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Novel quinoline and naphthalene derivatives as potent antimycobacterial agents.

European journal of medicinal chemistry (2010-02-09)
Ram Shankar Upadhayaya, Jaya Kishore Vandavasi, Ramakant A Kardile, Santosh V Lahore, Shailesh S Dixit, Hemantkumar S Deokar, Popat D Shinde, Manash P Sarmah, Jyoti Chattopadhyaya

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 microg/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 microg/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.

Product Number
Product Description

Isoniazid, analytical standard, ≥99% (TLC)