Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer

Takahiro Oka, Takuya Yasusa, Takashi Ando, Mayumi Watanabe, Fumio Yoneda, Toshimasa Ishida, J. Knoll

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Abstract

Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane ((-)-BPAP), which is a highly potent and selective catecholaminergic activity enhancer (CAE) substance, are described. The synthetic approach consists of the coupling reaction of benzofuran with (R)-N-tosyl-2-propylazirizine or (R)-N-methoxy-N-methylnorvaliamide, followed by appropriate modifications of the resulting coupling products. As the results, (-)-BPAP turned out to have the R configuration, which was finally confirmed by X-ray crystallographic analysis.

Original languageEnglish
Pages (from-to)1213-1219
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume9
Issue number5
DOIs
Publication statusPublished - May 2001

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1-(benzofuran-2-yl)-2-propylaminopentane
benzofuran

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer. / Oka, Takahiro; Yasusa, Takuya; Ando, Takashi; Watanabe, Mayumi; Yoneda, Fumio; Ishida, Toshimasa; Knoll, J.

In: Bioorganic and Medicinal Chemistry, Vol. 9, No. 5, 05.2001, p. 1213-1219.

Research output: Contribution to journalArticle

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AU - Yoneda, Fumio

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