莫西沙星去羧基类似物 | 1322062-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 莫西沙星去羧基类似物
• 英文名称: moxifloxacin
• 英文别名: Decarboxy Moxifloxacin；7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinolin-4-one
• CAS: 1322062-57-6
• 化学式: C₂₀H₂₄FN₃O₂
• 分子量: 357.428
• InChiKey: OULQTEYVKYNDBD-BLLLJJGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 储存条件：
  2-8°C

制备方法与用途

Decarboxy Moxifloxacin（化合物8）是莫西沙星的一种脱羧衍生物。Moxifloxacin 是一种口服有效的喹诺酮类抗菌药物，主要用于治疗急性细菌性鼻窦炎、慢性支气管炎的急性细菌性加重以及感染性肺炎。

反应信息

• 作为产物：
  描述：

  莫西沙星 在 sodium cyanide 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 以99%的产率得到莫西沙星去羧基类似物
  参考文献：
  名称：

  Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones

  摘要：

  Novel fluoroquinolone derivatives substituted with a 2-thioalkyl moiety, with and without a concomitant 3-carboxylate group, were synthesized to evaluate the effect of C-2 thioalkyl substituents on gyrase binding and inhibition. The presence of a 2-thioalkyl group universally decreased activity as compared to parent fluoroquinolones. However, with derivatives of moxifloxacin the presence of either a 2-thioalkyl group or a 3-carboxylate moiety increased activity over the 2,3-unsubstituted derivative. Energy minimization of structures provides an explanation for relative activities of fluoroquinolones having a C-2 thio moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.112

文献信息

• Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones
  作者：Kevin R. Marks、Muhammad Malik、Arkady Mustaev、Hiroshi Hiasa、Karl Drlica、Robert J. Kerns

  DOI：10.1016/j.bmcl.2011.05.112

  日期：2011.8

  Novel fluoroquinolone derivatives substituted with a 2-thioalkyl moiety, with and without a concomitant 3-carboxylate group, were synthesized to evaluate the effect of C-2 thioalkyl substituents on gyrase binding and inhibition. The presence of a 2-thioalkyl group universally decreased activity as compared to parent fluoroquinolones. However, with derivatives of moxifloxacin the presence of either a 2-thioalkyl group or a 3-carboxylate moiety increased activity over the 2,3-unsubstituted derivative. Energy minimization of structures provides an explanation for relative activities of fluoroquinolones having a C-2 thio moiety. (C) 2011 Elsevier Ltd. All rights reserved.