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

doi:10.1016/S0960-894X(01)00350-X

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 journal › Article

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 language	English
Pages (from-to)	1985-1988
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	11
Issue number	15
DOIs	https://doi.org/10.1016/S0960-894X(01)00350-X
Publication status	Published - 2001 Aug 6
Externally published	Yes

Fingerprint

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Organic Chemistry
Drug Discovery
Pharmaceutical Science

Cite this

Suhara, Y., Nakane, S., Arai, S., Takayama, H., Waku, K., Ishima, Y., & Sugiura, T. (2001). Synthesis and biological activities of novel structural analogues of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand. Bioorganic and Medicinal Chemistry Letters, 11(15), 1985-1988. https://doi.org/10.1016/S0960-894X(01)00350-X

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 journal › Article

@article{dc7088f8c7db445f8690164d7a2079cc,

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

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.",

author = "Yoshitomo Suhara and Shinji Nakane and Shunsuke Arai and Hiroaki Takayama and Keizo Waku and Yoshio Ishima and Takayuki Sugiura",

year = "2001",

month = "8",

day = "6",

doi = "10.1016/S0960-894X(01)00350-X",

language = "English",

volume = "11",

pages = "1985--1988",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "15",

}

TY - JOUR

T1 - Synthesis and biological activities of novel structural analogues of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand

AU - Suhara, Yoshitomo

AU - Nakane, Shinji

AU - Arai, Shunsuke

AU - Takayama, Hiroaki

AU - Waku, Keizo

AU - Ishima, Yoshio

AU - Sugiura, Takayuki

PY - 2001/8/6

Y1 - 2001/8/6

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0035817227&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035817227&partnerID=8YFLogxK

U2 - 10.1016/S0960-894X(01)00350-X

DO - 10.1016/S0960-894X(01)00350-X

M3 - Article

C2 - 11454463

AN - SCOPUS:0035817227

VL - 11

SP - 1985

EP - 1988

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 15

ER -

Access to Document

10.1016/S0960-894X(01)00350-X