3-(1H-imidazo[4,5-b]pyrydine-1-yl)propyl(methyl)carbamic acid tert-butyl ester | 273757-09-8

• 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: 3-(1H-imidazo[4,5-b]pyrydine-1-yl)propyl(methyl)carbamic acid tert-butyl ester
• 英文别名: 1-[3-(tert-butoxycarbonylmethylamino)propyl]-1H-imidazo[4,5-b]pyridine；tert-butyl 3-(1H-imidazo[4,5-b]pyridin-1-yl)propyl(methyl)carbamate；tert-butyl N-(3-imidazo[4,5-b]pyridin-1-ylpropyl)-N-methylcarbamate
• CAS: 273757-09-8
• 化学式: C₁₅H₂₂N₄O₂
• 分子量: 290.365
• InChiKey: FEBKNDJQRSYOQL-UHFFFAOYSA-N

物化性质

• 沸点：
  432.2±47.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1H-imidazo[4,5-b]pyrydine-1-yl)propyl(methyl)carbamic acid tert-butyl ester 在 盐酸 、 甲酸 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 1-(3-dimethylaminopropyl)-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
• 作为产物：
  描述：

  2,3-二氨基吡啶 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 3-(1H-imidazo[4,5-b]pyrydine-1-yl)propyl(methyl)carbamic acid tert-butyl ester
  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
• 作为试剂：
  描述：

  (6R,7R)-7-{2-(5-tert-Butoxycarbonylamino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-ethoxyimino]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 、 3-(1H-imidazo[4,5-b]pyrydine-1-yl)propyl(methyl)carbamic acid tert-butyl ester 在 3-(1H-imidazo[4,5-b]pyrydine-1-yl)propyl(methyl)carbamic acid tert-butyl ester 作用下， 以42的产率得到(6R,7R)-7-[[(2Z)-2-(5-amino-2,5-dihydro-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl]amino]-3-[[1-[3-(methylamino)propyl]imidazo[4,5-b]pyridin-4-ium-4-yl]methyl]-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid
  参考文献：
  名称：

  Imidazo[4,5-b]pyridiniummethyl-containing cephem compounds having broad antibacterial spectrum

  摘要：

  公式（I）的Cefem化合物具有广泛的抗菌谱，可对包括MRSA在内的各种致病菌产生作用。其中，X为N或CY，Y为H或卤素；R1为氨基或保护氨基；R2为氢或可选取代的较低烷基等；R3为氢等；R4为氢、可选取代的较低烷基或可选取代的含氮杂环基团等；R5为氢等；波浪线表示syn-或anti-异构或其混合物。

  公开号：

  US06518263B1

文献信息

• 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.
• EP2703406
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• J Antibiot 2002, 55, 975-992
  作者：

  DOI：——

  日期：——
• SULFATE OF CEPHEM COMPOUND
  申请人：SHIONOGI & CO., LTD.

  公开号：EP1382608B1

  公开（公告）日：2005-08-31