Tricyclic Pyrazoles. 4. Synthesis and Biological Evaluation of Analogues of the Robust and Selective CB2 Cannabinoid Ligand 1-(2‘,4‘-Dichlorophenyl)-6-methyl-N-piperidin-1-yl- 1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamide
New analogues (2a−p) of the previously reported CB2 ligands 6-methyl- and 6-chloro-1-(2‘,4‘-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) have been synthesized and evaluated for cannabinoid receptor affinity. One example, 1-(2‘,4‘-dichlorophenyl)-6-methyl-N-...
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| Published in | Journal of medicinal chemistry Vol. 49; no. 25; pp. 7502 - 7512 |
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| Main Authors | , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
14.12.2006
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-2623 1520-4804 |
| DOI | 10.1021/jm060920d |
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| Abstract | New analogues (2a−p) of the previously reported CB2 ligands 6-methyl- and 6-chloro-1-(2‘,4‘-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) have been synthesized and evaluated for cannabinoid receptor affinity. One example, 1-(2‘,4‘-dichlorophenyl)-6-methyl-N-cyclohexyilamine-1,4-dihydroindeno[1,2-c] pyrazole-3-carboxamide (2a) was shown to have single digit nanomolar affinity for cannabinoid CB2 receptors. Furthermore, compounds 2a and 2b, as well as lead structures 1a,b, were also shown to be agonist in an in vitro model based on human promyelocytic leukemia HL-60 cells. |
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| AbstractList | New analogues (2a-p) of the previously reported CB2 ligands 6-methyl- and 6-chloro-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) have been synthesized and evaluated for cannabinoid receptor affinity. One example, 1-(2',4'-dichlorophenyl)-6-methyl-N-cyclohexyilamine-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamide (2a) was shown to have single digit nanomolar affinity for cannabinoid CB2 receptors. Furthermore, compounds 2a and 2b, as well as lead structures 1a, b, were also shown to be agonist in an in vitro model based on human promyelocytic leukemia HL-60 cells. New analogues (2a−p) of the previously reported CB2 ligands 6-methyl- and 6-chloro-1-(2‘,4‘-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) have been synthesized and evaluated for cannabinoid receptor affinity. One example, 1-(2‘,4‘-dichlorophenyl)-6-methyl-N-cyclohexyilamine-1,4-dihydroindeno[1,2-c] pyrazole-3-carboxamide (2a) was shown to have single digit nanomolar affinity for cannabinoid CB2 receptors. Furthermore, compounds 2a and 2b, as well as lead structures 1a,b, were also shown to be agonist in an in vitro model based on human promyelocytic leukemia HL-60 cells. New analogues (2a-p) of the previously reported CB(2) ligands 6-methyl- and 6-chloro-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) have been synthesized and evaluated for cannabinoid receptor affinity. One example, 1-(2',4'-dichlorophenyl)-6-methyl-N-cyclohexyilamine-1,4-dihydroindeno[1,2-c] pyrazole-3-carboxamide (2a) was shown to have single digit nanomolar affinity for cannabinoid CB(2) receptors. Furthermore, compounds 2a and 2b, as well as lead structures 1a,b, were also shown to be agonist in an in vitro model based on human promyelocytic leukemia HL-60 cells. |
| Author | Loriga, Giovanni Pinna, Gérard A Lazzari, Paolo Chelucci, Giorgio Falzoi, Matteo Manca, Ilaria Murineddu, Gabriele Sanna, Angela Curzu, Maria M Dessì, Christian Pani, Luca Ruiu, Stefania |
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| Cites_doi | 10.1111/j.1460-9568.2006.04684.x 10.1073/pnas.1834309100 10.1016/j.brainres.2005.11.035 10.1038/sj.bjp.0706406 10.1002/syn.20050 10.1182/blood-2002-01-0098 10.1124/jpet.103.049924 10.1038/sj.ijo.0803272 10.1016/S0306-4522(03)00126-X 10.1016/j.brainres.2005.04.053 10.1093/jb/mvh063 |
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| Keywords | SR 144528 2-ARACHIDONOYLGLYCEROL ACTIVATION ANTAGONIST PHARMACOLOGY INVOLVEMENT INVERSE AGONIST MICROGLIAL CELLS EXPRESSION RECEPTOR CB2 Human Promyelocytic leukemia Ligand CB2 cannabinoid receptor Selectivity Tricyclic compound In vitro HL60 cell line Cell line Structure activity relation Piperidine derivatives Carboxamide Chemical synthesis Tumor cell |
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| SubjectTerms | Biological and medical sciences Chemistry, Medicinal HL-60 Cells Humans Indenes - chemical synthesis Indenes - chemistry Indenes - pharmacology Life Sciences & Biomedicine Ligands Medical sciences Miscellaneous Mitogen-Activated Protein Kinase 1 - biosynthesis Mitogen-Activated Protein Kinase 3 - biosynthesis Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Pharmacology & Pharmacy Pharmacology. Drug treatments Phosphorylation Piperidines - chemical synthesis Piperidines - chemistry Piperidines - pharmacology Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Radioligand Assay Receptor, Cannabinoid, CB2 - agonists Science & Technology Structure-Activity Relationship |
| Title | Tricyclic Pyrazoles. 4. Synthesis and Biological Evaluation of Analogues of the Robust and Selective CB2 Cannabinoid Ligand 1-(2‘,4‘-Dichlorophenyl)-6-methyl-N-piperidin-1-yl- 1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamide |
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