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Novel quinoline and naphthalene derivatives as potent antimycobacterial agents
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2010 (English)In: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 45, no 5, 1854-1867 p.Article in journal (Refereed) Published
Abstract [en]

We have designed and synthesized both the quinoline and naphthalene based molecules influenced by the unique structural make-up of mefloquine and TMC207, respectively. These compounds were evaluated for their anti-mycobacterial activity against drug sensitive Mycobacterium tuberculosis H37Rv in vitro at single-dose concentration (6.25 mu g/mL). The compounds 22,23, 26 and 27 inhibited the growth of M. tuberculosis H37Rv 99%, 90%, 98% and 91% respectively. Minimum inhibitory concentration of compounds 22, 23, 26 and 27 was found to be 6.25 mu g/mL.. Our molecular modeling and docking studies of designed compounds showed hydrogen bonding with Glu-61, Tyr-64 and Asn-190 amino acid residues at the putative binding site of ATP synthase, these interactions were coherent as shown by Mefloquine and TMC207, where hydrogen bonding was found with Tyr-64 and Glu-61 respectively. SAR analysis indicates importance of hydroxyl group and nature of substituents on piperazinyl-phenyl ring was critical in dictating the biological activity of newly synthesized compounds. (C) 2010 Elsevier Masson SAS. All rights reserved.

Place, publisher, year, edition, pages
2010. Vol. 45, no 5, 1854-1867 p.
Keyword [en]
ATP synthase, Naphthalene, Quinoline, TMC207, Mefloquine, Anti-tuberculosis drugs
National Category
Medical and Health Sciences Biological Sciences Pharmaceutical Sciences
URN: urn:nbn:se:uu:diva-136621DOI: 10.1016/j.ejmech.2010.01.024ISI: 000276695200021OAI: oai:DiVA.org:uu-136621DiVA: diva2:377165
Available from: 2010-12-13 Created: 2010-12-13 Last updated: 2010-12-13Bibliographically approved

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Bioorganic Chemistry
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