Asymmetric synthesis of isobenzofuranone derivatives and their unique character as protein kinase Cα (PKCα) activators

Go Hirai, Yosuke Ogoshi, Megumi Ohkubo, Yuki Tamura, Toru Watanabe, Tadashi Shimizu, Mikiko Sodeoka

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Efficient enantio-selective synthesis of conformationally constrained diacylglycerol analogues, 7-substituted isobenzofuranone derivatives, originally developed by us as PKCα ligands, was achieved by asymmetric dihydroxylation and γ-lactone formation via ortho-lithiation and carboxylation. A series of derivatives having straight and/or branched side chains were synthesized and evaluated, and low-nanomolar-concentration affinity ligands and highly potent PKCα activators were found among them. These potent ligands induced phenotypic change of K562 cells, which is characteristic of PKC activators.

Original languageEnglish
Pages (from-to)3609-3612
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - Jul 1 2009
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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