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

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- 5a-I- 5e and II- 5a-II- 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.

SUBMITTER: Wang S

PROVIDER: S-EPMC7649976 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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

Wang Shaochi S Han Xueqing X Yang Yun Y Chen Rui R Guo Zhaoyi Z Zhu Qihua Q Xu Yungen Y

RSC medicinal chemistry 20200616 7

A practical synthetic route, consisting of 5 steps, has been developed and applied successfully for converting limonin/deoxylimonin into the corresponding amino derivatives I- 5a-I- 5e and II- 5a-II- 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 ...[more]

PMID: 33479680

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