isobutyl pyrazinoate | 158905-14-7

• 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: isobutyl pyrazinoate
• 英文别名: 2-Methylpropyl pyrazine-2-carboxylate
• CAS: 158905-14-7
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: USUPZWMFSOZLLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲酸吡嗪 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 isobutyl pyrazinoate
  参考文献：
  名称：

  吡嗪酸酯具有广泛的体外抗分枝杆菌活性。

  摘要：

  已经制备了一系列取代的吡嗪酸酯，并检查了它们对鸟分枝杆菌和堪萨斯分枝杆菌以及结核分枝杆菌的体外活性。吡嗪核和酯官能团的修饰在扩展吡嗪酰胺的活性方面非常成功，从而使其扩展到包括通常不易受吡嗪酰胺影响的鸟鸟分支杆菌和堪萨斯分枝杆菌。这些化合物中的几种具有比吡嗪酰胺更高的抗结核分枝杆菌活性100-1000倍。

  DOI：

  10.1021/jm00020a003

文献信息

• JPH06211811A
  申请人：——

  公开号：JPH06211811A

  公开（公告）日：1994-08-02
• [EN] PYRAZINOIC ACID PRODRUGS ACTIVATED BY ESTERASES OF MYCOBACTERIA<br/>[FR] PROMÉDICAMENTS D'ACIDE PYRAZINOÏQUE ACTIVÉS PAR DES ESTÉRASES DE MYCOBACTÉRIES
  申请人：UNIV LISBOA

  公开号：WO2013084214A2

  公开（公告）日：2013-06-13

  Since pyrazinamide is in fact a prodrug of pyrazinoic acid, other prodrugs of pyrazinoic acid, like esters, could have activity against M. tuberculosis. These compounds should be resistant to the human plasma and liver enzymes, but must be readily hydrolyzed, by mycobacteria, at the site of action. Esters were proposed in the past as prodrugs of pyrazinoic acid. The main advantage of those compounds is that they are not activated by a specific enzyme (pirazinamidase) but by a large array of esterases preventing the onset of resistance by this mechanism. However, these compounds must reach the mycobacteria in the prodrug form otherwise they cannot penetrate the mycobacterial wall and since plasma has also esterases the compounds studied were rapidly hydrolysed. Amide prodrugs are resistant to plasma hydrolysis however the compounds cannot be activated efficiently by mycobacterial esterases and do not present activity. New branched lipophilic esters were synthesized in order to delay their hydrolysis through the human plasma and liver before reaching the target mycobacteria. Their pseudo-first order rate constants for the hydrolysis in human plasma were evaluated as well as their activity against M. tuberculosis H37Ra. Branches in the first alkyl carbon, adjacent to the ester function, unexpectedly increased the stability and maintained the activity. The good stability of these compounds along with their activity against M. tuberculosis were the main achievements of this invention.
• Pyrazinoic Acid Esters with Broad Spectrum in Vitro Antimycobacterial Activity
  作者：Michael H. Cynamon、Rayomand Gimi、Ferenc Gyenes、Cindy A. Sharpe、Kathryn E. Bergmann、Hye Jung Han、Livia B. Gregor、Radha Rapolu、Gregorio Luciano、John T. Welch

  DOI：10.1021/jm00020a003

  日期：1995.9

  A series of substituted pyrazinoic acid esters has been prepared and examined for their in vitro activity against Mycobacterium avium and Mycobacterium kansasii as well as Mycobacterium tuberculosis. Modification of both the pyrazine nucleus and the ester functionality have been very successful in expanding the activity of pyrazinamide to include M. avium and M. kansasii, organisms normally not susceptible

  已经制备了一系列取代的吡嗪酸酯，并检查了它们对鸟分枝杆菌和堪萨斯分枝杆菌以及结核分枝杆菌的体外活性。吡嗪核和酯官能团的修饰在扩展吡嗪酰胺的活性方面非常成功，从而使其扩展到包括通常不易受吡嗪酰胺影响的鸟鸟分支杆菌和堪萨斯分枝杆菌。这些化合物中的几种具有比吡嗪酰胺更高的抗结核分枝杆菌活性100-1000倍。