1-[3-[tert-butoxycarbonyl-(2-triethylsilanyloxyethyl)amino]propyl]-1H-imidazo[4,5-b]pyridine | 273757-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 1-[3-[tert-butoxycarbonyl-(2-triethylsilanyloxyethyl)amino]propyl]-1H-imidazo[4,5-b]pyridine
• 英文别名: tert-butyl N-(3-imidazo[4,5-b]pyridin-1-ylpropyl)-N-(2-triethylsilyloxyethyl)carbamate
• CAS: 273757-13-4
• 化学式: C₂₂H₃₈N₄O₃Si
• 分子量: 434.654
• InChiKey: SHPMEPXINNPZAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[3-[tert-butoxycarbonyl-(2-triethylsilanyloxyethyl)amino]propyl]-1H-imidazo[4,5-b]pyridine 在 sodium halide 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  S-3578, A New Broad Spectrum Parenteral Cephalosporin Exhibiting Potent Activity Against both Methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa Synthesis and Structure-activity Relationships.

  摘要：

  一系列具有1-(取代基)-1H-咪唑[4, 5-b]吡啶铵基团的7-氨基噻二唑基头孢菌素在头孢核的C-3'位点合成并评估其体外抗菌活性。在本研究中制备的头孢菌素中，7β-[2-(5-amino-1, 2, 4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[1-(3-methylaminopropyl)-1H-imidazo[4, 5-b]pyridinium-4-yl]methyl-3-头孢-4-羧酸盐硫酸盐(S-3578)对革兰氏阳性细菌（包括抗甲氧西林的金黄色葡萄球菌MRSA）和革兰氏阴性细菌（包括铜绿色假单胞菌）表现出极强的广谱活性，并且具有良好的水溶性。

  DOI：

  10.7164/antibiotics.55.975
• 作为产物：
  描述：

  N-(3-氨基-2-吡啶基)甲酰胺 在 吡啶硼烷 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 1-[3-[tert-butoxycarbonyl-(2-triethylsilanyloxyethyl)amino]propyl]-1H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  S-3578, A New Broad Spectrum Parenteral Cephalosporin Exhibiting Potent Activity Against both Methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa Synthesis and Structure-activity Relationships.

  摘要：

  一系列具有1-(取代基)-1H-咪唑[4, 5-b]吡啶铵基团的7-氨基噻二唑基头孢菌素在头孢核的C-3'位点合成并评估其体外抗菌活性。在本研究中制备的头孢菌素中，7β-[2-(5-amino-1, 2, 4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[1-(3-methylaminopropyl)-1H-imidazo[4, 5-b]pyridinium-4-yl]methyl-3-头孢-4-羧酸盐硫酸盐(S-3578)对革兰氏阳性细菌（包括抗甲氧西林的金黄色葡萄球菌MRSA）和革兰氏阴性细菌（包括铜绿色假单胞菌）表现出极强的广谱活性，并且具有良好的水溶性。

  DOI：

  10.7164/antibiotics.55.975

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.
• S-3578, A New Broad Spectrum Parenteral Cephalosporin Exhibiting Potent Activity Against both Methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa Synthesis and Structure-activity Relationships.
  作者：HIDENORI YOSHIZAWA、HIKARU ITANI、KOJI ISHIKURA、TADASHI IRIE、KATSUKI YOKOO、TADATOSHI KUBOTA、KYOJI MINAMI、TSUTOMU IWAKI、HIDEAKI MIWA、YASUHIRO NISHITANI

  DOI：10.7164/antibiotics.55.975

  日期：——

  A series of 7-aminothiadiazolylcephalosporins having a 1-(substituted)-1H-imidazo[4, 5-b]pyridinium group at the C-3' position of the cephem nucleus were synthesized and evaluated for in vitro antibacterial activities. Among the cephalosporins prepared in this study, 7β-[2-(5-amino-1, 2, 4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[1-(3-methylaminopropyl)-1H-imidazo[4, 5-b]pyridinium-4-yl]methyl-3-cephem-4-carboxylate sulfate (S-3578) showed extremely potent broad spectrum activity against both Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) and Gram-negative bacteria including Pseudomonas aeruginosa, and good water solubility.

  一系列具有1-(取代基)-1H-咪唑[4, 5-b]吡啶铵基团的7-氨基噻二唑基头孢菌素在头孢核的C-3'位点合成并评估其体外抗菌活性。在本研究中制备的头孢菌素中，7β-[2-(5-amino-1, 2, 4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[1-(3-methylaminopropyl)-1H-imidazo[4, 5-b]pyridinium-4-yl]methyl-3-头孢-4-羧酸盐硫酸盐(S-3578)对革兰氏阳性细菌（包括抗甲氧西林的金黄色葡萄球菌MRSA）和革兰氏阴性细菌（包括铜绿色假单胞菌）表现出极强的广谱活性，并且具有良好的水溶性。