2-[4-(6-methylpyridin-3-yl)imidazol-1-yl]isoindole-1,3-dione | 484673-43-0

• 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-[4-(6-methylpyridin-3-yl)imidazol-1-yl]isoindole-1,3-dione
• 英文别名: 2-[4-(6-methylpyridin-3-yl)-imidazol-1-ylbutyl]-isoindole-1,3-dione；2-[4-[4-(6-Methylpyridin-3-yl)imidazol-1-yl]butyl]isoindole-1,3-dione
• CAS: 484673-43-0
• 化学式: C₂₁H₂₀N₄O₂
• 分子量: 360.415
• InChiKey: UCDNCBPPLAHXAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  68.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-(6-methylpyridin-3-yl)imidazol-1-yl]isoindole-1,3-dione 在 肼 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以95%的产率得到4-[4-(6-methylpyridin-3-yl)-1H-imidazol-1-yl]butylamine
  参考文献：
  名称：

  [EN] PYRIDYL SUBSTITUTED KETOLIDE ANTIBIOTICS
  [FR] ANTIBIOTIQUES A BASE DE KETOLIDE A SUBSTITUTION PYRIDYLE

  摘要：

  公开号：

  WO2004096822A3
• 作为产物：
  描述：

  5-溴-2-甲基吡啶 在 盐酸 、 乙基溴化镁 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 2-[4-(6-methylpyridin-3-yl)imidazol-1-yl]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

• [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.