Potential anti-tubercular and in vitro anti-inflammatory agents: 9-substituted 1,8-dioxo-octahydroxanthenes through cascade/domino reaction by citric fruit juices
- 286 Downloads
A series of 9-substituted 1,8-dioxo-octahydroxanthenes, 3a–k 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.
Keywords1,8-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.
- Dharma Rao GB, Kaushik MP, Halve AK (2012) Zinc Oxide nanoparticles, An environmentally benign and reusable catalyst for the synthesis of 1,8-dioxooctahydroxanthene derivatives under solvent-free conditions. Heterocycl Lett 2(4):411–418Google Scholar
- Ellis GP (1977) The chemistry of heterocyclic compounds. In: Weissberger A, Taylor ECE (eds) Chromene, chromanes and chromone, vol 31. Wiley, New York, p 13Google Scholar
- Ilangovan A, Malayappasamy S, Muralidharan S, Maruthamuthu S (2011) A highly efficient green synthesis of 1, 8-dioxo-octahydroxanthenes. Chem Cent J 5(81):1–6Google Scholar
- Jin T-S, Qi N, Li M, Han L-S, Liu L-B, Li T-S (2007) Onepot synthesis of 9-aryl-1,8-dioxo-1,2,3,4,6,7,8-octahydroxanthenes catalysed by p-dodecyl benzene sulfonic acid in aqueous media. Asian J Chem 19(5):380–3809Google Scholar
- Manivel P, Mohana Roopan S, Sathish Kumar R, Nawaz Khan F (2009) Synthesis of 3 substituted isoquinolin-1-yl-2-(cycloalk-2-enylidene) hydrazines and their antimicrobial properties. J Chilean Chem Soc 54(2):183–185Google Scholar
- Roopan SM, Khan FRN (2010a) ZnO nanoparticles in the synthesis of AB ring core of camptothecin. Chem Pap 64(6):812–817Google Scholar
- Roopan SM, Khan FRN (2010b) ZnO nanorods catalyzed N-alkylation of piperidin-4-one, 4 (3H)-pyrimidone, and ethyl 6-chloro-1, 2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate. Chem pap 64(5):678–682Google Scholar
- Roopan SM, Reddy BR, Kumar AS, Khan FN (2009b) Synthesis of 3-substituted isocoumarins using montmorillonite K-10. Indian J Heterocycl Ch 19(1):81–82Google Scholar
- Sirkecioglu O, Talinli N, Akar A (1995) Chemical aspects of santalin as a histological stain. J Chem Res 2:502–507Google Scholar
- Toth M, Sohail A, Fridman R (2012) Assessment of gelatinases (MMP-2 and MMP-9) by gelatin zymography. Method Mol Biol 878:121–135Google Scholar
- Xue Yuan HU, FAN XS, Zhang XY, Wang JJ (2005) Green and efficient synthesis of Xanthenedione derivatives promoted by InCl3·4H2O in ionic liquid. Chin Chem Lett 16(3):293–295Google Scholar