ethyl (R)-3-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(2-(3-hydroxy-5-((1,4,5,6-tetrahydropyrimidin-2-yl)amino)benzamido)acetamido)propanoate | 951308-32-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: ethyl (R)-3-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(2-(3-hydroxy-5-((1,4,5,6-tetrahydropyrimidin-2-yl)amino)benzamido)acetamido)propanoate
• CAS: 951308-32-0
• 化学式: C₂₄H₂₇BrClN₅O₆
• 分子量: 596.865
• InChiKey: XLUNWDIIQKVCSM-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  161.38
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl (R)-3-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(2-(3-hydroxy-5-((1,4,5,6-tetrahydropyrimidin-2-yl)amino)benzamido)acetamido)propanoate 在 lithium hydroxide 、 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 (R)-3-bromo-5-chloro-2-hydroxy-β-[[2-[[[3-hydroxy-5-[(1,4,5,6-tetrahydropyrimidin-2-yl)amino]phenyl]carbonyl]amino]acetyl]amino]benzenepropionic acid trifluoroacetate salt
  参考文献：
  名称：

  [EN] THE R-ISOMER OF BETA AMINO ACID COMPOUNDS AS INTEGRIN RECEPTOR ANTAGONISTS DERIVATIVES
  [FR] ISOMERE R DE COMPOSES D'ACIDES AMINES BETA EN TANT QUE DERIVES ANTAGONISTES DU RECEPTEUR DES INTEGRINES

  摘要：

  本发明涉及一类由公式(I)表示的化合物或其药用可接受的盐，包含公式(I)化合物的药物组合物，以及在不显著抑制αVβ6整合素的情况下选择性抑制或拮抗αVβ3和/或αVβ5整合素的方法。

  公开号：

  WO2004060376A1
• 作为产物：
  描述：

  3-氨基-5-羟基苯甲酸 在 sodium methylate 、 1-羟基苯并三唑 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 53.5h， 生成 ethyl (R)-3-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(2-(3-hydroxy-5-((1,4,5,6-tetrahydropyrimidin-2-yl)amino)benzamido)acetamido)propanoate
  参考文献：
  名称：

  R-Isomers of Arg-Gly-Asp (RGD) mimics as potent αvβ3 inhibitors

  摘要：

  The integrin alpha(v)beta(3), vitronectin receptor, is expressed in a number of cell types and has been shown to mediate adhesion of osteoclasts to bone matrix, vascular smooth muscle cell migration, and angiogenesis. We recently disclosed the discovery of a tripeptide Arg-Gly-Asp (RGD) mimic, which has been shown to be a potent inhibitor of the integrin alpha(v)beta(3) and has excellent anti-angiogenic properties including its suppression of tumor growth in animal models. In other investigations involving RGD mimics, only compounds containing the S-isomers of the beta-amino acids have been shown to be potent. We were surprised to find the potencies of analogs containing enantiomerically pure S-isomers of beta-amino acids which were only marginally better than the corresponding racemic mixtures. We therefore synthesized RGD mimics containing R-isomers of beta-amino acids and found them to be relatively potent inhibitors of alpha(v)beta(3). One of the compounds was examined in tumor models in mice and has been shown to significantly reduce the rate of growth and the size of tumors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.034