Synthesis and antimycobacterial evaluation of novel 5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenyl-5,4-substituted phenyl methanone analogues

• Published in: Bioorganic & medicinal chemistry letters Vol. 19; no. 24; pp. 7000 - 7002
• Main Authors: Ali, Mohamed Ashraf, Samy, Jeyabalan Govinda, Manogaran, Elumalai, Sellappan, Velmurugan, Hasan, Mohamed Zaheen, Ahsan, Mohamed Jawed, Pandian, Suresh, ShaharYar, Mohammad
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 15.12.2009; Elsevier
• Subjects: Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antitubercular agents; Antitubercular Agents - chemical synthesis; Antitubercular Agents - chemistry; Antitubercular Agents - pharmacology; Biological and medical sciences; Diketone; Indenes - chemical synthesis; Indenes - chemistry; Indenes - pharmacology; Medical sciences; Mycobacterium tuberculosis; Mycobacterium tuberculosis - drug effects; Pharmacology. Drug treatments; Antitubercular agents; Diketone; Benzene derivatives; In vitro; Metabolic stability; Mycobacterium tuberculosis; Structure activity relation; Mycobacteriales; Mycobacteriaceae; Bicyclic compound; Bacteria; Actinomycetes; Antituberculous agent; Aromatic compound; Diether; Antibacterial agent; Chemical synthesis
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2009.10.034

In present investigation, a series of substituted phenyl-5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenylmethanone analogues were synthesized and were evaluated for antimycobacterial activity against Mycobacterium tuberculosis H57Rv and INH resistant M. tuberculosis. All the newly synthesized compounds were showing moderate to high inhibitory activities, with compound 5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenyl-4-fluorophenylmethanone (5g) produced was found to be the most promising compounds active against M. tuberculosis H57Rv and isoniazid (INH) resistant M. tuberculosis with Minimum inhibitory concentration 0.10 and 0.10μM. In present investigation, a series of substituted phenyl-5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenylmethanone analogues were synthesized and were evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Rv and INH resistant M. tuberculosis. All the newly synthesized compounds were showing moderate to high inhibitory activities. The compound 5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenyl-4-fluorophenylmethanone (5g) was found to be the most promising compounds active against M. tuberculosis H37Rv and isoniazid (INH) resistant M. tuberculosis with Minimum inhibitory concentration 0.10 and 0.10μM.