Computational Quantum Chemical Study, Insilco Molecular Docking and ADMET Study of (3E,5E)-3,5-Bis((1H-Indol-3-yl)Methylene)-1-Benzylpiperidin-4-One Derivatives

References

• F. F. Gan, K. K. Kaminska, H. Yang, C. Y. Liew, P. C. Leow, C. L. So, L. N. Tu, A. Roy, C. W. Yap, T. S. Kang, et al. “Identification of Michael Acceptor-Centric Pharmacophores with Substituents That Yield Strong Thioredoxin Reductase Inhibitory Character Correlated to Antiproliferative Activity,” Antioxidants & Redox Signaling 19, no. 11 (2013): 1149–1165. doi:10.1089/ars.2012.4909
   PubMed Web of Science ®Google Scholar
• S. N. A. Bukhari, I. Jantan, V. H. Masand, D. T. Mahajan, M. Sher, M. Naeem-Ul-Hassan, and M. W. Amjad, “Synthesis of α, β-Unsaturated Carbonyl-Based Compounds as Acetylcholinesterase and Butyrylcholinesterase Inhibitors: Characterization, Molecular Modeling, QSAR Studies and Effect against Amyloid β-Induced Cytotoxicity,” European Journal of Medicinal Chemistry 83, no. 83 (2014): 355–365. doi:10.1016/j.ejmech.2014.06.034
   PubMedGoogle Scholar
• S. Amslinger, “The Tunable Functionality of α, β-Unsaturated Carbonyl Compounds Enable Their Differential Application in Biological Systems,” ChemMedChem 5, no. 3 (2010): 351–356. doi:10.1002/cmdc.200900499
   PubMed Web of Science ®Google Scholar
• J. R. Dimmock, V. K. Arora, M. J. Duffy, R. S. Reid, T. M. Allen, and G. Y. Kao, “Evaluation of Some N-Acyl Analogues of 3,5-Bis (Arylidene)-4-Piperidones for Cytotoxic Activity, Drug Des,” Discovery 8, no. 4 (1992): 291–299.
   Google Scholar
• H. I. El-Subbagh, S. M. Abu-Zaid, M. A. Mahran, F. A. Badria, and A. M. Al-Obaid, “Synthesis and Biological Evaluation of Certain α, β-Unsaturated Ketones and Their Corresponding Fused Pyridines as Antiviral and Cytotoxic Agents,” Journal of Medicinal Chemistry 43, no. 15 (2000): 2915–2921. doi:10.1021/jm000038m
   PubMed Web of Science ®Google Scholar
• N. Li, W. Y. Xin, B. R. Yao, C. H. Wang, W. Cong, F. Zhao, H. J. Li, Y. Hou, Q. G. Meng, and G. G. Hou, “Novel Dissymmetric 3, 5-Bis (Arylidene)-4-Piperidones as Potential Antitumor Agents with Biological Evaluation in Vitro and in Vivo,” European Journal of Medicinal Chemistry 147, no. 147 (2018): 21–33. doi:10.1016/j.ejmech.2018.01.088
   PubMedGoogle Scholar
• Q. Chen, Y. Hou, G. G. Hou, J. F. Sun, N. Li, W. Cong, F. Zhao, H. J. Li, and C. H. Wang, “Synthesis Design, Anticancer Activity and Cytotoxicity of Novel 4-Piperi- Done/Cyclohexanone Derivatives,” Research on Chemical Intermediates 42, no. 12 (2016): 8119–8130. doi:10.1007/s11164-016-2583-y
   Web of Science ®Google Scholar
• S. Prakobwong, J. Khoontawad, P. Yongvanit, C. Pairojkul, Y. Hiraku, P. Sithithaworn, P. Pinlaor, B. B. Aggarwal, and S. Pinlaor, “Curcumin Decreases Cholangio Carcinogenesis in Hamsters by Suppressing Inflammation-Mediated Molecular Events Related to Multistep Carcinogenesis,” International Journal of Cancer 129, no. 1 (2011): 88–100. doi:10.1002/ijc.25656
   PubMed Web of Science ®Google Scholar
• J. A. Bush, K. J. J. Cheung, and G. Li, “Curcumin Induces Apoptosis in Human Melanoma Cells through a Fas Receptor/Caspase-8 Pathway Independent of p53,” Experimental Cell Research 271, no. 2 (2001): 305–314. doi:10.1006/excr.2001.5381
   PubMed Web of Science ®Google Scholar
• D. L. Yin, Y. J. Liang, T. S. Zheng, R. P. Song, J. B. Wang, B. S. Sun, S. H. Pan, L. D. Qu, J. R. Liu, H. C. Jiang, et al. “EF24 Inhibits Tumor Growth and Metastasis via Sup Pressing NF-kappaB Dependent Pathways in Human Cholangiocarcinoma,” Scientific Reports 6, no. 6 (2016): 32167. doi:10.1038/srep32167
   PubMedGoogle Scholar
• B. Yao, N. Li, C. Wang, G. Hou, Q. Meng, and K. Yan, “Novel Asymmetric 3,5-Bis (Arylidene) Piperidin-4-One Derivatives: Synthesis, Crystal Structures and Cyto- Toxicity,” Acta Crystallographica. Section C, Structural Chemistry 74, no. Pt 6 (2018): 659–665. doi:10.1107/S2053229618006605
   PubMedGoogle Scholar
• Xi-S. Wu, R. Wang, Y.-Li Xing, X.-Q. Xue, Y. Zhang, Y.-Z. Lu, Y. Song, X.-Yu Luo, C. Wu, Yu-L. Zhou, et al. “Discovery and Structural Optimization of 4-(4-(Benzyloxy) Phenyl)-3, 4-Dihydropyrimidin-2 (1H)-Ones as RORc Inhibitors,” Acta Pharmacologica Sinica 37, no. 11 (2016): 1516–1524. doi:10.1038/aps.2016.32
   PubMed Web of Science ®Google Scholar
• Q. Chen, F. Wang, and B. Zhou, “Investigations of Retinoic Acid Receptor-Related Orphan Receptor-Ramma t (ROR γt) Agonists: A Combination of 3D-QSAR, Molecular Docking and Molecular Dynamics,” Journal of Biomolecular Structure and Dynamics. 39, no. 10 (2020): 1–19.
   Web of Science ®Google Scholar
• H. B. Schlegel, “Optimization of Equilibrium Geometries and Transition Structures,” Advances in Chemical Physics. 67 (2007): 249–286.
   Google Scholar
• S. Ponnuswamy, R. Kayalvizhi, S. Sethuvasan, P. Sugumar, and M. N. Ponnuswamy, “Synthesis, Stereochemistry, Crystal Structure, Docking Study and Biological Evaluation of Some New N-Benzylpiperidin-4-Ones,” Journal of Molecular Structure. 1155 (2018): 654–665. doi:10.1016/j.molstruc.2017.11.024
   Web of Science ®Google Scholar
• K. Paulrasu, A. Duraikannu, M. Palrasu, A. Shanmugasundaram, M. Kuppusamy, and B. Thirunavukkarasu, “Synthesis of 4-methyl-N’-(3-Alkyl-2r,6cdiarylpiperidin-4-Ylidene)-1,2,3-thiadiazole5-Carbohydrazides with Antioxidant, Antitumor and Antimicrobial Activities,” Organic & Biomolecular Chemistry 12, no. 31 (2014): 5911–5921. doi:10.1039/c4ob00739e
   PubMed Web of Science ®Google Scholar
• G. Bitencourt-Ferreira, and W. Filgueira de Azevedo, “Molecular Docking Simulations with ArgusLab,” Methods in Molecular Biology. 2053 (2019): 203–220.
   PubMedGoogle Scholar
• S. Yadav, S. K. Pandey, V. K. Singh, Y. Goel, A. Kumar, and S. M.. Singh, “Molecular Docking Studies of 3-Bromopyruvate and Its Derivatives to Metabolic Regulatory Enzymes: Implication in Designing of Novel Anticancer Therapeutic Strategies,” PLoS One 12, no. 5 (2017): e0176403. doi:10.1371/journal.pone.0176403
   PubMed Web of Science ®Google Scholar
• G. Sundararajan, D. Rajaraman, T. Srinivasan, D. Velmurugan, and K. Krishnasamy, “Synthesis, Characterization, Computational Calculation and Biological Studies of Some 2,6-Diaryl-1-(Prop-2-yn-1-yl)Piperidin-4-One Oxime Derivatives Spectrochim,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 139 (2015): 108–118. doi:10.1016/j.saa.2014.12.014
   PubMed Web of Science ®Google Scholar
• S. Savithiri, “Synthesis, Spectral, Stereochemical, Biological, Molecular Docking and DFT Studies of 3-Alkyl/3,5-Dialkyl-2r,6c-di(Naphthyl)Piperidin-4-One Picrates Derivatives,” Journal of Molecular Structure. 1234 (2021): 130–145.
   Web of Science ®Google Scholar
• V. Mohanraj, and S. Ponnuswamy, “Synthesis, Characterization, Stereochemistry, Biological Investigation and DNA Binding Studies on N-Acyl-t-3-Ethyl-r-2,c-6-Bis(4-Methoxyphenyl)Piperidin-4-Ones,” Journal of Molecular Structure. 1171 (2018): 420–428. doi:10.1016/j.molstruc.2018.05.102
   Web of Science ®Google Scholar
• D. Rajaraman, G. Sundararajan, A. Kamaraj, H. Saleem, and K. Krishnasamy, “Synthesis, Computational and Spectroscopic Analysis on (E)-(4-(2-(Benzo[d]Thiazol-2-yl)Hydrazono)-3-Methyl-2,6-Diphenylpiperidine-1-yl)(Phenyl)Methanone Using DFT Approach, Spectrochim,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 151 (2015): 480–489. doi:10.1016/j.saa.2015.06.037
   PubMed Web of Science ®Google Scholar
• A. Ramalingam, “Hirshfeld Surface Analysis, Interaction Energy Calculation and Spectroscopical Study of 3-Chloro-3-Methyl-r(2),c(6)-Bis(p-Tolyl)Piperidin-4-One Using DFT Approaches,” Journal of Molecular Structure. 1248 (2022): 131–148.
   Web of Science ®Google Scholar
• F. Rizwana, S. Muthu, J. Christian Prasana, C. Susan Abraham, and M. Raja, “Spectroscopic (FT-IR, FT-RAMAN) Investigation, Topology (ESP, ELF, LOL) Analyses, Charge Transfer Excitation and Molecular Docking (Dengue, Hcv) Studies on Ribavirin,” Chemical Data Collections 17-18 (2018): 236–250. doi:10.1016/j.cdc.2018.09.003
   Google Scholar
• R. S.. Saji, J. C. Prasana, S. Muthu, J. George, T. K. Kuruvilla, and B. R. Raajaraman, “Spectroscopic and Quantum Computational Study on Naproxen Sodium,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 226 (2020): 117614. doi:10.1016/j.saa.2019.117614
   PubMed Web of Science ®Google Scholar
• G. Venkatesh, S. Haseena, J.. S.Al-Otaibi, Y. S.. Mary, P. Vennila, Y. Shyma Mary, and S. A.. Azad, “Observations into the Reactivity, Docking, DFT, and MD Simulations of Fludarabine and Clofarabine in Various Solvents,” Journal of Molecular Liquids. 383 (2023): 122076. doi:10.1016/j.molliq.2023.122076
   Web of Science ®Google Scholar
• R. Rajamanickam, R. Mannangatty, J. Sampathkumar, S. Kabilan, and B. Diravidamani, “Synthesis, Crystal Structure, DFT and Molecular Docking Studies of N-Acetyl-2,4-[Diaryl-3-Azabicyclo[3.3.1]Nonan-9-yl]-9-Spiro-4′-Acetyl-2′-(Acetylamino)-4′,9-Dihydro-[1′,3′,4′]-Thiadiazoles: A Potential SARS-nCoV-2 Mpro (COVID-19) Inhibitor,” Journal of Molecular Structure 1259 (2022): 132747. doi:10.1016/j.molstruc.2022.132747
   PubMed Web of Science ®Google Scholar
• R. V. Sakthivel, P. Sankudevan, P. Vennila, G. Venkatesh, S. Kaya, and G. Serdaroğlu, “Experimental and Theoretical Analysis of Molecular Structure, Vibrational Spectra and Biological Properties of the New Co(II), Ni(II) and Cu(II) Schiff Base Metal Complexes,” Journal of Molecular Structure. 1233 (2021): 130097. doi:10.1016/j.molstruc.2021.130097
   Web of Science ®Google Scholar
• X-Yu. Meng, “Molecular Docking: A Powerful Approach for Structure-Based Drug Discovery," Current Computer-Aided Drug Design, 7, no. 2 (2011): 146–157. doi: 10.2174/157340911795677602.
   Google Scholar
• P. Manjusha, J. Christian Prasana, S. Muthu, and B. F. Rizwana, “Spectroscopic Elucidation (FT-IR, FT-Raman and UV-Visible) with NBO, NLO, ELF, LOL, Drug Likeness and Molecular Docking Analysis on 1-(2-Ethylsulfonylethyl)-2-Methyl-5-Nitro-Imidazole: An Antiprotozoal Agent,” Computational Biology and Chemistry 88 (2020): 107330. doi:10.1016/j.compbiolchem.2020.107330
   PubMed Web of Science ®Google Scholar
• J. Morin, and J. Marie Pelletier, “Density Functional Theory Principles, Applications and Analysis,” 2013.
   Google Scholar
• G. Raja, G. Venkatesh, J. S. Al-Otaibi, P. Vennila, Y. S.. Mary, and Y. Sixto-López, “Synthesis, Characterization, Molecular Docking and Molecular Dynamics Simulations of Benzamide Derivatives as Potential anti-Ovarian Cancer Agents,” Journal of Molecular Structure. 1269, no. 5 (2022): 133785. doi:10.1016/j.molstruc.2022.133785
   Google Scholar
• P. Aravindan, K. Sivaraj, C. Kamal, P. Vennila, and G. Venkatesh, “Synthesis, Molecular Structure, Spectral Characterization, Molecular Docking and Biological Activities of (E)-N-(2-Methoxy Benzylidene) Anthracene-2-Amine and Co(II), Cu(II) and Zn(II) Complexes,” Journal of Molecular Structure. 1229 (2021): 129488. doi:10.1016/j.molstruc.2020.129488
   Web of Science ®Google Scholar
• P. Rajamani, V. Vijayakumar, N. Sundaraganesan, M. Jeeva, and M. Susai Boobalan, “FT-IR, FT-Raman, UV–Visible, NMR, DFT and Molecular Docking Investigation of 1-(Phenyl(Piperidin-1-yl)Methyl)Naphthalene-2-ol,” Results in Chemistry 3 (2021): 100096. doi:10.1016/j.rechem.2021.100096
   Google Scholar
• M. Alcolea Palafox, D. Bhat, Y. Goyal, S. Ahmad, I. Hubert Joe, and V. K. Rastogi, “FT-IR and FT-Raman Spectra, MEP and HOMO–LUMO of 2,5-Dichlorobenzonitrile: DFT Study,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 136 Pt B (2015): 464–472. doi:10.1016/j.saa.2014.09.058
   PubMed Web of Science ®Google Scholar
• C. Ravikumar, I. Huber Joe, and V. S. Jayakumar, “Charge Transfer Interactions and Nonlinear Optical Properties of Push–Pull Chromophore Benzaldehyde Phenylhydrazone: A Vibrational Approach,” Chemical Physics Letters. 460, no. 4-6 (2008): 552–558. doi:10.1016/j.cplett.2008.06.047
   Web of Science ®Google Scholar
• L. A. Anthony, D. Rajaraman, M. Shanmugam, and K. Krishnasamy, “Synthesis, Spectral Techniques, X-Ray Crystal Structure, DFT Method, Hirshfeld Surface Analysis and Molecular Docking Studies of 1-(Furan-2-yl)Methyl)-4,5-Diphenyl-2-(p-Tolyl)-1H-Imidazole,” Chemical Data Collections. 28 (2020): 100421. doi:10.1016/j.cdc.2020.100421
   Google Scholar
• F. Weinhold, C. R. Landis, and E. D. Glendening, “What is NBO Analysis and How is It Useful?,” International Reviews in Physical Chemistry 35, no. 3 (2016): 399–440. doi:10.1080/0144235X.2016.1192262
   Web of Science ®Google Scholar
• M. S. Almatairi, “Structural, Spectroscopic, Hirshfeld Surface and Charge Distribution Analysis of 3-(1H-Imidazole-1-yl)-1-Phenylpropan-1-ol Complemented by Molecular Docking Predictions: An Integrated Experimental and Computational Approach,” Journal of Molecular Structure. 1196 (2019): 578–591.
   Web of Science ®Google Scholar
• J. V. Turner, and S. Agatonovic-Kustrin, “Comprehensive Medicinal Chemistry II,” ISBN 978-0-08-045044 (2007).
   Google Scholar
• A. Pawełczyk, D. Olender, K. Sowa-Kasprzak, and L. Zaprutko, “Linked Drug-Drug Conjugates Based on Triterpene and Phenol Structures. Rational Synthesis, Molecular Properties, Toxicity and Bioactivity Prediction,” Arabian Journal of Chemistry 13, no. 12 (2020): 8793–8806. doi:10.1016/j.arabjc.2020.10.009
   Web of Science ®Google Scholar
• https://www.molinspiration.com/docu/miscreen/druglikeness.html.
   Google Scholar
• F. Cheng, W. Li, Y. Zhou, J. Shen, Z. Wu, G. Liu, P. W. Lee, and Y. Tang, “admetSAR: A Comprehensive Source and Free Tool for Assessment of Chemical ADMET Properties,” Journal of Chemical Information and Modeling 52, no. 11 (2012): 3099–3105. doi:10.1021/ci300367a
   PubMed Web of Science ®Google Scholar
• T. Hou, J. Wang, W. Zhang, and X. Xu, “ADME Evaluation in Drug discovery-Prediction of Oral Absorption by Correlation and Classification,” Journal of Chemical Information and Modeling 47, no. 1 (2007): 208–218. doi:10.1021/ci600343x
   PubMed Web of Science ®Google Scholar
• V. M. Alves, E. Muratov, D. Fourches, J. Strickland, N. Kleinstreuer, C. H. Andrade, and A. Tropsha, “Predicting Chemically-Induced Skin Reactions. Part II: QSAR Models of Skin Permeability and the Relationships between Skin Permeability and Skin Sensitization,” Toxicology and Applied Pharmacology 284, no. 2 (2015): 273–280. 15 no doi:10.1016/j.taap.2014.12.013
   PubMed Web of Science ®Google Scholar
• G. Berellini, C. Springer, N. J. Waters, and F. Lombardo, “In Silico Prediction of Volume of Distribution in Human Using Linear and Nonlinear Models on a 669 Compound Data Set,” Journal of Medicinal Chemistry 52, no. 14 (2009): 4488–4495. doi:10.1021/jm9004658
   PubMed Web of Science ®Google Scholar
• E. M. del Amo, L. Ghemtio, H. Xhaard, M. Yliperttula, A. Urtti, and H. Kidron, “Applying Linear and Non-Linear Methods for Parallel Prediction of Volume of Distribution and Fraction of Unbound Drug,” PloS One 8, no. 10 (2013): e74758. doi:10.1371/journal.pone.0074758
   PubMed Web of Science ®Google Scholar
• C. Suenderhauf, F. Hammann, and J. Huwyler, “Computational Prediction of Blood–Brain Barrier Permeability Using Decision Tree Induction,” Molecules (Basel, Switzerland) 17, no. 9 (2012): 10429–10445. doi:10.3390/molecules170910429
   PubMed Web of Science ®Google Scholar
• C. W. Yap, Z. R. Li, and Y. Z. Chen, “Quantitative Structure-Pharmacokinetic Relationships for Drug Clearance by Using Statistical Learning Methods,” Journal of Molecular Graphics & Modelling 24, no. 5 (2006): 383–395. doi:10.1016/j.jmgm.2005.10.004
   PubMed Web of Science ®Google Scholar
• R. Liu, G. Tawa, and A. Wallqvist, “Locally Weighted Learning Methods for Predicting Dose-Dependent Toxicity with Application to the Human Maximum Recommended Daily Dose,” Chemical Research in Toxicology 25, no. 10 (2012): 2216–2226. doi:10.1021/tx300279f
   PubMed Web of Science ®Google Scholar
• P. Mazzatorta, M. D. Estevez, M. Coulet, and B. Schilter, “Modeling Oral Rat Chronic Toxicity,” Journal of Chemical Information and Modeling 48, no. 10 (2008): 1949–1954. doi:10.1021/ci8001974
   PubMed Web of Science ®Google Scholar
• D. Fourches, J. C. Barnes, N. C. Day, P. Bradley, J. Z. Reed, and A. Tropsha, “Cheminformatics Analysis of Assertions Mined from Literature That Describe Drug-Induced Liver Injury in Different Species,” Chemical Research in Toxicology 23, no. 1 (2010): 171–183. doi:10.1021/tx900326k
   PubMed Web of Science ®Google Scholar
• V. M. Alves, E. Muratov, D. Fourches, J. Strickland, N. Kleinstreuer, C. H. Andrade, ““tropsha, predicting chemically-induced skin reactions. Part I: QSAR models of skin sensitization and their application to identify potentially hazardous compounds, toxicol,”. Appl. Pharmacol 284, no. 2 (2015): 262–272. doi:10.1016/j.taap.2014.12.014.
   PubMed Web of Science ®Google Scholar