2-Arachidonoylgylcerol: A Possible Endogenous Cannabinoid Receptor Ligand in Brain

Sugiura, Takayuki; Kondo, Sachiko; Sukagawa, Akihiro; Nakane, Shinji; Shinoda, Akira; Itoh, Kohji; Yamashita, Atsushi; Waku, Keizo

doi:10.1006/bbrc.1995.2437

Cited by 1,995 publications

(1,042 citation statements)

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“…The two main endocannabinoids, N-arachidonoylethanolamine (anandamide, AEA, 1) [1] and 2-arachidonoylglycerol (2-AG, 2) [2,3], bind to and activate both cannabinoid receptors, CB 1 [4,5] and CB 2 [6], that bind also exogenous cannabinoids like D 9 -tetrahydrocannabinol (D 9 -THC, 3) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors

Minkkilä

Myllymäki

Saario

et al. 2009

European Journal of Medicinal Chemistry

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Section: Introductionmentioning

confidence: 99%

The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors

Minkkilä

Myllymäki

Saario

et al. 2009

European Journal of Medicinal Chemistry

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“…The endocannabinoid system contains two major endogenous agonists, N-arachidonoylethanolamide (AEA) [1] and 2-arachidonoylglycerol (2-AG) [2,3]. These compounds, also called endocannabinoids, activate cannabinoid receptors CB1 and CB2.…”

Section: Introductionmentioning

confidence: 99%

Chiral 3-(4,5-dihydrooxazol-2-yl)phenyl alkylcarbamates as novel FAAH inhibitors: Insight into FAAH enantioselectivity by molecular docking and interaction fields

Myllymäki¹,

Käsnänen

Kataja³

et al. 2009

European Journal of Medicinal Chemistry

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Fatty acid amide hydrolase (FAAH) and monoglyceride lipase (MGL) are the main enzymes responsible for the hydrolysis of endogenous cannabinoids N-arachidonoylethanolamide (AEA) and 2-arachidonoylglycerol (2-AG), respectively. Phenyl alkylcarbamates are FAAH inhibitors with anxiolytic and analgesic activities in vivo. Herein we present for the first time the synthesis and biological evaluation of a series of chiral 3-(2-oxazoline)-phenyl N-alkylcarbamates as FAAH inhibitors. Furthermore, the structural background of chirality on the FAAH inhibition is explored by analyzing the protein-ligand interactions. Remarkably, 10-fold difference in potency was observed for (R)-and (S)-derivatives of 3-(5-methyl-4,5-dihydrooxazol-2-yl)phenyl cyclohexylcarbamate (6a vs. 6b). Molecular modelling indicated an important interaction between the oxazoline nitrogen and FAAH active site.

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“…Metabolism of anandamide happens rapidly by fatty acid amide hydrolase (FAAH) 31, 43. 2‐AG was discovered shortly after anandamide in 1995 44, 45. It is synthesized by the enzyme diacylglycerol lipase from arachidonic acid‐containing diacylglycerol and metabolized by soluble monoacylglycerol lipase 31, 46.…”

Section: The Endocannabinoid Systemmentioning

confidence: 99%

Cannabinoids, the Heart of the Matter

Alfulaij

Meiners

Michalek

et al. 2018

JAHA

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2-Arachidonoylgylcerol: A Possible Endogenous Cannabinoid Receptor Ligand in Brain

Cited by 1,995 publications

References 0 publications

The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors

The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors

Chiral 3-(4,5-dihydrooxazol-2-yl)phenyl alkylcarbamates as novel FAAH inhibitors: Insight into FAAH enantioselectivity by molecular docking and interaction fields

Cannabinoids, the Heart of the Matter

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