title: Design, synthesis and antitubercular evaluation of novel 2-substituted-3H-benzofuro benzofurans via palladium-copper catalysed Sonagashira coupling reaction.
abstract: A series of novel natural product like 2-substiuted-3H-benzofurobenzofurans designed by molecular hybridization were synthesized in very good yields. The key reactions involved in the synthesis are iodination of 2-dibenzofuranol using iodine monochloride followed by palladium-copper catalyzed Sonagashira-coupling of 1-iododibenzofuran-2-ol with various alkyl and aryl acetylenes. Among the all 10 new compounds screened for in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv, 2-(4-methoxy-2-methyl phenyl)-3H-benzofuro[3,2-e]benzofuran (7c) was found to be most active with MIC 3.12 μg/mL and has shown lower cytotoxicity with good therapeutic index.
authors: Organic Chemistry Division-II (CPC Division), CSIR-Indian Institute of Chemical Technology, Hyderabad, India.
authors: Thirumal
authors: T
authors: Yempala
authors: Jonnalagadda Padma
authors: JP
authors: Sridevi
authors: Perumal
authors: P
authors: Yogeeswari
authors: Darmarajan
authors: D
authors: Sriram
authors: Srinivas
authors: S
authors: Kantevari
mesh_terms: D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015195:Drug Design; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D010165:Palladium / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: C587541:2-(4-methoxy-2-methylphenyl)-3H-benzofuro(3,2-e)benzofuran; D000995:Antitubercular Agents; D001572:Benzofurans; D006576:Heterocyclic Compounds, 4 or More Rings; D010165:Palladium; D003300:Copper; C105430:benzofuran
keywords: Antimycobacterial activity; Benzofuran; Dibenzofuran; Molecular hybridization; Sonagashira reaction