Synthesis, Spectroscopic Characterization, Molecular Docking and in Vitro Cytotoxicity Evaluation Studies on 6-Methoxy-8-Nitroquinoline Hydrogen Sulphate: A Novel Cervical Cancer Drug

References

• S. Jain, V. Chandra, P. Kumar Jain, K. Pathak, D. Pathak, and A. Vaidya, “Comprehensive Review on Current Developments of Quinoline-Based Anticancer Agents,” Arabian Journal of Chemistry 12, no. 8 (2019): 4920–46. doi:10.1016/j.arabjc.2016.10.009.
   Web of Science ®Google Scholar
• A. Ganguly, K. Banerjee, P. Chakraborty, S. Das, A. Sarkar, A. Hazra, M. Banerjee, A. Maity, M. Chatterjee, N. B. Mondal, et al, “Overcoming Multidrug Resistance (MDR) in Cancer in Vitro and in Vivo by a Quinoline Derivative,” Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie 65, no. 6 (2011): 387–94. doi:10.1016/j.biopha.2011.04.024.
   PubMed Web of Science ®Google Scholar
• C. H. Tseng, C. C. Tzeng, K. Y. Chung, C. L. Kao, C. Y. Hsu, C. M. Cheng, K. S. Huang, and Y. L. Chen, “Synthesis and Antiproliferative Evaluation of 6-Aryl-11-Iminoindeno[1,2-c]Quinoline Derivatives,” Bioorganic & Medicinal Chemistry 19, no. 24 (2011): 7653–63. doi:10.1016/j.bmc.2011.10.014.
   PubMed Web of Science ®Google Scholar
• S. Sharma, K. Panjamurthy, B. Choudhary, M. Srivastava, M. S. Shahabuddin, R. Giri, G. M. Advirao, and S. C. Raghavan, “A Novel DNA Intercalator, 8-Methoxy Pyrimido[40,50:4,5]Thieno (2,3-b)Quinoline-4(3H)-One Induces Apoptosis in Cancer Cells, Inhibits the Tumor Progression and Enhances Lifespan in Mice with Tumor,” Molecular Carcinogenesis 52, no. 6 (2013): 413–25. doi:10.1002/mc.21867.
   PubMed Web of Science ®Google Scholar
• P. Jasinski, B. Welsh, J. Galvez, D. Land, P. Zwolak, L. Ghandi, K. Terai, and A. Z. Dudek, “A Novel Quinoline, MT477: suppresses Cell Signaling through Ras Molecular Pathway, Inhibits PKC Activity, and Demonstrates in Vivo anti-Tumor Activity against Human Carcinoma Cell Lines,” Investigational New Drugs 26, no. 3 (2008): 223–32. doi:10.1007/s10637-007-9096-x.
   PubMed Web of Science ®Google Scholar
• P. Jasinski, P. Zwolak, K. Terai, R. I. Vogel, D. Borja-Cacho, and A. Z. Dudek, “X-Ray-Activated Nanosystems for Theranostic Applications,” Anticancer Research 31 (2011): 41181–7.
   Google Scholar
• A. Jemal, R. Siegel, E. Ward, T. Murray, J. Xu, and M. J. Thun, “Cancer Statistics, 2007,” CA: A Cancer Journal for Clinicians 57, no. 1 (2007): 43–66. doi:10.3322/canjclin.57.1.43.
   PubMed Web of Science ®Google Scholar
• T. Nasr, S. Bondock, and M. Youns, “Anti-Cancer Activity of New Coumarin Substituted Ydrazide-Hydrazone Derivatives, Anticancer Activity of New Coumarin Substituted Hydrazide–Hydrazone Derivatives,” European Journal of Medicinal Chemistry 76 (2014): 539–48. doi:10.1016/j.ejmech.2014.02.026.
   PubMed Web of Science ®Google Scholar
• S. I. Alqasoumi, A. M. Al-Taweel, A. M. Alafeefy, M. M. Hamed, E. Noaman, and M. M. Ghorab, “Synthesis and Biological Evaluation of 2-Amino-7,7-Dimethyl 4-Substituted-5-Oxo-1-(3,4,5-Trimethoxy)-1,4,5,6,7,8-Hexahydro-Quinoline-3-Carbonitrile Derivatives as Potential Cytotoxic Agents,” Bioorganic & Medicinal Chemistry Letters 19, no. 24 (2009): 6939–42. doi:10.1016/j.bmcl.2009.10.065.
   PubMed Web of Science ®Google Scholar
• A. E. Rashad, W. A. El-Sayed, A. M. Mohamed, and M. M. Ali, “Synthesis of New Quinoline Derivatives as Inhibitors of Human Tumor Cells Growth,” Archiv der Pharmazie 343, no. 8 (2010): 440–8. doi:10.1002/ardp.201000002.
   PubMed Web of Science ®Google Scholar
• M. M. Ghorab, F. A. Ragab, H. I. Heiba, R. K. Arafa, and E. M. El-Hossary, “In Vitro Anticancer Screening and Radiosensitizing Evaluation of Some New Quinolines and Pyrimido[4,5-b]Quinolines Bearing a Sulfonamide Moiety,” European Journal of Medicinal Chemistry 45, no. 9 (2010): 3677–84. doi:10.1016/j.ejmech.2010.05.014.
   PubMed Web of Science ®Google Scholar
• Y. Wang, J. Ai, Y. Wang, Y. Chen, L. Wang, G. Liu, M. Geng, and A. Zhang, “Synthesis and c-Met Kinase Inhibition of 3,5-Disubstituted and 3,5,7-Trisubstituted Quinolines: Identification of 3-(4-Acetylpiperazin-1-yl)-5-(3-Nitrobenzylamino)-7-(Trifluoromethyl)Quinoline as a Novel Anticancer Agent,” Journal of Medicinal Chemistry 54, no. 7 (2011): 2127–42. doi:10.1021/jm101340q.
   PubMed Web of Science ®Google Scholar
• M. M. Ghorab, F. A. Ragab, H. I. Heiba, and W. M. Ghorab, “Design and Synthesis of Some Novel Quinoline Derivatives as Anticancer and Radiosensitizing Agents Targeting VEGFR Tyrosine Kinase,” Journal of Heterocyclic Chemistry 48, no. 6 (2011): 1269–79. doi:10.1002/jhet.749.
   Web of Science ®Google Scholar
• C. Tseng, Y. Chen, K. Chung, C. Wang, S. Peng, C. Cheng, and C. Tzeng, “Synthesis and Antiproliferative Evaluation of 2,3-Diarylquinoline Derivatives,” Organic & Biomolecular Chemistry 9, no. 9 (2011): 3205–16. doi:10.1039/c0ob01225d.
   PubMed Web of Science ®Google Scholar
• B. Heiniger, G. Gakha, K. Prasain, D. H. Hua, and T. A. Nguyen, “Second-Generation Substituted Quinolines as Anticancer Drugs for Breast Cancer,” Anticancer Research 30, no. 10 (2010): 3927–32.
   PubMed Web of Science ®Google Scholar
• M. Sechi, G. Rizzi, A. Bacchi, M. Carcelli, D. Rogolino, N. Pala, T. W. Sanchez, L. Taheri, R. Dayam, and N. Neamati, “Designand Synthesis of Novel Dihydroquinoline-3-Carboxylic Acidsas HIV-1 Integrase Inhibitors,” Bioorganic & Medicinal Chemistry 17, no. 7 (2009): 2925–35. doi:10.1016/j.bmc.2008.10.088.
   PubMed Web of Science ®Google Scholar
• R. Konakanchi, K. Prabhakara Rao, N. Reddy, and J. Prashanth, “Zinc(II) Complex: Spectroscopic, Physicochemical Calculations, anti-Inflammatory and in Silico Molecular Docking Studies,” Journal of Molecular Structure 1263 (2022): 133070. doi:10.1016/j.molstruc.2022.133070.
   Web of Science ®Google Scholar
• S. Konduri, V. Pogaku, J. Prashanth, V. Siva Krishna, D. Sriram, S. Basavoju, J. N. Behera, and K. Prabhakara. Rao, “Sacubitril-Based Urea and Thiourea Derivatives as Novel Inhibitors for anti-Tubercular against Dormant Tuberculosis,” ChemistrySelect 6, no. 16 (2021): 3869–74. doi:10.1002/slct.202004724.
   Web of Science ®Google Scholar
• T. Valarmathi, R. Premkumar, M. R. Meera, and A. Milton Franklin Benial, “Spectroscopic, Quantum Chemical and Molecular Docking Studies on 1-Amino-5-Chloroanthraquinone: A Targeted Drug Therapy for Thyroid Cancer,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 255 (2021): 119659. doi:10.1016/j.saa.2021.119659.
   PubMed Web of Science ®Google Scholar
• J. Prashanth, J. Kishan Ojha, B. Venkatram Reddy, and G. Ramana. Rao, “Experimental and Theoretical Study of 3-Methyl-4-Nitrobenzoic Acid Using DFT and IVP Methods,” Journal of Physics: Conference Series 759 (2016): 012057. doi:10.1088/1742-6596/759/1/012057.
   Google Scholar
• S. Konduri, J. Prashanth, V. Siva Krishna, D. Sriram, J. N. Behera, D. Siegel, and K. Prabhakara. Rao, “Design and Synthesis of Purine Connected Piperazine Derivatives as Novel Inhibitors of Mycobacterium tuberculosis,” Bioorganic & Medicinal Chemistry Letters 30, no. 22 (2020): 127512. doi:10.1016/j.bmcl.2020.127512.
   PubMed Web of Science ®Google Scholar
• J. Prashanth, R. Konakanchi, and B. Venkatram Reddy, “Barrier Potentials, Molecular Structure, Force Filed Calculations and Quantum Chemical Studies of Some Bipyridine di-Carboxylic Acids Using the Experimental and Theoretical Using (DFT, IVP) Approach,” Molecular Simulation 45, no. 16 (2019): 1353–83. doi:10.1080/08927022.2019.1634807.
   Web of Science ®Google Scholar
• Y. Yang, Y. Zhang, L. Yang, L. Zhao, L. Si, H. Zhang, Q. Liu, and J. Zhou, “Discovery of Imidazopyridine Derivatives as Novel c-Met Kinase Inhibitors: synthesis, SAR Study, and Biological Activity,” Bioorganic Chemistry 70 (2017): 126–32. doi:10.1016/j.bioorg.2016.12.002.
   PubMed Web of Science ®Google Scholar
• W. Zhu, W. Wang, S. Xu, J. Wang, Q. Tang, C. Wu, Y. Zhao, and P. Zheng, “Synthesis, and Docking Studies of Phenylpyrimidine-Carboxamide Derivatives Bearing 1H-Pyrrolo[2,3-b]Pyridine Moiety as c-Met Inhibitors,” Bioorganic & Medicinal Chemistry 24, no. 8 (2016): 1749–56. doi:10.1016/j.bmc.2016.02.046.
   PubMed Web of Science ®Google Scholar
• K. H. W. Sait, Q. Alam, N. Anfinan, O. Al-Ghamdi, A. Malik, R. Noor, F. Jahan, and M. Tarique, “Structure-Based Virtual Screening and Molecular Docking for the Identification of Potential Novel EGFR Kinase Inhibitors against Ovarian Cancer,” Bioinformation 15, no. 4 (2019): 287–94. doi:10.6026/97320630015287.
   PubMed Web of Science ®Google Scholar
• A. T. Negmeldin, G. Padige, A. V. Bieliauskas, and M. K. H. Pflum, “Structural Requirements of HDAC Inhibitors: SAHA Analogues Modified at the C2 Position Display HDAC6/8 Selectivity,” ACS Medicinal Chemistry Letters 8, no. 3 (2017): 281–6. doi:10.1021/acsmedchemlett.6b00124.
   PubMed Web of Science ®Google Scholar
• S. Celik, F. Ozkok, A. E. Ozel, Y. M. Sahin, S. Akyuz, B. D. Sigirci, B. B. Kahraman, H. Darici, and E. Karaoz, “Synthesis, FT-IR and NMR Characterization, Antimicrobial Activity, Cytotoxicity and DNA Docking Analysis of a New Anthraquinone Derivate Compound,” Journal of Biomolecular Structure & Dynamics 38, no. 3 (2020): 756–70. doi:10.1080/07391102.2019.1587513.
   PubMed Web of Science ®Google Scholar
• G. Rajagopal, N. Manivannan, M. Sundararaja, A. G. Kumar, S. Samuthirarajan, N. Mathivanan, and S. Ilango, “Biocompatibility Assessment of Silver Chloride Nanoparticles Derived from Padina Gymnospora and Its Therapeutic Potential,” Nano Express 2, no. 1 (2021): 010010. doi:10.1088/2632-959X/abd965.
   Google Scholar
• M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, et al, Gaussian 09, Revision C. 02 (Wallingford CT: Gaussian Inc., 2009).
   Google Scholar
• M. H. Jamroz, Vibrational Energy Distribution Analysis VEDA 4.0 Program (Warsaw, 2004).
   Google Scholar
• R. Dennington, T. Keith and J. Milam Gauss View, Version 5 (Shawnee, KS: Semichem Inc., 2009).
   Google Scholar
• G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, and A. J. Olson, “Automated Docking Using a Lamarckian Genetic Algorithm and an Empirical Binding Free Energy Function,” Journal of Computational Chemistry 19, no. 14 (1998): 1639–62. doi:10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B.
   Web of Science ®Google Scholar
• G. Pandimeena, R. Premkumar, T. Mathavan, and A. Milton Franklin. Benial, “Spectroscopic, Quantum Chemical and Molecular Docking Studies on Methyl 6-Aminopyridine-3-Carboxylate: A Potent Bioactive Agent for the Treatment of Sarcoidosis,” Journal of Molecular Structure 1231 (2021): 129996. doi:10.1016/j.molstruc.2021.129996.
   Web of Science ®Google Scholar
• C. S. Abraham, S. Muthu, J. C. Prasana, S. Armaković, S. J. Armaković, F. Rizwana B, B. Geoffrey, and H. Antony David R, “Computational Evaluation of the Reactivity and Pharmaceutical Potential of an Organic Amine: A DFT, Molecular Dynamics Simulations and Molecular Docking Approach,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 222 (2019): 117188. doi:10.1016/j.saa.2019.117188.
   PubMed Web of Science ®Google Scholar
• Li-Min Man, Ting Li, Xiao-Chun Wu, Kai-Xin Lu, Le-Min Yang, Xiao-Ping Liu, Zhuo-Hong Yang, Jia-Rong Zhou, and Chun-Lin Ni, “Synthesis, Crystal Structure, Vibrational Spectra, Nonlinear Optical Property of an Organic Charge-Transfer Compound―4-Nitrobenzyl Isoquinolinium Picrate Based on DFT Calculations,” Journal of Molecular Structure 1175 (2019): 971–8. doi:10.1016/j.molstruc.2018.07.054.
   Web of Science ®Google Scholar
• S. Premkumar, T. N. Rekha, B. J. M. Rajkumar, R. Mohamed. Asath, A. Jawahar, T. Mathavan, and A. Milton Franklin. Benial, “Vibrational Spectroscopic and Structural Investigations of 2-Amino-6-Methoxy-3-Nitropyridine: A DFT Approach,” Brazilian Journal of Physics 45, no. 6 (2015): 621–32. doi:10.1007/s13538-015-0365-4.
   Web of Science ®Google Scholar
• D. M. Suresh, M. Amalanathan, S. Sebastian, D. Sajan, I. Hubert. Joe, V. Bena Jothy, and I. Nemec, “Vibrational Spectral Investigation and Natural Bond Orbital Analysis of Pharmaceutical Compound 7-Amino-2,4-Dimethylquinolinium Formate – DFT Approach,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 115 (2013): 595–02. doi:10.1016/j.saa.2013.06.077.
   PubMed Web of Science ®Google Scholar
• M. Okuno, “Hyper-Raman Spectroscopy of Alcohols Excited at 532 nm: Methanol, Ethanol, 1-Propanol, and 2-Propanol,” Journal of Raman Spectroscopy 52, no. 4 (2021): 849–56. doi:10.1002/jrs.6066.
   Web of Science ®Google Scholar
• G. Varsanyi, Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives, Vol. I (London: Adam Hilger, 1974).
   Google Scholar
• R. Premkumar, Shamima. Hussain, Naidu Dhanpal. Jayram, Stève-Jonathan. Koyambo-Konzapa, M. S. Revathy, T. Mathavan, and A. Milton Franklin Benial, “Adsorption and Orientation Characteristics of 1-Methylpyrrole-2-Carbonyl Chloride Using SERS and DFT Investigations,” Journal of Molecular Structure 1253 (2022): 132201. doi:10.1016/j.molstruc.2021.132201.
   Web of Science ®Google Scholar
• R. Mohamed Asath, R. Premkumar, T. Mathavan, and A. Milton Franklin Benial, “Structural, Spectroscopic and Molecular Docking Studies on 2-Amino-3-Chloro-5-Trifluoromethyl Pyridine: A Potential Bioactive Agent,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 175 (2017): 51–60. doi:10.1016/j.saa.2016.11.037.
   PubMed Web of Science ®Google Scholar
• T. Koopmans, “Über Die Zuordnung Von Wellenfunktionen Und Eigenwerten zu Den Einzelnen Elektronen Eines Atoms,” Physica 1, no. 1–6 (1934): 104–13. doi:10.1016/S0031-8914(34)90011-2.
   Google Scholar
• T. Valarmathi, R. Premkumar, and A. Milton. Franklin Benial, “Spectroscopic and Molecular Docking Studies on 1-Hydroxyanthraquinone: A Potent Ovarian Cancer Drug,” Journal of Molecular Structure 1213 (2020): 128163. doi:10.1016/j.molstruc.2020.128163.
   Web of Science ®Google Scholar
• E. D. Glendening, A. E. Reed, J. E. Carpenter, and F. Weinhold, NBO Version 3.1 (Madison, WI: TCI, University of Wisconsin, 1998).
   Google Scholar
• M. Alcolea Palafox, D. Bhat, Y. Goyal, A. 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 (2015): 464–72. doi:10.1016/j.saa.2014.09.058.
   PubMed Web of Science ®Google Scholar
• Zeynep Demircioğlu, Çiğdem Albayrak Kaştaş, and Orhan Büyükgüngör, “Theoretical Analysis (NBO, NPA, Mulliken Population Method) and Molecular Orbital Studies (Hardness, Chemical Potential, Electrophilicity and Fukui Function Analysis) of (E)-2-((4-Hydroxy-2-Methylphenylimino)Methyl)-3-Methoxyphenol,” Journal of Molecular Structure 1091 (2015): 183–95. doi:10.1016/j.molstruc.2015.02.076.
   Web of Science ®Google Scholar
• R. Renjith, Y. Sheena Mary, H. T. Varghese, C. Yohannan Panicker, T. Thiemann, A. Shereef, and A. A. Al-Saadi, “Spectroscopic Investigation (FT-IR and FT-Raman), Vibrational Assignments, HOMO-LUMO Analysis and Molecular Docking Study of 1-Hydroxy-4,5,8-25 Tris(4-Methoxyphenyl) Anthraquinone,” Journal of Physics and Chemistry of Solids 87 (2015): 110–21. doi:10.1016/j.jpcs.2015.07.024.
   Web of Science ®Google Scholar