3-amino-3-[3,5-dibromophenyl]propanoic acid | 773125-62-5

• 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: 3-amino-3-[3,5-dibromophenyl]propanoic acid
• 英文别名: 3-Amino-3-(3,5-dibromophenyl)propanoic acid
• CAS: 773125-62-5
• 化学式: C₉H₉Br₂NO₂
• 分子量: 322.984
• InChiKey: BGOZWRSTHRDJSS-UHFFFAOYSA-N

物化性质

• 沸点：
  417.7±45.0 °C(Predicted)
• 密度：
  1.897±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-3-[3,5-dibromophenyl]propanoic acid 在 N-甲基吗啉 、 盐酸 、 immobilized Pseudomonas cepacia lipase 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 25.0h， 生成
  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
• 作为产物：
  描述：

  丙二酸 、 3,5-二溴苯甲醛 在 ammonium acetate 作用下， 以 异丙醇 为溶剂， 反应 14.0h， 以32.2 g的产率得到3-amino-3-[3,5-dibromophenyl]propanoic acid
  参考文献：
  名称：

  [EN] META-AZACYCLIC AMINO BENZOIC ACID DERIVATIVES AS PAN INTEGRIN ANTAGONISTS
  [FR] DÉRIVÉS D'ACIDE AMINOBENZOÏQUE MÉTA-AZACYCLIQUE À TITRE D'ANTAGONISTES DE PAN-INTÉGRINE

  摘要：

  本公开提供了以下公式的药物代理：其中变量在此处定义。还提供了包含这种药物代理的药物组合物、工具包和制造品。还提供了使用这种药物代理治疗各种疾病和疾病的方法。

  公开号：

  WO2017117538A1

文献信息

• META-AZACYCLIC AMINO BENZOIC ACID DERIVATIVES AS PAN INTEGRIN ANTAGONISTS WITH IMPROVED PHARMACOKINETIC PROPERTIES AND METHODS FOR THEIR MANUFACTURE
  申请人：Saint Louis University

  公开号：EP3738953A1

  公开（公告）日：2020-11-18

  The present disclosure provides pharmaceutical agents of the formula: wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such pharmaceutical agents. Methods of using the pharmaceutical agents for the treatment of a variety of diseases and disorders are also provided.

  本公开提供了式中的药剂： 其中的变量在此定义。还提供了包含此类药剂的药物组合物、试剂盒和制造品。还提供了使用这些药剂治疗各种疾病和失调的方法。
• Meta-azacyclic amino benzoic acid derivatives as pan integrin antagonists
  申请人：Saint Louis University

  公开号：US10035778B2

  公开（公告）日：2018-07-31

  The present disclosure provides pharmaceutical agents of the formula: wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such pharmaceutical agents. Methods of using the pharmaceutical agents for the treatment of a variety of diseases and disorders are also provided.

  本公开提供了式中的药剂： 其中的变量在此定义。此外，还提供了包含此类药剂的药物组合物、试剂盒和制成品。还提供了使用这些药剂治疗各种疾病和失调的方法。
• META-AZACYCLIC AMINO BENZOIC ACID DERIVATIVES AS PAN INTEGRIN ANTAGONISTS
  申请人：Saint Louis University

  公开号：EP3294716A1

  公开（公告）日：2018-03-21