song, L., Zhang, L., Luo, S., & Cheng, J.-P. (2014). Visible-light promoted catalyst-free imidation of arenes and heteroarenes. Chemistry—A European Journal, 20, 14231.
   PubMed Web of Science ®Google Scholar
• Spackman, M. A., & Jayatilaka, D. (2009). Hirshfeld surface analysis. Crystal Engineering Communications, 111(), 19, 32.
   Web of Science ®Google Scholar
• Spackman, M. A., McKinnon, J. J., Jayatilaka, D. (2008). Electrostatic potentials mapped on Hirshfeld surfaces provide direct insight into intermolecular interactions in crystals. Crystal Engineering Communications, 10, 377. https://doi.org/10.1007/BF00549096
   Google Scholar
• Sun, Q., Li, X., Su, J., Zhao, L., Ma, M., Zhu, Y., Zhao, Y., Zhu, R., Yan, W., Wang, K., & Wang, R. (2015). The Squaramide-Catalyzed 1,3-Dipolar Cycloaddition of Nitroalkenes with N-2,2,2-Trifluoroethylisatin Ketimines: An Approach for the Synthesis of 5′-Trifluoromethyl-spiro[pyrrolidin-3,2′-oxindoles]. Adv. Synth. Catal., 357, 3187.
   Google Scholar
• Sundberg, R., & Indoles, J. (1996). Academic Press, 175.
   Google Scholar
• Taheri-Ledari, R., Zhang, W., Radmanesh, M., Cathcart, N., Maleki, A., & Kitaev, V. (2021). Plasmonic photothermal release of docetaxel by gold nanoparticles incorporated onto halloysite nanotubes with conjugated 2D8-E3 antibodies for selective cancer therapy. Journal of Nanobiotechnology, 19, 1.
   PubMed Web of Science ®Google Scholar
• Takase, Y., Saeki, T., Watanabe, N., Adachi, H., Souda, S., Saito, I., Cyclic, G. M. P. (2007). Phosphodiesterase inhibitors requirement of 6-substitution of quinazoline derivatives for potent and selective inhibitory activity. Biochemical and Biophysical Research Communications, 37(1), 2106.
   Google Scholar
• Tavakolian, M., & Sarvari, M. H. (2022). Catalyst-free organic transformations under visible-light. ACS Sustainable Chemistry & Engineering., 38, 7, 34583–34598.
   Google Scholar
• Terryn, R. J., German, H. W., Kummerer, T. M., Sinden, R. R., Baum, J. C., & Novak, M. J. (2014). Novel computational study on π-stacking to understand mechanistic interactions of tryptanthrin analogues with DNA. Toxicology Mechanisms and Methods, 24, 73. https://doi.org/10.1016/S0014-2999(00)00674-9
   PubMed Web of Science ®Google Scholar
• Traxler, P., & Furet, P. (1999). Strategies toward the design of novel and selective protein tyrosine kinase inhibitors. Pharmacology & Therapeutics, 82, 195.
   PubMed Web of Science ®Google Scholar
• Uzun, S., Esen, Z., Koç, E., Usta, N.C., & Ceylan M. (2019). Experimental and density functional theory (MEP, FMO, NLO, Fukui functions) and antibacterial activity studies on 2-amino-4- (4-nitrophenyl) -5,6-dihydrobenzo [h] quinoline-3-carbonitrile. Journal of. Molecular Structure, 1178, 450.
   Google Scholar
• Venkatesan, P., Thamotharan, S., Ilangovan, A., Liang, H., & Sundius, T. (2016). Crystal structure, Hirshfeld surfaces and DFT computation of NLO Active (2E)-2-(ethoxycarbonyl)-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino]prop-2-enoic Acid. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 153, 625. https://doi.org/10.1039/B818330A
   PubMed Web of Science ®Google Scholar
• Wakeling, A. E., Guy, S. P., Woodburn, J. R., Ashton, S. E., Curry, B. J., Barker, A. J., & Gibson, K. H. (2002). ZD1839 (IressAn) orally active inhibitor of epidermal growth factor signaling with potential for cancer therapy. Cancer Research, 62, 5749. https://doi.org/10.1016/S0960-894X(01)00344-4
   PubMed Web of Science ®Google Scholar
• Wang, C., Qi, R., Xue, H., Shen, Y., Chang, M., Chen, Y., Wang, R., & Xu, Z. (2020). Visible-Light-Promoted C(sp3) H alkylation by intermolecular charge transfer: preparation of unnatural a-amino acids and late-stage modification of peptides. Angewandte Chemie International Edition, 59, 7461. https://doi.org/10.1021/j150499a001
   PubMed Web of Science ®Google Scholar
• Wang, C.-S., Zhu, R.-Y., Zheng, J., Shi, F., & Tu, S.-J. (2015). Enantioselective construction of spiro[indoline-3,2′-pyrrole] framework via catalytic asymmetric 1,3-dipolar cycloadditions using allenes as equivalents of alkynes. Journal of Organic Chemistry, 80, 512.
   Google Scholar
• Wang, H., Cheng, Y., Yu, S. (2016). Visible-light-promoted and photocatalyst-free trifluoromethylation of enamides. Science China Chemistry, 59, 195.
   Web of Science ®Google Scholar
• Wang, Y.-M., Zhang, H.-H., Li, C., Fanand, T., & Shi, F. (2016). Catalytic asymmetric chemoselective 1,3-dipolar cycloadditions of an azomethine ylide with Isatin-derived imines: diastereo- and enantioselective construction of a spiro[imidazolidine-2,3′-oxindole] framework. Chemisty Communication, 52, 1804.
   Google Scholar
• Wardle, K. A., Bingham, S., Ellis, E. S., Gaster, L. M., Rushant, B., Smith, M. I., & Sanger, G. J. B. (1996). Selective and functional 5-hydroxytryptamine4 receptor antagonism by SB 207266. Journal of Pharmacology, 118, 665.
   Google Scholar
• Wood, E. R., Truesdale, A. T., McDonald, O. B., Yuan, D., Hassell, A., Dickerson, S. H., Ellis, B., Pennisi, C., Horne, E., Lackey, K., Alligood, K. J., Rusnak, D. W., Gilmer, T. M., & Shewchuk, L. (2004). A Unique structure for epidermal growth factor receptor bound to GW572016 (Lapatinib) relationships among protein conformation, inhibitor off-rate, and receptor activity in tumor cells. Cancer Research, 64(18), 6652–6659. https://doi.org/10.1158/0008-5472.CAN-04-1168
   PubMed Web of Science ®Google Scholar
• Wu, J., Bär, R. M., Guo, L., Noble, A., & Aggarwal, V. K. (2019). Photoinduced deoxygenative borylations of aliphatic alcohols. Angewandte Chemie International Edition, 58, 18830. https://doi.org/10.1021/acs.orglett.0c03347
   PubMed Web of Science ®Google Scholar
• Wu, J., Grant, P. S., Li, X., Noble, A., & Aggarwal, V. K. (2019). Catalyst-free deaminative functionalizations of primary amines by photoinduced single-electron transfer. Angewandte Chemie International Edition, 58, 5697.
   PubMed Web of Science ®Google Scholar
• Xiao, J.-A., Liu, Q., Ren, J.-W., Liu, J., Carter, R. G., Chen, X.-Q., Yang, H. (2014). Highly enantioselective construction of polycyclic spirooxindoles by organocatalytic 1,3-dipolar cycloaddition of 2-cyclohexenone catalyzed by proline-sulfonamide. European Journal of Organic Chemistry, 2014, 5700.
   Google Scholar
• Yasutaka., T., Takao., S., Nobuhisa., W., Hideyuki., A., Shigeru., S., & Isao., S. (1994). Cyclic GMP Phosphodiesterase inhibitors. 2. Requirement of 6-substitution of quinazoline derivatives for potent and selective inhibitory activity. Journal of Medicinal Chemistry, 37, 2106.
   PubMed Web of Science ®Google Scholar
• Yu, S. T., Chen, T. M., Teng, S. Y., & Chen, Y. H. (2007). Tryptanthrin inhibits MDR1 and reverses doxorubicin resistance in breast cancer cells. Biochemical and Biophysical Research Communications., 358(1), 79–84.
   PubMed Web of Science ®Google Scholar
• Yu, S.-T., Chen, T.-M., Chem, J.-W., Tseng, S.-Y., & Chen, Y.-H. (2009). Downregulation of GSTπ Expression by tryptanthrin contributing to sensitization of doxorubicin-resistant MCF-7 cells through c-jun NH2-terminal kinase-mediated apoptosis. Anti-Cancer Drugs, 20, 382. https://doi.org/10.1248/bpb.28.260
   PubMed Web of Science ®Google Scholar
• Yu, S.-T., Chen, T.-M., Tseng, S.-Y., Chen, Y.-H. (2007). Tryptanthrin Inhibits MDR1 and Reverses Doxorubicin Resistance in Breast Cancer Cells. Biochemical and Biophysical Research Communications, 358, 79.
   PubMed Web of Science ®Google Scholar
• Yuan, Y.-Q., Majumder, S., Yang, M.-H., & Guo, S.-R. (2020). Recent advances in catalyst-free photochemical reactions via electron-donor–acceptor (EDA) complex process. Tetrahedron Letters, 61(8), 151506. https://doi.org/10.1016/j.tetlet.2019.151506
   Web of Science ®Google Scholar
• Zhang, J., Yang, P. L., & Gray, N. S. (2009). Targeting cancer with small molecule kinase inhibitors. Nature Reviews Cancer, 9, 28.
   PubMed Web of Science ®Google Scholar
• Zhao, H.-W., Yang, Z., Meng, W., Tian, T., Li, B., Song, X.-Q., Chen, X.-Q., & Pang, H.-L. (2015). Diastereo- and enantioselective synthesis of chiral pyrrolidine-fused spirooxindoles via organocatalytic [3 + 2] 1,3-dipolar cycloaddition of azomethine ylides with maleimides. Advanced Synthesis & Catalysis, 357, 2492.
   Web of Science ®Google Scholar
• Zhu, X., Zhang, X., Ma, G., Yan, J., Wang, H., & Yang, Q. (2011). Transport characteristics of Tryptanthrin and its inhibitory effect on P-gp and MRP2 in Caco-2 cells. Journal of Pharmacy & Pharmaceutical Sciences, 14(3), 325.
   PubMed Web of Science ®Google Scholar
• Zou, Y., Zhang, G., Li, C., Long, H., Chen, D., Li, Z., Ouyang, G., Zhang, W., Zhang, Y., & Wang, Z. (2023). Discovery of tryptanthrin and its derivatives and its activities against nsclc in vitro via both apoptosis and autophagy pathways. International Journal of Molecular Sciences, 24(2), 1450.
   PubMed Web of Science ®Google Scholar