title: Synthesis of novel 2-amino-4-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents.
abstract: As a part of systematic investigation of synthesis and biological activities of indole analogues linked to various heterocyclic systems, we have synthesized new compounds viz., 2-amino-4-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitriles (2a-i), 4,5-diamino-6-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-8-aryl-2-oxo-2,6-dihydrodipyrano [2,3-b:3,2-e]pyridine-3-carbonitriles (3a-i), 4-amino-5-(5'-substituted 2'-phenyl-1H-indol-3-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-ones (4a-i), 4-amino-5-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-thiones (5a-i), 4-(5'-subtituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-1,4-dihydropyrano[2,3-c]pyrazol-3-amines (6a-i) and 5-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-7-aryl-3H-pyrano[2,3-d]pyrimidin-4(5H)-ones (7a-i). Antibacterial activity results revealed that, compound 6a showed promising activity versus Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 6d exhibited good activity against S. aureus, K. pneumoniae and Pseudomonas aeruginosa. Antifungal activity results indicated that, compound 4d exhibited maximum zone of inhibition against Aspergillus oryzae and Aspergillus flavus. In case of antioxidant activity, compound 4a showed promising radical scavenging activity, ferric ions (Fe(3+)) reducing antioxidant power (FRAP) and metal chelating activity.
authors: Department of Post-Graduate Studies and Research in Chemistry, Gulbarga University, Gulbarga 585 106, Karnataka, India. arsaundane@rediff.com
authors: Anand R
authors: AR
authors: Saundane
authors: Katkar
authors: K
authors: Vijaykumar
authors: A Verma
authors: AV
authors: Vaijinath
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001231:Aspergillus flavus / Q000187:drug effects; D001236:Aspergillus oryzae / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004926:Escherichia coli / Q000187:drug effects; D007711:Klebsiella pneumoniae / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000975:Antioxidants; D009570:Nitriles; D011714:Pyrans