tert-butyl 3-(1H-pyrrolo[3,2-b]pyridin-1-yl)propyl(methyl)carbamate | 604002-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: tert-butyl 3-(1H-pyrrolo[3,2-b]pyridin-1-yl)propyl(methyl)carbamate
• 英文别名: tert-butyl N-methyl-N-(3-pyrrolo[3,2-b]pyridin-1-ylpropyl)carbamate
• CAS: 604002-29-1
• 化学式: C₁₆H₂₃N₃O₂
• 分子量: 289.378
• InChiKey: HJRIGBCEWNTGBM-UHFFFAOYSA-N

物化性质

• 沸点：
  423.6±28.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(1H-pyrrolo[3,2-b]pyridin-1-yl)propyl(methyl)carbamate 、 (6R,7R)-4-methoxybenzyl 7-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylate 5-oxide 在 sodium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  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
• 作为产物：
  描述：

  4-氮杂吲哚 、 3-[tert-butoxycarbonyl(methyl)amino]propyl methanesulfonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以54%的产率得到tert-butyl 3-(1H-pyrrolo[3,2-b]pyridin-1-yl)propyl(methyl)carbamate
  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

• EP1489084
  申请人：——

  公开号：——

  公开（公告）日：——
• Cephem Compounds Having Broad Antibacterial Spectrum
  申请人：Nishitani Yasuhiro

  公开号：US20090131655A1

  公开（公告）日：2009-05-21

  A compound of the formula: (wherein, T is S, SO or O; X is halogen, CN, carbamoyl optionally substituted with lower alkyl, lower alkyl, lower alkoxy, or lower alkylthio; A is substituted lower alkylene (wherein the substituent is optionally substituted mono lower alkyl, optionally substituted lower alkylidene, or optionally substituted lower alkylene) Z + is an optionally substituted, a cation and an N atom-containing heterocyclic group), ester, amino-protected compound wherein the amino bonds to a thiazole ring at the 7-position, or pharmaceutically acceptable salt or solvate thereof.
• US7384928B2
  申请人：——

  公开号：US7384928B2

  公开（公告）日：2008-06-10
• US7696354B2
  申请人：——

  公开号：US7696354B2

  公开（公告）日：2010-04-13
• 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.