4-[[3-(3-Carboxypropylcarbamoyl)benzoyl]amino]butanoic acid | 853755-35-8

• 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: 4-[[3-(3-Carboxypropylcarbamoyl)benzoyl]amino]butanoic acid
• CAS: 853755-35-8
• 化学式: C₁₆H₂₀N₂O₆
• 分子量: 336.345
• InChiKey: UJILDELNQBKFJB-UHFFFAOYSA-N

物化性质

• 沸点：
  734.3±55.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[[3-(3-Carboxypropylcarbamoyl)benzoyl]amino]butanoic acid 在 N-甲基吗啉 、 草酰氯 、 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 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 N1,N3-bis((R)-7-(N-isopropoxy-[1,1'-biphenyl]-4-sulfonamido)-2,2,3,3-tetramethyl-6,11-dioxo-4-oxa-5,10-diaza-3-silatetradecan-14-yl)isophthalamide
  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：

  间苯二甲酰氯 、 4-氨基丁酸 在 sodium hydroxide 作用下， 生成 4-[[3-(3-Carboxypropylcarbamoyl)benzoyl]amino]butanoic acid
  参考文献：
  名称：

  低聚胺的血小板聚集抑制和抗凝作用，XVIII：具有荧光特性的低聚胺，B 部分：分子外围的荧光团

  摘要：

  已经合成了 17 种具有荧光特性的 N, N' - 苯 - 1,3 - 二甲烷和九种 N, N ', N ' - 苯 - 1,3,5 - 三甲烷衍生物。其中三个在 <10 μmol / L 的浓度下显示出抗血小板活性（诱导剂胶原蛋白，IC50 Born 测试）。它们适用于与生物大分子以及合成和生物膜的相互作用研究。构效关系表明杂多环荧光团，即喹啉、二苯并呋喃或咔唑是实现此目的的有利替代品。

  DOI：

  10.1002/ardp.19943270611

文献信息

• DIAGNOSTIC AGENTS SELECTIVE AGAINST METALLOPROTEASES
  申请人：Bracco Imaging S.p.A.

  公开号：EP2320954B1

  公开（公告）日：2019-09-04
• Platelet Aggregation Inhibiting and Anticoagulant Effects of Oligoamines, XVIII: Oligoamines with Fluorescent Properties, Part B: Fluorophores in the Molecular Periphery
  作者：K. Rehse、T. Seidel

  DOI：10.1002/ardp.19943270611

  日期：——

  Seventeen N,N′‐benzene‐1,3‐dimethane and nine N,N′,N″‐benzene‐1,3,5‐trimethane derivatives with fluorescent properties have been synthesized. Three of them show antiplatelet activities (inducer collagen, IC50 Born‐test) in concentrations < 10 μmol/L. They are suitable for interaction studies with biological macromolecules and synthetical and biological membranes. Structure activity relationships demonstrate

  已经合成了 17 种具有荧光特性的 N, N' - 苯 - 1,3 - 二甲烷和九种 N, N ', N ' - 苯 - 1,3,5 - 三甲烷衍生物。其中三个在 <10 μmol / L 的浓度下显示出抗血小板活性（诱导剂胶原蛋白，IC50 Born 测试）。它们适用于与生物大分子以及合成和生物膜的相互作用研究。构效关系表明杂多环荧光团，即喹啉、二苯并呋喃或咔唑是实现此目的的有利替代品。
• A new development of matrix metalloproteinase inhibitors: twin hydroxamic acids as potent inhibitors of MMPs
  作者：Armando Rossello、Elisa Nuti、Maria Pia Catalani、Paolo Carelli、Elisabetta Orlandini、Simona Rapposelli、Tiziano Tuccinardi、Susan J. Atkinson、Gillian Murphy、Aldo Balsamo

  DOI：10.1016/j.bmcl.2005.03.002

  日期：2005.5

  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.