4-[4-(6-chloro-3-pyridyl)-2-methylimidazol-1-yl]butylamine | 790262-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[4-(6-chloro-3-pyridyl)-2-methylimidazol-1-yl]butylamine
• 英文别名: 4-[4-(6-chloro-(3-pyridyl))-2-methylimidazolyl]butylamine；4-[4-(6-Chloropyridin-3-yl)-2-methylimidazol-1-yl]butan-1-amine
• CAS: 790262-97-4
• 化学式: C₁₃H₁₇ClN₄
• 分子量: 264.758
• InChiKey: IKJQIGHSSFHHMI-UHFFFAOYSA-N

物化性质

• 沸点：
  479.5±40.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[4-(6-chloro-3-pyridyl)-2-methylimidazol-1-yl]butylamine 在 甲醇 作用下， 以 水 、 乙腈 为溶剂， 反应 28.0h， 生成 (1S,2R,5R,7R,8R,9R,11R,13R,14R)-15-[4-[4-(6-chloropyridin-3-yl)-2-methylimidazol-1-yl]butyl]-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-1-ethenyl-2-ethyl-9-methoxy-5,7,9,11,13-pentamethyl-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
  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：

  5-溴-2-氯吡啶 在 乙基溴化镁 、 potassium carbonate 、 三氟乙酸 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 4-[4-(6-chloro-3-pyridyl)-2-methylimidazol-1-yl]butylamine
  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

• [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
• [EN] NOVEL KETOLIDE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES DE KETOLIDES
  申请人：CHIRON CORP

  公开号：WO2004096823A3

  公开（公告）日：2005-02-10
• US7163924B2
  申请人：——

  公开号：US7163924B2

  公开（公告）日：2007-01-16
• US7332476B2
  申请人：——

  公开号：US7332476B2

  公开（公告）日：2008-02-19
• Synthesis and Antibacterial Activity of Novel C₁₂ Vinyl Ketolides
  作者：Matthew T. Burger、Xiaodong Lin、Daniel T. Chu、Christy Hiebert、Alice C. Rico、Mehran Seid、Georgia L. Carroll、Lynn Barker、Kay Huh、Mike Langhorne、Ribhi Shawar、Jolene Kidney、Kelly Young、Scott Anderson、Manoj C. Desai、Jacob J. Plattner

  DOI：10.1021/jm051157a

  日期：2006.3.1

  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.