An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[ 3,2-c]pyridine-3-carbonitriles
An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[ 3,2-c]pyridine-3-carbonitriles
复制标题
DOI：
10.1016/j.bmcl.2007.09.095
复制
发表时间：
2007-12-01
影响因子：
2.7
通讯作者：
Sriram, Dharmarajan
中科院分区：
文献类型：
--
作者：
Kumar, Raju Ranjith;Perumal, Subbu;Sriram, Dharmarajan
本文报道了一种原子效率高的绿色反应路线，在无溶剂条件下，由1-甲基-3，5-双[（E）-芳基亚甲基]四氢-4（1H）-吡啶酮与丙二腈反应，以定量的产率合成了15个2-氨基-6-甲基-4-芳基-8-[（E）-芳基亚甲基]-5，6，7，8-四氢-4H-吡喃并[3，2-c]吡啶-3-腈。使用琼脂稀释法测试化合物对结核分枝杆菌H37 Rv（MTB）、多药耐药结核（MDR-TB）和耻垢分枝杆菌的体外活性。发现2-氨基-4-[4-（二甲氨基）苯基]-8-（E）-[4（二甲氨基）苯基]亚甲基-6-甲基-5，6，7，8-四氢-4H-吡喃并[3，2-c]-吡啶-3-腈是抗MTB和MDR-TB最有效的化合物（MIC：0.43 μ M），比标准异烟肼抗MDRTB的活性高100倍。(c)2007爱思唯尔有限公司保留所有权利。
An atom efficient, green protocol for the synthesis of fifteen 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro4H-pyrano[3,2-c] pyridine-3-carbonitriles in quantitative yields from the reaction of 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones with malononitrile in presence of solid sodium ethoxide under solvent-free condition is described. The compounds were tested for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant tuberculosis (MDR-TB), and Mycobacterium smegmatis using agar dilution method. 2-Amino-4-[4-(dimethylamino) phenyl]-8-(E)-[4(dimethylamino) phenyl] methylidene-6-methyl-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]-pyridine-3-carbonitrile was found to be the most potent compound (MIC: 0.43 mu M) against MTB and MDR-TB, being 100 times more active than standard, isoniazid against MDRTB. (c) 2007 Elsevier Ltd. All rights reserved.