231
Views
0
CrossRef citations to date
0
Altmetric
Research Article

New2-((2-(2,4-dinitrophenyl)hydrazineeylidene) derivatives: design, synthesis, in silico, and in vitro anticancer studies

ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon show all
Pages 11681-11699 | Received 20 Sep 2022, Accepted 22 Dec 2022, Published online: 05 Jan 2023

References

  • Abd‐Elzaher, M. M., Hegazy, W. H., & Gaafar, A. E. D. M. (2005). Synthesis, characterization and biological studies of ferrocenyl complexes containing thiophene moiety. Applied Organometallic Chemistry, 19(8), 911–916. https://doi.org/10.1002/aoc.927
  • Abdelazeem, A. H., El-Saadi, M. T., Said, E. G., Youssif, B. G., Omar, H. A., & El-Moghazy, S. M. (2017). Novel diphenylthiazole derivatives with multi-target mechanism: Synthesis, docking study, anticancer and anti-inflammatory activities. Bioorganic Chemistry, 75, 127–138. https://doi.org/10.1016/j.bioorg.2017.09.009
  • Abonia, R., Insuasty, D., Castillo, J., Insuasty, B., Quiroga, J., Nogueras, M., & Cobo, J. (2012). Synthesis of novel quinoline-2-one based chalcones of potential anti-tumor activity. European Journal of Medicinal Chemistry, 57, 29–40. https://doi.org/10.1016/j.ejmech.2012.08.039
  • Abraham, M. J., Murtola, T., Schulz, R., Páll, S., Smith, J. C., Hess, B., & Lindahl, E. (2015). GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX, 1–2, 19–25. https://doi.org/10.1016/j.softx.2015.06.001
  • Alanazi, M. M., Elkady, H., Alsaif, N. A., Obaidullah, A. J., Alanazi, W. A., Al-Hossaini, A. M., Alharbi, M. A., Eissa, I. H., & Dahab, M. A. (2022). Discovery of new quinoxaline-based derivatives as anticancer agents and potent VEGFR-2 inhibitors: Design, synthesis, and in silico study. Journal of Molecular Structure, 1253, 132220. https://doi.org/10.1016/j.molstruc.2021.132220
  • An, H.-W., Qiao, S.-L., Hou, C.-Y., Lin, Y.-X., Li, L.-L., Xie, H.-Y., Wang, Y., Wang, L., & Wang, H. (2015). Self-assembled NIR nanovesicles for long-term photoacoustic imaging in vivo. Chemical Communications (Cambridge, England), 51(70), 13488–13491. https://doi.org/10.1039/C5CC05395A
  • Arora, P., Arora, V., Lamba, H. S., & Wadhwa, D. (2012). Importance of heterocyclic chemistry: A review. International Journal of Pharmaceutical Sciences and Research, 3(9), 2947.
  • Arunagiri, C., Anitha, A. G., Subashini, A., & Selvakumar, S. (2018). Synthesis, X-ray crystal structure, vibrational spectroscopy, DFT calculations, electronic properties and Hirshfeld analysis of (E)-4-Bromo-N'-(2, 4-dihydroxy-benzylidene) benzohydrazide. Journal of Molecular Structure, 1163, 368–378. https://doi.org/10.1016/j.molstruc.2018.03.023
  • Arunagiri, C., Subashini, A., Saranya, M., Muthiah, P. T., Thanigaimani, K., & Razak, I. A. (2015). Synthesis, crystal structure and theoretical studies of a Schiff base 2-[4-hydroxy benzylidene]-amino naphthalene. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 135, 307–316. https://doi.org/10.1016/j.saa.2014.07.016
  • Belal, A., Elanany, M. A., Santali, E. Y., Al-Karmalawy, A. A., Aboelez, M. O., Amin, A. H., Abdellattif, M. H., Mehany, A. B. M., & Elkady, H. (2022). Screening a panel of topical ophthalmic medications against MMP-2 and MMP-9 to investigate their potential in keratoconus management. Molecules, 27(11), 3584. https://doi.org/10.3390/molecules27113584
  • Belal, A., Abdel Gawad, N. M., Mehany, A. B., Abourehab, M. A., Elkady, H., Al‐Karmalawy, A. A., & Ismael, A. S. (2022). Design, synthesis and molecular docking of new fused 1 H-pyrroles, pyrrolo [3, 2-d] pyrimidines and pyrrolo [3, 2-e][1, 4] diazepine derivatives as potent EGFR/CDK2 inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 37(1), 1884–1902. https://doi.org/10.1080/14756366.2022.2096019
  • BIOVIA Discovery Studio. (2020). Discovery studio modeling environment. Discovery Studio visualizer v21.1.0.20298. San Diego, CA, USA: BIOVIA
  • Castillo, J.-C., Jiménez, E., Portilla, J., Insuasty, B., Quiroga, J., Moreno-Fuquen, R., Kennedy, A. R., & Abonia, R. (2018). Application of a catalyst-free Domino Mannich/Friedel-Crafts alkylation reaction for the synthesis of novel tetrahydroquinolines of potential antitumor activity. Tetrahedron, 74(9), 932–947. https://doi.org/10.1016/j.tet.2017.12.049
  • Buldurun, K., Turan, N., Bursal, E., Aras, A., Mantarcı, A., Çolak, N., Türkan, F., & Gülçin, İ. (2021). Synthesis, characterization, powder x-ray diffraction analysis, thermal stability, antioxidant properties and enzyme inhibitions of M (II)-Schiff base ligand complexes. Journal of Biomolecular Structure & Dynamics, 39(17), 6480–6487. https://doi.org/10.1080/07391102.2020.1802340
  • Celik, I., Abdellattif, M. H., & Tallei, T. E. (2022). An insight based on computational analysis of the interaction between the receptor-binding domain of the omicron variants and human angiotensin-converting enzyme 2. Biology, 11(5), 797. https://doi.org/10.3390/biology11050797
  • Çevik, U. A., Celik, I., Işık, A., Pillai, R. R., Tallei, T. E., Yadav, R., Özkay, Y., & Kaplancıklı, Z. A. (2022). Synthesis, molecular modeling, quantum mechanical calculations and ADME estimation studies of benzimidazole-oxadiazole derivatives as potent antifungal agents. Journal of Molecular Structure, 1252, 132095. https://doi.org/10.1016/j.molstruc.2021.132095
  • Chabner, B. A. (2004). The miracle of Iressa®. The Oncologist, 9(3), 245–246. https://doi.org/10.1634/theoncologist.9-3-245
  • Collins, I., Molife, R., Kaye, S. B., & Workman, P. (2005). Rational drug design of small molecule anticancer agents: Preclinical discovery. The Cancer Handbook, 14, 57e66. https://doi.org/10.1002/9780470025079.chap96.pub2
  • Dallakyan, S., & Olson, A. J. (2015). Small-molecule library screening by docking with PyRx. Chemical biology (pp. 243–250). Humana Press. https://doi.org/10.1007/978-1-4939-2269-7_19
  • Dennington, R D., Keith, T. A., & Millam, J. M. (2016). GaussView, version 6.0. 16. Semichem Inc.
  • Dembitsky, V. M. (2006). Anticancer activity of natural and synthetic acetylenic lipids. Lipids, 41(10), 883–924. https://doi.org/10.1007/s11745-006-5044-3
  • Elkaeed, E. B., Youssef, F. S., Eissa, I. H., Elkady, H., Alsfouk, A. A., Ashour, M. L., El Hassab, M. A., Abou-Seri, S. M., & Metwaly, A. M. (2022). Multi-step in silico discovery of natural drugs against COVID-19 targeting main protease. International Journal of Molecular Sciences, 23(13), 6912. https://doi.org/10.3390/ijms23136912
  • Elkaeed, E. B., Elkady, H., Belal, A., Alsfouk, B. A., Ibrahim, T. H., Abdelmoaty, M., Arafa, R. K., Metwaly, A. M., & Eissa, I. H. (2022). Multi-phase in silico discovery of potential SARS-CoV-2 RNA-dependent RNA polymerase inhibitors among 3009 clinical and FDA-approved related drugs. Processes, 10(3), 530. https://doi.org/10.3390/pr10030530
  • Farkona, S., Diamandis, E. P., & Blasutig, I. M. (2016). Cancer immunotherapy: The beginning of the end of cancer? BMC Medicine, 14(1), 1–18. https://doi.org/10.1186/s12916-016-0623-5
  • Fadda, A. A., Berghot, M. A., Amer, F. A., Badawy, D. S., & Bayoumy, N. M. (2012). Synthesis and antioxidant and antitumor activity of novel pyridine, chromene, thiophene and thiazole derivatives. Archiv Der Pharmazie, 345(5), 378–385. https://doi.org/10.1002/ardp.201100335
  • Frisch, M. E., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., & Fox, D. J. (2016). Gaussian. 16.
  • Gabr, M. T., El-Gohary, N. S., El-Bendary, E. R., & El-Kerdawy, M. M. (2014). Synthesis and in vitro antitumor activity of new series of benzothiazole and pyrimido [2, 1-b] benzothiazole derivatives. European Journal of Medicinal Chemistry, 85, 576–592. https://doi.org/10.1016/j.ejmech.2014.07.097
  • Gridelli, C., De Marinis, F., Di Maio, M., Cortinovis, D., Cappuzzo, F., & Mok, T. (2011). Gefitinib as first-line treatment for patients with advanced non-small-cell lung cancer with activating epidermal growth factor receptor mutation: Review of the evidence. Lung Cancer (Amsterdam, Netherlands), 71(3), 249–257. https://doi.org/10.1016/j.lungcan.2010.12.008
  • Guo, S., Colbert, L. S., McGlothen, T. Z., & Gonzalez-Perez, R. R. (2012). Regulation of angiogenesis in human cancer via vascular endothelial growth factor receptor-2 (VEGFR-2). Tumor Angiogenesis, 27–66. https://www.who.int/news-room/fact-sheets/detail/cancer.
  • Huang, J., Rauscher, S., Nawrocki, G., Ran, T., Feig, M., de Groot, B. L., Grubmüller, H., & MacKerell, A. D. (2017). CHARMM36m: An improved force field for folded and intrinsically disordered proteins. Nature Methods, 14(1), 71–73. https://doi.org/10.1038/nmeth.4067
  • Irfan, M., Aneja, B., Yadava, U., Khan, S. I., Manzoor, N., Daniliuc, C. G., & Abid, M. (2015). Synthesis, QSAR and anticandidal evaluation of 1, 2, 3-triazoles derived from naturally bioactive scaffolds. European Journal of Medicinal Chemistry, 93, 246–254. https://doi.org/10.1016/j.ejmech.2015.02.007
  • Jiménez-Pulido, S. B., Linares-Ordóñez, F. M., Martínez-Martos, J. M., Moreno-Carretero, M. N., Quirós-Olozábal, M., & Ramírez-Expósito, M. J. (2008). Metal complexes with the ligand derived from 6-acetyl-1, 3, 7-trimethyllumazine and benzohydrazide. Molecular structures of two new Co (II) and Rh (III) complexes and analysis of in vitro antitumor activity. Journal of Inorganic Biochemistry, 102(8), 1677–1683. https://doi.org/10.1016/j.jinorgbio.2008.04.004
  • Jo, S., Kim, T., Iyer, V. G., & Im, W. (2008). CHARMM‐GUI: A web‐based graphical user interface for CHARMM. Journal of Computational Chemistry, 29(11), 1859–1865. https://doi.org/10.1002/jcc.20945
  • Kajal, A., Bala, S., Kamboj, S., Sharma, N., & Saini, V. (2013). Schiff bases: A versatile pharmacophore. Journal of Catalysts, 2013, 1–14. https://doi.org/10.1155/2013/893512
  • Karabacak, M., & Yilan, E. (2012). Molecular structure, spectroscopic (FT-IR, FT-Raman, 13C and 1H NMR, UV), polarizability and first-order hyperpolarizability, HOMO and LUMO analysis of 4′-methylbiphenyl-2-carbonitrile. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 87, 273–285. https://doi.org/10.1016/j.saa.2011.11.051
  • Kargar, H., Kia, R., & Tahir, M. N. (2012). (E)-4-amino-N′-(2-hydroxy-5-methoxybenzylidene) benzohydrazide monohydrate. Acta Crystallographica. Section E, Structure Reports Online, 68(Pt 8), o2321–o2322. https://doi.org/10.1107/S1600536812026633
  • Karrouchi, K., Celik, I., Fettach, S., Karthick, T., Bougrin, K., Radi, S., Faouzi, M. E. A., Ansar, M., & Renjith, R. (2022). Synthesis and investigations of reactive properties, photophysical properties and biological activities of a pyrazole-triazole hybrid molecule. Journal of Molecular Structure, 1265, 133363. https://doi.org/10.1016/j.molstruc.2022.133363
  • Kolligs, F. T. (2016). Diagnostics and epidemiology of colorectal cancer. Visceral Medicine, 32(3), 158–164. https://doi.org/10.1159/000446488
  • Kumar, S., Saini, V., Maurya, I. K., Sindhu, J., Kumari, M., Kataria, R., & Kumar, V. (2018). Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents. PloS One, 13(4), e0196016. https://doi.org/10.1371/journal.pone.0196016
  • Krasinskas, A. M. (2011). EGFR signaling in colorectal carcinoma. Pathology Research International, 2011, 932932. https://doi.org/10.4061/2011/932932
  • Li, W., Zhou, J., & Xu, Y. (2015). Study of the in vitro cytotoxicity testing of medical devices. Biomedical Reports, 3(5), 617–620. https://doi.org/10.3892/br.2015.481
  • Li, Y., Yan, W., Yang, J., Yang, Z., Hu, M., Bai, P., Tang, M., & Chen, L. (2018). Discovery of novel β-carboline/acylhydrazone hybrids as potent antitumor agents and overcome drug resistance. European Journal of Medicinal Chemistry, 152, 516–526. https://doi.org/10.1016/j.ejmech.2018.05.003
  • Lone, S. H., Jameel, S., Bhat, M. A., Lone, R. A., Butcher, R. J., & Bhat, K. A. (2018). Synthesis of an unusual quinazoline alkaloid: Theoretical and experimental investigations of its structural, electronic, molecular and biological properties. RSC Advances, 8(15), 8259–8268. https://doi.org/10.1039/C8RA00138C
  • Lu, J. F. (2008). 4-Hydroxy-N′-(2-hydroxy-3-methoxybenzylidene) benzohydrazide monohydrate. Acta Crystallographica. Section E, Structure Reports Online, 64(Pt 10), o2032. https://doi.org/10.1107/S1600536808030894
  • Lopez, J. S., & Banerji, U. (2017). Combine and conquer: Challenges for targeted therapy combinations in early phase trial. Nature Reviews. Clinical Oncology, 14(1), 57–66. https://doi.org/10.1038/nrclinonc.2016.96
  • Luque, F. J., López, 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(3–4), 343–345. https://doi.org/10.1007/s002149900013
  • Mahdy, H. A., Ibrahim, M. K., Metwaly, A. M., Belal, A., Mehany, A. B. M., El-Gamal, K. M. A., El-Sharkawy, A., Elhendawy, M. A., Radwan, M. M., Elsohly, M. A., & Eissa, I. H. (2020). Design, synthesis, molecular modeling, in vivo studies and anticancer evaluation of quinazolin-4 (3H)-one derivatives as potential VEGFR-2 inhibitors and apoptosis inducers. Bioorganic Chemistry, 94, 103422. https://doi.org/10.1016/j.bioorg.2019.103422
  • Malik, M. A., Dar, O. A., Gull, P., Wani, M. Y., & Hashmi, A. A. (2018). Heterocyclic Schiff base transition metal complexes in antimicrobial and anticancer chemotherapy. MedChemComm, 9(3), 409–436. https://doi.org/10.1039/C7MD00526A
  • Miroslaw, B., Plech, T., & Wujec, M. (2015). Halogen bonding in the antibacterial 1, 2, 4-triazole-3-thione derivative–Spectroscopic properties, crystal structure and conformational analysis. Journal of Molecular Structure, 1083, 187–193. https://doi.org/10.1016/j.molstruc.2014.11.060
  • Mohamed, G. G., & Sharaby, C. M. (2007). Metal complexes of Schiff base derived from sulphametrole and o-vanilin: Synthesis, spectral, thermal characterization and biological activity. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 66(4–5), 949–958. https://doi.org/10.1016/j.saa.2006.04.033
  • O'Boyle, N. M., Banck, M., J., James C. A., Morley, C., Vandermeersch, T., & Hutchison, G. R. (2011). Open Babel: An open chemical toolbox. Journal of Cheminformatics, 3(1), 33. https://doi.org/10.1186/1758-2946-3-33
  • Odabaşoğlu, M., Albayrak, Ç., Koşar, B., & Büyükgüngör, O. (2012). Synthesis, spectroscopic characterizations and quantum chemical computational studies of (Z)-4-[(E)-p-tolyldiazenyl]-6-[(2-hydroxyphenylamino)methylene]-2-methoxycyclohexa-2,4-dienone. Spectrochim. Acta A, 92, 357–364. https://doi.org/10.1186/1758-2946-3-33
  • One-way ANOVA followed by Dinnett’s multiple comparisons test was performed using Graphpad Prism version 8.0.0 for windows. GraphPad Software, San Diego, California USA, www.graphpad.com.
  • Ozdemir, K. G., Yılmaz, H., & Yılmaz, S. (2009). In vitro evaluation of cytotoxicity of soft lining materials on L929 cells by MTT assay. Journal of Biomedical Materials Research. Part B, Applied Biomaterials, 90(1), 82–86. https://doi.org/10.1002/jbm.b.31256
  • Pearson, R. G. (1987). Recent advances in the concept of hard and soft acids and bases. Journal of Chemical Education, 64(7), 561. https://doi.org/10.1021/ed064p561
  • Pereshivko, O. P., Peshkov, V. A., & Van der Eycken, E. V. (2010). Unprecedented Cu (I)-catalyzed microwave-assisted three-component coupling of a ketone, an alkyne, and a primary amine. Organic Letters, 12(11), 2638–2641. https://doi.org/10.1021/ol1008312
  • Prathap, K. C., & Lokanath, N. K. (2018). Three novel coumarin-benzenesulfonylhydrazide hybrids: Synthesis, characterization, crystal structure, Hirshfeld surface, DFT and NBO studies. Journal of Molecular Structure, 1171, 564–577. https://doi.org/10.1016/j.molstruc.2018.06.022
  • Ruddarraju, R. R., Murugulla, A. C., Kotla, R., Tirumalasetty, M. C. B., Wudayagiri, R., Donthabakthuni, S., & Maroju, R. (2017). Design, synthesis, anticancer activity and docking studies of theophylline containing 1, 2, 3-triazoles with variant amide derivatives. MedChemComm, 8(1), 176–183. https://doi.org/10.1039/C6MD00479B
  • Sajjan, V. P., Anigol, L. B., Gurubasavaraj, P. M., Kotresha, D., Pradhan, S. S., Venkatesh, S., & Patil, D. (2022). Synthesis, characterization and molecular docking studies of phenoxyimine based ligands: Cytotoxicity, hemolytic activity and antioxidant assessment. Journal of Molecular Structure, 1265, 133457. https://doi.org/10.1016/j.molstruc.2022.133457
  • Sangani, C. B., Makawana, J. A., Duan, Y. T., Yin, Y., Teraiya, S. B., Thumar, N. J., & Zhu, H. L. (2014). Design, synthesis and molecular modeling of biquinoline–pyridine hybrids as a new class of potential EGFR and HER-2 kinase inhibitors. Bioorganic & Medicinal Chemistry Letters, 24(18), 4472–4476. https://doi.org/10.1016/j.bmcl.2014.07.094
  • Savcı, A., Buldurun, K., & Kırkpantur, G. (2021). A new Schiff base containing 5-FU and its metal complexes: Synthesis, characterization, and biological activities. Inorganic Chemistry Communications, 134, 109060. https://doi.org/10.1016/j.inoche.2021.109060
  • Schiff, H. (1864). Communications from the University laboratory in Pisa: A new range of organic bases. Annalen der Chemie und Pharmacie, 131(1), 118–119. https://doi.org/10.1002/jlac.18641310113
  • Scrocco, E., & Tomasi, J. (1973). The electrostatic molecular potential as a tool for the interpretation of molecular properties. New concepts II (pp. 95–170). Springer. https://doi.org/10.1007/3-540-06399-4_6
  • Sheldrick, G. M. (2015). Crystal structure refinement with SHELXL. Acta Crystallographica. Section C, Structural Chemistry, 71(Pt 1), 3–8. https://doi.org/10.1107/S2053273314026370
  • Taghour, M. S., Elkady, H., Eldehna, W. M., El-Deeb, N. M., Kenawy, A. M., Elkaeed, E. B., Alsfouk, A. A., Alesawy, M. S., Metwaly, A. M., & Eissa, I. H. (2022). Design and synthesis of thiazolidine-2, 4-diones hybrids with 1, 2-dihydroquinolones and 2-oxindoles as potential VEGFR-2 inhibitors: In-vitro anticancer evaluation and in-silico studies. Journal of Enzyme Inhibition and Medicinal Chemistry, 37(1), 1903–1917. https://doi.org/10.1080/14756366.2022.2085693
  • Turan, N., Buldurun, K., Türkan, F., Aras, A., Çolak, N., Murahari, M., Bursal, E., & Mantarcı, A. (2022). Some metal chelates with Schiff base ligand: Synthesis, structure elucidation, thermal behavior, XRD evaluation, antioxidant activity, enzyme inhibition, and molecular docking studies. Molecular Diversity, 26(5), 2459–2472. https://doi.org/10.1007/s11030-021-10344-x
  • van Wyk, J. L., Mapolie, S. F., Lennartson, A., Håkansson, M., & Jagner, S. (2008). The catalytic oxidation of phenol in aqueous media using cobalt (II) complexes derived from N-(aryl) salicylaldimines. Inorganica Chimica Acta, 361(7), 2094–2100. https://doi.org/10.1016/j.ica.2007.10.031
  • Vektariene, A., Vektaris, G., & Svoboda, J. (2009). A theoretical approach to the nucleophilic behavior of benzofused thieno [3, 2-b] furans using DFT and HF based reactivity descriptors. Arkivoc, 2009(7), 311–329. https://doi.org/10.3998/ark.5550190.0010.730
  • Venkatesan, P., Thamotharan, S., Kumar, R. G., & Ilangovan, A. (2015). Invariant and variable intermolecular interactions in functionalized malonic acid half-esters: X-ray, Hirshfeld surface and PIXEL energy analyses. CrystEngComm, 17(4), 904–915. https://doi.org/10.1039/C4CE02125H
  • 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, 625–636. https://doi.org/10.1016/j.saa.2015.09.002
  • Venkatesan, P., Rajakannan, V., Venkataramanan, N. S., Ilangovan, A., Sundius, T., & Thamotharan, S. (2016). Structural investigation of (2E)-2-(ethoxycarbonyl)-3-[(4-methoxyphenyl) amino] prop-2-enoic acid: X-ray crystal structure, spectroscopy and DFT. Journal of Molecular Structure, 1119, 259–268. https://doi.org/10.1016/j.molstruc.2016.04.090
  • Yeşilçayır, E., Çelik, İ., Şen, H. T., Gürpınar, S. S., Eryılmaz, M., & Kilcigil, G. (2022). Novel benzimidazole-based compounds as antimicrobials: Synthesis, molecular docking, molecular dynamics and in silico ADME profile studies. Acta Chimica Slovenica, 69(2), 419–429. https://doi.org/10.17344/acsi.2021.7314
  • Yu, Y. Y., Xian, H. D., Liu, J. F., & Zhao, G. L. (2009). Synthesis, characterization, crystal structure and antibacterial activities of transition metal (II) complexes of the Schiff base 2-[(4-methylphenylimino) methyl]-6-methoxyphenol. Molecules (Basel, Switzerland), 14(5), 1747–1754. https://doi.org/10.3390/molecules14051747
  • Zaout, S., Chafaa, S., Hellal, A., Boukhemis, O., Khattabi, L., Merazig, H., Chafai, N., Bensouici, C., & Bendjeddou, L. (2021). Hydroxyphenylamine phosphonate derivatives: Synthesis, x-ray crystallographic analysis, and evaluation of theirs anti-Alzheimer effects and antioxidant activities. Journal of Molecular Structure, 1225, 129121. https://doi.org/10.1016/j.molstruc.2020.129121
  • Zoete, V., Cuendet, M. A., Grosdidier, A., & Michielin, O. (2011). SwissParam: A fast force field generation tool for small organic molecules. Journal of Computational Chemistry, 32(11), 2359–2368. https://doi.org/10.1002/jcc.21816

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.