Facile One-Pot Multi-Component Synthesis, Characterization, Molecular Docking Studies, Biological Evaluation of 1,2,4-Triazolo Isoindoline-1,3-Diones and Their DFT Calculations

References

• S. H. Wrzesinski, Y. Y. Wan, and R. A. Flavell, “Transforming Growth factor-beta and the immune response: implications for anticancer therapy,” Clinical Cancer Research: An Official Journal of the American Association for Cancer Research 13, no. 18 Pt 1 (2007): 5262–70.
   PubMedGoogle Scholar
• J. Cortes, J. M. Perez‐García, A. Llombart‐Cussac, G. Curigliano, N. S. El Saghir, F. Cardoso, C. H. Barrios, S. Wagle, J. Roman, N. Harbeck, et al, “Enhancing Global Access to Cancer Medicines,” CA: a Cancer Journal for Clinicians 70, no. 2 (2020): 105–24.
   PubMedGoogle Scholar
• C. Yu, B. Liu, and L. Hu, “Efficient Baylis-Hillman reaction using stoichiometric base catalyst and an aqueous medium,” The Journal of Organic Chemistry 66, no. 16 (2001): 5413–8.
   PubMedGoogle Scholar
• Matthias Nuchter, Bernd Ondruschka, Anja Jungnickel, and Ute M⏧Ller, “Organic Processes Initiated by Non-Classical Energy Source,” Journal of Physical Organic Chemistry 13, no. 10 (2000): 579–86.
   Google Scholar
• M. B. Gawande, V. D. B. Bonifacio, R. Luque, P. S. Branco, and R. S. Varma, “Solvent-Free and Catalyst-Free Chemistry: A Benign Way to Sustainability,” Chemsuschem. 7, no. 1 (2014): 24–44.
   PubMed Web of Science ®Google Scholar
• S. Mamidala, R. K. Aravilli, K. Vaarla, and R. Vedula, “Microwave-Assisted Synthesis and Biological Evaluation of Some New Pyrazolothiazoles via Multicomponent Approach,” ChemistrySelect 4, no. 33 (2019): 9878–81.
   Web of Science ®Google Scholar
• K. Sujatha, R. P. Deshpande, R. K. Kesharwani, P. P. Babu, and R. R. Vedula, “An Efficient one- Pot Expeditious Synthesis of 3-Phenyl-1-(6-Phenyl-7H- [1,2,4] Triazolo[3,4-b] [1,3,4]Thiadiazine-3-yl)-1H-Pyrazol-5-Amines via Multicomponent Approach,” Synthetic Communications 49, no. 1 (2019): 49–55.
   Web of Science ®Google Scholar
• L. Banfi, A. Basso, G. Guanti, N. Kielland, C. Repetto, and R. Riva, “Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic substitution: convergent multicomponent synthesis of 1-sulfonyl 1,4-diazepan-5-ones and of their benzo-fused derivatives,” The Journal of Organic Chemistry 72, no. 6 (2007): 2151–60.
   PubMed Web of Science ®Google Scholar
• S. Maddila, R. Pagadala, and S. B. Jonnalagadda, “1,2,4 Triazoles a Review of Synthetic Approach and Biological Activity,” Letters in Organic Chemistry 10, no. 10 (2013): 693–14.
   Web of Science ®Google Scholar
• R. Pignatello, S. Mazzone, A. M. Panico, G. Mazzone, G. Pennisi, R. Castana, M. Matera, and G. Blandino, “Synthesis and Biological Evaluation of Thiazolo-Triazole Derivatives,” European Journal of Medicinal Chemistry. 26, no. 9 (1991): 929–38.
   Google Scholar
• I. A. Ai-Masoudi, Y. A. Ai-Soud, N. J. Ai-Salihi, and N. A. Ai-Masoudi, “1,2,4-triazoles Synthetic Approaches and Pharmacological Importance,” Chemistry of Heterocyclic Compounds. 42 (2006): 1377–403.
   Google Scholar
• Tomasz Plech, Barbara Kaproń, Agata Paneth, Urszula Kosikowska, Anna Malm, Aleksandra Strzelczyk, Paweł Stączek, Łukasz Świątek, Barbara Rajtar, Małgorzata Polz-Dacewicz, et al, “Search for Factors Affecting Antibacterial Activity and Toxicity of 1,2,4-triazole-ciprofloxacin hybrids,” European Journal of Medicinal Chemistry 97, no. 5 (2015): 94–103.
   PubMedGoogle Scholar
• E. M. Guantai, K. Ncokazi, T. J. Egan, J. Gut, P. J. Rosenthal, P. J. Smith, and K. Chibale, “Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds,” Bioorganic & Medicinal Chemistry 18, no. 23 (2010): 8243–56.
   PubMedGoogle Scholar
• C. Tratrat, M. Haroun, A. Paparisva, A. Geronikaki, Ch Kamoutsis, A. Ćirić, J. Glamočlija, M. Soković, Ch Fotakis, P. Zoumpoulakis, et al, “Design Synthesis and Biological Evaluation of New Substituted 5-Benzylideno-2-Adamantyl Thiazole[3,2-b] [1,2,4] Triazol-6(5H) Ones” Pharmacophore Models for Antifungal Activity,” Arabian Journal of Chemistry 11, no. 4 (2018): 573–90.
   Web of Science ®Google Scholar
• Harish Kumar, Sadique A. Javed, Suroor A. Khan, and Mohammad Amir, “1,3,4-oxadiazole/Thiadiazole and 1,2,4-Triazole Derivatives of Biphenyl-4-Yloxy Acetic Acid: Synthesis and Preliminary Evaluation of Biological Properties,” European Journal of Medicinal Chemistry 43, no. 12 (2008): 2688–98.
   PubMedGoogle Scholar
• A. A. Aly, A. A. Hassa, M. M. Makhlouf, and S. Brase, “Chemistry and Biological Activities of 1,2,4-Triazolethiones-Antiviral and anti-Infective Drugs,” Molecules 25, no. 13 (2020): 3036.
   PubMed Web of Science ®Google Scholar
• A. T. A. Boraei, P. K. Singh, M. Sechi, and S. Satta, “Discovery of Novel Functionalized 1,2,4-triazoles as PARP-1 inhibitors in breast cancer: Design, synthesis and antitumor activity evaluation,” European Journal of Medicinal Chemistry 182 (2019): 111621.
   PubMed Web of Science ®Google Scholar
• F. Safari, M. Bayat, S. Nasri, and S. Karami, “Synthesis and Evaluation of anti-Tumor Activity of Novel Triazolo[1,5-a] Pyrimidine on Cancer Cells by Induction of Cellular Apoptosis and Inhibition of Epithelial-to-Mesenchymal Transition Process,” Bioorganic & Medicinal Chemistry Letters 30, no. 10 (2020): 127111.
   PubMedGoogle Scholar
• Hany A. M. El-Sherief, Bahaa G. M. Youssif, Syed Nasir Abbas Bukhari, Ahmed H. Abdelazeem, Mohamed Abdel-Aziz, and Hamdy M. Abdel-Rahman, “Synthesis, Anticancer Activity and Molecular Modeling Studies of 1,2,4-Triazole Derivatives as EGFR Inhibitors,” European Journal of Medicinal Chemistry 156 (2018): 774–89.
   PubMed Web of Science ®Google Scholar
• Costanza Ceni, Daniela Catarzi, Flavia Varano, Diego Dal Ben, Gabriella Marucci, Michela Buccioni, Rosaria Volpini, Andrea Angeli, Alessio Nocentini, Paola Gratteri, et al, “Discovery of First-in-Class Multi Target Adenosine A2A Receptor Antagonists-Carbonic Anhydrase IX and XII Inhibitors. 8 Amino-6-Aryl-2-Phenyl 1,2,4-Triazolo [4,3-a] Pyrazine-3-One Derivatives as New Potential Antitumor Agents,” European Journal of Medicinal Chemistry. 201 (2020): 112478.
   PubMed Web of Science ®Google Scholar
• Nisha Aggarwal, Rajesh Kumar, Prem Dureja, and J. M. Khurana, “Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1,2,4-triazole derivatives,” European Journal of Medicinal Chemistry 46, no. 9 (2011): 4089–99.
   PubMedGoogle Scholar
• Samir M. El-Moghazy, Flora F. Barsoum, Hamdy M. Abdel-Rahman, and Adel A. Marzouk, “Synthesis and anti-Inflammatory Activity of Some Pyrazole Derivatives,” Medicinal Chemistry Research 21, no. 8 (2012): 1722–33.
   Web of Science ®Google Scholar
• K. Speck, and T. Magauer, “The Chemistry of Isoindole Natural Products,” Beilstein Journal of Organic Chemistry 9 (2013): 2048–78.
   PubMed Web of Science ®Google Scholar
• P. L. Zhao, W. F. Ma, A. N. Duan, M. Zou, Y. C. Yan, W. W. You, and S. G. Wu, “One-pot synthesis of novel isoindoline-1,3-dione derivatives bearing 1,2,4-triazole moiety and their preliminary biological evaluation,” European Journal of Medicinal Chemistry 54 (2012): 813–22.
   PubMedGoogle Scholar
• P. Lamie, J. Philoppes, A. E. I. Gendy, L. Rarova, and J. Gruz, “Design Synthesis and Evaluation Phthalimide Derivatives as Invitro anti-Microbial, anti-Oxidant, and anti-Inflammatory Agents,” Molecules 20, no. 9 (2015): 16620–42.
   PubMedGoogle Scholar
• J. A. Ai-Qaisi, T. M. Alhussainy, N. A. Qinna, K. Z. Matalka, E. N. Ai-Kaissi, and Z. A. Muhi-Eldeen, “Synthesis and Pharmacological Evaluation of Amino Acetylenic Isoindoline-1,3-Dione Derivatives as anti-Inflammatory Agents,” Arabian Journal of Chemistry 7, no. 6 (2014): 1024–30.
   Google Scholar
• Stanton Hon Lung Kok, Roberto Gambari, Chung Hin Chui, Marcus Chun Wah Yuen, Eva Lin, Raymond Siu Ming Wong, Fung Yi Lau, Gregory Yin Ming Cheng, Wing Sze Lam, Sau Hing Chan, et al, “Synthesis and anti-Cancer Activity of Benzo Thiazole Containing Phthalimide on Human Carcinoma Cell Lines,” Bioorganic and Medicinal Chemistry Letters. 16, no. 7 (2008): 3626–31.
   Google Scholar
• K. Saravanan, R. Elancheran, S. Divakar, S. Athavan Alias Anand, M. Ramanathan, Jibon Kotoky, N. K. Lokanath, and S. Kabilan, “Design, synthesis and biological evaluation of 2-(4-phenylthiazol-2-yl) isoindoline-1,3-dione derivatives as anti-prostate cancer agents,” Bioorganic & Medicinal Chemistry Letters 27, no. 5 (2017): 1199–04.
   PubMed Web of Science ®Google Scholar
• M. S. A. Ei-Gaby, M. A. Zahran, M. M. F. Ismail, and Y. A. Ammar, “A Novel Synthesis of Dibenzo [c, f] Chromenesdibenzo [c, h] Chromenes and Benzo [7,8] Chromeno [3,4, f] Isoindoles as Antimicrobial Agents,” FARMACO 3, no. 3 (2000): 227–32.
   Google Scholar
• S. Rajasekaran, G. K. Rao, S. Pai, and A. Ranjan, “Design Synthesis Antibacterial and Invitro Antioxidant Activity of Substituted 2-H Benzopyrane-2-One Derivatives,” Int. J. ChemTech Res 3, no. 2 (2011): 555–9.
   Google Scholar
• Alaa A.-M. Abdel-Aziz, Adel S. El-Azab, Mohamed A. Abu El-Enin, Abdulrahman A. Almehizia, Claudiu T. Supuran, and Alessio Nocentini, “Synthesis of Novel isoindoline-1,3-dione-based oximes and benzenesulfonamide hydrazones as selective inhibitors of the tumor-associated carbonic anhydrase IX,” Bioorganic Chemistry 80 (2018): 706–13.
   PubMed Web of Science ®Google Scholar
• Noriyasu Kato, Mitsuru Oka, Takayo Murase, Masahiro Yoshida, Masao Sakairi, Mirensha Yakufu, Satoko Yamashita, Yoshika Yasuda, Aya Yoshikawa, Yuji Hayashi, et al, “Synthesis and Pharmacological Characterization of Potent, selective, and orally bioavailable isoindoline class dipeptidyl peptidase IV inhibitors,” Organic and Medicinal Chemistry Letters 1, no. 1 (2011): 7.
   PubMedGoogle Scholar
• A. A. Abu-Hashem, and M. A. Gouda, “Synthesis, anti-inflammatory and analgesic evaluation of certain new 3a,4,9,9a-tetrahydro-4,9-benzenobenz[f]isoindole-1,3-diones,” Archiv Der Pharmazie 344, no. 8 (2011): 543–51.
   PubMedGoogle Scholar
• H. E. A. Ahmed, H. A. Abdel-Salam, and M. A. Shaker, “Synthesis, Characterization, Molecular Modeling, and Potential Antimicrobial and Anticancer Activities of Novel 2-aminoisoindoline-1,3-dione derivatives,” Bioorganic Chemistry 66 (2016): 1–11.
   PubMed Web of Science ®Google Scholar
• Sara Azimi, Afsaneh Zonouzi, Omidreza Firuzi, Aida Iraji, Mina Saeedi, Mohammad Mahdavi, and Najmeh Edraki, “Discovery of Imidazopyridines Containing Isoindoline-1,3-Dione Framework as a New Class of BACE1 Inhibitors: Design, Synthesis and SAR Analysis,” European Journal of Medicinal Chemistry 138 (2017): 729–37.
   PubMed Web of Science ®Google Scholar
• P. Santhosh, G. Kranthi Kumar, B. Srinivas, and R. R. Vedula, “An Efficient One-Pot Synthesis of Pyrazolyl- [1,2,4] Triazolo[3,4-b][1,3,4] Thiadiazin-6-yl)-2H-Pyran-2-One Derivatives via Multicomponent Approach and Their Potential Antimicrobial and Nematicidal Activities,” Tetrahedron Letters. 54, no. 42 (2013): 5663–66.
   Google Scholar
• P. C. Jilloju, L. Persoons, S. K. Kurapati, D. Schols, S. De Jonghe, D. Daelemans, and R. R. Vedula, “Discovery of (±)-3-(1 H -Pyrazol-1-yl)-6,7-Dihydro-5H-[1,2,4]Triazolo [3,4- b][1,3,4[3,4- b] [1,3,4] Thiadiazine Derivatives with Promising in Vitro Anticoronavirus and Antitumoral Activity,” Mol. Divers 169 (2021): 1–15.
   Google Scholar
• C. J. Burchell, S. M. Aucott, H. L. Milton, A. M. Z. Slawin, and J. Derek Woollins, “Synthesis and Characterization of Cyanodithioimidocarbonate [C2N2S2] 2-Complexes,” Dalton Transactions. 3 (2004): 369–74.
   Google Scholar
• T. Wang, T. H. Zhang, S. Yu, H. Ji, Y. S. Lai, and S. X. Peng, “Synthesis and Biological Evaluation of Novel Thalidomide Analogues as Potential Anticancer Drugs,” Chinese Chemical Letters. 19, no. 8 (2008): 928–30.
   Google Scholar
• Y. Chen, J. Ma, F. Wang, J. Hu, A. Cui, C. Wei, Q. Yang, and F. Li, “Amygdalin Induces Apoptosis in Human Cervical Cancer Cell Line HeLa Cells,” Immunopharmacology and Immunotoxicology 35, no. 1 (2013): 43–51.
   PubMed Web of Science ®Google Scholar
• K. Wu, J. Ai, Q. Liu, T. T. Chen, A. Zhao, X. Peng, Y. Wang, Y. Ji, Q. Yao, Y. Xu, et al, “Multisubstituted Quinoxaline and Pyrido[2,3-d] Pyrimidines: synthesis and SAR Study as Tyrosine Kinase c-Met Inhibitors,” Bioorganic and Medicinal Chemistry Letters. 22, no. 20 (2012): 6368–72.
   PubMedGoogle Scholar
• D. Becke, “A New Mixing of Hartree-Fock and Local Density-Functional Theories,” The Journal of Chemical Physics 98, no. 2 (1993): 1372–77.
   Web of Science ®Google Scholar
• C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical Review. B, Condensed Matter 37, no. 2 (1988): 785–89.
   PubMed Web of Science ®Google Scholar
• Gaussian 16, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, and J. R. Cheeseman, 2016. Gaussian, Inc., Wallingford CT.
   Google Scholar