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Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones

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Abstract

A novel series of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-one (7a–i) were synthesized by the condensation between the appropriately substituted 5-substituted-1,3,4-oxadiazolyl-2-thione (4a–i) derived from various existing NSAIDs and 3-(2-bromoacetyl)-2H-chromen-2-one (6) under reflux in the presence of sodium ethoxide. Structure of the synthesized compounds was established on the basis of physicochemical, elemental analysis, and spectral data. The title compounds were screened for in vivo acute anti-inflammatory and analgesic activities at a dose of 200 mg/kg bw. Among the series, four compounds 7c, 7e, 7f, and 7h were found to possess a significant anti-inflammatory and analgesic activity profile. In addition, these compounds were also found to possess a less degree of ulcerogenic potential as compared to standard NSAIDs.

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Acknowledgments

The authors are thankful to The Principal, KLES College of Pharmacy, Hubli, for providing necessary facilities to carry out this research study. We sincerely express our gratitude to Dr. M. N. A. Rao, General Manager (R&D), Divi’s Laboratory, Hyderabad, and Dr. Y. S. Agasimundin, Professor, K.L.E.S College of Pharmacy Hubli, for their encouragement. We are grateful to The Director, SAIF, Punjab University, for providing elemental and spectral analysis. The authors sincerely thank the AICTE, New Delhi (India), for their financial support under MODROBS Scheme (File No. 8023/RID/BOR/MOD/201/7/8). The authors also express special thanks to Fourrts (India) Lab. Pvt. Ltd., Chennai (Tamil Nadu, India), and Elvina Pharmaceuticals Pvt. Ltd. Kotur, Dharwad, for providing gift samples of NSAIDs.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, KLES’ College of Pharmacy, Vidyanagar, Hubli, 580031, Karnataka, India

    Nista Ingale, Veeresh Maddi, Mahesh Palkar, Pradeepkumar Ronad & Shivalingrao Mamledesai

  2. Department of Pharmacology, KLES’ College of Pharmacy, Vidyanagar, Hubli, 580031, Karnataka, India

    A. H. M. Vishwanathswamy

  3. Department of Pharmaceutical Chemistry, NGSM Institute of Pharmaceutical Sciences, Paneer, Deralakatte, Mangalore, Karnataka, India

    Darbhamulla Satyanarayana

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  1. Nista Ingale
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  2. Veeresh Maddi
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  3. Mahesh Palkar
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  4. Pradeepkumar Ronad
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  5. Shivalingrao Mamledesai
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  6. A. H. M. Vishwanathswamy
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  7. Darbhamulla Satyanarayana
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Correspondence to Veeresh Maddi.

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Ingale, N., Maddi, V., Palkar, M. et al. Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones. Med Chem Res 21, 16–26 (2012). https://doi.org/10.1007/s00044-010-9494-z

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  • DOI: https://doi.org/10.1007/s00044-010-9494-z

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