1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists
Duen Ren Hou, Safiul Alam, Ting Chun Kuan, Mani Ramanathan, Tsung Pang Lin, Ming Shiu Hung
This letter reports the new entry of novel 1,2,3-triazole derivatives as CB1 receptor antagonists. The design, synthesis and biological evaluation of N1 and N2 substituted 1,2,3-trizoles are described. The N2 substituted, symmetrical 1,2,3-triazoles are more potent ligands than the unsymmetrical analogues. The in vitro activity of these triazoles is further improved by inserting a methylene group between the central core and the carbonyl side chain. The most potent antagonists prepared in this series (IC50 < 20 nM) are the triazoles containing benzyl amides. These triazoles also show excellent selectivity between CB1 and CB2 receptors (IC50 > 10 μM for CB2; CB2/CB1 > 1000).
Bioorganic and Medicinal Chemistry Letters
https://doi.org/10.1016/j.bmcl.2008.11.029
Published - 1 Feb 2009
Cannabinoid
Triazole
10.1016/j.bmcl.2008.11.029
Dive into the research topics of '1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists'. Together they form a unique fingerprint.
Cannabinoid 1 Receptor Antagonist Chemical Compounds 100%
Cannabinoid Receptor Antagonists Medicine & Life Sciences 81%
Triazoles Medicine & Life Sciences 77%
1,2,3-triazole Chemical Compounds 67%
Methylene Group Chemical Compounds 30%
Antagonist Chemical Compounds 26%
Cannabinoid Receptor CB1 Medicine & Life Sciences 24%
Inhibitory Concentration 50 Medicine & Life Sciences 17%
Hou, D. R., Alam, S., Kuan, T. C., Ramanathan, M., Lin, T. P., & Hung, M. S. (2009). 1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists. Bioorganic and Medicinal Chemistry Letters, 19(3), 1022-1025. https://doi.org/10.1016/j.bmcl.2008.11.029
Hou, Duen Ren ; Alam, Safiul ; Kuan, Ting Chun ; Ramanathan, Mani ; Lin, Tsung Pang ; Hung, Ming Shiu. / 1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists. In: Bioorganic and Medicinal Chemistry Letters. 2009 ; Vol. 19, No. 3. pp. 1022-1025.
@article{1f7056f194074247a360d31761b443b1,
title = "1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists",
abstract = "This letter reports the new entry of novel 1,2,3-triazole derivatives as CB1 receptor antagonists. The design, synthesis and biological evaluation of N1 and N2 substituted 1,2,3-trizoles are described. The N2 substituted, symmetrical 1,2,3-triazoles are more potent ligands than the unsymmetrical analogues. The in vitro activity of these triazoles is further improved by inserting a methylene group between the central core and the carbonyl side chain. The most potent antagonists prepared in this series (IC50 < 20 nM) are the triazoles containing benzyl amides. These triazoles also show excellent selectivity between CB1 and CB2 receptors (IC50 > 10 μM for CB2; CB2/CB1 > 1000).",
keywords = "Cannabinoid, Obesity, Triazole",
author = "Hou, {Duen Ren} and Safiul Alam and Kuan, {Ting Chun} and Mani Ramanathan and Lin, {Tsung Pang} and Hung, {Ming Shiu}",
note = "Funding Information: This research was supported by the National Science Council (NSC 95-2323-B-007-005, NSC 96-2323-B-007-001 and NSC 95-2133-M-008-007-MY3), and National Health Research Institutes (NHRI), Taiwan, ROC. We are grateful to Ms. Ping-Yu Lin at the Institute of Chemistry, Academia Sinica, Ms. Wen-Chi Hsiao at NHRI, and Valuable Instrument Center in National Central University for obtaining mass analysis. ",
doi = "10.1016/j.bmcl.2008.11.029",
journal = "Bioorganic and Medicinal Chemistry Letters",
Hou, DR, Alam, S, Kuan, TC, Ramanathan, M, Lin, TP & Hung, MS 2009, '1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists', Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 3, pp. 1022-1025. https://doi.org/10.1016/j.bmcl.2008.11.029
1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists. / Hou, Duen Ren; Alam, Safiul; Kuan, Ting Chun; Ramanathan, Mani; Lin, Tsung Pang; Hung, Ming Shiu.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 3, 01.02.2009, p. 1022-1025.
T1 - 1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists
AU - Hou, Duen Ren
AU - Alam, Safiul
AU - Kuan, Ting Chun
AU - Ramanathan, Mani
AU - Lin, Tsung Pang
AU - Hung, Ming Shiu
N1 - Funding Information: This research was supported by the National Science Council (NSC 95-2323-B-007-005, NSC 96-2323-B-007-001 and NSC 95-2133-M-008-007-MY3), and National Health Research Institutes (NHRI), Taiwan, ROC. We are grateful to Ms. Ping-Yu Lin at the Institute of Chemistry, Academia Sinica, Ms. Wen-Chi Hsiao at NHRI, and Valuable Instrument Center in National Central University for obtaining mass analysis.
N2 - This letter reports the new entry of novel 1,2,3-triazole derivatives as CB1 receptor antagonists. The design, synthesis and biological evaluation of N1 and N2 substituted 1,2,3-trizoles are described. The N2 substituted, symmetrical 1,2,3-triazoles are more potent ligands than the unsymmetrical analogues. The in vitro activity of these triazoles is further improved by inserting a methylene group between the central core and the carbonyl side chain. The most potent antagonists prepared in this series (IC50 < 20 nM) are the triazoles containing benzyl amides. These triazoles also show excellent selectivity between CB1 and CB2 receptors (IC50 > 10 μM for CB2; CB2/CB1 > 1000).
AB - This letter reports the new entry of novel 1,2,3-triazole derivatives as CB1 receptor antagonists. The design, synthesis and biological evaluation of N1 and N2 substituted 1,2,3-trizoles are described. The N2 substituted, symmetrical 1,2,3-triazoles are more potent ligands than the unsymmetrical analogues. The in vitro activity of these triazoles is further improved by inserting a methylene group between the central core and the carbonyl side chain. The most potent antagonists prepared in this series (IC50 < 20 nM) are the triazoles containing benzyl amides. These triazoles also show excellent selectivity between CB1 and CB2 receptors (IC50 > 10 μM for CB2; CB2/CB1 > 1000).
KW - Cannabinoid
KW - Obesity
KW - Triazole
U2 - 10.1016/j.bmcl.2008.11.029
DO - 10.1016/j.bmcl.2008.11.029
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
Hou DR, Alam S, Kuan TC, Ramanathan M, Lin TP, Hung MS. 1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists. Bioorganic and Medicinal Chemistry Letters. 2009 Feb 1;19(3):1022-1025. https://doi.org/10.1016/j.bmcl.2008.11.029