Synthesis of Novel Pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine Derivatives: Potent and Selective Adenosine A3 Receptor Antagonists

被引：10

作者：

Banda, Veeraswamy ^{[1
]}

Chandrasekaran, Balakumar ^{[2
,3
]}

Koese, Meryem ^{[4
]}

Vielmuth, Christin ^{[4
]}

Mueller, Christa E. ^{[4
]}

Chavva, Kurumurthy ^{[1
]}

Gautham, Santhosh Kumar ^{[1
]}

Pillalamarri, Sambasivarao ^{[1
]}

Mylavaram, Raghuprasad ^{[5
]}

Akkinepally, Raghuramarao ^{[6
]}

Pamulaparthy, Shanthanrao ^{[1
]}

Banda, Narsaiah ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Fluoroorgan Div, Hyderabad 500007, Andhra Pradesh, India

[2] Panjab Univ, Univ Inst Pharmaceut Sci, Chandigarh 160014, Punjab, India

[3] Panjab Univ, UGC Ctr Adv Study Pharmaceut Sci UGC CAS, Chandigarh 160014, Punjab, India

[4] Univ Bonn, Inst Pharmaceut, PharmaCtr Bonn, Bonn, Germany

[5] Vishnu Coll Pharm, West Godavari, Andhra Pradesh, India

[6] Univ Coll Pharmaceut Sci, Warangal, Andhra Pradesh, India

来源：

ARCHIV DER PHARMAZIE | 2013年 / 346卷 / 10期

关键词：

Adenosine receptors; 2-Aminonicotinonitrile; Aroyl hydrazide; Orthoacetate; Orthoformate; RADIOLIGAND; MEMBRANES; AFFINITY;

D O I：

10.1002/ardp.201300003

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives 5 was prepared from 2-amino-3-cyano-4-trifluoromethyl-6-phenylpyridine 1 in two steps via formation of iminoether 3 followed by reaction with different aroylhydrazides 4. Representative products 5 were evaluated for their affinity towards all four subtypes of human adenosine receptors. Compounds 2-(3-fluorophenyl)-8-phenyl-10-(trifluoromethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (5b), 2-(furan-2-yl)-8-phenyl-10-(trifluoromethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (5d), and 2-(furan-2-yl)-5-methyl-8-phenyl-10-(trifluoromethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (5j) showed high affinity for the A(3) receptors, with K-i values of 8.1, 10.4, and 12.1nM, respectively, and were >1000-fold selective versus all other adenosine receptor subtypes.

引用

页码：699 / 707

页数：9

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