(S,Z)-2-(1-(benzhydryloxycarbonyl)ethoxyimino)-2-(2-(tert-butoxycarbonylamino)-5-chlorothiazol-4-yl)acetic acid | 604002-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,Z)-2-(1-(benzhydryloxycarbonyl)ethoxyimino)-2-(2-(tert-butoxycarbonylamino)-5-chlorothiazol-4-yl)acetic acid
• 英文别名: (2Z)-2-[(2S)-1-benzhydryloxy-1-oxopropan-2-yl]oxyimino-2-[5-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]acetic acid
• CAS: 604002-41-7
• 化学式: C₂₆H₂₆ClN₃O₇S
• 分子量: 560.027
• InChiKey: KEXSHYUIPHLHIF-CKZUHEGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S,Z)-2-(1-(benzhydryloxycarbonyl)ethoxyimino)-2-(2-(tert-butoxycarbonylamino)-5-chlorothiazol-4-yl)acetic acid 、 7-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester hydrochloride 在 吡啶 、 1-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  EP1489084

  摘要：

  公开号：
• 作为产物：
  描述：

  2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)-2-oxoacetic acid 、 benzhydryl (S)-2-(aminooxy)propanoate 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以44.9 g的产率得到(S,Z)-2-(1-(benzhydryloxycarbonyl)ethoxyimino)-2-(2-(tert-butoxycarbonylamino)-5-chlorothiazol-4-yl)acetic acid
  参考文献：
  名称：

  A novel series of parenteral cephalosporins exhibiting potent activities against Pseudomonas aeruginosa and other Gram-negative pathogens: Synthesis and structure–activity relationships

  摘要：

  A series of 7p-[2-(2-aminothiazol-4-yl)-2-(Z)-(carboxymethoxyimino)acetamido]cephalosporins bearing a 1-(substituted)-1H-pyrrolo[3,2-b]pyridinium group at C-3' position was synthesized and their in vitro antibacterial activities against Pseltdomollas aeruginosa and other Gram-negative pathogens were evaluated. Among the cephalosporins prepared, 7 beta-[2-(2-amino-5-chlorothiazol-4yl)-2(Z)-((S)-1-carboxyethoxyimino)acetamido]cephalosporins (42d) showed potent antibacterial activities against P. aeruginosa and other Gram-negative pathogens including the strains which produce class C P-lactamase and extended spectrum beta-lactamase (ESBL). These results imply that both the C1 atom on the C-7 aminothiazole moiety and the alpha-substituent at the iminoether moiety are essential for the stability against beta-lactamase and the potent activity against Gram-negative bacteria including P. aeruginosa. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.001

文献信息

• NOVEL CEPHALOSPORIN DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF
  申请人：CHO Young Lag

  公开号：US20120264727A1

  公开（公告）日：2012-10-18

  The present invention relates to novel cephalosporin derivatives represented by Chemical Formula 1. Wherein, X, Y, L, R 1 , and R 2 are as same as defined in the description of the invention. The present invention also relates to pharmaceutical antibiotic compositions comprising a novel celphalosporin derivative represented by Chemical Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient. According to the present invention, novel cephalosporin derivatives, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient for the broad spectrum of antibiotic resistant, low toxicity, particularly in Gram-negative bacteria, which can be useful with strong antimicrobial activity.

  本发明涉及由化学公式1表示的新型头孢菌素衍生物。其中，X、Y、L、R1和R2与发明描述中定义的相同。本发明还涉及包含由化学公式1表示的新型头孢菌素衍生物、前药、水合物、溶剂化物、异构体或药用可接受盐作为有效成分的药物抗生素组合物。根据本发明，新型头孢菌素衍生物、前药、水合物、溶剂化物、异构体或药用可接受盐作为广谱抗生素耐药、低毒性的有效成分，特别是在革兰氏阴性细菌中，可以具有强大的抗菌活性。
• NOVEL CEPHALOSPORIN DERIVATIVE AND PHARMACEUTICAL COMPOSITION THEREOF
  申请人：LegoChem Biosciences, Inc.

  公开号：EP2706062A2

  公开（公告）日：2014-03-12

  The present invention relates to novel cephalosporin derivatives represented by Chemical Formula 1. Wherein, X, Y, L, R1, and R2 are as same as defined in the description of the invention. The present invention also relates to pharmaceutical antibiotic compositions comprising a novel celphalosporin derivative represented by Chemical Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient. According to the present invention, novel cephalosporin derivatives, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient for the broad spectrum of antibiotic resistant, low toxicity, particularly in Gram-negative bacteria, which can be useful with strong antimicrobial activity.

  本发明涉及化学式 1 所代表的新型头孢菌素衍生物。 其中，X、Y、L、R1 和 R2 与本发明描述中所定义的相同。 本发明还涉及药物抗生素组合物，该组合物包含化学式 1 所代表的新型头孢菌素衍生物、其原药、其水合物、其溶液、其异构体或其药学上可接受的盐作为有效成分。 根据本发明，新型头孢菌素衍生物、其原药、其水合物、其溶物、其异构体或其药学上可接受的盐作为有效成分，可用于广谱抗抗生素、低毒性，特别是革兰氏阴性菌，具有很强的抗菌活性。
• US8329684B2
  申请人：——

  公开号：US8329684B2

  公开（公告）日：2012-12-11
• US9630977B2
  申请人：——

  公开号：US9630977B2

  公开（公告）日：2017-04-25
• A novel series of parenteral cephalosporins exhibiting potent activities against Pseudomonas aeruginosa and other Gram-negative pathogens: Synthesis and structure–activity relationships
  作者：Kenji Yamawaki、Takashi Nomura、Tatsuro Yasukata、Koichi Uotani、Hideaki Miwa、Kei Takeda、Yasuhiro Nishitani

  DOI：10.1016/j.bmc.2007.08.001

  日期：2007.11

  A series of 7p-[2-(2-aminothiazol-4-yl)-2-(Z)-(carboxymethoxyimino)acetamido]cephalosporins bearing a 1-(substituted)-1H-pyrrolo[3,2-b]pyridinium group at C-3' position was synthesized and their in vitro antibacterial activities against Pseltdomollas aeruginosa and other Gram-negative pathogens were evaluated. Among the cephalosporins prepared, 7 beta-[2-(2-amino-5-chlorothiazol-4yl)-2(Z)-((S)-1-carboxyethoxyimino)acetamido]cephalosporins (42d) showed potent antibacterial activities against P. aeruginosa and other Gram-negative pathogens including the strains which produce class C P-lactamase and extended spectrum beta-lactamase (ESBL). These results imply that both the C1 atom on the C-7 aminothiazole moiety and the alpha-substituent at the iminoether moiety are essential for the stability against beta-lactamase and the potent activity against Gram-negative bacteria including P. aeruginosa. (C) 2007 Elsevier Ltd. All rights reserved.