Synthesis of spiro-tetrahydrothiopyran-oxindoles by Michael–aldol cascade reactions: discovery of potential P53-MDM2 inhibitors with good antitumor activity

Literature Information

Publication Date 2017-12-21
DOI 10.1039/C7OB02726E
Impact Factor 3.876
Authors

Shengzheng Wang, Shuqiang Chen, Zhongjie Guo, Shipeng He, Fan Zhang, Xueying Liu, Weiping Chen, Shengyong Zhang, Chunquan Sheng


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Abstract

Using proline as the catalyst, an organocatalytic Michael–aldol cascade reaction was developed for the synthesis of spiro-tetrahydrothiopyran oxindoles. The highly functionalized scaffold was assembled in moderate to good yields (51–78%) and excellent diastereoselectivities (>20 : 1 dr). Interestingly, the oxindoles displayed moderate to good in vitro antitumor activities and were validated as p53-MDM2 inhibitors, which represented promising lead compounds for antitumor drug discovery.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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