Solvent-Dependent Chemoselective and Stereoselective Approach to Synthesis of Spiro-γ-Lactams with Potent Anticancer Activity

Jie Lei, Liu Jun He, Dian Yong Tang, Jingyuan Wen, Wei Yan, Hong yu Li, Zhong Zhu Chen, Zhi Gang Xu

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Chemoselective approaches were developed for derivatizing diastereoselective chromanone spiro-γ-lactams through the Michael-type addition by using amide as a weak nucleophile to construct the spiro-carbon center under basic conditions. To expand the scope of this post-Ugi cascade reaction, a new series of oxidized chromone derivatives was synthesized by altering solvent from EtOH to DMF. Compounds 7 a and 7 b which could be synthesized in one day, demonstrated comparable anticancer activities with legendary anticancer drug paclitaxel in the PANC and U87 cell lines. This methodology offers a new approach to construct spiro-carbon centers with functionalized chromanones or chromones under mild reaction conditions. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)2996-3000
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume363
Issue number12
DOIs
StatePublished - Jun 21 2021
Externally publishedYes

Keywords

  • Anticancer activity
  • Michael addition
  • Multicomponent reactions (MCRs)
  • Spiro-carbon center
  • Spiro-γ-lactams

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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