4-((p-Aminophenyl)thio)azetidin-2-one | 129287-21-4

• 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: 4-((p-Aminophenyl)thio)azetidin-2-one
• 英文别名: 4-(4-aminophenylthio)azetidin-2-one；4-(4-Aminophenyl)sulfanylazetidin-2-one
• CAS: 129287-21-4
• 化学式: C₉H₁₀N₂OS
• 分子量: 194.257
• InChiKey: JEBJEIPJXWATLG-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C(Solvent: Ethyl acetate)
• 沸点：
  501.6±40.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((p-Aminophenyl)thio)azetidin-2-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 、 Potassium p-aminothiophenolate
  参考文献：
  名称：

  Base-catalyzed elimination of para-substituted thiophenoxides from 4-(arylthio)azetidin-2-ones

  摘要：

  DOI：

  10.1021/jo00308a027
• 作为产物：
  描述：

  4-乙酰氧基-2-氮杂环丁酮 、 4-氨基苯硫酚 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以51%的产率得到4-((p-Aminophenyl)thio)azetidin-2-one
  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

文献信息

• GU, HUIZHONG;FEDOR, LEO R. (JR), J. ORG. CHEM., 55,(1990) N1, C. 5655-5657
  作者：GU, HUIZHONG、FEDOR, LEO R. (JR)

  DOI：——

  日期：——
• Base-catalyzed elimination of para-substituted thiophenoxides from 4-(arylthio)azetidin-2-ones
  作者：Huizhong Gu、Leo R. Fedor

  DOI：10.1021/jo00308a027

  日期：1990.10
• C4-Alkylthiols with activity against Moraxella catarrhalis and Mycobacterium tuberculosis
  作者：Maya B. Kostova、Carey J. Myers、Tim N. Beck、Balbina J. Plotkin、Jacalyn M. Green、Helena I.M. Boshoff、Clifton E. Barry、Jeffrey R. Deschamps、Monika I. Konaklieva

  DOI：10.1016/j.bmc.2011.09.030

  日期：2011.11

  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.