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A practical synthesis of amino limonin/deoxylimonin derivatives as effective mitigators against inflammation and nociception

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Abstract

A practical synthetic route, consisting of 5 steps, has been developed and applied successfully for converting limonin/deoxylimonin into the corresponding amino derivatives I-5aI-5e and II-5aII-5e. Deoxylimonin analogs II-5a and II-5b bearing an open A ring structure underwent ring closure reaction by employing the Mitsunobu procedure to afford II-6a and II-6b. All of the 12 newly synthesized compounds were subjected to preliminary screening for evaluating their inflammation and nociception inhibition efficacy. The most promising compounds, I-5b and II-5d, were selected for further investigation by a carrageenan-induced mouse paw edema model, both of which displayed a dose–response dependent manner and demonstrated superior anti inflammation capacity to that of indomethacin in the first 2 hours.

Graphical abstract: A practical synthesis of amino limonin/deoxylimonin derivatives as effective mitigators against inflammation and nociception

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Article information


Submitted
12 Apr 2020
Accepted
12 May 2020
First published
16 Jun 2020

RSC Med. Chem., 2020, Advance Article
Article type
Research Article

A practical synthesis of amino limonin/deoxylimonin derivatives as effective mitigators against inflammation and nociception

S. Wang, X. Han, Y. Yang, R. Chen, Z. Guo, Q. Zhu and Y. Xu, RSC Med. Chem., 2020, Advance Article , DOI: 10.1039/D0MD00117A

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