(αZ)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-α-(ethoxyimino)-4-thiazoleacetic acid | 185312-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (αZ)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-α-(ethoxyimino)-4-thiazoleacetic acid
• 英文别名: (2Z)-2-ethoxyimino-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]acetic acid
• CAS: 185312-26-9
• 化学式: C₁₂H₁₇N₃O₅S
• 分子量: 315.35
• InChiKey: XNAYPJROSUFQGD-NVNXTCNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 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：

  (αZ)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-α-(ethoxyimino)-4-thiazoleacetic acid 在 吡啶 、 N,O-双三甲硅基乙酰胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 为溶剂， 生成 (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-ethoxyimino]-acetylamino}-3-(2,6-diamino-pyrimidin-4-ylsulfanyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins including against respiratory tract pathogens

  摘要：

  The variety of cephalosporins 1 and 2 which possessed C(3)-aminopyrimidinyl substituents were prepared and evaluated for their antibacterial activities. They exhibited excellent in vitro activities especially against respiratory tract pathogens such as penicillin resistant Streptococus pneumonia, Moraxella catarrhalis and Haemophilus influenza. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00425-x
• 作为产物：
  描述：

  (2-tert-Butoxycarbonylamino-thiazol-4-yl)-[(Z)-ethoxyimino]-acetic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (αZ)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-α-(ethoxyimino)-4-thiazoleacetic acid
  参考文献：
  名称：

  Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins including against respiratory tract pathogens

  摘要：

  The variety of cephalosporins 1 and 2 which possessed C(3)-aminopyrimidinyl substituents were prepared and evaluated for their antibacterial activities. They exhibited excellent in vitro activities especially against respiratory tract pathogens such as penicillin resistant Streptococus pneumonia, Moraxella catarrhalis and Haemophilus influenza. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00425-x

文献信息

• A novel tricyclic β-lactam exhibiting potent antibacterial activities against carbapenem-resistant Enterobacterales: Synthesis and structure-activity-relationships
  作者：Jun Sato、Hiroki Kusano、Toshiaki Aoki、Satoru Shibuya、Katsuki Yokoo、Kazuo Komano、Takuya Oguma、Shuhei Matsumoto、Takafumi Sato、Kazuya Yasuo、Kenji Yamawaki

  DOI：10.1016/j.bmc.2021.116343

  日期：2021.9

  evaluated for in vitro antibacterial activities against carbapenem-resistant Enterobacterales (CREs). Starting from a reported tricyclic β-lactam that combined the cephalosporin skeleton having a γ-lactone ring with a carboxylic acid group, which was reported as a unique partial structure of Lactivicin, we identified the compound which shows potent antibacterial activities against all tested CREs by introducing

  合成了一系列三环 β-内酰胺并进行了体外评价对耐碳青霉烯肠杆菌 (CRE) 的抗菌活性。从报道的三环 β-内酰胺开始，该三环 β-内酰胺将具有 γ-内酯环的头孢菌素骨架与羧酸基团结合起来，据报道，这是 Lactivicin 的独特部分结构，我们确定了对所有测试的 CRE 显示有效抗菌活性的化合物引入亚砜。此外，亚砜引入的三环 β-内酰胺在中性粒细胞减少的小鼠肺部感染模型中也显示出很强的治疗效果。这些结果表明，三环 β-内酰胺骨架在临床使用中将显示出足够的治疗性能，因此可以作为寻找针对 CRE 的新型抗菌剂的支架。
• Novel broad-spectrum and long-acting parenteral cephalosporins having an acyl cyanamide moiety at the C-3 terminal: Synthesis and structure-activity relationships
  作者：Katsuki Yokoo、Kenji Yamawaki、Yutaka Yoshida、Shuji Yonezawa、Yoshinori Yamano、Masakatsu Tsuji、Toshihiko Hori、Rio Nakamura、Koji Ishikura

  DOI：10.1016/j.ejmech.2016.09.015

  日期：2016.11

  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.
• PENICILLIN-BINDING PROTEIN INHIBITORS
  申请人：VenatoRx Pharmaceuticals, Inc.

  公开号：US20200102331A1

  公开（公告）日：2020-04-02

  Described herein are certain boron-containing compounds, compositions, preparations and their use as modulators of the transpeptidase function of bacterial penicillin-binding proteins and as antibacterial agents. In some embodiments, the compounds described herein inhibit penicillin-binding proteins. In certain embodiments, the compounds described herein are useful in the treatment of bacterial infections.