Synthesis and biological activities of novel structural analogues of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand

Yoshitomo Suhara, Shinji Nakane, Shunsuke Arai, Hiroaki Takayama, Keizo Waku, Yoshio Ishima, Takayuki Sugiura

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Novel analogues of 2-arachidonoylglycerol (2-AG), an endogenous cannabinoid receptor ligand, were developed. Chemical synthesis of these analogues (2-AGA105 and 2-AGA109) was accomplished starting from 2-octyn-1-ol and diethyl malonate and employing Wittig coupling of triene phosphonate with an aldehyde intermediate in a convergent and stereoselective manner. These analogues should be useful lead compounds for the development of novel 2-AG mimetics.

Original languageEnglish
Pages (from-to)1985-1988
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume11
Issue number15
DOIs
Publication statusPublished - 2001 Aug 6
Externally publishedYes

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Cannabinoid Receptors
Bioactivity
Ligands
Lead compounds
Organophosphonates
Aldehydes
2-arachidonylglycerol
diethyl malonate

ASJC Scopus subject areas

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

Cite this

Synthesis and biological activities of novel structural analogues of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand. / Suhara, Yoshitomo; Nakane, Shinji; Arai, Shunsuke; Takayama, Hiroaki; Waku, Keizo; Ishima, Yoshio; Sugiura, Takayuki.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 11, No. 15, 06.08.2001, p. 1985-1988.

Research output: Contribution to journalArticle

Suhara, Yoshitomo ; Nakane, Shinji ; Arai, Shunsuke ; Takayama, Hiroaki ; Waku, Keizo ; Ishima, Yoshio ; Sugiura, Takayuki. / Synthesis and biological activities of novel structural analogues of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand. In: Bioorganic and Medicinal Chemistry Letters. 2001 ; Vol. 11, No. 15. pp. 1985-1988.
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