Ethanaminium, N-(carboxymethyl)-2-[[2-[(3S)-1-[8-[[[4-(1,1-dimethylethyl)-2-thiazolyl]amino]carbonyl]-4-oxo-3-[(1E)-2-(2H-tetrazol-5-yl)ethenyl]-4H-pyrido[1,2-a]pyrimidin-2-yl]-3-piperidinyl]acetyl]amino]-N,N-dimethyl-, inner salt | 957472-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: Ethanaminium, N-(carboxymethyl)-2-[[2-[(3S)-1-[8-[[[4-(1,1-dimethylethyl)-2-thiazolyl]amino]carbonyl]-4-oxo-3-[(1E)-2-(2H-tetrazol-5-yl)ethenyl]-4H-pyrido[1,2-a]pyrimidin-2-yl]-3-piperidinyl]acetyl]amino]-N,N-dimethyl-, inner salt
• 英文别名: 2-[2-[[2-[(3S)-1-[8-[(4-tert-butyl-1,3-thiazol-2-yl)carbamoyl]-4-oxo-3-[(E)-2-(2H-tetrazol-5-yl)ethenyl]pyrido[1,2-a]pyrimidin-2-yl]piperidin-3-yl]acetyl]amino]ethyl-dimethylazaniumyl]acetate
• CAS: 957472-00-3
• 化学式: C₃₂H₄₁N₁₁O₅S
• 分子量: 691.814
• InChiKey: QWFJRLBPTOAJDW-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  230
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  在 盐酸 、 苯甲醚 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以550 mg的产率得到Ethanaminium, N-(carboxymethyl)-2-[[2-[(3S)-1-[8-[[[4-(1,1-dimethylethyl)-2-thiazolyl]amino]carbonyl]-4-oxo-3-[(1E)-2-(2H-tetrazol-5-yl)ethenyl]-4H-pyrido[1,2-a]pyrimidin-2-yl]-3-piperidinyl]acetyl]amino]-N,N-dimethyl-, inner salt
  参考文献：
  名称：

  MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 7: Highly soluble and in vivo active quaternary ammonium analogue D13-9001, a potential preclinical candidate

  摘要：

  A series of 4-oxo-4H-pyrido[1,2-a]pyrimidine derivatives, Substituted at the 2-position with piperidines bearing quaternary ammonium salt side chains, were synthesized and evaluated for their ability to potentiate the activity of the fluoroquinolone levofloxacin (LVFX) and the beta-lactam aztreonam (AZT) in Pseudomonas aeruginosa. Attachment of the charged entity using an N-ethylcarbamoyloxy linker led to the discovery of the highly soluble compound 22 (D13-9001), which maintained good potency in vitro and displayed excellent activity in vivo in a rat pneumonia model of P. aeruginosa. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.039

文献信息

• MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 7: Highly soluble and in vivo active quaternary ammonium analogue D13-9001, a potential preclinical candidate
  作者：Ken-ichi Yoshida、Kiyoshi Nakayama、Masami Ohtsuka、Noriko Kuru、Yoshihiro Yokomizo、Atsunobu Sakamoto、Makoto Takemura、Kazuki Hoshino、Hiroko Kanda、Hironobu Nitanai、Kenji Namba、Kumi Yoshida、Yuichiro Imamura、Jason Z. Zhang、Ving J. Lee、William J. Watkins

  DOI：10.1016/j.bmc.2007.07.039

  日期：2007.11

  A series of 4-oxo-4H-pyrido[1,2-a]pyrimidine derivatives, Substituted at the 2-position with piperidines bearing quaternary ammonium salt side chains, were synthesized and evaluated for their ability to potentiate the activity of the fluoroquinolone levofloxacin (LVFX) and the beta-lactam aztreonam (AZT) in Pseudomonas aeruginosa. Attachment of the charged entity using an N-ethylcarbamoyloxy linker led to the discovery of the highly soluble compound 22 (D13-9001), which maintained good potency in vitro and displayed excellent activity in vivo in a rat pneumonia model of P. aeruginosa. (C) 2007 Elsevier Ltd. All rights reserved.