2-(4-(1H-benzo[d]imidazol-2-ylamino)phenyl)acetic acid | 917763-67-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(4-(1H-benzo[d]imidazol-2-ylamino)phenyl)acetic acid
• 英文别名: {4-[(1H-Benzimidazol-2-yl)amino]phenyl}acetic acid；2-[4-(1H-benzimidazol-2-ylamino)phenyl]acetic acid
• CAS: 917763-67-8
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: MBKKBGPJQYJLRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-[4-(1H-benzimidazol-2-ylamino)phenyl]acetate 在 lithium hydroxide 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以4.82 g的产率得到2-(4-(1H-benzo[d]imidazol-2-ylamino)phenyl)acetic acid
  参考文献：
  名称：

  Highly Potent, Water Soluble Benzimidazole Antagonist for Activated α₄β₁ Integrin

  摘要：

  The cell surface receptor alpha(4)beta(1), integrin, activated constitutively in lymphoma, can be targeted with the bisaryl urea peptidomimetic antagonist 1 (LLP2A). However, concerns on its preliminary pharmacokinetc (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzimidazole moiety, resulting in improved solubility while maintaining picomolar potency [5 (KLCA4); IC50 = 305 pM]. With exceptional solubility, this finding has the potential for improving PK to help diagnose and treat lymphomas.

  DOI：

  10.1021/jm070790o

文献信息

• Heterocyclic Ligands for Integrin Imaging and Therapy
  申请人：Carpenter Richard D.

  公开号：US20100310455A1

  公开（公告）日：2010-12-09

  The present invention provides α 4 β 1 integrin ligands that display high binding affinity, specificity, and stability. The ligands comprise a peptide having n independently selected amino acids, wherein at least one amino acid is an unnatural amino acid or a D-amino acid, and wherein n is an integer of from 3 to 20. Methods are provided for administering the ligands for treating cancer, inflammatory diseases, and autoimmune diseases. Also provided are methods for administering the ligands for imaging a tumor, organ, or tissue in a subject.
• US8486370B2
  申请人：——

  公开号：US8486370B2

  公开（公告）日：2013-07-16
• [EN] HETEROCYCLIC LIGANDS FOR INTEGRIN IMAGING AND THERAPY<br/>[FR] LIGANDS HÉTÉROCYCLIQUES D'INTÉGRINE, IMAGERIE ET THÉRAPIE
  申请人：UNIV CALIFORNIA

  公开号：WO2008031016A2

  公开（公告）日：2008-03-13

  [EN] The present invention provides a ₄ß₁ integrin ligands that display high binding affinity, specificity, and stability. The ligands comprise a peptide having n independently selected amino acids, wherein at least one amino acid is an unnatural amino acid or a D-amino acid, and wherein n is an integer of from 3 to 20. Methods are provided for administering the ligands for treating cancer, inflammatory diseases, and autoimmune diseases. Also provided are methods for administering the ligands for imaging a tumor, organ, or tissue in a subject.
  [FR] La présente invention fournit des ligands d'intégrine ₄b₁ affichant une affinité, une spécificité et une stabilité de liaison élevées. Les ligands comprennent un peptide ayant n acides aminés sélectionnés indépendamment, au moins un acide aminé étant un acide aminé non naturel ou un acide aminé D, et n étant un entier de 3 à 20. Des procédés sont fournis pour administrer les ligands pour traiter le cancer, des maladies inflammatoires et des maladies auto-immunes. Des procédés sont également fournis pour administrer les ligands pour visualiser une tumeur, un organe, ou un tissu chez un sujet.
• Highly Potent, Water Soluble Benzimidazole Antagonist for Activated α₄β₁ Integrin
  作者：Richard D. Carpenter、Mirela Andrei、Edmond Y. Lau、Felice C. Lightstone、Ruiwu Liu、Kit S. Lam、Mark J. Kurth

  DOI：10.1021/jm070790o

  日期：2007.11.1

  The cell surface receptor alpha(4)beta(1), integrin, activated constitutively in lymphoma, can be targeted with the bisaryl urea peptidomimetic antagonist 1 (LLP2A). However, concerns on its preliminary pharmacokinetc (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzimidazole moiety, resulting in improved solubility while maintaining picomolar potency [5 (KLCA4); IC50 = 305 pM]. With exceptional solubility, this finding has the potential for improving PK to help diagnose and treat lymphomas.