- Synthesis and structure activity relationship investigation of triazolo[1,5-a]pyrimidines as CB2 cannabinoid receptor inverse agonists
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CB2 cannabinoid receptor ligands are known to be therapeutically important for the treatment of numerous diseases. Recently, we have identified the heteroaryl-4-oxopyridine/7-oxopyrimidine derivatives as highly potent and selective CB2 receptor ligands, showing that the pharmakodynamics of the new compounds was controlled by the nature of the heterocycle core. In this paper we describe the synthesis and biological evaluation of 7-oxo-4-pentyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide derivatives that led to the identification of novel CB2 receptor inverse agonists. Cyclic AMP experiments on CB2 receptors expressed in CHO cells revealed that introduction of structural modifications at position 2 of triazolopyrimidine template changes the functional activity from partial to inverse agonism. The molecular docking analysis of the novel structures is reported.
- Aghazadeh Tabrizi, Mojgan,Baraldi, Pier Giovanni,Ruggiero, Emanuela,Saponaro, Giulia,Baraldi, Stefania,Poli, Giulio,Tuccinardi, Tiziano,Ravani, Annalisa,Vincenzi, Fabrizio,Borea, Pier Andrea,Varani, Katia
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- Efficient regioselective three-component domino synthesis of 3-(1,2,4-Triazol-5-yl)-1,3-thiazolidin-4-ones as potent antifungal and antituberculosis agents
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In research for promising antibacterial and antifungal compounds, a series of 2-aryl 3-[1,2,4]triazol-5-yl 4-thiazolidinones 1 were synthesized by a domino reaction of 5-amino-1H-[1,2,4]triazoles 3, aromatic aldehydes, and α-mercaptoacids in boiling tolue
- El Bialy, Serry A.,Nagy, Maria M.,Abdel-Rahman, Hamdy M.
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p. 821 - 829
(2012/03/08)
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- On Triazoles. XXVIII. Synthesis of Isomeric 1,2,4-Triazolylcarbothiohydrazides
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Different 3a, 3b, 9, 10 and 12 type 5-amino-1,2,4-triazolylcarbothiohydrazide isomers representing all possible isomeric types derived from 5-amino-1,2,4-triazoles were synthesised from the corresponding 5-amino-1,2,4-triazolyldithiocarbonates and hydrazines.HPLC measurements proved that in case of monosubstituted hydrazines the steric press in the intermediate 6 caused besides formation of the expected derivative 3a the formation of compounds 4 and 5, too, while the intermediate 7 yielded only 3b.Thermal rearangement of derivatives 3a in acetic acid led to isomers 9 and 10, respectively.
- Barkoczy, Jozsef,Reiter, Jozsef
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p. 1677 - 1683
(2007/10/02)
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- 5-(1-Piperazinyl)-1H-1,2,4-triazol-3-amines as antihypertensive agents
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A series of 5-(1-piperazinyl)-1H-1,2,4-triazol-3-amines was synthesized and screened for antihypertensive and diuretic activity in spontaneously hypertensive rats (SHR). One compound, 5-[4-[(3-chlorophenyl)methyl]-1-piperazinyl]-1H-1,2,4-triazol-3-amine (8), was selected to define the mechanism of its antihypertensive activity. Studies in SHR suggest ganglionic blocking activity. Short-lived antihypertensive activity was observed in conscious renal hypertensive dogs.
- Meyer,Tomcufcik,Chan,Haug
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p. 593 - 597
(2007/10/02)
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- On Triazoles. V . Synthesis of 1- and 2-R1-3-R2,R3-Amino-5-amino-1,2,4-triazoles
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The correct isomeric and tautomeric structure of different 1- and 2-R1-3-R2,R3-amino-5-amino-1,2,4-triazole derivatives prepared from the corresponding N-cyano-N'-R2,R3-S-methyl-isothioureas and the corresponding hydrazines was proved with the help of their ir, uv, 1H-nmr and 13C-nmr spectra as well as the uv spectra of the Schiff bases of an isomeric pair.
- Reiter, Jozsef,Pongo, Laszlo,Somorai, Tamas,Dvortsak, Peter
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p. 401 - 408
(2007/10/02)
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