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Tetrahedron Lett. 2013 Mar 20;54(12):1546-1549.

Efficient Synthesis of ESI-09, A Novel Non-cyclic Nucleotide EPAC Antagonist.

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1
Department of Pharmacology and Toxicology, University of Texas Medical Branch, Galveston, Texas 77555, United States.

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:

EPAC antagonist; ESI-09; cyanomethyl ketone; isoxazole; modified Kowalski's protocol

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