2-(2-(methyl-((2-(pyridin-3-yl)thiazol-5-yl)methyl)amino)ethyl)isoindole-1,3-dione | 882032-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2-(methyl-((2-(pyridin-3-yl)thiazol-5-yl)methyl)amino)ethyl)isoindole-1,3-dione
• 英文别名: 2-[2-[Methyl-[(2-pyridin-3-yl-1,3-thiazol-5-yl)methyl]amino]ethyl]isoindole-1,3-dione
• CAS: 882032-78-2
• 化学式: C₂₀H₁₈N₄O₂S
• 分子量: 378.455
• InChiKey: YPNJASVIPJWHND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-(methyl-((2-(pyridin-3-yl)thiazol-5-yl)methyl)amino)ethyl)isoindole-1,3-dione 在 肼 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以100%的产率得到N1-methyl-N1-((2-(pyridin-3-yl)-1,3-thiazol-5-yl)methyl)ethane-1,2-diamine
  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：

  二乙基(3-吡啶基)-硼烷 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 、 三乙酰氧基硼氢化钠 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.0h， 生成 2-(2-(methyl-((2-(pyridin-3-yl)thiazol-5-yl)methyl)amino)ethyl)isoindole-1,3-dione
  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.