Tropical Journal of Pharmaceutical Research

Original Research Article | OPEN ACCESS

Synthesis, Characterization and Evaluation of Analgesic and Anti-inflammatory Activities of Some Novel Indoles

Rajashree S Chavan¹ , Harinath N More², Ashok V Bhosale¹

¹PDEA's Seth Govind Raghunath Sable College of Pharmacy, Saswad, Dist- Pune; ²Bharati Vidyapeeth's College of Pharmacy, Kolhapur, Maharashtra, India.

For correspondence:- Rajashree Chavan Email: rajchavan18@yahoo.co.in Tel:+9102115 222212

Received: 3 November 2010 Accepted: 10 June 2011 Published: 20 August 2011

Citation: Chavan RS, More HN, Bhosale AV. Synthesis, Characterization and Evaluation of Analgesic and Anti-inflammatory Activities of Some Novel Indoles. Trop J Pharm Res 2011; 10(4):463-473 doi: 10.4314/tjpr.v10i4.12

© 2011 The authors.
This is an Open Access article that uses a funding model which does not charge readers or their institutions for access and distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0) and the Budapest Open Access Initiative (http://www.budapestopenaccessinitiative.org/read), which permit unrestricted use, distribution, and reproduction in any medium, provided the original work is properly credited..

Abstract

Purpose: Long-term clinical usage of nonsteroidal anti-inflammatory drugs (NSAIDs) is associated with significant side effects - gastrointestinal lesions, bleeding and nephrotoxicity. Therefore, the discovery of new safer antiinflammatory drugs represents a challenging goal for this research area.

Methods: Various derivatives of 3-(2-aminopyrimidin-4-yl) indoles viz. 4-(4-substitutedphenyl)-6-(2-(4-substitutedphenyl)-1H-indol-3-yl) pyrimidin-2-amine (4a-4r) were synthesized by cyclization of (3-(4-substitutedphenyl)-1-(2-(4-substitutedphenyl)-1H-indol-3-yl) prop-2-en-1-one) of indole with guanidine hydrochloride in the presence of sodium isopropoxide. Their structures were confirmed by FTIR, ¹H NMR and elemental analysis. These compounds were investigated for their analgesic, inflammatory and ulcerogenic activities.

Results: All the compounds tested (4a-4r) showed analgesic and inflammatory activities. Seven compounds (4d, e, h, j, k, q, p) out of 18 compounds showed antiinflammatory activity comparable to that of the reference standard, indomethacin, but with much lower ulcerogenic action. Compounds 4j and 4k showed 87.4 and 88.2 % inhibition of paw edema, 78.5 and 76.6 % protection against acetic acid-induced writhings and 0.89 and 1.12 of severity index, respectively, compared to 92.7 %, 82.8 % and 2.2, respectively, for indomethacin.

Conclusion: The results show that incorporation of an appropriately substituted pyrimidine ring in indole nucleus can afford molecules with good analgesic and anti-inflammatory activities but with reduced gastric irritation.

Keywords: Synthesis, Indole, Pyrimidine, Anti-inflammatory activity, Analgesic activity, Ulcerogenic effect