New tetrahydroisoquinoline-4-carbonitrile derivatives as potent agents against cyclin-dependent kinases, crystal structures, and computational studies

References

• Acar Çevik, U., Celik, I., İnce, U., Maryam, Z., Ahmad, I., Patel, H., Özkay, Y., & Asım Kaplancıklı, Z. (2023). Synthesis, biological evaluation, and molecular modeling studies of new 1, 3, 4‐thiadiazole derivatives as potent antimicrobial agents. Chemistry & Biodiversity, 20(3), e202201146. https://doi.org/10.1002/cbdv.202201146
   PubMed Web of Science ®Google Scholar
• Agwupuye, J. A., Louis, H., Gber, T. E., Ahmad, I., Agwamba, E. C., Samuel, A. B., Ejiako, E. J., Patel, H., Ita, I. T., & Bassey, V. M. (2022). Molecular modeling and DFT studies of diazenylphenyl derivatives as a potential HBV and HCV antiviral agents. Chemical Physics Impact, 5, 100122. https://doi.org/10.1016/j.chphi.2022.100122
   Google Scholar
• Akintunde, J. K., Akomolafe, V. O., Taiwo, O. A., Ahmad, I., Patel, H., Osifeso, A., Olusegun, A. O., & Ojo, O. A. (2022). Antihypertensive activity of roasted cashew nut in mixed petroleum fractions-induced hypertension: An in vivo and in silico approaches. Heliyon, 8(12), e12339. https://doi.org/10.1016/j.heliyon.2022.e12339
   PubMed Web of Science ®Google Scholar
• Ali, G.-C., Ryan, G., & De Silva, M. J. (2016). Validated screening tools for common mental disorders in low and middle income countries: A systematic review. PloS One, 11(6), e0156939. https://doi.org/10.1371/journal.pone.0156939
   PubMed Web of Science ®Google Scholar
• Aljuhani, A., Ahmed, H. E. A., Ihmaid, S. K., Omar, A. M., Althagfan, S. S., Alahmadi, Y. M., Ahmad, I., Patel, H., Ahmed, S., Almikhlafi, M. A., El-Agrody, A. M., Zayed, M. F., Turkistani, S. A., Abulkhair, S. H., Almaghrabi, M., Salama, S. A., Al-Karmalawy, A. A., & Abulkhair, H. S. (2022). In vitro and computational investigations of novel synthetic carboxamide-linked pyridopyrrolopyrimidines with potent activity as SARS-CoV-2-M Pro inhibitors. RSC Advances, 12(41), 26895–26907. https://doi.org/10.1039/d2ra04015h
   PubMed Web of Science ®Google Scholar
• Alsagaby, S. A., Iqbal, D., Ahmad, I., Patel, H., Mir, S. A., Madkhali, Y. A., Oyouni, A. A. A., Hawsawi, Y. M., Alhumaydhi, F. A., Alshehri, B., Alturaiki, W., Alanazi, B., Mir, M. A., & Al Abdulmonem, W. (2022). In silico investigations identified butyl xanalterate to competently target CK2α (CSNK2A1) for therapy of chronic lymphocytic leukemia. Scientific Reports, 12(1), 17648. https://doi.org/10.1038/s41598-022-21546-0
   PubMed Web of Science ®Google Scholar
• Asghar, U., Witkiewicz, A. K., Turner, N. C., & Knudsen, E. S. (2015). The history and future of targeting cyclin-dependent kinases in cancer therapy. Nature Reviews. Drug Discovery, 14(2), 130–146. https://doi.org/10.1038/nrd4504
   PubMed Web of Science ®Google Scholar
• Ayers, P. W., Anderson, J. S. M., & Bartolotti, L. J. (2005). Perturbative perspectives on the chemical reaction prediction problem. International Journal of Quantum Chemistry, 101(5), 520–534. https://doi.org/10.1002/qua.20307
   Web of Science ®Google Scholar
• Ayers, P. W., Morell, C., De Proft, F., & Geerlings, P. (2007). Understanding the Woodward–Hoffmann rules by using changes in electron density. Chemistry (Weinheim an Der Bergstrasse, Germany), 13(29), 8240–8247. https://doi.org/10.1002/chem.200700365
   PubMed Web of Science ®Google Scholar
• Ayipo, Y. O., Ahmad, I., Alananzeh, W., Lawal, A., Patel, H., & Mordi, M. N. (2022). Computational modelling of potential Zn-sensitive non-β-lactam inhibitors of imipenemase-1 (IMP-1). Journal of Biomolecular Structure and Dynamics, 40, 1–21. https://doi.org/10.1080/07391102.2022.2153168
   PubMedGoogle Scholar
• Ayipo, Y. O., Ahmad, I., Chong, C. F., Zainurin, N. A., Najib, S. Y., Patel, H., & Mordi, M. N. (2023). Carbazole derivatives as promising competitive and allosteric inhibitors of human serotonin transporter: Computational pharmacology. Journal of Biomolecular Structure and Dynamics, 41, 1–22. https://doi.org/10.1080/07391102.2023.2198016
   PubMedGoogle Scholar
• Bakhite, E. A., Marae, I. S., Gad, M. A., Mohamed, S. K., Mague, J. T., & Abuelhassan, S. (2022). Pyridine derivatives as insecticides. Part 3. Synthesis, crystal structure, and toxicological evaluation of some new partially hydrogenated isoquinolines against Aphis gossypii (Glover, 1887). Journal of Agricultural and Food Chemistry, 70(31), 9637–9644. https://doi.org/10.1021/acs.jafc.2c02776
   PubMed Web of Science ®Google Scholar
• Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review. A, General Physics, 38(6), 3098–3100. https://doi.org/10.1103/physreva.38.3098
   PubMedGoogle Scholar
• Bruker, A. S. X. (2016). APEX3, SAINT and SADABS.
   Google Scholar
• Chaudhary, M. K., Karthick, T., Joshi, B. D., Prajapati, P., de Santana, M. S. A., Ayala, A. P., Reeda, V. S. J., & Tandon, P. (2021). Molecular structure and quantum descriptors of cefradine by using vibrational spectroscopy (IR and Raman), NBO, AIM, chemical reactivity and molecular docking. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 246, 118976. https://doi.org/10.1016/j.saa.2020.118976
   PubMed Web of Science ®Google Scholar
• Cheong, J. E., Zaffagni, M., Chung, I., Xu, Y., Wang, Y., Jernigan, F. E., Zetter, B. R., & Sun, L. (2018). Synthesis and anticancer activity of novel water soluble benzimidazole carbamates. European Journal of Medicinal Chemistry, 144, 372–385. https://doi.org/10.1016/j.ejmech.2017.11.037
   PubMed Web of Science ®Google Scholar
• Cohen, N., & Benson, S. W. (1993). Estimation of heats of formation of organic compounds by additivity methods. Chemical Reviews, 93(7), 2419–2438. https://doi.org/10.1021/cr00023a005
   Web of Science ®Google Scholar
• Cremer, D. T., & Pople, J. A. (1975). General definition of ring puckering coordinates. Journal of the American Chemical Society, 97(6), 1354–1358. https://doi.org/10.1021/ja00839a011
   Web of Science ®Google Scholar
• Cruz, J. C., & Tsai, L.-H. (2004). Cdk5 deregulation in the pathogenesis of Alzheimer’s disease. Trends in Molecular Medicine, 10(9), 452–458. https://doi.org/10.1016/j.molmed.2004.07.001
   PubMed Web of Science ®Google Scholar
• Daina, A., Michielin, O., & Zoete, V. (2019). SwissTargetPrediction: Updated data and new features for efficient prediction of protein targets of small molecules. Nucleic Acids Research, 47(W1), W357–W364. https://doi.org/10.1093/nar/gkz382
   PubMed Web of Science ®Google Scholar
• De Proft, F., Ayers, P. W., Fias, S., & Geerlings, P. (2006). Woodward-Hoffmann rules in density functional theory: Initial hardness response. The Journal of Chemical Physics, 125(21), 214101. https://doi.org/10.1063/1.2387953
   PubMed Web of Science ®Google Scholar
• Demange, L., Abdellah, F. N., Lozach, O., Ferandin, Y., Gresh, N., Meijer, L., & Galons, H. (2013). Potent inhibitors of CDK5 derived from roscovitine: Synthesis, biological evaluation and molecular modelling. Bioorganic & Medicinal Chemistry Letters, 23(1), 125–131. https://doi.org/10.1016/j.bmcl.2012.10.141
   PubMed Web of Science ®Google Scholar
• Desai, N. C., Jadeja, D. J., Jethawa, A. M., Ahmad, I., Patel, H., & Dave, B. P. (2023). Design and synthesis of some novel hybrid molecules based on 4-thiazolidinone bearing pyridine-pyrazole scaffolds: Molecular docking and molecular dynamics simulations of its major constituent onto DNA gyrase inhibition. Molecular Diversity, 27, 1–17. https://doi.org/10.1007/s11030-023-10612-y
   PubMedGoogle Scholar
• Eitrich, T., Kless, A., Druska, C., Meyer, W., & Grotendorst, J. (2007). Classification of highly unbalanced CYP450 data of drugs using cost sensitive machine learning techniques. Journal of Chemical Information and Modeling, 47(1), 92–103. https://doi.org/10.1021/ci6002619
   PubMed Web of Science ®Google Scholar
• Emamian, S., Lu, T., Kruse, H., & Emamian, H. (2019). Exploring nature and predicting strength of hydrogen bonds: A correlation analysis between atoms‐in‐molecules descriptors, binding energies, and energy components of symmetry‐adapted perturbation theory. Journal of Computational Chemistry, 40(32), 2868–2881. https://doi.org/10.1002/jcc.26068
   PubMed Web of Science ®Google Scholar
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Petersson, G. A., & Nakatsuji, H. (2016). Gaussian 16. Gaussian.
   Google Scholar
• Garadi, W. A., Bakri, Y. E., Lai, C., Karthikeyan, S., Ghayati, L. E., Mague, J. T., & Essassi, E. M. (2020). Synthesis, crystal structure and computational investigation of new 4‐phenyl‐decahydro‐1h‐1, 5‐benzodiazepin‐2‐one as potent inhibitor of Mu‐opioid receptor. ChemistrySelect, 5(15), 4601–4607. https://doi.org/10.1002/slct.202000356
   Web of Science ®Google Scholar
• Geerlings, P., Ayers, P. W., Toro-Labbe, A., Chattaraj, P. K., & De Proft, F. (2012). The Woodward-Hoffmann rules reinterpreted by conceptual density functional theory. Accounts of Chemical Research, 45(5), 683–695. https://doi.org/10.1021/ar200192t
   PubMed Web of Science ®Google Scholar
• Geerlings, P., De Proft, F., & Langenaeker, W. (2003). Conceptual density functional theory. Chemical Reviews, 103(5), 1793–1873. https://doi.org/10.1021/cr990029p
   PubMed Web of Science ®Google Scholar
• Groom, C. R., Bruno, I. J., Lightfoot, M. P., & Ward, S. C. (2016). The Cambridge structural database. Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 72(Pt 2), 171–179. https://doi.org/10.1107/S2052520616003954
   PubMedGoogle Scholar
• Halder, S. K., Ahmad, I., Shathi, J. F., Mim, M. M., Hassan, M. R., Jewel, M. J. I., Dey, P., Islam, M. S., Patel, H., Morshed, M. R., Shakil, M. S., & Hossen, M. S. (2022). A comprehensive study to unleash the putative inhibitors of serotype2 of dengue virus: Insights from an in silico structure-based drug discovery. Molecular Biotechnology, 1–14. https://doi.org/10.1007/s12033-022-00582-1
   PubMed Web of Science ®Google Scholar
• Helal, C. J., Sanner, M. A., Cooper, C. B., Gant, T., Adam, M., Lucas, J. C., Kang, Z., Kupchinsky, S., Ahlijanian, M. K., Tate, B., Menniti, F. S., Kelly, K., & Peterson, M. (2004). Discovery and SAR of 2-aminothiazole inhibitors of cyclin-dependent kinase 5/p25 as a potential treatment for Alzheimer’s disease. Bioorganic & Medicinal Chemistry Letters, 14(22), 5521–5525. https://doi.org/10.1016/j.bmcl.2004.09.006
   PubMed Web of Science ®Google Scholar
• Jain, P., Flaherty, P. T., Yi, S., Chopra, I., Bleasdell, G., Lipay, J., Ferandin, Y., Meijer, L., & Madura, J. D. (2011). Design, synthesis, and testing of an 6-O-linked series of benzimidazole based inhibitors of CDK5/p25. Bioorganic & Medicinal Chemistry, 19(1), 359–373. https://doi.org/10.1016/j.bmc.2010.11.022
   PubMed Web of Science ®Google Scholar
• Javan, M. J. (2021). Effect of multiple & cooperative intramolecular hydrogen bonding on polyhydroxylated thiopyrans acidities: Detailed view from AIM & NBO analyses. Computational and Theoretical Chemistry, 1205, 113440.
   Web of Science ®Google Scholar
• Jazayeri, S. B., Beygi, S., Shokraneh, F., Hagen, E. M., & Rahimi-Movaghar, V. (2015). Incidence of traumatic spinal cord injury worldwide: A systematic review. European Spine Journal: Official Publication of the European Spine Society, the European Spinal Deformity Society, and the European Section of the Cervical Spine Research Society, 24(5), 905–918. https://doi.org/10.1007/s00586-014-3424-6
   PubMed Web of Science ®Google Scholar
• Jeffrey, P. D., Russo, A. A., Polyak, K., Gibbs, E., Hurwitz, J., Massagué, J., & Pavletich, N. P. (1995). Mechanism of CDK activation revealed by the structure of a cyclinA-CDK2 complex. Nature, 376(6538), 313–320. https://doi.org/10.1038/376313a0
   PubMed Web of Science ®Google Scholar
• Johnson, E. R., Keinan, S., Mori-Sánchez, P., Contreras-García, J., Cohen, A. J., & Yang, W. (2010). Revealing noncovalent interactions. Journal of the American Chemical Society, 132(18), 6498–6506. https://doi.org/10.1021/ja100936w
   PubMed Web of Science ®Google Scholar
• Kaller, M. R., Zhong, W., Henley, C., Magal, E., Nguyen, T., Powers, D., Rzasa, R. M., Wang, W., Xiong, X., & Norman, M. H. (2009). Design and synthesis of 6-oxo-1, 6-dihydropyridines as CDK5 inhibitors. Bioorganic & Medicinal Chemistry Letters, 19(23), 6591–6594. https://doi.org/10.1016/j.bmcl.2009.10.027
   PubMed Web of Science ®Google Scholar
• Karthikeyan, S., Bharanidharan, G., Mangaiyarkarasi, R., Chinnathambi, S., Sriram, R., Gunasekaran, K., Saravanan, K., Gopikrishnan, M., Aruna, P., Ganesan, S. (2018). A cytotoxicity, optical spectroscopy and computational binding analysis of 4-[3-acetyl-5-(acetylamino)-2-methyl-2,3-dihydro-1,3,4-thiadiazole-2-yl]phenyl benzoate in calf thymus DNA. Luminescence, 33, 731–741. https://doi.org/10.1002/bio.3470.
   Google Scholar
• Kikiowo, B., Ahmad, I., Alade, A. A., Ijatuyi, T., Iwaloye, O., & Patel, H. M. (2022). Molecular dynamics simulation and pharmacokinetics studies of ombuin and quercetin against human pancreatic α-amylase. Journal of Biomolecular Structure and Dynamics, 40, 1–8. https://doi.org/10.1080/07391102.2022.2155699
   PubMed Web of Science ®Google Scholar
• Koch, U., & Popelier, P. L. A. (1995). Characterization of CHO hydrogen bonds on the basis of the charge density. The Journal of Physical Chemistry, 99(24), 9747–9754. https://doi.org/10.1021/j100024a016
   Web of Science ®Google Scholar
• Kolesnikova, I. N., Chegodaev, N. A., Sharanov, P. Y., & Shishkov, I. F. (2022). Equilibrium molecular structure and intramolecular interactions of picolinic acid hydrazide. Chemical Physics Letters, 793, 139447. https://doi.org/10.1016/j.cplett.2022.139447
   Web of Science ®Google Scholar
• Krause, L., Herbst-Irmer, R., Sheldrick, G. M., & Stalke, D. (2015). Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination. Journal of Applied Crystallography, 48(Pt 1), 3–10. https://doi.org/10.1107/S1600576714022985
   PubMedGoogle Scholar
• Kunick, C., Lauenroth, K., Wieking, K., Xie, X., Schultz, C., Gussio, R., Zaharevitz, D., Leost, M., Meijer, L., Weber, A., Jørgensen, F. S., & Lemcke, T. (2004). Evaluation and comparison of 3D-QSAR CoMSIA models for CDK1, CDK5, and GSK-3 inhibition by paullones. Journal of Medicinal Chemistry, 47(1), 22–36. https://doi.org/10.1021/jm0308904
   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, Condensed Matter, 37(2), 785–789. https://doi.org/10.1103/physrevb.37.785
   PubMed Web of Science ®Google Scholar
• Louet, M., Labbé, C. M., Fagnen, C., Aono, C. M., Homem-de-Mello, P., Villoutreix, B. O., & Miteva, M. A. (2018). Insights into molecular mechanisms of drug metabolism dysfunction of human CYP2C9* 30. PloS One, 13(5), e0197249. https://doi.org/10.1371/journal.pone.0197249
   PubMed Web of Science ®Google Scholar
• Lu, T., & Chen, F. (2012). Multiwfn: A multifunctional wavefunction analyzer. Journal of Computational Chemistry, 33(5), 580–592. https://doi.org/10.1002/jcc.22885
   PubMed Web of Science ®Google Scholar
• Mackenzie, C. F., Spackman, P. R., Jayatilaka, D., & Spackman, M. A. (2017). CrystalExplorer model energies and energy frameworks: Extension to metal coordination compounds, organic salts, solvates and open-shell systems. IUCrJ, 4(Pt 5), 575–587. https://doi.org/10.1107/S205225251700848X
   PubMedGoogle Scholar
• Mapelli, M., Massimiliano, L., Crovace, C., Seeliger, M. A., Tsai, L.-H., Meijer, L., & Musacchio, A. (2005). Mechanism of CDK5/p25 binding by CDK inhibitors. Journal of Medicinal Chemistry, 48(3), 671–679. https://doi.org/10.1021/jm049323m
   PubMed Web of Science ®Google Scholar
• Mathew, B., Ravichandran, V., Raghuraman, S., Rangarajan, T. M., Abdelgawad, M. A., Ahmad, I., Patel, H. M., & Kim, H. (2022). Two dimensional-QSAR and molecular dynamics studies of a selected class of aldoxime-and hydroxy-functionalized chalcones as monoamine oxidase-B inhibitors. Journal of Biomolecular Structure and Dynamics, 1–11. https://doi.org/10.1080/07391102.2022.2146198
   Google Scholar
• Mazanetz, M. P., & Fischer, P. M. (2007). Untangling tau hyperphosphorylation in drug design for neurodegenerative diseases. Nature Reviews. Drug Discovery, 6(6), 464–479. https://doi.org/10.1038/nrd2111
   PubMed Web of Science ®Google Scholar
• McKinnon, J. J., Spackman, M. A., & Mitchell, A. S. (2004). Novel tools for visualizing and exploring intermolecular interactions in molecular crystals. Acta Crystallographica. Section B, Structural Science, 60(Pt 6), 627–668. https://doi.org/10.1107/S0108768104020300
   PubMedGoogle Scholar
• McLean, A. D., & Chandler, G. S. (1980). Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z = 11-18. The Journal of Chemical Physics, 72(10), 5639–5648. https://doi.org/10.1063/1.438980
   Web of Science ®Google Scholar
• Mettey, Y., Gompel, M., Thomas, V., Garnier, M., Leost, M., Ceballos-Picot, I., Noble, M., Endicott, J., Vierfond, J., & Meijer, L. (2003). Aloisines, a new family of CDK/GSK-3 inhibitors. SAR study, crystal structure in complex with CDK2, enzyme selectivity, and cellular effects. Journal of Medicinal Chemistry, 46(2), 222–236. https://doi.org/10.1021/jm020319p
   PubMed Web of Science ®Google Scholar
• Miehlich, B., Savin, A., Stoll, H., & Preuss, H. (1989). Results obtained with the correlation energy density functionals of Becke and Lee, Yang and Parr. Chemical Physics Letters, 157(3), 200–206. https://doi.org/10.1016/0009-2614(89)87234-3
   Web of Science ®Google Scholar
• Morell, C., Ayers, P. W., Grand, A., Gutiérrez-Oliva, S., & Toro-Labbe, A. (2008). Rationalization of Diels–Alder reactions through the use of the dual reactivity descriptor Δ f (r). Physical Chemistry Chemical Physics: PCCP, 10(48), 7239–7246. https://doi.org/10.1039/b810343g
   PubMed Web of Science ®Google Scholar
• Osmaniye, D., Ahmad, I., Sağlık, B. N., Levent, S., Patel, H. M., Ozkay, Y., & Kaplancıklı, Z. A. (2022). Design, synthesis and molecular docking and ADME studies of novel hydrazone derivatives for AChE inhibitory, BBB permeability and antioxidant effects. Journal of Biomolecular Structure and Dynamics, 40, 1–17. https://doi.org/10.1080/07391102.2022.2139762
   PubMedGoogle Scholar
• Pandey, R., Dubey, I., Ahmad, I., Mahapatra, D. K., Patel, H., & Kumar, P. (2022). In silico study of some dexamethasone analogs and derivatives against SARs-CoV-2 Target: A cost-effective alternative to remdesivir for various COVID phases. Current Chinese Science, 2(4), 294–309. https://doi.org/10.2174/2210298102666220404102217
   Google Scholar
• Parr, R. G., & Pearson, R. G. (1983). Absolute hardness: Companion parameter to absolute electronegativity. Journal of the American Chemical Society, 105(26), 7512–7516. https://doi.org/10.1021/ja00364a005
   Web of Science ®Google Scholar
• Patel, J. S., Berteotti, A., Ronsisvalle, S., Rocchia, W., & Cavalli, A. (2014). Steered molecular dynamics simulations for studying protein–ligand interaction in cyclin-dependent kinase 5. Journal of Chemical Information and Modeling, 54(2), 470–480. https://doi.org/10.1021/ci4003574
   PubMed Web of Science ®Google Scholar
• Patel, K. B., Mukherjee, S., Bhatt, H., Rajani, D., Ahmad, I., Patel, H., & Kumari, P. (2023). Synthesis, docking, and biological investigations of new coumarin-piperazine hybrids as potential antibacterial and anticancer agents. Journal of Molecular Structure, 1276, 134755. https://doi.org/10.1016/j.molstruc.2022.134755
   Web of Science ®Google Scholar
• Poon, R. C., Lew, J., & Hunter, T. (1997). Identification of functional domains in the neuronal Cdk5 activator protein. The Journal of Biological Chemistry, 272(9), 5703–5708. https://doi.org/10.1074/jbc.272.9.5703
   PubMed Web of Science ®Google Scholar
• Puri, S., Ahmad, I., Patel, H., Kumar, K., & Juvale, K. (2023). Evaluation of oxindole derivatives as a potential anticancer agent against breast carcinoma cells: In vitro, in silico, and molecular docking study. Toxicology in Vitro: An International Journal Published in Association with BIBRA, 86, 105517. https://doi.org/10.1016/j.tiv.2022.105517
   PubMed Web of Science ®Google Scholar
• Roy, D. R., Parthasarathi, R., Maiti, B., Subramanian, V., Chattaraj, P. K. (2005). Electrophilicity as a possible descriptor for toxicity prediction. Bioorganic & Medicinal Chemistry, 13, 3405–3412. https://doi.org/10.1016/j.bmc.2005.03.011.
   Google Scholar
• Saeed, A., Bolte, M., Erben, M. F., & Pérez, H. (2015). Intermolecular interactions in crystalline 1-(adamantane-1-carbonyl)-3-substituted thioureas with Hirshfeld surface analysis. CrystEngComm, 17(39), 7551–7563. https://doi.org/10.1039/C5CE01373A
   Web of Science ®Google Scholar
• Sanguinetti, M. C., & Tristani-Firouzi, M. (2006). hERG potassium channels and cardiac arrhythmia. Nature, 440(7083), 463–469. https://doi.org/10.1038/nature04710
   PubMed Web of Science ®Google Scholar
• Schrödinger, L. (2020). Desmond molecular dynamics system. DE Shaw research, New York, Maestro-Desmond interoperability tools. Schrödinger.
   Google Scholar
• Sheldrick, G. M. (2015a). Crystal structure refinement with SHELXL. Acta Crystallographica. Section C, Structural Chemistry, 71(Pt 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
• Sherman, W., Beard, H. S., & Farid, R. (2006). Use of an induced fit receptor structure in virtual screening. Chemical Biology & Drug Design, 67(1), 83–84. https://doi.org/10.1111/j.1747-0285.2005.00327.x
   PubMed Web of Science ®Google Scholar
• Spackman, M. A., & Byrom, P. G. (1997). A novel definition of a molecule in a crystal. Chemical Physics Letters, 267(3–4), 215–220. https://doi.org/10.1016/S0009-2614(97)00100-0
   Web of Science ®Google Scholar
• Spackman, M. A., & Jayatilaka, D. (2009). Hirshfeld surface analysis. CrystEngComm, 11(1), 19–32. https://doi.org/10.1039/B818330A
   Web of Science ®Google Scholar
• Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D., & Spackman, M. A. (2021). CrystalExplorer: A program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals. Journal of Applied Crystallography, 54(3), 1006–1011. https://doi.org/10.1107/S1600576721002910
   PubMedGoogle Scholar
• Stukenbrock, H., Mussmann, R., Geese, M., Ferandin, Y., Lozach, O., Lemcke, T., Kegel, S., Lomow, A., Burk, U., Dohrmann, C., Meijer, L., Austen, M., & Kunick, C. (2008). 9-Cyano-1-azapaullone (cazpaullone), a glycogen synthase kinase-3 (GSK-3) inhibitor activating pancreatic β cell protection and replication. Journal of Medicinal Chemistry, 51(7), 2196–2207. https://doi.org/10.1021/jm701582f
   PubMed Web of Science ®Google Scholar
• Sudevan, S. T., Oh, J. M., Abdelgawad, M. A., Abourehab, M. A. S., Rangarajan, T. M., Kumar, S., Ahmad, I., Patel, H., Kim, H., & Mathew, B. (2022). Introduction of benzyloxy pharmacophore into aryl/heteroaryl chalcone motifs as a new class of monoamine oxidase B inhibitors. Scientific Reports, 12(1), 22404. https://doi.org/10.1038/s41598-022-26929-x
   PubMed Web of Science ®Google Scholar
• Tabti, K., Ahmad, I., Zafar, I., Sbai, A., Maghat, H., Bouachrine, M., & Lakhlifi, T. (2023). Profiling the structural determinants of pyrrolidine derivative as gelatinases (MMP-2 and MMP-9) inhibitors using in silico approaches. Computational Biology and Chemistry, 104, 107855. https://doi.org/10.1016/j.compbiolchem.2023.107855
   PubMed Web of Science ®Google Scholar
• Tan, S. L., Jotani, M. M., & Tiekink, E. R. T. (2019). Utilizing Hirshfeld surface calculations, non-covalent interaction (NCI) plots and the calculation of interaction energies in the analysis of molecular packing. Acta Crystallographica. Section E, Crystallographic Communications, 75(Pt 3), 308–318. https://doi.org/10.1107/S2056989019001129
   PubMedGoogle Scholar
• Terkeltaub, R. A., Furst, D. E., DiGiacinto, J. L., Kook, K. A., & Davis, M. W. (2011). Novel evidence‐based colchicine dose‐reduction algorithm to predict and prevent colchicine toxicity in the presence of cytochrome P450 3A4/P‐glycoprotein inhibitors. Arthritis and Rheumatism, 63(8), 2226–2237. https://doi.org/10.1002/art.30389
   PubMed Web of Science ®Google Scholar
• Ul Haq, Z., Uddin, R., Wai, L. K., Wadood, A., & Lajis, N. H. (2011). Docking and 3D-QSAR modeling of cyclin-dependent kinase 5/p25 inhibitors. Journal of Molecular Modeling, 17(5), 1149–1161. https://doi.org/10.1007/s00894-010-0817-2
   PubMed Web of Science ®Google Scholar
• Zala, A. R., Rajani, D. P., Ahmad, I., Patel, H., & Kumari, P. (2023). Synthesis, characterization, molecular dynamic simulation, and biological assessment of cinnamates linked to imidazole/benzimidazole as a CYP51 inhibitor. Journal of Biomolecular Structure and Dynamics, 41, 1–17. https://doi.org/10.1080/07391102.2023.2170918
   PubMed Web of Science ®Google Scholar
• Zukerberg, L. R., Patrick, G. N., Nikolic, M., Humbert, S., Wu, C.-L., Lanier, L. M., Gertler, F. B., Vidal, M., Van Etten, R. A., & Tsai, L.-H. (2000). Cables links Cdk5 and c-Abl and facilitates Cdk5 tyrosine phosphorylation, kinase upregulation, and neurite outgrowth. Neuron, 26(3), 633–646. https://doi.org/10.1016/s0896-6273(00)81200-3
   PubMed Web of Science ®Google Scholar