4-(β-hydroxyethylthio)azetidin-2-one | 73845-13-3

• 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-(β-hydroxyethylthio)azetidin-2-one
• 英文别名: 4-(2-hydroxyethylthio)-2-oxoazetidine；4-(2-hydroxyethylthio)azetidin-2-one；4-[(2-Hydroxyethyl)sulfanyl]azetidin-2-one；4-(2-hydroxyethylsulfanyl)azetidin-2-one
• CAS: 73845-13-3
• 化学式: C₅H₉NO₂S
• mdl: MFCD19217945
• 分子量: 147.198
• InChiKey: ZDORRTORSGJIIM-UHFFFAOYSA-N

物化性质

• 沸点：
  446.4±35.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-(β-hydroxyethylthio)azetidin-2-one 在 三氟化硼乙醚 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 3.67h， 生成 2,2-dimethyl-trans-8-(α-hydroxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane
  参考文献：
  名称：

  The penems, a new class of .beta.-lactam antibiotics. 5. Total synthesis of racemic 6-.alpha.-hydroxyethylpenemcarboxylic acids

  摘要：

  DOI：

  10.1021/ja00526a045
• 作为产物：
  描述：

  4-乙酰氧基-2-氮杂环丁酮 、 2-巯基乙醇 以46%的产率得到4-(β-hydroxyethylthio)azetidin-2-one
  参考文献：
  名称：

  Azetidinone derivatives for the treatment of atherosclerosis

  摘要：

  式（I）中的Azetidinone衍生物，其中R.sup.1和R.sup.2，可能相同也可能不同，每个都选择自氢或C.sub.(1-8)烷基；R.sup.3是C.sub.(1-8)烷基或C.sub.(3-8)环烷基，每个都可以选择性地取代；X是连接基团；Y是芳基团；n为0、1或2；不包括苄基（4-甲硫基-2-氧代-氮杂环丙酮-1-基）乙酸酯是Lp PLA2酶的抑制剂，并且在治疗中有用，特别用于治疗动脉粥样硬化。

  公开号：

  US06071899A1

文献信息

• 3-Substituted bicyclic azetidinone derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US04436661A1

  公开（公告）日：1984-03-13

  Subject of the present invention are compounds of the formula ##STR1## which can be used as intermediates, wherein R represents hydrogen or R.sub.a, which represents an organic radical bonded to the ring carbon atom via a carbon atom, each of the radicals R.sub.b and R.sub.c represents hydrogen or an organic radical bonded to the ring carbon atom via a carbon atom, it being possible for the two radicals to be bonded to one another, A represents a lower alkylene radical having 2 or 3 carbon atoms between the two hetero atoms, and n represents 0 or 2, the stereoisomers thereof and mixtures of these stereoisomers and also processes for the manufacture of such compounds of the formula I. From compounds of the formula I it is possible to manufacture 6-R.sub.a -2-penem-4-carboxylic acid compounds having antibiotic properties.

  本发明的主题是化合物的公式为##STR1##，可用作中间体，其中R代表氢或R.sub.a，R.sub.a代表通过碳原子与环碳原子结合的有机基团，每个基团R.sub.b和R.sub.c代表氢或通过碳原子与环碳原子结合的有机基团，两个基团可能相互结合，A代表两个杂原子之间有2或3个碳原子的低烷基基团，n代表0或2，其立体异构体及这些立体异构体的混合物，以及制备该公式I化合物的方法。从公式I的化合物中可以制备具有抗生素性质的6-R.sub.a-2-庚基-4-羧基环己烯酸化合物。
• 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.
• Azetidinone derivatives for the treatment of atherosclerosis
  申请人：SmithKline Beecham p.l.c.

  公开号：US06071899A1

  公开（公告）日：2000-06-06

  Azetidinone derivatives of formula (I) in which R.sup.1 and R.sup.2, which may be the same or different, is each selected from hydrogen or C.sub.(1-8) alkyl; R.sup.3 is C.sub.(1-8) alkyl or C.sub.(3-8) cycloalkyl each of which may be optionally substituted; X is a linker group; Y is an aryl group; and n is 0, 1 or 2; and excluding benzyl (4-methylthio-2-oxo-azetidin-1-yl)acetate are inhibitors of the enzyme Lp PLA2 and are of use in therapy, in particular treating atherosclerosis.

  式（I）中的Azetidinone衍生物，其中R.sup.1和R.sup.2，可能相同也可能不同，每个都选择自氢或C.sub.(1-8)烷基；R.sup.3是C.sub.(1-8)烷基或C.sub.(3-8)环烷基，每个都可以选择性地取代；X是连接基团；Y是芳基团；n为0、1或2；不包括苄基（4-甲硫基-2-氧代-氮杂环丙酮-1-基）乙酸酯是Lp PLA2酶的抑制剂，并且在治疗中有用，特别用于治疗动脉粥样硬化。
• The penems, a new class of .beta.-lactam antibiotics. 5. Total synthesis of racemic 6-.alpha.-hydroxyethylpenemcarboxylic acids
  作者：H. R. Pfaendler、J. Gosteli、R. B. Woodward

  DOI：10.1021/ja00526a045

  日期：1980.3