1-(4-aminobutyl)-1H-indol-4-ylamine | 882032-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(4-aminobutyl)-1H-indol-4-ylamine
• 英文别名: 1-(4-Aminobutyl)indol-4-amine
• CAS: 882032-53-3
• 化学式: C₁₂H₁₇N₃
• 分子量: 203.287
• InChiKey: YNSWNCVTCKKOQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-aminobutyl)-1H-indol-4-ylamine 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-aminoindol-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：

  4-硝基吲哚 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 肼 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.0h， 生成 1-(4-aminobutyl)-1H-indol-4-ylamine
  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

• Synthesis and antibacterial activity of C12 des-methyl ketolides
  作者：Xiaodong Lin、Alice C. Rico、Daniel T. Chu、Georgia L. Carroll、Lynn Barker、Ribhi Shawar、Manoj C. Desai、Jacob J. Plattner

  DOI：10.1016/j.bmcl.2006.05.104

  日期：2006.9

  Synthesis of C-12 des-methyl ketolide is developed featuring an intramolecular epoxide formation/elimination process to establish the C-12 stereocenter. These ketolides are potent against several key respiratory pathogens, including erythromycin resistant erm- and mef-containing strains of Streptococcus pneumoniae. (c) 2006 Elsevier Ltd. All rights reserved.