Medicinal Chemistry Research

, Volume 23, Issue 11, pp 4749–4760 | Cite as

Potential anti-tubercular and in vitro anti-inflammatory agents: 9-substituted 1,8-dioxo-octahydroxanthenes through cascade/domino reaction by citric fruit juices

  • Ayyakannu Arumugam Napoleon
  • Fazlur-Rahman Nawaz KhanEmail author
Original Research


A series of 9-substituted 1,8-dioxo-octahydroxanthenes, 3ak were synthesized and evaluated for their anti-tubercular and in vitro anti-inflammatory potential. Compounds 3b, 3d, 3e, 3f, 3g, and 3k demonstrated their potential anti-tubercular activity at 0.4 μg/ml comparable to streptomycin and pyrazinamide (standard drugs) screened by Microplate Alamar Blue assay against Mycobacterium tuberculosis H37 Ra. Compounds 3j, 3e, 3f, and 3c showed good in vitro anti-inflammatory activity by the inhibition of enzyme MMP-2 75, 65, 70, and 60 % and inhibition of enzyme MMP-9 by 90, 70, 60, and 60 %, respectively by gelatin zymography on gel electrophoresis. Standard drug tetracycline (300 μg/ml) is used as positive control which showed 90 % inhibition. The percentage inhibition was determined by a gel documentation system. DMSO was used as solvent control which did not show any inhibition.


1,8-Dioxo-octahydroxanthene In vitro anti-tubercular Anti-inflammatory activities Gelatin zymography Gel electrophoresis 



The authors thank VIT University for providing research funding and laboratory facilities. DST for FIST funding and SIF-VIT is acknowledged for providing the NMR and GCMS facilities.

Supplementary material

44_2014_1033_MOESM1_ESM.doc (13.7 mb)
Supplementary material 1 (DOC 14046 kb)


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Ayyakannu Arumugam Napoleon
    • 1
    • 2
  • Fazlur-Rahman Nawaz Khan
    • 1
    Email author
  1. 1.Organic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced SciencesVIT-UniversityVelloreIndia
  2. 2.Pharmaceutical Chemistry Division, School of Advanced SciencesVIT UniversityVelloreIndia

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