(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetyl chloride;hydrochloride | 124219-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetyl chloride;hydrochloride
• CAS: 124219-60-9
• 化学式: C₇H₈ClN₃O₂S*ClH
• 分子量: 270.139
• InChiKey: JPPYLDJCQACNKU-JIBDQCPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetyl chloride;hydrochloride 在 苯磺酰胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 为溶剂， 反应 3.0h， 生成 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(ethoxyimino)acetamido]-3-[(4-pyrazolyl)methylthio]-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Orally Active Cephalosporins. Part 4: Synthesis, Structure–Activity Relationships and Oral Absorption of Novel 3-(4-Pyrazolylmethylthio)cephalosporins with Various C-7 Side Chains

  摘要：

  A series of 3-(4-pyrazolylmethylthio)cephalosporins with various C-7 side chains was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity against Haemophilus influenzae was markedly increased by the C-7 oxime moiety. Deamination at the 2 position of, or introduction of a substituent such as halogen or methyl to, the 5 position of the (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino) moiety improved oral absorption. Among these compounds, FR192752 (40a) having a (Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-hydroxyiminoacetam do moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including H. influenzae and penicillin G-resistant Streptococcus pneumoniae (PRSP). Further, it showed higher oral absorption than CFDN and FK041. (C) 2002 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00416-3
• 作为产物：
  描述：

  2-(2-amino-4-thiazolyl)-(Z)-2-ethoxyiminoacetic acid 在 五氯化磷 、 N,N-二甲基甲酰胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以53%的产率得到(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetyl chloride;hydrochloride
  参考文献：
  名称：

  Mandel, Martin; Novak, Ludvik; Rajsner, Miroslav, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 6, p. 1734 - 1745

  摘要：

  DOI：

文献信息

• MANDEL, MARTIN;NOVAK, LUDVIK;RAJSNER, MIROSLAV;HOLUBEK, JIRI;HOLA, VLADIS+, COLLECT. CZECHOSL. CHEM. COMMUN., 54,(1989) N, C. 1734-1745
  作者：MANDEL, MARTIN、NOVAK, LUDVIK、RAJSNER, MIROSLAV、HOLUBEK, JIRI、HOLA, VLADIS+

  DOI：——

  日期：——
• Mandel, Martin; Novak, Ludvik; Rajsner, Miroslav, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 6, p. 1734 - 1745
  作者：Mandel, Martin、Novak, Ludvik、Rajsner, Miroslav、Holubek, Jiri、Hola, Vladislava

  DOI：——

  日期：——
• Orally Active Cephalosporins. Part 4: Synthesis, Structure–Activity Relationships and Oral Absorption of Novel 3-(4-Pyrazolylmethylthio)cephalosporins with Various C-7 Side Chains
  作者：Hirofumi Yamamoto、Yoshiteru Eikyu、Shinya Okuda、Kohji Kawabata、Hisashi Takasugi、Hirokazu Tanaka、Satoru Matsumoto、Yoshimi Matsumoto、Shuichi Tawara

  DOI：10.1016/s0968-0896(01)00416-3

  日期：2002.5

  A series of 3-(4-pyrazolylmethylthio)cephalosporins with various C-7 side chains was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity against Haemophilus influenzae was markedly increased by the C-7 oxime moiety. Deamination at the 2 position of, or introduction of a substituent such as halogen or methyl to, the 5 position of the (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino) moiety improved oral absorption. Among these compounds, FR192752 (40a) having a (Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-hydroxyiminoacetam do moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including H. influenzae and penicillin G-resistant Streptococcus pneumoniae (PRSP). Further, it showed higher oral absorption than CFDN and FK041. (C) 2002 Elsevier Science Ltd, All rights reserved.