{(R)-3-Benzyloxycarbamoyl-3-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-propyl}-carbamic acid benzyl ester | 849773-61-1

• 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-Benzyloxycarbamoyl-3-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-propyl}-carbamic acid benzyl ester
• CAS: 849773-61-1
• 化学式: C₃₄H₃₇N₃O₇S
• 分子量: 631.75
• InChiKey: OUGJYAUEYZOMEF-JGCGQSQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  45.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  123.27
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  {(R)-3-Benzyloxycarbamoyl-3-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-propyl}-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 (R)-4-Amino-2-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-N-hydroxy-butyramide
  参考文献：
  名称：

  N-i-Propoxy-N-biphenylsulfonylaminobutylhydroxamic acids as potent and selective inhibitors of MMP-2 and MT1-MMP

  摘要：

  Structural manipulation of the pharmacophoric model of type A selective MMP inhibitors (MMPi), obtained by the insertion of some alkyl substituents R-2 possessing an appropriate geometry, steric bulkiness and lipophilicity, is able to improve potency, in the subnanomolar range on MMP-2, and to give a good MMP inhibition on MMP-14 (MT1-MMP) in the designed MMPi of type C, while maintaining a good MMP-1/MMP-2 selectivity profile. The simultaneous inhibition of these two enzymes yields type C compounds, which are potent antiangiogenic agents, able to block a chemoinvasion model on HUVEC cells in the micromolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.024
• 作为产物：
  描述：

  (R)-tert-butyl 8-(biphenyl-4-ylsulfonyl)-10-methyl-3-oxo-1-phenyl-2,9-dioxa-4,8-diazaundecane-7-carboxylate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 {(R)-3-Benzyloxycarbamoyl-3-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-propyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  N-i-Propoxy-N-biphenylsulfonylaminobutylhydroxamic acids as potent and selective inhibitors of MMP-2 and MT1-MMP

  摘要：

  Structural manipulation of the pharmacophoric model of type A selective MMP inhibitors (MMPi), obtained by the insertion of some alkyl substituents R-2 possessing an appropriate geometry, steric bulkiness and lipophilicity, is able to improve potency, in the subnanomolar range on MMP-2, and to give a good MMP inhibition on MMP-14 (MT1-MMP) in the designed MMPi of type C, while maintaining a good MMP-1/MMP-2 selectivity profile. The simultaneous inhibition of these two enzymes yields type C compounds, which are potent antiangiogenic agents, able to block a chemoinvasion model on HUVEC cells in the micromolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.024