4-(4-hydroxyphenylthio)-azetidin-2-one | 1350644-74-4

• 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-(4-hydroxyphenylthio)-azetidin-2-one
• 英文别名: 4-(4-Hydroxyphenyl)sulfanylazetidin-2-one
• CAS: 1350644-74-4
• 化学式: C₉H₉NO₂S
• 分子量: 195.242
• InChiKey: XLQZJQOPSGDIKI-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxyphenylthio)-azetidin-2-one 、 四丁基硫酸氢铵 在 三氧化硫 N,N-二甲基甲酰胺络合物 、 potassium phosphate 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 2.0h， 以50%的产率得到2-(4-hydroxyphenylthio)-4-oxo-azetidine-1-sulfonic acid tetra-n-butylammonium salt
  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：

  4-乙酰氧基-2-氮杂环丁酮 、 4-羟基苯硫酚 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以66%的产率得到4-(4-hydroxyphenylthio)-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

• 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.