methyl-(2-pyrazolo[4,5-b]pyridin-1-ylethyl)carbamic acid tert-butyl ester | 753483-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: methyl-(2-pyrazolo[4,5-b]pyridin-1-ylethyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl (2-(1H-pyrazolo[4,3-b]pyridin-1-yl)ethyl)(methyl)carbamate；tert-butyl N-methyl-N-(2-pyrazolo[4,3-b]pyridin-1-ylethyl)carbamate
• CAS: 753483-47-5
• 化学式: C₁₄H₂₀N₄O₂
• 分子量: 276.338
• InChiKey: IIKQCLOTPWNZOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.25
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl-(2-pyrazolo[4,5-b]pyridin-1-ylethyl)carbamic acid tert-butyl ester 在 三氯化铝 作用下， 以 二氯甲烷 、 二甲基亚砜 、 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  New broad-spectrum parenteral cephalosporins exhibiting potent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa. Part 2: Synthesis and structure–activity relationships in the S-3578 series

  摘要：

  Among the prepared novel cephalosporin derivatives related to S-3578, a series of 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z) -ethoxyiminoacetamido]-3-[1-(aminoalkyl)-1H-pyrazoIo[4,3-b]pyridinium-4-yl]methyl-3-cephem-4-carboxylate showed potent activity against both MRSA and Pseudomonas aeruginosa, and displayed good water solubility. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.022
• 作为产物：
  描述：

  3-氟吡啶-2-醛 在 sodium hydride 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 methyl-(2-pyrazolo[4,5-b]pyridin-1-ylethyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  New broad-spectrum parenteral cephalosporins exhibiting potent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa. Part 2: Synthesis and structure–activity relationships in the S-3578 series

  摘要：

  Among the prepared novel cephalosporin derivatives related to S-3578, a series of 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z) -ethoxyiminoacetamido]-3-[1-(aminoalkyl)-1H-pyrazoIo[4,3-b]pyridinium-4-yl]methyl-3-cephem-4-carboxylate showed potent activity against both MRSA and Pseudomonas aeruginosa, and displayed good water solubility. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.022

文献信息

• A novel series of parenteral cephalosporins exhibiting potent activities against both Pseudomonas aeruginosa and other Gram-negative pathogens. Part 2: Synthesis and structure–activity relationships
  作者：Kenji Yamawaki、Takashi Nomura、Tatsuro Yasukata、Norihiko Tanimoto、Koichi Uotani、Hideaki Miwa、Yoshinori Yamano、Kei Takeda、Yasuhiro Nishitani

  DOI：10.1016/j.bmc.2007.11.028

  日期：2008.2.15

  A novel series of 7 beta-[2-(2-amino-5-chloro-thiazol-4-yl)-2(Z)-((S)-1-carboxyethoxyimino)acetamido]cephalosporins bearing various pyridinium groups at the C-3' position were synthesized and their in vitro antibacterial activities against Gram-negative pathogens including Pseudomonas aeruginosa and several Gram-positive pathogens were evaluated. Among the cephalosporins prepared, we found that a cephalosporin bearing the 2- amino-1-(3-methylamino-propyl)-1H-imidazo[4,5-b] pyridinium group at the C-3' position (8a) showed potent and well-balanced antibacterial activities against P. aeruginosa and other Gram-negative pathogens including the strains which produce class C beta-lactamase and extended spectrum beta-lactamase (ESBL). Compound 8a also showed efficacious in vivo activity and high stability against AmpC beta-lactamase. These findings indicate that 2-aminoimidazopyridinium having an aminoalkyl group at the 1-position as a C-3' side chain is suitable for cephalosporins bearing an aminochlorothiazolyl moiety and a carboxyethoxyimino moiety on the C-7 side chain. (C) 2007 Elsevier Ltd. All rights reserved.