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Structural modifications of the cannabinoid side chain towards C3-aryl and 1',1'-cycloalkyl-1'-cyano cannabinoids.
Bioorg Med Chem Lett. 2006 Mar 15; 16(6):1616-20.BM

Abstract

The compounds reported in this study are Delta(8)-THC analogues in which the C3 five-carbon linear side chain of Delta(8)-THC was replaced with aryl and 1',1'-cycloalkyl substituents. Of the compounds described here analogues 2d (CB(1), K(i)=11.7 nM. CB(2), K(i)=9.39 nM) and 2f (CB(1), K(i)=8.26 nM. CB(2), K(i)=3.86 nM) exhibited enhanced binding affinities for CB(1) and CB(2), exceeding that of Delta(8)-THC. Efficient procedures for the synthesis of these novel cannabinoid analogues are described.

Authors+Show Affiliations

Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation, 48 Vass. Constantinou, Athens 116-35, Greece. dpapah@eie.grNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16387492

Citation

Papahatjis, Demetris P., et al. "Structural Modifications of the Cannabinoid Side Chain Towards C3-aryl and 1',1'-cycloalkyl-1'-cyano Cannabinoids." Bioorganic & Medicinal Chemistry Letters, vol. 16, no. 6, 2006, pp. 1616-20.
Papahatjis DP, Nahmias VR, Andreou T, et al. Structural modifications of the cannabinoid side chain towards C3-aryl and 1',1'-cycloalkyl-1'-cyano cannabinoids. Bioorg Med Chem Lett. 2006;16(6):1616-20.
Papahatjis, D. P., Nahmias, V. R., Andreou, T., Fan, P., & Makriyannis, A. (2006). Structural modifications of the cannabinoid side chain towards C3-aryl and 1',1'-cycloalkyl-1'-cyano cannabinoids. Bioorganic & Medicinal Chemistry Letters, 16(6), 1616-20.
Papahatjis DP, et al. Structural Modifications of the Cannabinoid Side Chain Towards C3-aryl and 1',1'-cycloalkyl-1'-cyano Cannabinoids. Bioorg Med Chem Lett. 2006 Mar 15;16(6):1616-20. PubMed PMID: 16387492.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structural modifications of the cannabinoid side chain towards C3-aryl and 1',1'-cycloalkyl-1'-cyano cannabinoids. AU - Papahatjis,Demetris P, AU - Nahmias,Victoria R, AU - Andreou,Thanos, AU - Fan,Pusheng, AU - Makriyannis,Alexandros, Y1 - 2006/01/04/ PY - 2005/09/09/received PY - 2005/11/29/revised PY - 2005/12/07/accepted PY - 2006/1/3/pubmed PY - 2006/4/18/medline PY - 2006/1/3/entrez SP - 1616 EP - 20 JF - Bioorganic & medicinal chemistry letters JO - Bioorg Med Chem Lett VL - 16 IS - 6 N2 - The compounds reported in this study are Delta(8)-THC analogues in which the C3 five-carbon linear side chain of Delta(8)-THC was replaced with aryl and 1',1'-cycloalkyl substituents. Of the compounds described here analogues 2d (CB(1), K(i)=11.7 nM. CB(2), K(i)=9.39 nM) and 2f (CB(1), K(i)=8.26 nM. CB(2), K(i)=3.86 nM) exhibited enhanced binding affinities for CB(1) and CB(2), exceeding that of Delta(8)-THC. Efficient procedures for the synthesis of these novel cannabinoid analogues are described. SN - 0960-894X UR - https://www.unboundmedicine.com/medline/citation/16387492/Structural_modifications_of_the_cannabinoid_side_chain_towards_C3_aryl_and_1'1'_cycloalkyl_1'_cyano_cannabinoids_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-894X(05)01594-5 DB - PRIME DP - Unbound Medicine ER -