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

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

doi:10.1016/j.tetlet.2013.01.024

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

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

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

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 language	English (US)
Pages (from-to)	1546-1549
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2013.01.024
State	Published - Mar 20 2013

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.01.024

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

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\%.",

keywords = "Cyanomethyl ketone, EPAC antagonist, ESI-09, Isoxazole, Modified Kowalski's protocol",

author = "Haijun Chen and Chunyong Ding and Christopher Wild and Huiling Liu and Tianzhi Wang and White, \{Mark A.\} and Xiaodong Cheng and Jia Zhou",

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T1 - Efficient synthesis of ESI-09, a novel non-cyclic nucleotide EPAC antagonist

AU - Chen, Haijun

AU - Ding, Chunyong

AU - Wild, Christopher

AU - Liu, Huiling

AU - Wang, Tianzhi

AU - White, Mark A.

AU - Cheng, Xiaodong

AU - Zhou, Jia

PY - 2013/3/20

Y1 - 2013/3/20

N2 - 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%.

AB - 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%.

KW - Cyanomethyl ketone

KW - EPAC antagonist

KW - ESI-09

KW - Isoxazole

KW - Modified Kowalski's protocol

UR - https://www.scopus.com/pages/publications/84873716320

UR - https://www.scopus.com/pages/publications/84873716320#tab=citedBy

U2 - 10.1016/j.tetlet.2013.01.024

DO - 10.1016/j.tetlet.2013.01.024

M3 - Article

C2 - 23459418

AN - SCOPUS:84873716320

SN - 0040-4039

VL - 54

SP - 1546

EP - 1549

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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