Home LiteratureArticle Details

PMID: 11741470 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't

Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors.

Journal of medicinal chemistry ·Vol. 44 ·No. 26 ·2001-12-20 ·Pages 4505-8

López-Rodríguez ML, Viso A, Ortega-Gutiérrez S, Lastres-Becker I, González S, Fernández-Ruiz J, Ramos JA

Abstract

In the present work, we have designed and synthesized a series of arachidonic acid derivatives of general structure I which have been characterized as highly potent and selective inhibitors of anandamide transporter (IC(50) = 24-0.8 microM, K(i) > 1000-5000 nM for CB(1) and CB(2) cannabinoid receptors and vanilloid VR(1) receptor). Among them, N-(3-furylmethyl)eicosa-5,8,11,14-tetraenamide deserves special attention as being the most potent endocannabinoid transporter inhibitor (IC(50) = 0.8 microM) described to date.

MeSH Terms

Animals Arachidonic Acids/chemical synthesis,chemistry,metabolism,pharmacology Cannabinoid Receptor Modulators Cannabinoids/metabolism Carrier Proteins/antagonists & inhibitors,metabolism Cell Line Cerebellum/metabolism Drug Design Endocannabinoids Furans/chemical synthesis,chemistry,pharmacology Humans In Vitro Techniques Membranes Polyunsaturated Alkamides Radioligand Assay Receptors, Cannabinoid Receptors, Drug/metabolism Spinal Cord/metabolism Structure-Activity Relationship

Chemicals

Arachidonic Acids Cannabinoid Receptor Modulators Cannabinoids Carrier Proteins Endocannabinoids Furans N-(3-furylmethyl)eicosa-5,8,11,14-tetraenamide Polyunsaturated Alkamides Receptors, Cannabinoid Receptors, Drug anandamide

Authors & Affiliations

7 authors, click to expand affiliations / ORCID

López-Rodríguez M L

Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain. [email protected]

Viso A

Ortega-Gutiérrez S

Lastres-Becker I

González S

Fernández-Ruiz J

Ramos J A

Article Info

Journal

Journal of medicinal chemistry

Abbr.

J Med Chem

ISSN

0022-2623

DOI

10.1021/jm015545y

[email protected]

Published

2001-12-20

Pages

4505-8

Language

English

Region

United States

NLM ID

9716531

Subset

External Links

PubMed source DOI: 10.1021/jm015545y View journal details

Analysis Services

Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors.

Contact

WeChat Official Account