(R)-2-[(Biphenyl-4-sulfonyl)-isopropoxy-amino]-4-{4-[3-(3-{(R)-3-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-3-carboxy-propylcarbamoyl}-propylcarbamoyl)-benzoylamino]-butyrylamino}-butyric acid | 853755-40-5

• 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: (R)-2-[(Biphenyl-4-sulfonyl)-isopropoxy-amino]-4-{4-[3-(3-{(R)-3-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-3-carboxy-propylcarbamoyl}-propylcarbamoyl)-benzoylamino]-butyrylamino}-butyric acid
• CAS: 853755-40-5
• 化学式: C₅₄H₆₄N₆O₁₄S₂
• 分子量: 1085.27
• InChiKey: QNTFHUNNQAFDBU-URZIEALYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  76.0
• 可旋转键数：
  30.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  284.22
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[(Biphenyl-4-sulfonyl)-isopropoxy-amino]-4-{4-[3-(3-{(R)-3-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-3-carboxy-propylcarbamoyl}-propylcarbamoyl)-benzoylamino]-butyrylamino}-butyric acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N,N'-Bis(4-{[(3r)-3-[(Biphenyl-4-Ylsulfonyl)(Propan-2-Yloxy)amino]-4-(Hydroxyamino)-4-Oxobutyl]amino}-4-Oxobutyl)benzene-1,3-Dicarboxamide
  参考文献：
  名称：

  A new development of matrix metalloproteinase inhibitors: twin hydroxamic acids as potent inhibitors of MMPs

  摘要：

  Starting from the observation that the CbzNH(CH2)(2) side chain of the potent MMP-2/MMP-14 inhibitor, benzyl-(3R)-4-(hydroxyamino)-3-[isopropoxy(1,1'-biphenyl-4yl-sulfonyl)amino]-4-oxobutylcarbamate, (R)-1 lies in a hydrophobic region (S1) exposed to the solvent of the protease active site, we hypothesized that an aminoethylcarboxamido chain structurally related to that of (R)-1 might be an useful tool to bind another linker stretching out from the protein. This would be able to interact either with a enzyme region adjacent to the active site, or with other molecules of matrix metalloproteinases (MMPs), or other proteins of the extracellular matrix (ECM) that may be involved in the enzyme activation. On these basis we describe new dimeric compounds of type 2, twin hydroxamic acids, obtained by the joint of two drug entities of (R)-1 linked in PI by extendable semirigid linkers. Type 2 compounds are potentially able to undergo more complex inhibitor enzyme interactions than those occurring with monomeric compounds of type 1, thus influencing positively the potency, selectivity and/or cytotoxicity of the new compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.002
• 作为产物：
  描述：

  4-[3-(3-Chlorocarbonyl-propylcarbamoyl)-benzoylamino]-butyryl chloride 在 N-甲基吗啉 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-2-[(Biphenyl-4-sulfonyl)-isopropoxy-amino]-4-{4-[3-(3-{(R)-3-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-3-carboxy-propylcarbamoyl}-propylcarbamoyl)-benzoylamino]-butyrylamino}-butyric acid
  参考文献：
  名称：

  A new development of matrix metalloproteinase inhibitors: twin hydroxamic acids as potent inhibitors of MMPs

  摘要：

  Starting from the observation that the CbzNH(CH2)(2) side chain of the potent MMP-2/MMP-14 inhibitor, benzyl-(3R)-4-(hydroxyamino)-3-[isopropoxy(1,1'-biphenyl-4yl-sulfonyl)amino]-4-oxobutylcarbamate, (R)-1 lies in a hydrophobic region (S1) exposed to the solvent of the protease active site, we hypothesized that an aminoethylcarboxamido chain structurally related to that of (R)-1 might be an useful tool to bind another linker stretching out from the protein. This would be able to interact either with a enzyme region adjacent to the active site, or with other molecules of matrix metalloproteinases (MMPs), or other proteins of the extracellular matrix (ECM) that may be involved in the enzyme activation. On these basis we describe new dimeric compounds of type 2, twin hydroxamic acids, obtained by the joint of two drug entities of (R)-1 linked in PI by extendable semirigid linkers. Type 2 compounds are potentially able to undergo more complex inhibitor enzyme interactions than those occurring with monomeric compounds of type 1, thus influencing positively the potency, selectivity and/or cytotoxicity of the new compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.002