(2R,3R)-2-[(Methanesulfonyl-methyl-amino)-methyl]-5-methyl-3-(piperidine-1-carbonyl)-hexanoic acid benzyl ester | 206554-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-2-[(Methanesulfonyl-methyl-amino)-methyl]-5-methyl-3-(piperidine-1-carbonyl)-hexanoic acid benzyl ester
• 英文别名: benzyl (2R,3R)-5-methyl-2-[[methyl(methylsulfonyl)amino]methyl]-3-(piperidine-1-carbonyl)hexanoate
• CAS: 206554-01-0
• 化学式: C₂₃H₃₆N₂O₅S
• 分子量: 452.615
• InChiKey: SFIIHXFAWBTTPH-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-[(Methanesulfonyl-methyl-amino)-methyl]-5-methyl-3-(piperidine-1-carbonyl)-hexanoic acid benzyl ester 在 palladium on activated charcoal N-甲基吗啉 、 甲酸 、 盐酸羟胺 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2R,3R)-2-[(Methanesulfonyl-methyl-amino)-methyl]-5-methyl-3-(piperidine-1-carbonyl)-hexanoic acid hydroxyamide
  参考文献：
  名称：

  The synthesis and biological evaluation of non-peptidic matrix metalloproteinase inhibitors

  摘要：

  Novel sulfonamide matrix metalloproteinase inhibitors of general formula (9) were synthesised by a route involving a stereoselective conjugate addition reaction. Enzyme selectivity was found to be dependant on the nature of the sulfonamide substituents. Compounds (9f, 9q) are potent selective collagenase inhibitors with good oral bioavailability. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00494-1
• 作为产物：
  描述：

  (2R,3R)-2-Isobutyl-3-methylaminomethyl-succinic acid 4-benzyl ester 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R)-2-[(Methanesulfonyl-methyl-amino)-methyl]-5-methyl-3-(piperidine-1-carbonyl)-hexanoic acid benzyl ester
  参考文献：
  名称：

  The synthesis and biological evaluation of non-peptidic matrix metalloproteinase inhibitors

  摘要：

  Novel sulfonamide matrix metalloproteinase inhibitors of general formula (9) were synthesised by a route involving a stereoselective conjugate addition reaction. Enzyme selectivity was found to be dependant on the nature of the sulfonamide substituents. Compounds (9f, 9q) are potent selective collagenase inhibitors with good oral bioavailability. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00494-1