Synthesis of crambescin B carboxylic acid, a potent inhibitor of voltage-gated sodium channels

Atsuo Nakazaki; Yuki Ishikawa; Yusuke Sawayama; Mari Yotsu-Yamashita; Toshio Nishikawa

doi:10.1039/c3ob42017e

Synthesis of crambescin B carboxylic acid, a potent inhibitor of voltage-gated sodium channels

Atsuo Nakazaki, Yuki Ishikawa, Yusuke Sawayama, Mari Yotsu-Yamashita, Toshio Nishikawa

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

15 Citations (Scopus)

Abstract

The stereocontrolled synthesis of a racemic carboxylic acid of crambescin B, a marine alkaloid, is described. The synthesis features two highly stereoselective reactions: (i) palladium-catalyzed hydroxymethylation of an alkynyl aziridine having an N-guanidino group and (ii) cascade bromocyclization providing a spiro-hemiaminal structure. The cell-based colorimetric assay showed that the synthesized carboxylic acid exhibited a potent inhibitory activity on voltage-gated sodium channels.

Original language	English
Pages (from-to)	53-56
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	1
DOIs	https://doi.org/10.1039/c3ob42017e
Publication status	Published - 2014 Jan 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "The stereocontrolled synthesis of a racemic carboxylic acid of crambescin B, a marine alkaloid, is described. The synthesis features two highly stereoselective reactions: (i) palladium-catalyzed hydroxymethylation of an alkynyl aziridine having an N-guanidino group and (ii) cascade bromocyclization providing a spiro-hemiaminal structure. The cell-based colorimetric assay showed that the synthesized carboxylic acid exhibited a potent inhibitory activity on voltage-gated sodium channels.",

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AU - Nakazaki, Atsuo

AU - Ishikawa, Yuki

AU - Sawayama, Yusuke

AU - Yotsu-Yamashita, Mari

AU - Nishikawa, Toshio

PY - 2014/1/7

Y1 - 2014/1/7

N2 - The stereocontrolled synthesis of a racemic carboxylic acid of crambescin B, a marine alkaloid, is described. The synthesis features two highly stereoselective reactions: (i) palladium-catalyzed hydroxymethylation of an alkynyl aziridine having an N-guanidino group and (ii) cascade bromocyclization providing a spiro-hemiaminal structure. The cell-based colorimetric assay showed that the synthesized carboxylic acid exhibited a potent inhibitory activity on voltage-gated sodium channels.

AB - The stereocontrolled synthesis of a racemic carboxylic acid of crambescin B, a marine alkaloid, is described. The synthesis features two highly stereoselective reactions: (i) palladium-catalyzed hydroxymethylation of an alkynyl aziridine having an N-guanidino group and (ii) cascade bromocyclization providing a spiro-hemiaminal structure. The cell-based colorimetric assay showed that the synthesized carboxylic acid exhibited a potent inhibitory activity on voltage-gated sodium channels.

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JF - Organic and Biomolecular Chemistry

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Synthesis of crambescin B carboxylic acid, a potent inhibitor of voltage-gated sodium channels

Abstract

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