{2-[1-ethyl-1-(1-ethyl-1-formyl-propyldisulfanyl)-propyl]-3-methoxy-4-oxo-azetidin-1-yl}-acetic acid ethyl ester | 1350644-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: {2-[1-ethyl-1-(1-ethyl-1-formyl-propyldisulfanyl)-propyl]-3-methoxy-4-oxo-azetidin-1-yl}-acetic acid ethyl ester
• 英文别名: Ethyl 2-[2-[3-(3-formylpentan-3-yldisulfanyl)pentan-3-yl]-3-methoxy-4-oxoazetidin-1-yl]acetate
• CAS: 1350644-66-4
• 化学式: C₁₉H₃₃NO₅S₂
• 分子量: 419.607
• InChiKey: GUYKHEUKZKYPRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {2-[1-ethyl-1-(1-ethyl-1-formyl-propyldisulfanyl)-propyl]-3-methoxy-4-oxo-azetidin-1-yl}-acetic acid ethyl ester 在 盐酸 、 锌 作用下， 以 乙醇 、 水 为溶剂， 以70%的产率得到[2-(1-ethyl-1-mercapto-propyl)-3-methoxy-4-oxo-azetidin-1-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  C4-Alkylthiols with activity against Moraxella catarrhalis and Mycobacterium tuberculosis

  摘要：

  Antimicrobial resistance represents a global threat to healthcare. The ability to adequately treat infectious diseases is increasingly under siege due to the emergence of drug-resistant microorganisms. New approaches to drug development are especially needed to target organisms that exhibit broad antibiotic resistance due to expression of beta-lactamases which is the most common mechanism by which bacteria become resistant to beta-lactam antibiotics. We designed and synthesized 20 novel monocyclic beta-lactams with alkyl-and aryl-thio moieties at C4, and subsequently tested these for antibacterial activity. These compounds demonstrated intrinsic activity against serine beta-lactamase producing Mycobacterium tuberculosis wild type strain (Mtb) and multiple (n = 6) beta-lactamase producing Moraxella catarrhalis clinical isolates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.030
• 作为产物：
  描述：

  2,2,5,5-tetraethyl-3,4-dithiahexane-1,6-dial 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 84.0h， 生成 {2-[1-ethyl-1-(1-ethyl-1-formyl-propyldisulfanyl)-propyl]-3-methoxy-4-oxo-azetidin-1-yl}-acetic acid ethyl ester
  参考文献：
  名称：

  C4-Alkylthiols with activity against Moraxella catarrhalis and Mycobacterium tuberculosis

  摘要：

  Antimicrobial resistance represents a global threat to healthcare. The ability to adequately treat infectious diseases is increasingly under siege due to the emergence of drug-resistant microorganisms. New approaches to drug development are especially needed to target organisms that exhibit broad antibiotic resistance due to expression of beta-lactamases which is the most common mechanism by which bacteria become resistant to beta-lactam antibiotics. We designed and synthesized 20 novel monocyclic beta-lactams with alkyl-and aryl-thio moieties at C4, and subsequently tested these for antibacterial activity. These compounds demonstrated intrinsic activity against serine beta-lactamase producing Mycobacterium tuberculosis wild type strain (Mtb) and multiple (n = 6) beta-lactamase producing Moraxella catarrhalis clinical isolates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.030