Experimental, computational investigations and biological evaluation on 1-(3-acetamidophenyl)-5-mercaptotetrazole-cytotoxicity MTT assay

Kushwaha, 2019, Synthesis, biological evaluation and molecular dynamic simulations of novel benzofuran-tetrazole derivatives as potential agents against Alzheimer’s disease, Bioorg. Med. Chem. Lett., 29, 66, 10.1016/j.bmcl.2018.11.005 Popova, 2017, Tetrazole derivatives as promising anticancer agents, Anti-Cancer Agents Med. Chem. (Formerly Current Medicinal Chemistry-Anti-Cancer Agents), 17, 1856 Gao, 2019, Current scenario of tetrazole hybrids for antibacterial activity, Eur. J. Med. Chem., 184, 10.1016/j.ejmech.2019.111744 Zhan, 2009, Sulfanyltriazole/tetrazoles: a promising class of HIV-1 NNRTIs, Mini Rev. Med. Chem., 9, 1014, 10.2174/138955709788681618 Roh, 2017, Development of water-soluble 3,5-dinitrophenyl tetrazole and oxadiazole antitubercular agents, Bioorg. Med. Chem., 25, 5468, 10.1016/j.bmc.2017.08.010 Wang, 2019, Tetrazole hybrids and their antifungal activities, Eur. J. Med. Chem., 170, 225, 10.1016/j.ejmech.2019.03.023 Mohite, 2011, Potential pharmacological activities of tetrazoles in the new millennium, Int. J. PharmTech Res., 3, 1557 R.J. Herr, 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods, Bioorg. Med. Chem. 10(11) (2002) 3379–3394. Crossref, Medline, CAS, Google Scholar. Gao, 2019, Recent advances of tetrazole derivatives as potential anti-tubercular and anti-malarial agents, Eur. J. Med. Chem., 163, 404, 10.1016/j.ejmech.2018.12.001 Zou, 2020, Bioisosteres in drug discovery: focus on tetrazole, Future Med. Chem., 12, 91, 10.4155/fmc-2019-0288 Dai, 2015, Synthesis of tetrazole compounds as a novel type of potential antimicrobial agents and their synergistic effects with clinical drugs and interactions with calf thymus DNA, MedChemComm, 6, 147, 10.1039/C4MD00266K Stone, 1970, Convulsant actions of tetrazole derivatives, Pharmacology, 3, 367, 10.1159/000136093 Frisch, 2016 R. Dennington, T.A. Keith, J.M. Millam, GaussView 6.0. 16, Semichem Inc., Shawnee Mission, KS, USA, 2016. G.A. Zhurko, D.A. Zhurko, Chemcraft. Version 1.7 (Build 132), 2014, HTML: www.chemcraftprog.com. Bassey, 2022, Vibrational characterization and molecular electronic investigations of 2-acetyl-5-methylfuran using FT-IR, FT-Raman, UV–VIS, NMR, and DFT methods, J. Fluoresc., 32, 1005, 10.1007/s10895-022-02903-8 M.H. Jamroz, Vibrational Energy Distribution Analysis: VEDA 4 Program, Warasaw, Poland, 2004, 11. Roy D, Keith T, Mi. Tian, 2012, Multiwfn: a multifunctional wavefunction analyzer, J. Comp. Chem, 33, 580, 10.1002/jcc.22885 Filimonov, 2014, Prediction of the biological activity spectra of organic compounds using the Pass online web resource, ChemHeterocycl. Compd., 50, 444, 10.1007/s10593-014-1496-1 Dassault Systemes BIOVIA: Discovery Studio Visualizer 21.1.0.20298, 2020. The PyMOL Molecular Graphics Development Component, Version 1.8, PYMOL Mol. Graph. Dev. Component, Version 1.8, Schrodinger LLC. Louis, 2021, Synthesis, characterization, DFT, and TD-DFT studies of (E)-5-((4, 6-dichloro-1, 3, 5-triazin-2-yl) amino)-4-hydroxy-3-(phenyldiazenyl) naphthalene-2, 7-diylbis (hydrogen sulfite), SN Appl. Sci., 3, 1, 10.1007/s42452-021-04688-0 Parakkal, 2022, Computational investigation into structural, topological, electronic properties, and biological evaluation of spiro [1H-indole-3, 2′-3H-1, 3-benzothiazole]-2-one, J. Mol. Liq., 359, 10.1016/j.molliq.2022.119234 Bisong, 2020, Vibrational, electronic, spectroscopic properties, and NBO analysis of p-xylene, 3, 6-difluoro-p-xylene, 3, 6-dichloro-p-xylene and 3, 6-dibromo-pxylene: DFT study, Heliyon, 6, 10.1016/j.heliyon.2020.e05783 Obu, 2021, Synthesis, spectra (FT-IR, NMR) investigations, DFT study, in silico ADMET and molecular docking analysis of 2-amino-4-(4-aminophenyl) thiophene-3-carbonitrile as a potential anti-tubercular agent, J. Mol. Struct., 1244, 10.1016/j.molstruc.2021.130880 Saral, 2022, Molecular structure spectroscopic Elucidation, IEFPCM solvation (UV–Vis, MEP, FMO, NBO, NLO), molecular docking and biological assessment studies of lepidine (4-Methylquinoline), J. Mol. Liq., 345, 10.1016/j.molliq.2021.118249 Ali, 2018, DFT study for the spectroscopic and structural analysis of p-dimethylaminoazobenzene, J. Spectrosc., 10.1155/2018/9365153 Jeelani, 2022, Experimental spectroscopic, molecular structure, electronic solvation, biological prediction and topological analysis of 2, 4, 6-tri (propan-2-yl) benzenesulfonyl chloride: an antidepressant agent, J. Mol. Liq., 358, 10.1016/j.molliq.2022.119166 Basha, 2021, Elaborated molecular structure, molecular docking and vibrational spectroscopic investigation of N-((4-aminophenyl) sulfonyl) benzamide with density functional theory, Chem. Data Collect., 31, 10.1016/j.cdc.2020.100609 Daisy Magdaline, 2015, Vibrational spectra (FT-IR, FT-Raman) NBO and HOMO-LUMO studies of 2-thiophene carboxylic acid based on density functional method, J. Appl. Chem., 8, 6 Barnes, 1985, The resonance Raman spectra of Orange II and Para Red: molecular structure and vibrational assignment, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 41, 629, 10.1016/0584-8539(85)80050-7 B. Sureshkumar, Y.S. Mary, K.S. Resmi, C.Y. Panicker, S. Armakovic ́, S.J. Armakovic ́, C. Van Alsenoy, B. Narayana, S. Suma, Spectroscopic analysis of 8-hydroxyquinoline derivatives and investigation of its reactive properties by DFT and molecular dynamics simulations, J. Mol. Struct. 1156 (2018) 336–347. Gümüş, 2022, Discovery of sulfadrug–pyrrole conjugates as carbonic anhydrase and acetylcholinesterase inhibitors, Archiv Der Pharmazie, 355, 10.1002/ardp.202100242 Mubarik, 2021, Computational study of structural, molecular orbitals, optical and thermodynamic parameters of thiophene sulfonamide derivatives, Crystals, 11, 211, 10.3390/cryst11020211 Eunice, 2023, Molecular structure, spectroscopic, quantum computational, and molecular docking investigations on propyl gallate, Polycycl. Aromat. Compd. S. El-Taher, M. Metwaly, DFT and PCM-TD-DFT investigation of the electronic structures and spectra of 5-(3-phenyl-2-propenylidene)-2-thioxo-4-thiazolidinone derivatives, J. Mol. Struct. 1134 (2017) 840–850, doi: 10.1016/j.molstruc.2017.01.014. Khanum, 2022, Synthesis, spectroscopic, quantum chemical, and molecular docking studies of 2-Cyano-N-cyclopropylacetamide and 2-cyano-N-(1-phenylethyl) acetamide, Polycycl. Aromat. Compd., 1, 10.1080/10406638.2022.2157452 B. Chandralekha, S. Hemamalini Rajagopal, Muthu, Quantum mechanical, spectroscopic and molecular docking studies of N-[4-cyano-3-(trifluoromethyl) phenyl]-3-[(4-fluorophenyl) sulfonyl]-2-hydroxy-2-methylpropanamide, Chem. Data Collect. 19 (2019). Akram, 2020, Spectroscopic, quantum chemical and molecular docking studies of 2-Hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone: a potent anti-Alzheimer's drug, Chem. Data Collect., 29, 10.1016/j.cdc.2020.100495 Ben Geoffrey, 2019, Structure-activity relationship studies of two dietary flavonoids and their nitric oxide synthase inhibition activity by spectroscopic and quantum/classical computational techniques, J. Theor. Comput. Chem., 18, 10.1142/S0219633619500317 Mahmudov, 2022, Synthesis and inhibition profiles of N-benzyl- and N-Allyl aniline derivatives against carbonic anhydrase and acetylcholinesterase – a molecular docking study, Arab. J. Chem., 10.1016/j.arabjc.2021.103645 Muthu, 2012, Molecular structure, vibrational spectra, first order hyper polarizability, NBO and HOMO-LUMO analysis of 4-amino-3 (4-chlorophenyl) butanoic acid, Solid State Sci., 14, 476, 10.1016/j.solidstatesciences.2012.01.028 Mansha, 2020, efficient synthesis of novel tricyclic benzoxazine derivative via ring opening of epoxide along the MP and DFT studies of structural, spectroscopic (IR, Raman, UV-VIS), thermodynamic, orbitals and NLO properties of desired tricyclic benzoxazine derivative, J. Chil. Chem. Soc., 65, 4769, 10.4067/S0717-97072020000204769 Isac Paulraj, 2013, Spectroscopic studies (FTIR, FT-Raman and UV), potential energy surface scan, normal coordinate analysis and NBO analysis of (2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl) piperidine-3,4,5-triol by DFT methods, Spectrochim. Acta Part A: Mol. Biomol. Spectrosc., 108, 38, 10.1016/j.saa.2013.01.061 Hermann, 1973, Optical nonlinearities in conjugated systems: β-carotene, Appl. Phys. Lett., 23, 178, 10.1063/1.1654850 B. Silvi, A. Savin, Classification of chemical bonds based on topological analysis of electron localization functions, Nature 371 (1994) 683–686, doi: 10.1038/371683a0. Sagaama, 2020, Design, molecular docking analysis of an anti-inflammatory drug, computational analysis and intermolecular interactions energy studies of 1-benzothiophene-2-carboxylic acid, J. Comput. Biol. Chem., 88 N.K. Nkungli, J.N. Ghogomu, Theoretical analysis of the binding of iron (III) protoporphyrin IX to 4-methoxyacetophenone thiosemicarbazone via DFT-D3, MEP, QTAIM, NCI, ELF, and LOL studies, J. Mol. Model. 23 (7) (2017) 1–20. Selvakumari, 2023, Solvent–solute interactions, electronic properties, topological and biological explorations of 6-Bromo-7-methylimidazo [1, 2-a] pyridine, J. Mol. Liq., 376, 10.1016/j.molliq.2023.121437 Selvakumari, 2023, Vibrational spectroscopic, electronic influences, reactivity analysis and molecular docking studies of 2-Fluoro-4-iodo-5-methylpyridine, Spectrosc. Lett., 56, 14, 10.1080/00387010.2022.2160462 Lipinski, 2004, Lead- and drug-like compounds: the rule-of-five revolution, Drug Discov. Today Technol., 1, 337, 10.1016/j.ddtec.2004.11.007 Sumithra, 2023, Effect of green solvents physical, chemical, biological and bonding nature on 5-acetyl-thiophene-2-carboxylic acid by DFT and TD-DFT approach–an antiviral agent, J. Indian Chem. Soc., 100, 10.1016/j.jics.2022.100867 Daina, 2014, iLOGP: a simple, robust, and efficient description of n-octanol/water partition coefficient for drug design using the GB/SA approach, J. Chem. Inf. Model., 54, 3284, 10.1021/ci500467k Vimala, 2021, Quantum computational studies on optimization, donor-acceptor analysis and solvent effect on reactive sites, global descriptors, non-linear optical parameters of Methyl N-Boc-piperidine-3-carboxylate, J. Mol. Liq., 343, 10.1016/j.molliq.2021.117608 Lovell, 2003, Structure validation by Ca geometry: /, w and Cb deviation, Proteins: Struct. Funct. Bioinform., 50, 437, 10.1002/prot.10286 Morris, 2008, Using AutoDock for ligand-receptor docking, Curr. Protoc. Bioinf., 24, 1 Thirunavukkarasu, 2021, Chem. Data Collect., 31, 10.1016/j.cdc.2020.100622 Arulaabaranam, 2021, Conformational study, FT-IR, FT-Raman, solvent effect on UV–Vis, charge transfer and protein–ligand interactions of Methyl-2-pyrazinecarboxylate, J. Mol. Liq., 341, 10.1016/j.molliq.2021.116934 Dege, 2022, Quantum computational, spectroscopic investigations on N-(2-((2-chloro-4, 5-dicyanophenyl) amino) ethyl)-4-methylbenzenesulfonamide by DFT/TD-DFT with different solvents, molecular docking and drug-likeness researches, Colloids Surf. A: Physicochem. Eng. Asp., 638, 10.1016/j.colsurfa.2022.128311 Asogwa, 2022, Structural benchmarking, density functional theory simulation, spectroscopic investigation and molecular docking of N-(1H-pyrrol-2-yl) methylene)-4-methylaniline as castration-resistant prostate cancer chemotherapeutic agent, Chem. Phys. Impact, 5, 10.1016/j.chphi.2022.100091 Denizot, 1986, Rapid colorimetric assay for cell growth and survival: modifications to the tetrazolium dye procedure giving improved sensitivity and reliability, J. Immunol. Methods, 89, 271, 10.1016/0022-1759(86)90368-6