4-(5-(pyridin-3-yl)thiophen-2-yl)butylamine | 882032-76-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(5-(pyridin-3-yl)thiophen-2-yl)butylamine
• 英文别名: 4-(5-(3-pyridyl)-2-thienyl)butylamine；4-(5-Pyridin-3-ylthiophen-2-yl)butan-1-amine
• CAS: 882032-76-0
• 化学式: C₁₃H₁₆N₂S
• 分子量: 232.349
• InChiKey: QTICQYNTMBOGPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-(pyridin-3-yl)thiophen-2-yl)butylamine 在 甲醇 作用下， 以 乙腈 为溶剂， 反应 62.0h， 生成 (1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-5,7,9,11,13-pentamethyl-15-[4-(5-pyridin-3-ylthiophen-2-yl)butyl]-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 C12 des-methyl ketolides

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.05.104
• 作为产物：
  描述：

  3-(5-溴噻吩-2-)吡啶 在 palladium on activated charcoal copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 氢气 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 58.0h， 生成 4-(5-(pyridin-3-yl)thiophen-2-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

• 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.
• 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.