2-Methoxyimino-2-(thien-2-yl)acetic acid | 79227-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-Methoxyimino-2-(thien-2-yl)acetic acid
• 英文别名: 2-methoxyimino-2-thiophen-2-ylacetic acid
• CAS: 79227-04-6
• 化学式: C₇H₇NO₃S
• 分子量: 185.203
• InChiKey: QAYOLNPUTNADNO-UHFFFAOYSA-N

物化性质

• 沸点：
  319.9±34.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Methoxyimino-2-(thien-2-yl)acetic acid 在 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 [[(2E)-2-methoxyimino-2-thiophen-2-ylacetyl]amino]methylphosphonic acid
  参考文献：
  名称：

  Thiophenyl oxime-derived phosphonates as nano-molar class C beta-lactamase inhibitors reducing MIC of imipenem against Pseudomonas aeruginosa and Acinetobacter baumannii

  摘要：

  The preparation and characterization of a series of thiophenyl oxime phosphonate beta-lactamase inhibitors is described. A number of these analogs were potent and selective inhibitors of class C beta-lactamases from Pseudomonas aeruginosa and Enterobacter cloacae. Compounds 3b and 7 reduced the MIC of imipenem against an AmpC expressing strain of imipenem-resistant P. aeruginosa. A number of the title compounds retained micromolar potency against the class D OXA-40 beta-lactamase from Acinetobacter baumannii and at high concentrations compound 3b was shown to reduce the MIC of imipenem against a highly imipenem-resistant strain of A. baumanii expressing the OXA-40 beta-lactamase. In mice compound 3b exhibited phamacokinetics similar to imipenem. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.122
• 作为产物：
  描述：

  2-噻酚乙酯乙酸乙酯 在 吡啶 、 盐酸羟胺 、 水 、 caesium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Methoxyimino-2-(thien-2-yl)acetic acid
  参考文献：
  名称：

  Thiophenyl oxime-derived phosphonates as nano-molar class C beta-lactamase inhibitors reducing MIC of imipenem against Pseudomonas aeruginosa and Acinetobacter baumannii

  摘要：

  The preparation and characterization of a series of thiophenyl oxime phosphonate beta-lactamase inhibitors is described. A number of these analogs were potent and selective inhibitors of class C beta-lactamases from Pseudomonas aeruginosa and Enterobacter cloacae. Compounds 3b and 7 reduced the MIC of imipenem against an AmpC expressing strain of imipenem-resistant P. aeruginosa. A number of the title compounds retained micromolar potency against the class D OXA-40 beta-lactamase from Acinetobacter baumannii and at high concentrations compound 3b was shown to reduce the MIC of imipenem against a highly imipenem-resistant strain of A. baumanii expressing the OXA-40 beta-lactamase. In mice compound 3b exhibited phamacokinetics similar to imipenem. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.122

文献信息

• .alpha.-(Etherified oximino) carboxylic acids and acid chlorides
  申请人：Glaxo Laboratories Limited

  公开号：US04017515A1

  公开（公告）日：1977-04-12

  .alpha.-(Etherified oximino)carboxylic acids, represented by the formula:- ##STR1## where R is hydrogen or an organic group having 1-20 carbon atoms and R.sup.a is an etherifying monovalent organic group having 1-16 carbon atoms linked to the oxygen atom through a carbon atom, and the corresponding acid chlorides, are useful intermediates in the preparation of highly active, highly .beta.-lactamase-stable 7.beta.-[.alpha.-(etherified oximino)acylamido]-ceph-3-em-4-carboxylic acid antibiotics. The compounds are syn isomers or exist as mixtures of syn and anti isomers containing at least 75% of the syn isomer.

  .alpha.-(醚化氧肟基)羧酸，化学式表示为：##STR1## 其中R表示氢或具有1-20个碳原子的有机基团，R.sup.a是具有1-16个碳原子的醚化一价有机基团，通过碳原子连接到氧原子，相应的酸氯化物是制备高活性、高β-内酰胺酶稳定性7.β-[.alpha.-(醚化氧肟基)酰胺基]-头孢-3-酰基-4-羧酸类抗生素的有用中间体。这些化合物是syn异构体或存在至少75％syn异构体的syn和anti异构体混合物。