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Synthesis of novel isoxazolines via 1,3-dipolar cycloaddition and evaluation of anti-stress activity

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Abstract

We have synthesized a series of novel isoxazolines via 1,3-dipolar cycloaddition of in situ generated nitrile oxide from 2,4-dimethoxy benzaldoxime and naphthaldehyde oxime with 4-allyl-2-methoxyphenol derivatives. The synthesized compounds were evaluated for anti-stress activity in acute stress (AS) induced peripheral changes. Adult male Sprague–Dawley rats, subjected to AS, cause a significant increase in gastric ulceration, adrenal gland weight, plasma glucose, corticosterone levels, and creatine kinase activity. Compounds 3d, 3g, 5b, 5c, 5d, and 5g displayed most promising anti-stress effect by reverting these peripheral stress parameters at a dose of 40 mg/kg p.o.

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Acknowledgments

The authors are grateful to SAIF for spectral data and Indian Council of Medicinal Research, New Delhi, for the award of senior research fellowship to P. Gupta. Kailash and Ausaf Ahmad are thankful to UGC for financial support.

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Correspondence to Rakesh Maurya.

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CDRI communication no. 7613.

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Maurya, R., Ahmad, A., Gupta, P. et al. Synthesis of novel isoxazolines via 1,3-dipolar cycloaddition and evaluation of anti-stress activity. Med Chem Res 20, 139–145 (2011). https://doi.org/10.1007/s00044-010-9299-0

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  • DOI: https://doi.org/10.1007/s00044-010-9299-0

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