title: Design, synthesis, antimicrobial, anti-inflammatory and analgesic activity of novel isoxazolyl pyrimido[4,5-b]quinolines and isoxazolyl chromeno[2,3-d]pyrimidin-4-ones.
abstract: Novel series of 2-methyl-3-{3-methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl}-3,4-dihydropyrimido[4,5-b]quinolin-4-ones 5 and 3-{3-methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl}-3,4-dihydro-2H-chromeno[2,3-d]pyrimidin-4-ones 7 have been synthesized from isoxazolyl cyanoacetamide synthon 2. Compound 2 was obtained by reaction of 4-amino-3-methyl-5-styrylisoxazole 1 with ethyl cyanoacetate. Isoxazolyl pyrimido[4,5-b]quinolin-4-ones 5 were obtained from compounds 2 by condensation with o-nitro benzaldehyde followed by treatment with SnCl(2) and subsequent tandem N-acetylation and cyclodehydration with acetic anhydride. Compounds 2 were converted to isoxazolyl chromeno[2,3-d]pyrimidin-4-ones 7 by reaction with salicylaldehydes and subsequent cyclization with formaldehyde. Compounds 2-7 were characterized by IR, (1)H NMR, (13)C NMR, and Mass spectral data. The title compounds 5a-f and 7a-g were evaluated for their antimicrobial, anti-inflammatory and analgesic activity. Compounds 5d and 7e exhibited significant antimicrobial activity, potent anti-inflammatory and analgesic activities as that of standard drugs.
authors: Department of Chemistry, Kakatiya University, Vidyaranyapuri, Warangal 506 009, AP, India. rajanarendareligeti@gmail.com
authors: E
authors: E
authors: Rajanarendar
authors: M
authors: M
authors: Nagi Reddy
authors: S
authors: S
authors: Rama Krishna
authors: K
authors: K
authors: Rama Murthy
authors: Y N
authors: YN
authors: Reddy
authors: M V
authors: MV
authors: Rajam
mesh_terms: D000700:Analgesics / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D001419:Bacteria / Q000187:drug effects; D001522:Behavior, Animal / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D004487:Edema / Q000188:drug therapy; D005658:Fungi / Q000187:drug effects; D007555:Isoxazoles / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D051381:Rats
chemical_list: D000700:Analgesics; D000890:Anti-Infective Agents; D000893:Anti-Inflammatory Agents; D007555:Isoxazoles; D011744:Pyrimidinones; D011804:Quinolines