Studies on substituted benzo[h]quinazolines, benzo[g]indazoles, pyrazoles, 2,6-diarylpyridines as anti-tubercular agents

Bioorg Med Chem Lett. 2013 Nov 1;23(21):5844-9. doi: 10.1016/j.bmcl.2013.08.101. Epub 2013 Sep 5.

Abstract

Various substituted 5,6-dihydro-8-methoxybenzo[h]quinazolin-2-amine, 1-(3-(4-alkoxyphenyl)-7-methoxy-3,3a,4,5-tetrahydro-2H benzo[g]indazol-2-yl)ethanone, pyrazole and 2,6-diarylpyridine derivatives have been synthesized in good yields by an efficient methodology. The synthesized compounds (4-23) were evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain. Compounds 6a, 6c, 8a, 19a and 19e exhibited significant anti-tubercular activity at MIC values 50, 100, 50, 25 and 100μM concentration. In vitro cytotoxicity data using THP-1 cells indicated that most active compound 19a is safe as its MIC value is much lower than the cytotoxic value.

Keywords: AFRWBGJRWRHQOV-UHFFFAOYSA-N; AJTJGWQHYALTSC-UHFFFAOYSA-N; AKKATVMDHBEASX-UHFFFAOYSA-N; AYZGFAJCOVMXLA-UHFFFAOYSA-N; Antitubercular; CFOCPVQZZLPMIO-UHFFFAOYSA-N; CMWJZWOGUWCFQV-UHFFFAOYSA-N; CTEHHBOBZOCAIT-UHFFFAOYSA-N; CTODEFQZHRGULH-UHFFFAOYSA-N; DBXRLXVTWNUHCR-UHFFFAOYSA-N; DSCMLTAZYFVUPH-UHFFFAOYSA-N; DSLIJABHAVBSDV-UHFFFAOYSA-N; DWRUNZAIXLCFIP-UHFFFAOYSA-N; DXBULVYHTICWKT-UHFFFAOYSA-N; DXPKJYJXQICXLT-UHFFFAOYSA-N; Diarylpyridine; FIGVJXMTQDHJMQ-UHFFFAOYSA-N; GYXWNSDLDXGMGU-UHFFFAOYSA-N; HJBWBXRSRQEPRF-UHFFFAOYSA-N; ICSNLGPSRYBMBD-UHFFFAOYSA-N; IEVUNGKXTAPNJR-UHFFFAOYSA-N; ITENFASQOQYRFM-UHFFFAOYSA-N; Indazole; JADFRCNEVYMOAL-UHFFFAOYSA-N; KGHNKNWLMDRAQN-UHFFFAOYSA-N; KXDAEFPNCMNJSK-UHFFFAOYSA-N; LFUDVFOVNMIIIB-UHFFFAOYSA-N; LONGYNYRAPHNDS-UHFFFAOYSA-N; LOQHWUSEIHJYSE-UHFFFAOYSA-N; MHOUKRXEYUPHQG-UHFFFAOYSA-N; MKOXPFXGJVHBRH-UHFFFAOYSA-N; MMVNARZZQWUGQI-UHFFFAOYSA-N; MZCGMLMIRVVUSZ-UHFFFAOYSA-N; MZWNQLWLROXGST-UHFFFAOYSA-N; NFJFJJLADCFCHO-UHFFFAOYSA-N; NKPNESPVSMHQPA-ZRDIBKRKSA-N; NQRYJNQNLNOLGT-UHFFFAOYSA-N; NXWRCPFWNLSYMG-UHFFFAOYSA-N; PAEYRUAPLGXYIJ-UHFFFAOYSA-N; PLGIFHJDPLCSPL-UHFFFAOYSA-N; POMGSLQHWNDZAP-UHFFFAOYSA-N; Pyrazole; QLIZWGWIQMJGMB-UHFFFAOYSA-N; QXQPWPCSFNZDEU-JLHYYAGUSA-N; Quinazoline; RLGJGDBTBWUXKU-UHFFFAOYSA-N; RMGFLMXDCGQKPS-UHFFFAOYSA-N; STGYTXNBWMZKBA-UHFFFAOYSA-N; UBABLIWJMXJJNH-UHFFFAOYSA-N; UPFBAUZYKBLCEO-ZRDIBKRKSA-N; VGLWVBWXBZWXJE-WUKNDPDISA-N; VMNKGGRIISDZAU-UHFFFAOYSA-N; VOISDZHTKJQPAM-UHFFFAOYSA-N; WDWWEAMPRRKLGH-UHFFFAOYSA-N; WGCBFZZUJQDDSF-UHFFFAOYSA-N; WJNQRYCMQPMUDS-PKNBQFBNSA-N; WNRWEBKEQARBKV-UHFFFAOYSA-N; WQMAANNAZKNUDL-UHFFFAOYSA-N; XBPOBCXHALHJFP-UHFFFAOYSA-N; XPAKBGQUORPCMO-PKNBQFBNSA-N; XRWQAJSVMIKRKF-UHFFFAOYSA-N; YNAVUWVOSKDBBP-UHFFFAOYSA-N; YWQRMQADBLJRKZ-UHFFFAOYSA-N; ZVGCJBIDARLIMB-UHFFFAOYSA-N; ZWKKHRLWUFOSPA-UHFFFAOYSA-N; ZXANSLBVWCBHPP-UHFFFAOYSA-N.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemistry*
  • Antitubercular Agents / pharmacology
  • Cell Line
  • Humans
  • Indazoles / chemistry*
  • Indazoles / pharmacology
  • Mycobacterium tuberculosis / drug effects*
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology
  • Pyridines / chemistry*
  • Pyridines / pharmacology
  • Quinazolines / chemistry*
  • Quinazolines / pharmacology
  • Tuberculosis / drug therapy

Substances

  • Antitubercular Agents
  • Indazoles
  • Pyrazoles
  • Pyridines
  • Quinazolines