2-Azetidinone derivatives: Design, synthesis, in vitro anti-microbial, cytotoxic activities and DNA cleavage study (Retracted article. See vol. 46, pg. 3177, 2011)

• Published in: European journal of medicinal chemistry Vol. 44; no. 12; pp. 5123 - 5130
• Main Authors: Keri, Rangappa S., Hosamani, Kallappa M., Shingalapur, Ramya V., Reddy, Harisha R. Seetharama
• Format: Journal Article
• Language: English
• Published: PARIS Elsevier 01.12.2009
• Subjects: Animals; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Artemia; Azetidines - chemistry; Biological and medical sciences; Chemistry, Medicinal; Coumarins - chemistry; DNA Cleavage - drug effects; Drug Design; Electrophoresis, Agar Gel; General aspects; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Medical sciences; Microbial Sensitivity Tests; Molecular Structure; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; Anti-microbial activity; MECHANISM; ELASTASE; Cytotoxicity; DNA cleavage; 2-Azetidinone; HUMAN CYTOMEGALOVIRUS PROTEASE; INHIBITORS; Coumarin; EFFICIENT; BETA-LACTAMS; Nitrogen heterocycle; Toxicity; Coumarine derivatives; Lactam; Oxygen heterocycle; Antimicrobial agent; Scission; Crustacea; Antifungal agent; Structure activity relation; Chlorine Organic compounds; Bicyclic compound; Cleavage; Aromatic compound; Chemical synthesis; Branchiopoda; Artemia salina; Four membered ring; Benzene derivatives; Lactone; Tricyclic compound; In vitro; Arthropoda; DNA; Azetidine derivatives; Invertebrata; Antibacterial agent
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2009.09.011

A novel series of 3-chloro-4-[4-(2-oxo-2H-chromen-4-ylmethoxy)-phenyl]-1-phenyl-azetidin-2-one derivatives (5a-j) have been synthesized from 4-aryloxymethylcoumarins (la-e) and 4-aryliminomethylphenols (3a-b). The title compounds were screened for their in vitro anti-bacterial and anti-fungal activities. Results revealed that, compounds (5c), (5f), (5h) and (5j) showed excellent anti-microbial activity against a panel of microorganisms. Brine shrimp bioassay was also carried out to study their in vitro cytotoxic properties among which (5h) and (5j) displayed potent cytotoxic activity against Artemia salina. The DNA cleavage activity of some compounds was studied by agarose gel electrophoresis method. All synthesized compounds were characterized using IR, H-1 NMR, C-13 NMR, MS and elemental analysis. (C) 2009 Elsevier Masson SAS. All rights reserved.