Efficient synthesis of ESI-09, a novel non-cyclic nucleotide EPAC antagonist

Haijun Chen, Chunyong Ding, Christopher Wild, Huiling Liu, Tianzhi Wang, Mark White, Xiaodong Cheng, Jia Zhou

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A concise and efficient synthetic approach to producing a novel non-cyclic nucleotide EPAC antagonist ESI-09 and its new analogs is reported. Key features of the synthesis include a mild and reliable one-pot procedure for an isoxazole synthon, as well as a modified one-pot protocol for the cyanomethyl ketone key intermediate. The synthesis requires inexpensive starting materials and only three linear steps for the completion in a total yield of 53%.

Original languageEnglish (US)
Pages (from-to)1546-1549
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number12
DOIs
StatePublished - Mar 20 2013

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Isoxazoles
Ketones
Nucleotides
3-(5-tert-butylisoxazol-3-yl)-2-((3-chlorophenyl)hydrazono)-3-oxopropionitrile
erythromycin propionate-N-acetylcysteinate

Keywords

  • Cyanomethyl ketone
  • EPAC antagonist
  • ESI-09
  • Isoxazole
  • Modified Kowalski's protocol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Efficient synthesis of ESI-09, a novel non-cyclic nucleotide EPAC antagonist. / Chen, Haijun; Ding, Chunyong; Wild, Christopher; Liu, Huiling; Wang, Tianzhi; White, Mark; Cheng, Xiaodong; Zhou, Jia.

In: Tetrahedron Letters, Vol. 54, No. 12, 20.03.2013, p. 1546-1549.

Research output: Contribution to journalArticle

Chen, Haijun ; Ding, Chunyong ; Wild, Christopher ; Liu, Huiling ; Wang, Tianzhi ; White, Mark ; Cheng, Xiaodong ; Zhou, Jia. / Efficient synthesis of ESI-09, a novel non-cyclic nucleotide EPAC antagonist. In: Tetrahedron Letters. 2013 ; Vol. 54, No. 12. pp. 1546-1549.
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AU - Cheng, Xiaodong

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