2-imidazo[4,5-b]pyridin-1-yl-2-methylpropan-1-ol | 484673-62-3

• 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: 2-imidazo[4,5-b]pyridin-1-yl-2-methylpropan-1-ol
• 英文别名: 2-Imidazo [4,5-b]pyridin-1-yl-2-methyl-propan-1-ol；2-Imidazo[4,5-b]pyridin-1-yl-2-methyl-propan-1-ol
• CAS: 484673-62-3
• 化学式: C₁₀H₁₃N₃O
• 分子量: 191.233
• InChiKey: LZJRGIPZSOSZSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-imidazo[4,5-b]pyridin-1-yl-2-methylpropan-1-ol 在 palladium on activated charcoal 草酰氯 、 氢气 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 49.5h， 生成 4-Imidazo[4,5-b]pyridin-1-yl-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel C₁₂ Vinyl Ketolides

  摘要：

  A novel series Of C-12 vinyl erythromycin derivatives have been discovered which exhibit in vitro and in vivo potency against key respiratory pathogens. The C-12 modification involves replacing the natural C-12 methyl group in the erythromycin core with a vinyl group via chemical synthesis. From the C-12 vinyl macrolide core, a series Of C-12 vinyl ketolides was prepared. Several compounds were found to be potent against macrolide-sensitive and -resistant bacteria. The C-12 vinyl ketolides 6j and 6k showed a similar antimicrobial spectrum and comparable activity to the commercial ketolide telithromycin. However, the pharmacokinetic profiles Of C-12 vinyl ketolides 6j and 6k in rats differ from that of telithromycin by having higher lung-to-plasma ratios, larger volumes of distribution, and longer half-lives. These pharmacokinetic differences have a pharmacodynamic effect as both 6j and 6k exhibited better in vivo efficacy than telithromycin in rat lung infection models against Streptococcus pneumoniae and Haemophilus influenzae.

  DOI：

  10.1021/jm051157a
• 作为产物：
  描述：

  4-氮杂苯并咪唑 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 2-imidazo[4,5-b]pyridin-1-yl-2-methylpropan-1-ol
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel C₁₂ Vinyl Ketolides

  摘要：

  A novel series Of C-12 vinyl erythromycin derivatives have been discovered which exhibit in vitro and in vivo potency against key respiratory pathogens. The C-12 modification involves replacing the natural C-12 methyl group in the erythromycin core with a vinyl group via chemical synthesis. From the C-12 vinyl macrolide core, a series Of C-12 vinyl ketolides was prepared. Several compounds were found to be potent against macrolide-sensitive and -resistant bacteria. The C-12 vinyl ketolides 6j and 6k showed a similar antimicrobial spectrum and comparable activity to the commercial ketolide telithromycin. However, the pharmacokinetic profiles Of C-12 vinyl ketolides 6j and 6k in rats differ from that of telithromycin by having higher lung-to-plasma ratios, larger volumes of distribution, and longer half-lives. These pharmacokinetic differences have a pharmacodynamic effect as both 6j and 6k exhibited better in vivo efficacy than telithromycin in rat lung infection models against Streptococcus pneumoniae and Haemophilus influenzae.

  DOI：

  10.1021/jm051157a

文献信息

• C12 Modified erythromycin macrolides and ketolides having antibacterial activity
  申请人：——

  公开号：US20030125266A1

  公开（公告）日：2003-07-03

  Antimicrobial macrolide compounds are provided having formulas II: 1 as well as pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  提供具有II:1式的抗微生物大环内酯化合物，以及其药用盐、酯或前药；包含这类化合物的药物组合物；通过给予这类化合物治疗细菌感染的方法；以及这类化合物的制备方法。
• Pyridyl substituted ketolide antibiotics
  申请人：Burger T. Matthew

  公开号：US20050009764A1

  公开（公告）日：2005-01-13

  Antimicrobial macrolide and ketolide compounds are provided having formulas XII: as well as pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  提供具有XII式的抗微生物大环内酯和酮内酯化合物，以及其药学上可接受的盐、酯或前药；包含这些化合物的药物组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。
• C12 modified erythromycin macrolides and ketolides having antibacterial activity
  申请人：Chiron Corporation

  公开号：US06756359B2

  公开（公告）日：2004-06-29

  Antimicrobial macrolide compounds are provided having formulas II: as well as pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  本发明提供具有II式的抗微生物大环内酯化合物，以及其药学上可接受的盐、酯或前药；包含这些化合物的药物组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。
• [EN] PYRIDYL SUBSTITUTED KETOLIDE ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES A BASE DE KETOLIDE A SUBSTITUTION PYRIDYLE
  申请人：CHIRON CORP

  公开号：WO2004096822A3

  公开（公告）日：2004-12-16
• C12 MODIFIED ERYTHROMYCIN MACROLIDES AND KETOLIDES HAVING ANTIBACTERIAL ACTIVITY
  申请人：CHIRON CORPORATION

  公开号：EP1404693A2

  公开（公告）日：2004-04-07