Solid-phase synthesis of anandamide analogues

Longwu Qi; Michael M. Meijler; Sang Hyeup Lee; Chengzao Sun; Kim D. Janda

doi:10.1021/ol049474j

Solid-phase synthesis of anandamide analogues

Longwu Qi, Michael M. Meijler, Sang Hyeup Lee, Chengzao Sun, Kim D. Janda

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

18 Scopus citations

Abstract

The endocannabinoids are amides and esters of arachidonic acid that can mimic the pharmacological properties of Δ⁹-tetrahydrocannabinol (Δ⁹-THC). Anandamide, the most prominent of the endocannabinoids, has been implicated in both metabolic/physiological roles of the central nervous system, making it an attractive medicinal target. As such, we report the first solid-phase methodology that expedites access to various anandamide analogues. Our synthesis features a repetitive Cu-mediated coupling reaction between terminal alkynes and propargyl halides or allylic halides.

Original language	English
Pages (from-to)	1673-1675
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	10
DOIs	https://doi.org/10.1021/ol049474j
State	Published - 13 May 2004
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol049474j

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abstract = "The endocannabinoids are amides and esters of arachidonic acid that can mimic the pharmacological properties of Δ9-tetrahydrocannabinol (Δ9-THC). Anandamide, the most prominent of the endocannabinoids, has been implicated in both metabolic/physiological roles of the central nervous system, making it an attractive medicinal target. As such, we report the first solid-phase methodology that expedites access to various anandamide analogues. Our synthesis features a repetitive Cu-mediated coupling reaction between terminal alkynes and propargyl halides or allylic halides.",

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T1 - Solid-phase synthesis of anandamide analogues

AU - Qi, Longwu

AU - Meijler, Michael M.

AU - Lee, Sang Hyeup

AU - Sun, Chengzao

AU - Janda, Kim D.

PY - 2004/5/13

Y1 - 2004/5/13

N2 - The endocannabinoids are amides and esters of arachidonic acid that can mimic the pharmacological properties of Δ9-tetrahydrocannabinol (Δ9-THC). Anandamide, the most prominent of the endocannabinoids, has been implicated in both metabolic/physiological roles of the central nervous system, making it an attractive medicinal target. As such, we report the first solid-phase methodology that expedites access to various anandamide analogues. Our synthesis features a repetitive Cu-mediated coupling reaction between terminal alkynes and propargyl halides or allylic halides.

AB - The endocannabinoids are amides and esters of arachidonic acid that can mimic the pharmacological properties of Δ9-tetrahydrocannabinol (Δ9-THC). Anandamide, the most prominent of the endocannabinoids, has been implicated in both metabolic/physiological roles of the central nervous system, making it an attractive medicinal target. As such, we report the first solid-phase methodology that expedites access to various anandamide analogues. Our synthesis features a repetitive Cu-mediated coupling reaction between terminal alkynes and propargyl halides or allylic halides.

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VL - 6

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JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Solid-phase synthesis of anandamide analogues

Abstract

ASJC Scopus subject areas

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