3R-[2,2-Dimethyl-1S-(methylcarbamoyl)propylcarbamoyl]-5-methyl-2S-(1-methyl piperidin-4-yl)hexanoic acid | 191613-74-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3R-[2,2-Dimethyl-1S-(methylcarbamoyl)propylcarbamoyl]-5-methyl-2S-(1-methyl piperidin-4-yl)hexanoic acid
• 英文别名: (2S,3R)-3-[[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]carbamoyl]-5-methyl-2-(1-methylpiperidin-4-yl)hexanoic acid
• CAS: 191613-74-8
• 化学式: C₂₁H₃₉N₃O₄
• 分子量: 397.558
• InChiKey: BOTHQQKCHFOJKQ-IXDOHACOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  98.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3R-[2,2-Dimethyl-1S-(methylcarbamoyl)propylcarbamoyl]-5-methyl-2S-(1-methyl piperidin-4-yl)hexanoic acid 在 N-甲基吗啉 、 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 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3S)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N'-hydroxy-3-(1-methylpiperidin-4-yl)-2-(2-methylpropyl)butanediamide
  参考文献：
  名称：

  The synthesis of novel matrix metalloproteinase inhibitors employing the Ireland-Claisen rearrangement

  摘要：

  Matrix metalloproteinase inhibitors of general formula (1) were synthesised by a route involving an Ireland-Claisen rearrangement which enables systematic modification of the substituent alpha to the hydroxamic acid. An analogue (12c) possessing an alpha-cyclopentyl group is a potent broad spectrum inhibitor that displays high and sustained blood levels following oral dosing in both the rat and marmoset ex-vivo bioassays. This compound and analogues are also potent inhibitors of TNF alpha release. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00218-2
• 作为产物：
  描述：

  L-叔亮氨酸甲酰胺 在 palladium on activated charcoal 氢气 、 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 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 3R-[2,2-Dimethyl-1S-(methylcarbamoyl)propylcarbamoyl]-5-methyl-2S-(1-methyl piperidin-4-yl)hexanoic acid
  参考文献：
  名称：

  The synthesis of novel matrix metalloproteinase inhibitors employing the Ireland-Claisen rearrangement

  摘要：

  Matrix metalloproteinase inhibitors of general formula (1) were synthesised by a route involving an Ireland-Claisen rearrangement which enables systematic modification of the substituent alpha to the hydroxamic acid. An analogue (12c) possessing an alpha-cyclopentyl group is a potent broad spectrum inhibitor that displays high and sustained blood levels following oral dosing in both the rat and marmoset ex-vivo bioassays. This compound and analogues are also potent inhibitors of TNF alpha release. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00218-2

文献信息

• The synthesis of novel matrix metalloproteinase inhibitors employing the Ireland-Claisen rearrangement
  作者：Lisa M Pratt、R.Paul Beckett、Claire L Bellamy、Dominic J Corkill、Judy Cossins、Paul F Courtney、Stephen J Davies、Alan H Davidson、Alan H Drummond、Karen Helfrich、Christopher N Lewis、Matthew Mangan、Fionna M Martin、Karen Miller、Prakash Nayee、Michelle L Ricketts、Wayne Thomas、Richard S Todd、Mark Whittaker

  DOI：10.1016/s0960-894x(98)00218-2

  日期：1998.6

  Matrix metalloproteinase inhibitors of general formula (1) were synthesised by a route involving an Ireland-Claisen rearrangement which enables systematic modification of the substituent alpha to the hydroxamic acid. An analogue (12c) possessing an alpha-cyclopentyl group is a potent broad spectrum inhibitor that displays high and sustained blood levels following oral dosing in both the rat and marmoset ex-vivo bioassays. This compound and analogues are also potent inhibitors of TNF alpha release. (C) 1998 Elsevier Science Ltd. All rights reserved.