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Synthesis of Naamidine A and Selective Access to N(2)-Acyl-2-aminoimidazole Analogues.

ABSTRACT: A short and scalable synthesis of naamidine A, a marine alkaloid with a selective ability to inhibit epidermal growth factor receptor (EGFR)-dependent cellular proliferation, has been achieved. A key achievement in this synthesis was the development of a regioselective hydroamination of a monoprotected propargylguanidine to deliver N(3)-protected cyclic ene-guanidines. This permits the extension of this methodology to prepare N(2)-acyl analogues in a fashion that obviates the troublesome acylation of the free 2-aminoimidazoles, which typically yields mixtures of N(2)- and N(2),N(2)-diacylated products.

SUBMITTER: Gibbons JB

PROVIDER: S-EPMC5117189 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Synthesis of Naamidine A and Selective Access to N(2)-Acyl-2-aminoimidazole Analogues.

Gibbons Joseph B JB Salvant Justin M JM Vaden Rachel M RM Kwon Ki-Hyeok KH Welm Bryan E BE Looper Ryan E RE

The Journal of organic chemistry 20150924 20

A short and scalable synthesis of naamidine A, a marine alkaloid with a selective ability to inhibit epidermal growth factor receptor (EGFR)-dependent cellular proliferation, has been achieved. A key achievement in this synthesis was the development of a regioselective hydroamination of a monoprotected propargylguanidine to deliver N(3)-protected cyclic ene-guanidines. This permits the extension of this methodology to prepare N(2)-acyl analogues in a fashion that obviates the troublesome acylati ...[more]

PMID: 26360634

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