4-(3-(2-trifluoromethyl)-phenylureido)-phenylacetic acid | 317356-45-9

• 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: 4-(3-(2-trifluoromethyl)-phenylureido)-phenylacetic acid
• 英文别名: 4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetic acid；[4-({[2-(Trifluoromethyl)phenyl]carbamoyl}amino)phenyl]acetic acid；2-[4-[[2-(trifluoromethyl)phenyl]carbamoylamino]phenyl]acetic acid
• CAS: 317356-45-9
• 化学式: C₁₆H₁₃F₃N₂O₃
• 分子量: 338.286
• InChiKey: VMJUBYSIBVIQQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3-(2-trifluoromethyl)-phenylureido)-phenylacetic acid 、 Methyl 3-(5-amino-2-hydroxyphenyl)propanoate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 以87%的产率得到methyl 3-[2-hydroxy-5-(2-{4-[3-(2-trifluoromethyl-phenyl)-ureido]-phenyl}-acetylamino)-phenyl]-propionate
  参考文献：
  名称：

  A graftable LDV peptidomimetic: Design, synthesis and application to a blood filtration membrane

  摘要：

  A graftable LDV (Leu-Asp-Val) peptidomimetic molecule (B-c) has been prepared from 3-(5-amino-2-hydroxy)phenylpropionic acid, as alpha(4)beta(1) (VLA-4) integrin ligand. For that purpose, the mechanism of 3-(4-azidophenyl)propionic acid rearrangement has been revisited. Activation of Durapore DVPP-hydrophilic membrane, by surface wet chemistry using triazine trifluoride, followed by covalent coupling of B-c produced a modified filter (0.8% of derivatisation from XPS analysis) with improved capacity of leukocyte retention. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.006
• 作为产物：
  描述：

  ethyl 4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetate 以 四氢呋喃 为溶剂， 以51%的产率得到4-(3-(2-trifluoromethyl)-phenylureido)-phenylacetic acid
  参考文献：
  名称：

  VLA-4 inhibitor compounds

  摘要：

  本发明公开了选择性抑制配体与α4β1整合素（VLA-4）结合的化合物及其制备方法。在一个实施例中，本发明的化合物由式I表示： 1 作为VLA-4介导的细胞粘附的选择性抑制剂，本发明的化合物可用于治疗与该粘附相关的疾病，包括但不限于炎症和自身免疫反应、糖尿病、哮喘、银屑病、炎症性肠病、移植排斥和肿瘤转移。还公开了包含式I化合物的药物组合物、抑制VLA-4介导的细胞粘附的方法以及治疗与VLA-4介导的细胞粘附相关疾病的方法。

  公开号：

  US20030078249A1

文献信息

• VLA-4 INHIBITOR COMPOUNDS
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：EP1189612A1

  公开（公告）日：2002-03-27
• EP1189612A4
  申请人：——

  公开号：EP1189612A4

  公开（公告）日：2005-02-16
• US6756378B2
  申请人：——

  公开号：US6756378B2

  公开（公告）日：2004-06-29
• US7179819B2
  申请人：——

  公开号：US7179819B2

  公开（公告）日：2007-02-20
• [EN] VLA-4 INHIBITOR COMPOUNDS<br/>[FR] COMPOSES INHIBITEURS DE VLA-4
  申请人：DAIICHI SEIYAKU CO

  公开号：WO2001000206A1

  公开（公告）日：2001-01-04

  Compounds that selectively inhibit the binding of ligands to α4β1 integrin (VLA-4) and methods for their preparation are disclosed. In one embodiment, compounds of the invention are represented by formula (I). As selective inhibitors of VLA-4 mediated cell adhesion, compounds of the present invention are useful in the treatment of conditions associated with such adhesion, including, but not limited to, such conditions as inflammatory and autoimmune responses, diabetes, asthma, psoriasis, inflammatory bowel disease, transplantation rejection, and tumor metastasis. Also disclosed are methods of inhibiting VLA-4 mediated cell adhesion and methods of treating conditions associated with LA-4 mediated cell adhesion.