(Z)-2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)-2-(ethoxyimino)acetic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)-2-(ethoxyimino)acetic acid
• 英文别名: (2Z)-2-[5-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-ethoxyiminoacetic acid
• 化学式: C₁₂H₁₆ClN₃O₅S
• 分子量: 349.795
• InChiKey: BGOBVOGVDHCRLB-APSNUPSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (Z)-2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)-2-(ethoxyimino)acetic acid 在 N-甲基吗啉 、 二氯磷酸苯酯 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 3.58h， 生成
  参考文献：
  名称：

  Novel broad-spectrum and long-acting parenteral cephalosporins having an acyl cyanamide moiety at the C-3 terminal: Synthesis and structure-activity relationships

  摘要：

  A series of novel 7 beta-[2-(2-aminothiazole-4-yl)-2-(Z)-(alkoxyimino)acetamidol-cephalosporins having pyridinium-linked acyl cyanamide at the C-3 position were prepared and their antibacterial activities and pharmacokinetics profiles were evaluated. Most of the compounds exhibited potent antibacterial activities against penicillin-resistant Streptococcus pneumoniae (PRSP) and beta-lactamase non-producing penicillin-resistant Haemophilus influenzae (BLNAR). Introduction of a propenyl group between the cephalospoin core and the side chains at the C-3 position improved the pharmacokinetics profile. Among these compounds, 7 beta-[2-(2-aminothiazole-4-y1)-2-(Z)- (alkoxyimino)acetamido1-3-(pyridin-1-ium-1-yl) prop-1-en-1-yl)cephalosporins (32j) showed well-balanced antibacterial activity against S. pneumoniae and H. influenzae which included resistant strains and also other Gram-positive or Gram-negative pathogens. Furthermore, 32j showed a long half-life comparable to that of Ceftriaxone in mice and monkeys. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.015
• 作为产物：
  描述：

  2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)-2-oxoacetic acid 、 O-乙基羟胺 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.67h， 以78%的产率得到(Z)-2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)-2-(ethoxyimino)acetic acid
  参考文献：
  名称：

  Novel broad-spectrum and long-acting parenteral cephalosporins having an acyl cyanamide moiety at the C-3 terminal: Synthesis and structure-activity relationships

  摘要：

  A series of novel 7 beta-[2-(2-aminothiazole-4-yl)-2-(Z)-(alkoxyimino)acetamidol-cephalosporins having pyridinium-linked acyl cyanamide at the C-3 position were prepared and their antibacterial activities and pharmacokinetics profiles were evaluated. Most of the compounds exhibited potent antibacterial activities against penicillin-resistant Streptococcus pneumoniae (PRSP) and beta-lactamase non-producing penicillin-resistant Haemophilus influenzae (BLNAR). Introduction of a propenyl group between the cephalospoin core and the side chains at the C-3 position improved the pharmacokinetics profile. Among these compounds, 7 beta-[2-(2-aminothiazole-4-y1)-2-(Z)- (alkoxyimino)acetamido1-3-(pyridin-1-ium-1-yl) prop-1-en-1-yl)cephalosporins (32j) showed well-balanced antibacterial activity against S. pneumoniae and H. influenzae which included resistant strains and also other Gram-positive or Gram-negative pathogens. Furthermore, 32j showed a long half-life comparable to that of Ceftriaxone in mice and monkeys. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.015