Design and synthesis of certain mesoionic sydnonyl styrylketones as potential nonsteroidal antiinflammatory agents

Shreenivas Ramachandrarao Deshpande; Karkala Vasantakumar Pai; Ranganath Sridhar Pai

doi:10.1055/s-0031-1296186

Arzneimittelforschung, Table of Contents

Arzneimittelforschung 2011; 61(3): 180-185
DOI: 10.1055/s-0031-1296186

Analgesics · Anti-inflammatories · Antiphlogistics · Antirheumatic Drugs

Editio Cantor Verlag Aulendorf (Germany)

Design and synthesis of certain mesoionic sydnonyl styrylketones as potential nonsteroidal antiinflammatory agents

Shreenivas Ramachandrarao Deshpande

¹Departments of Medicinal & Pharmaceutical Chemistry, HSK College of Pharmacy, BVVS Campus, Bagalkote, Karnataka, India

,

Karkala Vasantakumar Pai

²Department of Industrial Chemistry, Kuvempu University, Shankaraghatta, Shivamogga District, Karnataka, India

,

Ranganath Sridhar Pai

³Department of Pharmacology, Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, Udupi District, Karnataka, India

› Author Affiliations

Abstract

In an attempt to develop effective and safer analgesic anti-inflammatory agents, nine compounds belonging to 4-[1-oxo-3-(substituted aryl)-2-propenyl]-3-(4-methoxyphenyl) sydnones, containing the structural features of mesoionic sydnone and styrylketone, have been designed and synthesized by condensing 4-acetyl-3-(4-methoxyphenyl)sydnone with various substituted aryl aldehydes and characterized by spectral studies. They have been tested for analgesic activity by acetic acid induced writhing in mice and for anti-inflammatory activity by carrageenan induced rat paw edema at 100 mg/kg body weight p.o. The compounds containing furyl and chloro substituents showed highly significant analgesic effect, while those with dimethylamino, chloro and nitro substituents exhibited highly significant anti-inflammatory effect at the end of 3 h. The compounds that showed good analgesic and anti-inflammatory activities were evaluated for ulcerogenicity in rats to assess their gastric side effects at 100 mg/kg body weight p.o. They were found to be less ulcerogenic than the standard drug.

Key words

Analgesic effect - Anti-inflammatory effect - Mesoionic compounds - 3-(4-Methoxyphenyl)sydnone - Styrylketone - Ulcerogenicity

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References

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