methyl 4-bromo-2-methoxyimino-3-oxobutanoate | 84208-78-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 4-bromo-2-methoxyimino-3-oxobutanoate
• 英文别名: methyl 4-bromo-3-oxo-2-methoxy-iminobutyrate；methyl 4-bromo-2-methoxyimino-3-oxobutyrate；methyl (2Z)-4-bromo-2-methoxyimino-3-oxobutanoate
• CAS: 84208-78-6
• 化学式: C₆H₈BrNO₄
• 分子量: 238.038
• InChiKey: GJHFBYADZNZZED-YVMONPNESA-N

物化性质

• 沸点：
  250.7±42.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-bromo-2-methoxyimino-3-oxobutanoate 在 碳酸氢钠 、 sodium acetate trihydrate 、 硫脲 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (Z)-2-氨基-alpha-(甲氧基亚胺)噻唑-4-乙酸甲酯
  参考文献：
  名称：

  [3-Heterocyclic-7-(2-methoxyimino-2-aminothiazolyl)

  摘要：

  公式为7-[2-(2-氨基噻唑-4-基)-2-(同)-甲氧基亚硝基乙酰氨基]头孢菌素酸衍生物；其中R.sup.1 NH是一个氨基，可以选择性地被保护；COOR.sup.2是一个可以选择性酯化的羧基；X是氧、硫或一个可以选择性替代的亚硝基；B是氢或一个可以选择性替代的羟基、氨基、硫醇或碳氢基团，或其盐，是新颖的、β-内酰胺酶抗性和低毒性的化合物，对包括大肠杆菌、马尔色葡萄球菌、雷氏变形杆菌、肠臭臭肠杆菌、弗伦德氏柠檬杆菌在内的广谱微生物表现出优异的活性。因此，这些化合物可用于治疗用抗菌剂。

  公开号：

  US04197298A1
• 作为产物：
  描述：

  (Z)-2-(甲氧基亚胺)-3-氧代丁酸甲酯 在 碳酸氢钠 、 溴 作用下， 以 氯仿 、 水 为溶剂， 生成 methyl 4-bromo-2-methoxyimino-3-oxobutanoate
  参考文献：
  名称：

  [3-Heterocyclic-7-(2-methoxyimino-2-aminothiazolyl)

  摘要：

  公式为7-[2-(2-氨基噻唑-4-基)-2-(同)-甲氧基亚硝基乙酰氨基]头孢菌素酸衍生物；其中R.sup.1 NH是一个氨基，可以选择性地被保护；COOR.sup.2是一个可以选择性酯化的羧基；X是氧、硫或一个可以选择性替代的亚硝基；B是氢或一个可以选择性替代的羟基、氨基、硫醇或碳氢基团，或其盐，是新颖的、β-内酰胺酶抗性和低毒性的化合物，对包括大肠杆菌、马尔色葡萄球菌、雷氏变形杆菌、肠臭臭肠杆菌、弗伦德氏柠檬杆菌在内的广谱微生物表现出优异的活性。因此，这些化合物可用于治疗用抗菌剂。

  公开号：

  US04197298A1

文献信息

• 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido] cephalosporins
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04278671A1

  公开（公告）日：1981-07-14

  A 7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido] cephalosporin derivative of the formula; ##STR1## wherein R.sub.3 is hydrogen or a residue of a nucleophilic compound; R.sub.2 NH is an amino group which may optionally be protected, pharmaceutically acceptable salt or ester thereof, is found to have excellent anti-bacterial activity against a broad spectrum of bacteria inclusive of gram-negative bacteria such as Escherichia coli, Serratia marcescens, Proteus rettgeri, Enterobacter cloacae and Citrobacter freundii. Thus, this compound may be used for an antibacterial agent in therapeutical purposes.

  一种7-[2-(2-氨基噻唑-4-基)-2-(syn)-甲氧基亚硝基乙酰胺基]头孢菌素衍生物的化学式如下：##STR1##其中R.sub.3为氢或亲核化合物的残基；R.sub.2 NH为可能被保护的氨基团，其药用盐或酯，发现对包括大肠杆菌、马尔色菌、雷特格氏变形杆菌、克雷伯氏菌和弗伦德氏细菌在内的广谱细菌具有出色的抗菌活性。因此，该化合物可用作治疗目的中的抗菌剂。
• [3-Heterocyclic-7-(2-methoxyimino-2-aminothiazolyl)
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04197298A1

  公开（公告）日：1980-04-08

  7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]cephalosporanic acid derivatives of the formula; ##STR1## wherein R.sup.1 NH is an amino group which may optionally be protected; COOR.sup.2 is a carboxyl group which may optionally be esterified; X is oxygen, sulfur or an imino group which may optionally be substituted; B is hydrogen or a hydroxyl, amino, thiol or hydrocarbon group which may optionally be substituted, or a salt thereof, are novel, .beta.-lactamase-resistant and low-toxicity compounds which display excellent activity against a broad spectrum of microorganisms including Gram-negative bacteria such as Escherichia coli, Serratia marcescens, Proteus rettgeri, Enterobacter cloacae, Citrobacter freundii. Thus, these compounds can be used for antibacterial agents in therapeutical purpose.

  公式为7-[2-(2-氨基噻唑-4-基)-2-(同)-甲氧基亚硝基乙酰氨基]头孢菌素酸衍生物；其中R.sup.1 NH是一个氨基，可以选择性地被保护；COOR.sup.2是一个可以选择性酯化的羧基；X是氧、硫或一个可以选择性替代的亚硝基；B是氢或一个可以选择性替代的羟基、氨基、硫醇或碳氢基团，或其盐，是新颖的、β-内酰胺酶抗性和低毒性的化合物，对包括大肠杆菌、马尔色葡萄球菌、雷氏变形杆菌、肠臭臭肠杆菌、弗伦德氏柠檬杆菌在内的广谱微生物表现出优异的活性。因此，这些化合物可用于治疗用抗菌剂。
• 4-halogeno-2-oxyimino-3-oxobutyric acids and derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04845257A1

  公开（公告）日：1989-07-04

  A method of producing a 4-halo-2-(substituted or unsubstituted)hydroxyimino-3-oxobutyric acid ester or amide, which is a synthetic intermediate of value for the production of cephalosporins containing an aminothiazole group, characterized by reacting a 2-(substituted or unsubstituted)-hydroxyimino-3-oxobutyric acid or an ester or amide thereof with a silylating agent and reacting the resulting novel 2-(substituted)hydroxyimino-3-silyloxy-3-butenoic acid ester or amide with a halogenating agent.

  生产4-卤代-2-(取代或未取代)羟基亚胺基-3-氧代丁酸酯或酰胺的方法，该方法是一种用于生产含有氨基噻唑基团头孢菌素的合成中间体，其特征在于将2-(取代或未取代)羟基亚胺基-3-氧代丁酸或其酯或酰胺与硅化剂反应，然后将所得的新型2-(取代)羟基亚胺基-3-硅氧基-3-丁烯酸酯或酰胺与卤代试剂反应。
• 4-Halogeno-2-Oxyimino-3-Oxobutyric acids
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0246603A2

  公开（公告）日：1987-11-25

  A method of producing a 4-halo-2-(substituted or unsubstituted)hydroxyimino-3-oxobutyric acid ester or amide, which is a synthetic intermediate of value for the production of cephalosporins containing an aminothiazole group, characterized by reacting a 2-(substituted or unsubstituted)­hydroxyimino-3-oxobutyric acid or an ester or amide thereof with a silylating agent and reacting the resulting novel 2-­(substituted)hydroxyimino-3-silyloxy-3-butenoic acid ester or amide with a halogenating agent.

  一种生产 4-卤代-2-(取代或未取代)羟基亚氨基-3-氧代丁酸酯或酰胺的方法，它是生产含有氨基噻唑基团的头孢菌素的重要合成中间体、其特征是将 2-(取代或未取代)羟基亚氨基-3-氧代丁酸或其酯或酰胺与硅烷化剂反应，并将所得的新型 2-(取代)羟基亚氨基-3-硅氧基-3-丁烯酸酯或酰胺与卤化剂反应。
• 2-Amino-5-thiazolyl motif: A novel scaffold for designing anti-inflammatory agents of diverse structures
  作者：P.X. Franklin、Ajay D. Pillai、Parendu D. Rathod、Swapnil Yerande、Manish Nivsarkar、Harish Padh、Kamala K. Vasu、V. Sudarsanam

  DOI：10.1016/j.ejmech.2007.02.008

  日期：2008.1

  Substituted thiazoles with different structural features were synthesized and screened for their anti-inflammatory activity in acute carrageenin induced rat paw edema model and chronic formalin induced rat paw edema model. The compounds 1-5 showed 83, 30, 63, 69 and 73% protection, respectively, in acute carrageenin induced rat paw edema model. In 5-day chronic formalin induced rat paw edema model on the fifth day 1 and 5 gave 66 and 41% protection. Both studies were carried out at a dose of 100 mg/kg body weight. The activity was compared with that of Ibuprofen, Rofecoxib, and Dexamethasone both in acute and chronic anti-inflammatory models. Compound 1 without COX-1 and COX-2 inhibitory activity showed good activity profile almost mimicking the gold standard Dexamethasone in terms of efficacy. A 7-day study in rats at dose of 100 mg/kg showed that this compound does not have any ulcerogenic activity and toxicity. The activity of 5 shows that incorporating two pharmacophoric features in one molecule can be a good drug designing strategy. 2,4-Diaminothiazoles with an aliphatic oxime esters attached via a ketone bridge to the 5th position of thiazole was identified as a novel scaffold for designing anti-inflammatory agents. (C) 2007 Elsevier Masson SAS. All rights reserved.