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Investigations on the 4-quinolone-3-carboxylic acid motif. 4. Identification of new potent and selective ligands for the cannabinoid type 2 receptor with diverse substitution patterns and antihyperalgesic effects in mice.
J Med Chem. 2011 Aug 11; 54(15):5444-53.JM

Abstract

Experimental evidence suggests that selective CB2 receptor modulators may provide access to antihyperalgesic agents devoid of psychotropic effects. Taking advantage of previous findings on structure-activity/selectivity relationships for a class of 4-quinolone-3-carboxamides, further structural modifications of the heterocyclic scaffold were explored, leading to the discovery of the 8-methoxy derivative 4a endowed with the highest affinity and selectivity ever reported for a CB2 ligand. The compound, evaluated in vivo in the formalin test, behaved as an inverse agonist by reducing at a dose of 6 mg/kg the second phase of the formalin-induced nocifensive response in mice.

Authors+Show Affiliations

Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Siena, Italy.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

21702498

Citation

Pasquini, Serena, et al. "Investigations On the 4-quinolone-3-carboxylic Acid Motif. 4. Identification of New Potent and Selective Ligands for the Cannabinoid Type 2 Receptor With Diverse Substitution Patterns and Antihyperalgesic Effects in Mice." Journal of Medicinal Chemistry, vol. 54, no. 15, 2011, pp. 5444-53.
Pasquini S, De Rosa M, Pedani V, et al. Investigations on the 4-quinolone-3-carboxylic acid motif. 4. Identification of new potent and selective ligands for the cannabinoid type 2 receptor with diverse substitution patterns and antihyperalgesic effects in mice. J Med Chem. 2011;54(15):5444-53.
Pasquini, S., De Rosa, M., Pedani, V., Mugnaini, C., Guida, F., Luongo, L., De Chiaro, M., Maione, S., Dragoni, S., Frosini, M., Ligresti, A., Di Marzo, V., & Corelli, F. (2011). Investigations on the 4-quinolone-3-carboxylic acid motif. 4. Identification of new potent and selective ligands for the cannabinoid type 2 receptor with diverse substitution patterns and antihyperalgesic effects in mice. Journal of Medicinal Chemistry, 54(15), 5444-53. https://doi.org/10.1021/jm200476p
Pasquini S, et al. Investigations On the 4-quinolone-3-carboxylic Acid Motif. 4. Identification of New Potent and Selective Ligands for the Cannabinoid Type 2 Receptor With Diverse Substitution Patterns and Antihyperalgesic Effects in Mice. J Med Chem. 2011 Aug 11;54(15):5444-53. PubMed PMID: 21702498.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Investigations on the 4-quinolone-3-carboxylic acid motif. 4. Identification of new potent and selective ligands for the cannabinoid type 2 receptor with diverse substitution patterns and antihyperalgesic effects in mice. AU - Pasquini,Serena, AU - De Rosa,Maria, AU - Pedani,Valentina, AU - Mugnaini,Claudia, AU - Guida,Francesca, AU - Luongo,Livio, AU - De Chiaro,Maria, AU - Maione,Sabatino, AU - Dragoni,Stefania, AU - Frosini,Maria, AU - Ligresti,Alessia, AU - Di Marzo,Vincenzo, AU - Corelli,Federico, Y1 - 2011/07/06/ PY - 2011/6/28/entrez PY - 2011/6/28/pubmed PY - 2011/10/8/medline SP - 5444 EP - 53 JF - Journal of medicinal chemistry JO - J Med Chem VL - 54 IS - 15 N2 - Experimental evidence suggests that selective CB2 receptor modulators may provide access to antihyperalgesic agents devoid of psychotropic effects. Taking advantage of previous findings on structure-activity/selectivity relationships for a class of 4-quinolone-3-carboxamides, further structural modifications of the heterocyclic scaffold were explored, leading to the discovery of the 8-methoxy derivative 4a endowed with the highest affinity and selectivity ever reported for a CB2 ligand. The compound, evaluated in vivo in the formalin test, behaved as an inverse agonist by reducing at a dose of 6 mg/kg the second phase of the formalin-induced nocifensive response in mice. SN - 1520-4804 UR - https://www.unboundmedicine.com/medline/citation/21702498/Investigations_on_the_4_quinolone_3_carboxylic_acid_motif__4__Identification_of_new_potent_and_selective_ligands_for_the_cannabinoid_type_2_receptor_with_diverse_substitution_patterns_and_antihyperalgesic_effects_in_mice_ L2 - https://doi.org/10.1021/jm200476p DB - PRIME DP - Unbound Medicine ER -