title: Biologically active perspective synthesis of heteroannulated 8-nitroquinolines with green chemistry approach.
abstract: A new class of pyrazolo[4,3-c]quinoline (5a-i, 7a-b) and pyrano[3,2-c]quinoline (9a-i) derivatives were designed and synthesized in moderate to good yields by microwave conditions. To enhance the yield of pyrano[3,2-c]quinoline derivatives, multicomponent one-pot synthesis has been developed. The synthesized compounds were identified by spectral and elemental analyses. Compounds 9a and 9i showed good antibacterial activity against Gram-positive and Gram-negative bacterial strains. All of the new compounds exhibited weak to moderate antioxidant activity, compound 9d exerted significant antioxidant power. The cytotoxicity of these compounds were also evaluated against MCF-7 (breast) and A549 (Lung) cancer cell lines. Most of the compounds displayed moderate to good cytotoxic activity against these cell lines. Compound 9i was found to be significantly active in this assay and also induced cell death by apoptosis. Molecular docking studies were carried out using EGFR inhibitor in order to determine the molecular interactions.
authors.affiliation: School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India; Department of Chemistry, Richardson College for the Environmental Science Complex, The University of Winnipeg, 599 Portage Avenue, Winnipeg, Manitoba R3B 2G3, Canada.
authors.forename: Thangaraj
authors.initials: T
authors.lastname: Arasakumar
authors.affiliation: School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India.
authors.forename: Sadasivam
authors.initials: S
authors.lastname: Mathusalini
authors.affiliation: School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India.
authors.forename: Subashini
authors.initials: S
authors.lastname: Gopalan
authors.affiliation: School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India.
authors.forename: Selvaraj
authors.initials: S
authors.lastname: Shyamsivappan
authors.affiliation: Department of Chemistry, Richardson College for the Environmental Science Complex, The University of Winnipeg, 599 Portage Avenue, Winnipeg, Manitoba R3B 2G3, Canada. Electronic address: a.ata@uwinnipeg.ca.
authors.forename: Athar
authors.initials: A
authors.lastname: Ata
authors.affiliation: School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, Tamil Nadu, India. Electronic address: psmohan59@gmail.com.
authors.forename: Palathurai Subramaniam
authors.initials: PS
authors.lastname: Mohan
mesh_terms: D000072283:A549 Cells; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D001713:Biphenyl Compounds / Q000737:chemistry; D020134:Catalytic Domain; D066246:ErbB Receptors / Q000737:chemistry; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D055772:Green Chemistry Technology; D006801:Humans; D061986:MCF-7 Cells; D062105:Molecular Docking Simulation; D009600:Nitroquinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010851:Picrates / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D009600:Nitroquinolines; D010851:Picrates; D011714:Pyrans; D011720:Pyrazoles; C004931:1,1-diphenyl-2-picrylhydrazyl; D066246:ErbB Receptors
keywords: Antibacterial; Anticancer; Antioxidant; Molecular docking; Pyrano[3,2-c]quinoline; Pyrazolo[4,3-c]quinoline