title: Synthesis and spectroscopic characterization of fluorescent 4-aminoantipyrine analogues: Molecular docking and in vitro cytotoxicity studies.
abstract: Two substituted aromatic carbonyl compounds (compounds 1 and 2) of 4-aminoantipyrine were synthesized by condensation of fluorine substituted benzoyl chlorides and 4-aminoantipyrine. The structures of synthesized derivatives were established on the basis of UV-Vis, IR, and Mass, (1)H, (13)C NMR and Fluorescence spectroscopy. Both compounds showed significant fluorescence emission and two broad emission bands were observed in the region at 340 nm and 450 nm on excitation at 280 nm. Theoretically to prove that the molecule has anticancer activity against cervical cancer cells, the compounds were analyzed for molecular docking interactions with HPV16-E7 target protein by Glide protocol. Furthermore, 4-aminoantipyrine derivatives were evaluated for their in vitro cytotoxic activity against human cervical cancer cells (SiHa) by MTT assay. Compound 1 showed two fold higher activity (IC50=0.912 μM) over compound 2, and its activity was similar to that of Pazopanib, suggesting that although the two compounds were chemically very similar the difference in substituent on the phenyl moiety caused changes in properties.
authors: Department of Bioinformatics, School of Biotechnology and Health Science, Karunya University, Coimbatore 641114, Tamilnadu, India. Electronic address: prems.bioinfo@gmail.com.
authors: D
authors: D
authors: Premnath
authors: Department of Chemistry, School of Science and Humanities, Karunya University, Coimbatore 641114, Tamilnadu, India.
authors: P Mosae
authors: PM
authors: Selvakumar
authors: Department of Chemistry, School of Science and Humanities, Karunya University, Coimbatore 641114, Tamilnadu, India.
authors: P
authors: P
authors: Ravichandiran
authors: Department of Chemistry, School of Science and Humanities, Karunya University, Coimbatore 641114, Tamilnadu, India.
authors: G Tamil
authors: GT
authors: Selvan
authors: Department of Bio Technology, Mepco Schlenk Engineering College, Sivakasi, Tamilnadu, India.
authors: M
authors: M
authors: Indiraleka
authors: Department of Bioinformatics, School of Biotechnology and Health Science, Karunya University, Coimbatore 641114, Tamilnadu, India.
authors: J Jannet
authors: JJ
authors: Vennila
mesh_terms: D000675:Ampyrone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000494:pharmacology; D045744:Cell Line, Tumor; D005453:Fluorescence; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D062105:Molecular Docking Simulation; D012015:Reference Standards; D013050:Spectrometry, Fluorescence; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000970:Antineoplastic Agents; D000675:Ampyrone
keywords: 4-Aminoantipyridine; Cytotoxic activity; Fluorescence; Molecular docking; Spectroscopy