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  CB1 and CB2 cannabinoid ligands
 

Cannabinoid CB1 and CB2 receptors are part of an important signalling system, the endocannabinoid system. They are involved in the modulation of different functions such as appetite, pain, immune response, cognition and others. Due to the interest generated by CB1 and CB2 receptors as therapeutic targets, different synthetic compounds belonging to different chemical families which could act as agonists or antagonists are currently investigated.

The chemical structures with cannbinoid properties are diverse and include the natural phytocannbinoids, the endogenous ligands derived from fatty acid amides and a great variety of heterocyclic compounds.

In this project we deal with the design, synthesis and optimization of novel cannabinoid ligands to be studied in obesity, analgesia, and neuroprotection.
 
CB1 and CB2 cannabinoid ligads
 

References:

 

- Hernandez-Folgado, L.; Cumella, J.M.; Morales, P.; Alkorta, I.; Elguero, J.; Jagerovic, N.
“Tautomerism of hydroxychromenopyrazoles”  
J. Mol. Struct. 2012, 1015, 162-165.

 

- Cumella, J.; Hernandez-Folgado, L.; Giron, R.; Sanchez, E.; Morales, P.; Hurst, D.P.; Gomez-Cañas, M.; Gomez-Ruiz, M.; Pinto, D.C.G.A.; Goya, P.; Reggio, P.H.; Martin, M.I.; Fernandez-Ruiz, J.; Silva, A.M.S.; Jagerovic N.
“Chromenopyrazoles: non-psychoactive and selective CB1 cannabinoid agonists with peripheral antinociceptive properties”  
ChemMedChem 2012, 7(3), 452-463.

 

- Oliva, C.G.; Jagerovic, N.; Goya, P.; Alkorta, I.; Elguero, J.; Cuberes, Rosa; Dordal, Alberto
“N-Substituted-1,2,3-triazoles: synthesis, characterization and evaluation as cannabinoid ligands”
ARKIVOC (2010), 2, 127-147.

 

- Jagerovic, N., Fernández-Fernández, C., Goya, P.

CB1 Cannabinoid antagonists: structure-activity relationships and potential therapeutic applications
Curr. Top. Med. Chem. 2008, 8, 205-230


- Pavón, F. J., Serrano, A., Pérez-Valero, V., Jagerovic, N., Hernández-Folgado, L., Macías, M., Goya, P., Rodríguez de Fonseca, F. J.
Central versus peripheral antagonism of cannabinoid CB1 receptor in obesity: effect of LH-21, a peripherally acting neutral cannabinoid receptor antagonist, in zucker rats
J. Neuroendocrinology 2008, 20 (suppl. 1), 116-123.

 

- Hernandez-Folgado, L., Goya, P., Frigola, J., Cuberes, M. R., Dordal, A., Holenz, J., Jagerovic, N.

Novel derivatives of 3-alkyl-1,5-diaryl-1 H - 1,2,4-triazoles and their pharmacological evaluation as CB1 cannabinoid ligands
Monatsh. Chem. 2008, 139, 1073-1081

 

- Cano, C, Goya, P, Paez, JA, Giron, R, Sanchez, E, Martin, M. I.

Discovery of 1,1-dioxo-1,2,6-thiadiazine 5-carboxamide derivatives as cannabinoid-like molecules with agonist and antagonist activity.

Bioorg. Med. Chem. 2007, 15, 7480-7493.

 

- Silva, V. L. M., Silva, A. M. S., Pinto, D. C .G. A., Jagerovic, N., Callado, L. F., Cavaleiro, J. A. S., Elguero, J.

Synthesis and pharmacological evaluation of chlorinated N-alkyl-3- and -5-(2-hydroxyphenyl)pyrazoles as CB1 cannabinoid ligands
Monatsh. Chem. 2007, 138, 97-811

 

- Pavón, F. J., Bilbao, A., Hernández-Folgado, L.; Cippitelli, A., Jagerovic, N., Abellán, G., Rodríguez-Franco, M. I., Serrano, A., Macias, M., Gómez, R., Navarro, M., Goya, P., Rodríguez de Fonseca, F.
Antiobesity effects of the novel in vivo neutral cannabinoid receptor antagonist 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1H-1,2,4-triazole - LH 21.
Neuropharmacol. 2006, 51, 358-366.

 

- Jagerovic, N., Hernandez-Folgado, L.., Alkorta, I., Goya, P., Martin, M. I., Dannert, M. T., Alsasua, A., Frigola, J., Cuberes, M. R., Dordal, A., Holenz, J.
Structure-activity relationship study on C4-carbon of the CB1 antagonist SR141716: synthesis and pharmacological evaluation of 1,2,4-triazole-3-carboxamides.
Eur. J. Med. Chem. 2006, 41, 114-120.

 

- Campillo, N. E.; Montero, C., Goya, P., Páez, J. A.
Homology models of the cannabinoid CB1 and CB2 receptors. A docking analysis study.
Eur. J. Med. Chem. 2005, 40, 75-83.

 

- Jagerovic, N.; Hernandez-Folgado, L.; Alkorta, I.; Goya, P.; Navarro, M.; Serrano, A.; de Fonseca, F. R., Dannert, M. T.; Alsasua, A.; Suardiaz, M.; Pascual, D.; Martín, M. I.
Discovery of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1H-1,2,4-triazole, a novel in vivo cannabinoid antagonist containing a 1,2,4-triazole motif .
J. Med. Chem. 2004, 47, 2939-2942.

 

Patents:

• Jagerovic N., Morales P., Goya P., Diaz Laviada I., Vara D., Fernández Ruiz J., Gómez-Ruiz M., Gómez-Cañas M.
“Cromenopirazoldionas como derivados cannabinoides de quinonas con actividad antitumoral”
Application number: ES P201231126
(Titular entity: CSIC/Universidad de Alcala/Universidad Cumplutense de Madrid)

 

• Jagerovic, N.; Cumella Montanchez, J.M.; Goya Laza, M.P.; Fernandez Ruiz, J.; Gomez Ruiz, M.; Rodriguez Valsero, P.
“Chromenopyrazole derivatives as cannabinoid receptor ligands and their preparation and use in the treatment of CB receptor-mediated diseases”
Application number: ES200900802, WO2010109050
(Titular entity: CSIC/UCM)

 

• Jagerovic N, Cumella J. M., Goya P., Fernández Ruiz J., Gómez M., Rodríguez P.

"Derivados de cromenopirazoles como ligandos de receptores cannabinoides"

Application number: ES P200900802

(Titular entity: CSIC/UCM)

 

• Páez J. A., Goya P., Cano C., Martín M. I., Girón R., Goicoechea C.

"1,1-Dioxo-1,2,6-thadiazine 2-substituted 5-carboxylate and 5- carboxamide derivatives with cannabinoid properties"

Application number: ES2274729, ES20050002759, WO2006ES70172, WO2007054601

(Titular entity: CSIC/URJC)

 

• Jagerovic N., Gómez-de la Oliva C. A., Goya P., Dordal A., Cuberes M.

"1,2,3-Triazole derivatives as cannabinoid-receptor modulators"

Application number: EP20060380290; EP1921072  

(Titular entity: Lab Dr Esteve S.A.)

 

• Holenz J., Frigola J., Cuberes R., Dordal A., Goya P., Jagerovic N., Hernández-Folgado L., Martin M. I., Alsasua A.
"New 1,2,4-triazole-3-carboxamide derivatives"

Application number: ES2255834; ES200402232; WO2005IB02720; WO2006030285.

(Titular entity: Lab. Dr. Esteve S.A.)

 

• Jagerovic N., Goya P., Hernandez-Folgado L., Alcorta I., Martin M. I., Suardiaz M., Dannert M. T.

"1,2,4-Triazole with cannabinoid properties"

Application number: ES2192494; WO03082833; AU2003215687-A1

(Titular entity: CSIC/UCM)