7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>ceph-3-em-4-carboxylic acid | 118680-12-9

• 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: 7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>ceph-3-em-4-carboxylic acid
• 英文别名: [6R,7R]-7-[Z-2-(2-Aminothiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetamido]-3-(3,4-dihydroxybenzoyloxy)methylceph-3-em-4-carboxylic acid；(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-3-[(3,4-dihydroxybenzoyl)oxymethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 118680-12-9
• 化学式: C₂₄H₂₃N₅O₁₁S₂
• 分子量: 621.606
• InChiKey: KLYMJTRPLLECHE-VHSHMJAOSA-N

物化性质

• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  305
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  diphenylmethyl 7β-(2-thienylacetamido)-3-(hydroxymethyl)-cephem-4-carboxylate 在 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 1,3-丁二醇 、 五氯化磷 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.92h， 生成 7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>ceph-3-em-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues

  摘要：

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.

  DOI：

  10.1021/jm00092a014

文献信息

• Cephalosporins, processes for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0265185A2

  公开（公告）日：1988-04-27

  Antibacterial agents have the formula (Ia) or are pharmaceutically acceptable salts or in vivo hydrolysable esters thereof: wherein R¹ is an acyl group, in particular that of an antibacterially active cephalosporin; R² is hydrogen, methoxy, or formamido; Y is S, SO, SO₂, O or CH₂; X is oxygen, sulphur, or -NH- and R⁴ is a group of the formula CO Z R⁵ wherein Z is -CH=CH-, -(CH₂)n- or -NH-; n is 0, 1 or 2; and R⁵ is: wherein R⁶ and R⁷ are the same or different, each representing hydroxy or protected hydroxy and R⁸ is hydroxy, amino, halogen or carboxy. The use of the compounds of formula (Ia) and intermediates for their preparation are also disclosed.

  抗菌剂具有式 (Ia) 或其药学上可接受的盐或体内可水解的酯： 其中 R¹ 是酰基，特别是抗菌活性头孢菌素的酰基；R² 是氢、甲氧基或甲酰胺基；Y 是 S、SO、SO₂、O 或 CH₂；X 是氧、硫或-NH-，R⁴ 是式 CO Z R⁵ 的基团，其中 Z 是-CH=CH-、-(CH₂)n- 或-NH-；n 是 0、1 或 2；R⁵ 是： 其中 R⁶ 和 R⁷ 相同或不同，各自代表羟基或受保护的羟基，而 R⁸ 是羟基、氨基、卤素或羧基。 还公开了式 (Ia) 化合物的用途及其制备中间体。
• Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues
  作者：J. C. Arnould、A. Bertrandie、T. G. C. Bird、D. Boucherot、F. Jung、J. J. Lohmann、A. Olivier、J. P. Bailey、W. Bell、G. M. Davies

  DOI：10.1021/jm00092a014

  日期：1992.7

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.