Design, synthesis, structural and molecular characterization, toxicity, psychotropic activity and molecular docking evaluation of a novel phenytoin derivative: 3-decyl-5,5-diphenylimidazolidine-2,4-dione

References

• Ajao, M. Y., & Akindele, A. J. (2013). Anxiolytic and sedative properties of hydroethanolic extract of Telfairia occidentalis leaves in mice. Revista Brasileira de Farmacognosia, 23(2), 301–309. https://doi.org/10.1590/S0102-695X2012005000138
   Google Scholar
• Alavijeh, M. S., Chishty, M., Qaiser, M. Z., & Palmer, A. M. (2005). Drug metabolism and pharmacokinetics, the blood-brain barrier, and central nervous system drug discovery. Neurorx: The Journal of the American Society for Experimental Neurotherapeutics, 2(4), 554–571. https://doi.org/10.1602/neurorx.2.4.554
   PubMedGoogle Scholar
• Alguacil, L. F., & Pérez-García, C. (2003). Histamine H3 receptor: A potential drug target for the treatment of central nervous system disorders. Current Drug Targets CNS and Neurological Disorders, 2(5), 303–313. https://doi.org/10.2174/1568007033482760
   PubMedGoogle Scholar
• Bagnéris, C., DeCaen, P. G., Naylor, C. E., Pryde, D. C., Nobeli, I., Clapham, D. E., & Wallace, B. A. (2014). Prokaryotic NavMs channel as a structural and functional model for eukaryotic sodium channel antagonism. Proceedings of the National Academy of Sciences of the United States of America, 111(23), 8428–8433. https://doi.org/10.1073/pnas.1406855111
   PubMed Web of Science ®Google Scholar
• Boissier, J. R., Pagny, J., Ratouis, R., & Dumont, C. (1961). Tentative de pharmacologie previsionnelle dans le domaine des neuroleptiques-actions sedative centrale et adrenolytique de la n (dimethoxy-3, 4 phenethyl) n’(chloro-2 phenyl) piperazine. Archives Internationales de Pharmacodynamie et de Therapie, 133(1–2), 29.
   Google Scholar
• Brandenburg, K., & Putz, H. (2006). DIAMOND. Crystal Impact GbR. Bonn, Germany.
   Google Scholar
• Bruker, A. X. S. (2016). “APEX3 Package, APEX3, SAINT and SADABS”.
   Google Scholar
• Cabral, L., & Santos, D. (2005). synthèse et évaluation de l’activité biologique de nouveau dérivés imidazolidinique 2,3,5-trisubstitués. Université de la mediterranée faculté de pharmacie de marseille, france.
   Google Scholar
• Ceylan-Ünlüsoy, M., Verspohl, E. J., & Ertan, R. (2010). Synthesis and antidiabetic activity of some new chromonyl-2,4-thiazolidinediones. Journal of Enzyme Inhibition and Medicinal Chemistry, 25(6), 784–789. ” https://doi.org/10.3109/14756360903357544
   PubMed Web of Science ®Google Scholar
• Cho, S., Kim, S.-H., & Shin, D. (2019). Recent applications of hydantoin and thiohydantoin in medicinal chemistry. European Journal of Medicinal Chemistry, 164, 517–545. https://doi.org/10.1016/j.ejmech.2018.12.066
   PubMed Web of Science ®Google Scholar
• Crawley, J., & Goodwin, F. K. (1980). Preliminary report of a simple animal behavior model for the anxiolytic effects of benzodiazepines. Pharmacology, Biochemistry, and Behavior, 13(2), 167–170. https://doi.org/10.1016/0091-3057(80)90067-2
   PubMed Web of Science ®Google Scholar
• Domínguez, A., Álvarez, A., Hilario, E., Suarez-Merino, B., & Goñi-de-Cerio, F. (2013). Central nervous system diseases and the role of the blood-brain barrier in their treatment. Neuroscience Discovery, 1(1), 3. https://doi.org/10.7243/2052-6946-1-3
   Google Scholar
• Dominguez, A., Alvarez, A., Suarez-Merino, B., & Goni-de-Cerio, F. (2014). Neurological disorders and the blood-brain barrier. Strategies and limitations for drug delivery to the brain. Revue Neurologique, 58(5), 213–224.
   Google Scholar
• File, S. E., & Pellow, S. (1985). The effects of triazolobenzodiazepines in two animal tests of anxiety and in the holeboard. British Journal of Pharmacology, 86(3), 729–735. https://doi.org/10.1111/j.1476-5381.1985.tb08952.x
   PubMed Web of Science ®Google Scholar
• Fleming, I., & Wiley, J. (1979). Frontier orbitals and organic chemical reactions. Journal of Molecular Structure, 56, 306. https://doi.org/10.1016/0022-2860(79)80172-6
   Google Scholar
• Frisch, AE. (2007). GaussView 4. Gaussian Inc. www.gaussian.com.
   Google Scholar
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., … Johnson, B. A. (2004). GAUSSIAN 03. Gaussian, Inc.
   Google Scholar
• Gautam, B. P. S., Srivastava, M., Prasad, R. L., & Yadav, R. A. (2014). Synthesis, characterization and quantum chemical investigation of molecular structure and vibrational spectra of 2,5-dichloro-3,6-bis-(methylamino)1,4-benzoquinone. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 129, 241–254. https://doi.org/10.1016/j.saa.2014.02.082
   PubMed Web of Science ®Google Scholar
• Gilman, J. J. (2007). Bond modulus and stability of covalent solids. Philosophical Magazine Letters, 87(2), 121–124. https://doi.org/10.1080/09500830601166974
   Web of Science ®Google Scholar
• Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T., & Ramli, Y. (2018). 3-Benzyl-5,5-diphenylimidazolidine-2,4-dione. IUCrData, 3(1), x171832. https://doi.org/10.1107/S2414314617018326
   Google Scholar
• Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T., & Ramli, Y. (2017a). 3-Methyl-5,5-diphenylimidazolidine-2,4-dione. IUCrData, 2(10), x171534. https://doi.org/10.1107/S2414314617015346
   Google Scholar
• Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T., & Ramli, Y. (2017b). 3-Ethyl-5,5-diphenylimidazolidine-2,4-dione. IUCrData, 2(11), x171591. https://doi.org/10.1107/S2414314617015917
   Google Scholar
• Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T., & Ramli, Y. (2017c). 3-n-Pentyl-5,5-diphenylimidazolidine-2,4-dione. IUCrData, 2(11), x171693. https://doi.org/10.1107/S2414314617016935
   Google Scholar
• Guerrab, W., Mague, J., Akrad, T. R., Ansar, M., Taoufik, J., & Ramli, Y. (2017d). 5,5-Diphenyl-3-propylimidazolidine-2,4-dione. IUCrData, 2(12), x171808. https://doi.org/10.1107/S2414314617018089
   Google Scholar
• Guerrab, W., Chung, I.-M., Kansiz, S., Mague, J. T., Dege, N., Taoufik, J., Salghi, R., Ali, I. H., Khan, M. I., Lgaz, H., & Ramli, Y. (2019). Synthesis, structural and molecular characterization of 2, 2-diphenyl-2H, 3H, 5H, 6H, 7H-imidazo [2, 1-b][1, 3] thiazin-3-one. Journal of Molecular Structure, 1197, 369–376. https://doi.org/10.1016/j.molstruc.2019.07.081
   Web of Science ®Google Scholar
• Guerrab, W., Lgaz, H., Kansiz, S., Mague, J. T., Dege, N., Ansar, M., Marzouki, R., Taoufik, J., Ali, I. H., Chung, I.-M., & Ramli, Y. (2020). Synthesis of a novel phenytoin derivative: Crystal structure, Hirshfeld surface analysis and DFT calculations. Journal of Molecular Structure, 1205, 127630. https://doi.org/10.1016/j.molstruc.2019.127630
   Web of Science ®Google Scholar
• Guerrab, W., Mague, J. T., Akrad, R., Ansar, M., Taoufik, J., & Ramli, Y. (2018). 3-Butyl-5, 5-diphenylimidazolidine-2, 4-dione. IUCrData, 3(1), x180050. https://doi.org/10.1107/S2414314618000500
   Google Scholar
• Guerrab, W., Mague, J. T., & Ramli, Y. (2020). Synthesis and crystal structure of 3-octyl-5, 5-diphenylimidazolidine-2, 4-dione, C23H28N2O2. Zeitschrift Für Kristallographie - New Crystal Structures, 235(6), 1425–1427. https://doi.org/10.1515/ncrs-2020-0347
   Web of Science ®Google Scholar
• Guerrab, W., Mague, J. T., Taoufik, J., & Ramli, Y. (2018). 3-Hexyl-5,5-diphenylimidazolidine-2,4-dione. IUCrData, 3(1), x180057. https://doi.org/10.1107/S2414314618000573
   Google Scholar
• Hajji, R., Hajji, S., Ahmed, A. B., Nasri, M., & Hlel, F. (2020). Synthesis, physical characterization, thermal studies, biological activities and DFT computations on the molecular structure and vibrational spectra of [C7H12N2]2Bi2Br10·4H2O compound. Journal of Solid State Chemistry, 288, 121402. https://doi.org/10.1016/j.jssc.2020.121402
   Web of Science ®Google Scholar
• Hondeghem, L. M., & Katzung, B. G. (1984). Antiarrhythmic agents: The modulated receptor mechanism of action of sodium and calcium channel-blocking drugs. Annual Review of Pharmacology and Toxicology, 24(1), 387–423. https://doi.org/10.1146/annurev.pa.24.040184.002131
   PubMedGoogle Scholar
• Jain, K. K. (2007). Nanobiotechnology-based drug delivery to the central nervous system. Neuro-Degenerative Diseases, 4(4), 287–291. https://doi.org/10.1159/000101884
   PubMed Web of Science ®Google Scholar
• Kosower, E. M., & Miyadera, T. (1972). Glutathione. 6. Probable mechanism of action of diazene antibiotics. Journal of Medicinal Chemistry, 15(3), 307–312. https://doi.org/10.1021/jm00273a023
   PubMed Web of Science ®Google Scholar
• Kownacki, G., Guilhaumou, R., Glaizal, M., Tichadou, L., Hayek-Lantois, M., & De Haro, L. (2012). Persistance sur plusieurs jours de taux élevés de phénytoïne et de symptômes neurologiques au cours d’une intoxication volontaire au Di-hydan ®. Therapies, 67(3), 267–269. https://doi.org/10.2515/therapie/2012030
   PubMedGoogle Scholar
• Kulkarni, S. K. (1999). Handbook of Experimental Pharmacology (pp. 122–123). Vallabh Prakashan.
   Google Scholar
• Lakshmi Praveen, P., & Ojha, D. P. (2014). Photosensitivity, substituent and solvent-induced shifts in UV-visible absorption bands of naphthyl-ester liquid crystals: A comparative theoretical approach. Liquid Crystals., 41(6), 872–882. https://doi.org/10.1080/02678292.2014.882423
   Web of Science ®Google Scholar
• Langmead, C. J., Watson, J., & Reavill, C. (2008). Muscarinic acetylcholine receptors as CNS drug targets. Pharmacology & Therapeutics., 117(2), 232–243. https://doi.org/10.1016/j.pharmthera.2007.09.009
   PubMed Web of Science ®Google Scholar
• Laverty, D., Desai, R., Uchański, T., Masiulis, S., Stec, W. J., Malinauskas, T., Zivanov, J., Pardon, E., Steyaert, J., Miller, K. W., & Aricescu, A. R. (2019). Cryo-EM structure of the human α1β3γ2 GABA A receptor in a lipid bilayer. Nature, 565(7740), 516–520. https://doi.org/10.1038/s41586-018-0833-4
   PubMed Web of Science ®Google Scholar
• Ledwon, P., Motyka, R., Ivaniuk, K., Pidluzhna, A., Martyniuk, N., Stakhira, P., Baryshnikov, G., Minaev, B. F., & Ågren, H. (2020). The effect of molecular structure on the properties of quinoxaline-based molecules for OLED applications. Dyes and Pigments, 173, 108008. https://doi.org/10.1016/j.dyepig.2019.108008
   Web of Science ®Google Scholar
• Lipnick, R. L., Cotruvo, J. A., Hill, R. N., Bruce, R. D., Stitzel, K. A., Walker, A. P., Chu, I., Goddard, M., Segal, L., Springer, J. A., & Myers, R. C. (1995). Comparison of the up-and-down, conventional LD50, and fixed-dose acute toxicity procedures. Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association, 33(3), 223–231. https://doi.org/10.1016/0278-6915(94)00136-C
   PubMed Web of Science ®Google Scholar
• Lourenço da Silva, A., & Elisabetsky, E. (2001). Interference of propylene glycol with the hole-board test. Brazilian Journal of Medical and Biological Research, 34(4), 545–547. https://doi.org/10.1590/S0100-879X2001000400016
   PubMed Web of Science ®Google Scholar
• Luo, Y. H., & Sun, B. W. (2013). Pharmaceutical co-crystals of pyrazinecarboxamide (PZA) with various carboxylic acids: Crystallography, hirshfeld surfaces, and dissolution study. Crystal Growth and Design., 13, 5. https://doi.org/10.1021/cg400167w
   Web of Science ®Google Scholar
• Mahadevan, D., Periandy, S., Karabacak, M., Ramalingam, S., & Puviarasan, N. (2012). Spectroscopic (FT-IR, FT-Raman and UV–vis) investigation and frontier molecular orbitals analysis on 3-methyl-2-nitrophenol using hybrid computational calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 86, 139–151. https://doi.org/10.1016/j.saa.2011.10.020
   PubMed Web of Science ®Google Scholar
• Meng, L., Chen, F., Bai, F.-Q., Bai, B., Wang, H., & Li, M. (2019). The effect of molecular structure on intramolecular charge-transfer in 1,3,4-oxadiazole derivatives. Journal of Photochemistry and Photobiology A: Chemistry, 377, 309–317. https://doi.org/10.1016/j.jphotochem.2019.04.011
   Web of Science ®Google Scholar
• Messasma, Z., Aggoun, D., Houchi, S., Ourari, A., Ouennoughi, Y., Keffous, F., & Mahdadi, R. (2021). Biological activities, DFT calculations and docking of imines tetradentates ligands, derived from salicylaldehydic compounds as metallo-beta-lactamase inhibitors. Journal of Molecular Structure, 1228, 129463. https://doi.org/10.1016/j.molstruc.2020.129463
   Web of Science ®Google Scholar
• Meusel, M., & Gütschow, M. (2004). Recent developments in hydantoin chemistry. A review. Organic Preparations and Procedures International, 36(5), 391–443. https://doi.org/10.1080/00304940409356627
   Web of Science ®Google Scholar
• Obradović, A., Žižić, J., Trišović, N., & Božić, B. (2013). Evaluation of antioxidative effects of twelve 3-substituted-5,5-diphenylhydantoins on human colon cancer cell line {HCT}-116. Turkish Journal of Biology, 37(6), 741–747.
   Web of Science ®Google Scholar
• Organisation for Economic Co-operation and Development, (2002). Acute oral toxicity-acute toxic class method. OECD Publication.
   Google Scholar
• Pardridge, W. M. (2006). Molecular Trojan horses for blood–brain barrier drug delivery. Current Opinion in Pharmacology, 6(5), 494–500. https://doi.org/10.1016/j.coph.2006.06.001
   PubMed Web of Science ®Google Scholar
• Prasad, S., & Ojha, D. P. (2017). Vibrational spectra, electronic properties and effect of alkyl chain length on chemical stability of nematogens – A comparison using DFT and HF methods. Molecular Crystals & Liquid Crystals, 658(1), 69–80. https://doi.org/10.1080/15421406.2017.1415656
   Web of Science ®Google Scholar
• Prasad, S., & Ojha, D. (2018). Molecular structure, vibrational spectroscopic, electronic properties and chemical stability of p-n-alkylbenzoic acids (nBAC) – A comparison using DFT and HF methods. Acta Physica Polonica A, 134(2), 557–563. https://doi.org/10.12693/APhysPolA.134.557
   Web of Science ®Google Scholar
• Saeed, A., Ashraf, S., White, J. M., Soria, D. B., Franca, C. A., & Erben, M. F. (2015). Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations. Spectrochimica Acta Part A: Molecular Spectroscopy; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 150, 409–418. https://doi.org/10.1016/j.saa.2015.05.068
   PubMed Web of Science ®Google Scholar
• Sakr, M. A. S., Mohamed, A. A., Abou Kana, M. T. H., Elwahy, A. H. M., El-Daly, S. A., & Ebeid, E.-Z M. (2021). Synthesis, characterization, DFT and TD-DFT study of novel bis(5,6-diphenyl-1,2,4-triazines. Journal of Molecular Structure, 1226, 129345. https://doi.org/10.1016/j.molstruc.2020.129345
   Web of Science ®Google Scholar
• Sax, N. I. (1989). Dangerous properties of industrial materials.
   Google Scholar
• Seth, S. K., Maity, G. C., & Kar, T. (2011). Structural elucidation, Hirshfeld surface analysis and quantum mechanical study of para-nitro benzylidene methyl arjunolate. Journal of Molecular Structure, 1000, 120–126. https://doi.org/10.1016/j.molstruc.2011.06.003
   Web of Science ®Google Scholar
• Shaaban, I. A. (2019). Conformational analysis, infrared/Raman spectral assignment, and electronic structural studies of 1,3-dimethyl-2-imidazolidinone using quantum chemical calculations. Journal of Molecular Structure, 1175, 708–720. https://doi.org/10.1016/j.molstruc.2018.08.015
   Web of Science ®Google Scholar
• Sheldrick, G. M. (2015a). Crystal structure refinement with SHELXL. Acta Crystallographica Section C Structural Chemistry, 71(1), 3–8. https://doi.org/10.1107/S2053229614024218
   PubMed Web of Science ®Google Scholar
• Sheldrick, G. M. (2015b). SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallographica. Section A, Foundations and Advances, 71(Pt 1), 3–8. https://doi.org/10.1107/S2053273314026370
   PubMed Web of Science ®Google Scholar
• Sproule, B. A., Naranjo, C. A., Bremner, K. E., & Hassan, P. C. (1997). Selective serotonin reuptake inhibitors and CNS drug interactions. Clinical Pharmacokinetics, 33(6), 454–471. https://doi.org/10.2165/00003088-199733060-00004
   PubMed Web of Science ®Google Scholar
• Stockwell, J., Abdi, N., Lu, X., Maheshwari, O., & Taghibiglou, C. (2014). Novel central nervous system drug delivery systems. Chemical Biology & Drug Design, 83(5), 507–520. https://doi.org/10.1111/cbdd.12268
   PubMed Web of Science ®Google Scholar
• Szymańska, E., Kieć-Kononowicz, K., Białecka, A., & Kasprowicz, A. (2002). Antimicrobial activity of 5-arylidene aromatic derivatives of hydantoin. Part 2. Il Farmaco, 57(1), 39–44. https://doi.org/10.1016/S0014-827X(01)01172-7
   PubMedGoogle Scholar
• Trišović, N., Valentić, N., & Ušćumlić, G. (2011). Solvent effects on the structure-property relationship of anticonvulsant hydantoin derivatives: A solvatochromic analysis. Chemistry Central Journal, 5(1), 62.
   PubMedGoogle Scholar
• Trott, O., & Olson, A. J. (2010). AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry, 31(2), 455–461. https://doi.org/10.1002/jcc.21334
   PubMed Web of Science ®Google Scholar
• Whiting, P. J. (2003). GABA – A receptor subtypes in the brain: A paradigm for CNS drug discovery? Drug Discovery Today, 8(10), 445–450. https://doi.org/10.1016/S1359-6446(03)02703-X
   PubMed Web of Science ®Google Scholar
• Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., & Spackman, M. A. (2012). CrystalExplorer (Version 3.1). University of Western Australia.
   Google Scholar
• Wong, H. L., Wu, X. Y., & Bendayan, R. (2012). Nanotechnological advances for the delivery of CNS therapeutics. Advanced Drug Delivery Reviews, 64(7), 686–700. https://doi.org/10.1016/j.addr.2011.10.007
   PubMed Web of Science ®Google Scholar