(R)-3-(4-Methoxy-benzenesulfonyl)-1-methyl-6-oxo-hexahydro-pyrimidine-4-carboxylic acid hydroxyamide | 350697-43-7

• 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: (R)-3-(4-Methoxy-benzenesulfonyl)-1-methyl-6-oxo-hexahydro-pyrimidine-4-carboxylic acid hydroxyamide
• 英文别名: (4R)-Hexahydro-N-hydroxy-3-[(4-methoxyphenyl)sulfonyl]-1-methyl-6-oxo-4-pyrimidinecarboxamide；(4R)-N-hydroxy-3-(4-methoxyphenyl)sulfonyl-1-methyl-6-oxo-1,3-diazinane-4-carboxamide
• CAS: 350697-43-7
• 化学式: C₁₃H₁₇N₃O₆S
• 分子量: 343.36
• InChiKey: DRWHINQPSIPRHF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-2-(4-Methoxy-benzenesulfonylamino)-succinic acid 1-methyl ester 在 氢氧化钾 、 硫酸 、 羟胺 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-3-(4-Methoxy-benzenesulfonyl)-1-methyl-6-oxo-hexahydro-pyrimidine-4-carboxylic acid hydroxyamide
  参考文献：
  名称：

  Heterocycle-based MMP Inhibitors with P2′ Substituents

  摘要：

  Potent and selective inhibition of matrix metalloproteinases was demonstrated fur a series of sulfonamide-based hydroxamic acids. The design of the heterocyclic sulfonamides incorporates a six- or seven-member central ring with a P2 ' substituent that can be modified. Binding interactions of this substituent at the S2 ' site are believed to contribute to high inhibitory potency against stromelysin, collagenase-3 and gelatinases A and B, and to provide selectivity against collagenase-1 and matrilysin. An X-ray structure of a stromelysin-inhibitor complex was obtained to provide insights into the SAR and selectivity trends observed for the series. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00137-8

文献信息

• Heterocycle-based MMP Inhibitors with P2′ Substituents
  作者：Stanislaw Pikul、Kelly McDow Dunham、Neil G Almstead、Biswanath De、Michael G Natchus、Yetunde O Taiwo、Lisa E Williams、Barbara A Hynd、Lily C Hsieh、Michael J Janusz、Fei Gu、Glen E Mieling

  DOI：10.1016/s0960-894x(01)00137-8

  日期：2001.4

  Potent and selective inhibition of matrix metalloproteinases was demonstrated fur a series of sulfonamide-based hydroxamic acids. The design of the heterocyclic sulfonamides incorporates a six- or seven-member central ring with a P2 ' substituent that can be modified. Binding interactions of this substituent at the S2 ' site are believed to contribute to high inhibitory potency against stromelysin, collagenase-3 and gelatinases A and B, and to provide selectivity against collagenase-1 and matrilysin. An X-ray structure of a stromelysin-inhibitor complex was obtained to provide insights into the SAR and selectivity trends observed for the series. (C) 2001 Elsevier Science Ltd. All rights reserved.