5-chloro-N-(4-bromobenzyl)pyrazine-2-carboxamide | 1438853-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-chloro-N-(4-bromobenzyl)pyrazine-2-carboxamide
• 英文别名: N-[(4-bromophenyl)methyl]-5-chloro-pyrazine-2-carboxamide；N-[(4-bromophenyl)methyl]-5-chloropyrazine-2-carboxamide
• CAS: 1438853-94-1
• 化学式: C₁₂H₉BrClN₃O
• 分子量: 326.58
• InChiKey: MEHRTHGAJPXSAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-羟基吡嗪-2-羧酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 5-chloro-N-(4-bromobenzyl)pyrazine-2-carboxamide
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of N-substituted 5-chloropyrazine-2-carboxamides

  摘要：

  To develop new potential antimycobacterial drugs, a series of pyrazinamide derivatives was designed, synthesized and tested for their ability to inhibit the growth of selected mycobacterial strains (Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two strains of Mycobacterium avium). This Letter is focused on binuclear pyrazinamide analogues containing the -CONH-CH2-bridge, namely on N-benzyl-5-chloropyrazine-2-carboxamides with various substituents on the phenyl ring and their comparison with some analogously substituted 5-chloro-N-phenylpyrazine-2-carboxamides. Compounds from the N-benzyl series exerted lower antimycobacterial activity against M. tuberculosis H37Rv then corresponding anilides, however comparable with pyrazinamide (12.5-25 mu g/mL). Remarkably, 5-chloro-N-(4-methylbenzyl)pyrazine-2-carboxamide (8, MIC = 3.13 mu g/mL) and 5-chloro-N-(2-chloro-benzyl)pyrazine-2-carboxamide (1, MIC = 6.25 mu g/mL) were active against M. kansasii, which is naturally unsusceptible to PZA. Basic structure-activity relationships are presented. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.04.021

文献信息

• Synthesis and antimycobacterial evaluation of N-substituted 5-chloropyrazine-2-carboxamides
  作者：Barbora Servusová、Jana Vobicková、Pavla Paterová、Vladimír Kubíček、Jiří Kuneš、Martin Doležal、Jan Zitko

  DOI：10.1016/j.bmcl.2013.04.021

  日期：2013.6

  To develop new potential antimycobacterial drugs, a series of pyrazinamide derivatives was designed, synthesized and tested for their ability to inhibit the growth of selected mycobacterial strains (Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two strains of Mycobacterium avium). This Letter is focused on binuclear pyrazinamide analogues containing the -CONH-CH2-bridge, namely on N-benzyl-5-chloropyrazine-2-carboxamides with various substituents on the phenyl ring and their comparison with some analogously substituted 5-chloro-N-phenylpyrazine-2-carboxamides. Compounds from the N-benzyl series exerted lower antimycobacterial activity against M. tuberculosis H37Rv then corresponding anilides, however comparable with pyrazinamide (12.5-25 mu g/mL). Remarkably, 5-chloro-N-(4-methylbenzyl)pyrazine-2-carboxamide (8, MIC = 3.13 mu g/mL) and 5-chloro-N-(2-chloro-benzyl)pyrazine-2-carboxamide (1, MIC = 6.25 mu g/mL) were active against M. kansasii, which is naturally unsusceptible to PZA. Basic structure-activity relationships are presented. (C) 2013 Published by Elsevier Ltd.