4-(5-methyl-1H-benzo[d]imidazol-2-ylamino)benzoic acid | 1011268-87-3

• 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: 4-(5-methyl-1H-benzo[d]imidazol-2-ylamino)benzoic acid
• 英文别名: 4-[(6-methyl-1H-benzimidazol-2-yl)amino]benzoic acid
• CAS: 1011268-87-3
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: YIOKHASCPJGWFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 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 4-[(6-methyl-1H-benzimidazol-2-yl)amino]benzoate 在 lithium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 以74%的产率得到4-(5-methyl-1H-benzo[d]imidazol-2-ylamino)benzoic acid
  参考文献：
  名称：

  Selectively Targeting T- and B-Cell Lymphomas: A Benzothiazole Antagonist of α₄β₁ Integrin

  摘要：

  Current cancer chemotherapeutic agents clinically deployed today are designed to be indiscriminately cytotoxic, however. achieving selective targeting of cancer malignancies would allow for improved diagnostic and chemotherapeutic tools. Integrin alpha(4)beta(1), a heterodimeric cell surface receptor, is believed to have a low-affinity conformation in resting normal lymphocytes and an activated high-affinity conformation in cancerous cells, specifically T- and B-cell lymphomas. This highly attractive yet poorly understood receptor has been selectively targeted with the bisaryl urea peptidomimetic antagonist 1. However. concerns regarding its preliminary pharmacokinetic (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzothiazole moiety, resulting in an analogue with improved physicochemical properties, solubility, and kidney:tumor ratio while maintaining potency (6; IC50 = 53 pM). The results presented herein utilized heterocyclic and solid-phase chemistry, cell adhesion assay, and in vivo optical imaging using the cyanine dye Cy5.5 conjugate.

  DOI：

  10.1021/jm800313f

文献信息

• Selectively Targeting T- and B-Cell Lymphomas: A Benzothiazole Antagonist of α₄β₁ Integrin
  作者：Richard D. Carpenter、Mirela Andrei、Olulanu H. Aina、Edmond Y. Lau、Felice C. Lightstone、Ruiwu Liu、Kit S. Lam、Mark J. Kurth

  DOI：10.1021/jm800313f

  日期：2009.1.8

  Current cancer chemotherapeutic agents clinically deployed today are designed to be indiscriminately cytotoxic, however. achieving selective targeting of cancer malignancies would allow for improved diagnostic and chemotherapeutic tools. Integrin alpha(4)beta(1), a heterodimeric cell surface receptor, is believed to have a low-affinity conformation in resting normal lymphocytes and an activated high-affinity conformation in cancerous cells, specifically T- and B-cell lymphomas. This highly attractive yet poorly understood receptor has been selectively targeted with the bisaryl urea peptidomimetic antagonist 1. However. concerns regarding its preliminary pharmacokinetic (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzothiazole moiety, resulting in an analogue with improved physicochemical properties, solubility, and kidney:tumor ratio while maintaining potency (6; IC50 = 53 pM). The results presented herein utilized heterocyclic and solid-phase chemistry, cell adhesion assay, and in vivo optical imaging using the cyanine dye Cy5.5 conjugate.