- 2-Amino[1,2,4]triazolo[1,5-c]quinazolines and Derived Novel Heterocycles: Syntheses and Structure–Activity Relationships of Potent Adenosine Receptor Antagonists
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2-Amino[1,2,4]triazolo[1,5-c]quinazolines were identified as potent adenosine receptor (AR) antagonists. Synthetic strategies were devised to gain access to a broad range of derivatives including novel polyheterocyclic compounds. Potent and selective A3AR antagonists were discovered, including 3,5-diphenyl[1,2,4]triazolo[4,3-c]quinazoline (17, Kihuman A3AR 1.16 nm) and 5′-phenyl-1,2-dihydro-3′H-spiro[indole-3,2′-[1,2,4]triazolo[1,5-c]quinazolin]-2-one (20, Kihuman A3AR 6.94 nm). In addition, multitarget antagonists were obtained, such as the dual A1/A3antagonist 2,5-diphenyl[1,2,4]triazolo[1,5-c]quinazoline (13 b, Kihuman A1AR 51.6 nm, human A3AR 11.1 nm), and the balanced pan-AR antagonists 5-(2-thienyl)[1,2,4]triazolo[1,5-c]quinazolin-2-amine (11 c, Kihuman A1AR 131 nm, A2AAR 32.7 nm, A2BAR 150 nm, A3AR 47.5 nm) and 9-bromo-5-phenyl[1,2,4]triazolo[1,5-c]quinazolin-2-amine (11 q, Kihuman A1AR 67.7 nm, A2AAR 13.6 nm, A2BAR 75.0 nm, A3AR 703 nm). In many cases, significantly different affinities for human and rat receptors were observed, which emphasizes the need for caution in extrapolating conclusions between different species.
- Burbiel, Joachim C.,Ghattas, Wadih,Küppers, Petra,K?se, Meryem,Lacher, Svenja,Herzner, Anna-Maria,Kombu, Rajan Subramanian,Akkinepally, Raghuram Rao,Hockemeyer, J?rg,Müller, Christa E.
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p. 2272 - 2286
(2016/10/25)
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- Synthesis and Benzodiazepine Binding Activity of a Series of Novel Triazoloquinazolin-5(6H)-ones
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Investigation of tricyclic heterocycles related to the 2-arylpyrazoloquinolin-3(5H)-ones, structures with high affinity for the benzodiazepine (BZ) receptor, led to the synthesis of 2-phenyl-triazoloquinazolin-5(6H)-one, a compound wi
- Francis, John E.,Cash, William D.,Barbaz, Beverly S.,Bernard, Patrick S.,Lovell, Richard A.,et al.
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p. 281 - 290
(2007/10/02)
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- REACTION OF 4-THIOXO-1,3-BENZOTHIAZINES WITH AMIDRAZONES: SYNTHESIS OF 1,2,4-TRIAZOLOQUINAZOLINE DERIVATIVES
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2-Aryl-4-thioxo-1,3-benzothiazines react with unsubstituted amidrazones to give the corresponding amidinoquinazolinthiones which by action of methyl iodide cyclize to 2,5-diaryl-1,2,4-triazoloquinazolines.Reaction of amidinoquinazolinthiones with h
- Molina, Pedro,Arques, Antonio,Cartagena, Inmaculada,Valcarcel, Maria Victoria
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p. 2357 - 2362
(2007/10/02)
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- Quinazoline Derivatives from 2-Phenyl-4-quinazolinylhydrazine
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Formic acid and acetyl and benzoyl chloride were treated with 2-phenyl-4-quinazolinylhydrazine (1) under mild conditions to afford the corresponding hydrazides which were converted into 5-phenyltriazoloquinazoline, 2-methyl-5-phenyltr
- El-Sherief, Hassan Ahmed,Mahmoud, Abdalla Mohamed,Esmaiel, Ahmed Ahmed
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p. 1138 - 1142
(2007/10/02)
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