title: Synthesis, molecular docking and biological evaluation of novel 6-(4-(4-aminophenylsulfonyl)phenylamino)-5H-benzo[a]phenothiazin-5-one derivatives.
abstract: A novel series of 6-(4-(4-aminophenylsulfonyl)phenylamino)-5H-benzo[a]phenothiazin-5-one derivatives have been synthesized and examined for their in vitro antibacterial activity against a panel of Gram-positive and Gram-negative bacteria. Among these, N-(4-(4-(5-oxo-5H-benzo[a]phenothiazin-6-ylamino)phenylsulfonyl)phenyl)-3,5-bis(trifluoromethyl)benzamide (3n) (0.4 μg/mL) and 4-ethyl-N-(4-(4-(5-oxo-5H-benzo[a]phenothiazin-6-ylamino)phenylsulfonyl)phenyl)benzamide (3l) (0.6 μg/mL) systems exhibited a potent inhibitory activity against Gram-positive organism Bacillus subtilis, when compare to the other synthesized compounds. Sparfloxacin (9.76 μg/mL), Norfloxacin (no activity) were employed as the standard drugs. An evaluation of the cytotoxicity of the title compounds (1, 2, 3a-n) revealed that they displayed low toxicity (26-115 mg/L) against cervical cancer cell line (SiHa). The results of these studies suggest that, phenothiazin-5-one derivatives are interesting binding agents for the development of new Gram-positive and Gram-negative antibacterial agents. To understand the interactions with protein receptors, docking simulation was done with crystal structures of B.subtilis (YmaH) and histone deacetylase (HDAC8) to determine the probable binding conformation.
authors.affiliation: Department of Chemistry, School of Science & Humanities, Karunya University, Coimbatore 641 114, India. Electronic address: ravichandru55@gmail.com.
authors.forename: Palanisamy
authors.initials: P
authors.lastname: Ravichandiran
authors.affiliation: Department of Nanosciences & Technology, School of Nanosciences & Technology, Karunya University, Coimbatore 641 114, India; Nanobiotechnology and Molecular Biology Research Lab, Department of Food Science and Nutrition, College of Food Sciences and Agriculture, King Saud University, P.O. Box 2460, Riyadh 11451, Kingdom of Saudi Arabia.
authors.forename: Jegan
authors.initials: J
authors.lastname: Athinarayanan
authors.affiliation: Department of Bioinformatics, School of Biotechnology and Health Sciences, Karunya University, Coimbatore 641 114, India.
authors.forename: Dhanaraj
authors.initials: D
authors.lastname: Premnath
authors.affiliation: Nanobiotechnology and Molecular Biology Research Lab, Department of Food Science and Nutrition, College of Food Sciences and Agriculture, King Saud University, P.O. Box 2460, Riyadh 11451, Kingdom of Saudi Arabia.
authors.forename: Vaiyapuri Subbarayan
authors.initials: VS
authors.lastname: Periasamy
authors.affiliation: Nanobiotechnology and Molecular Biology Research Lab, Department of Food Science and Nutrition, College of Food Sciences and Agriculture, King Saud University, P.O. Box 2460, Riyadh 11451, Kingdom of Saudi Arabia.
authors.forename: Ali A
authors.initials: AA
authors.lastname: Alshatwi
authors.affiliation: Department of Chemistry, School of Science & Humanities, Karunya University, Coimbatore 641 114, India. Electronic address: kumar2359@yahoo.com.
authors.forename: Samuel
authors.initials: S
authors.lastname: Vasanthkumar
mesh_terms: D000900:Anti-Bacterial Agents / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001665:Binding Sites; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D006801:Humans; D006877:Hydroxamic Acids / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D010640:Phenothiazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011809:Quinones / Q000737:chemistry; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000077337:Vorinostat
chemical_list: D000900:Anti-Bacterial Agents; D006877:Hydroxamic Acids; D010640:Phenothiazines; D011809:Quinones; D013450:Sulfones; D000077337:Vorinostat
keywords: Anticancer; SiHa; Solfones; Water as solvent