2-(4'-Carboxyanilin)-benzoxazol | 20852-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-(4'-Carboxyanilin)-benzoxazol
• 英文别名: N-(2-Benzoxazolyl)-p-aminobenzoic acid；4-(benzo[d]oxazol-2-ylamino)benzoic acid；4-benzooxazol-2-ylamino-benzoic acid；2-(4-carboxyanilino)benzoxazole；4-(2-Benzoxazolylamino)benzoic acid；4-(1,3-benzoxazol-2-ylamino)benzoic acid
• CAS: 20852-35-1
• 化学式: C₁₄H₁₀N₂O₃
• mdl: MFCD00598641
• 分子量: 254.245
• InChiKey: LNIYQPFVNDECDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  、 2-(4'-Carboxyanilin)-benzoxazol 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成
  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
• 作为产物：
  描述：

  2-氯苯并恶唑 在 sodium hydroxide 作用下， 生成 2-(4'-Carboxyanilin)-benzoxazol
  参考文献：
  名称：

  潜在的抗肿瘤药：N-（2-苯并恶唑基）氨基酸酯

  摘要：

  描述了由氨基酸和酯与2-氯苯并恶唑或2-苯并恶唑啉酮反应制备N-（2-苯并恶唑基）氨基酸和酯的研究。

  DOI：

  10.1002/jps.2600571013

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.
• VARMA R., CURR. SCI. (INDIA) <CUSC-AM>, 1976, 45, NO 2, 53-54
  作者：VARMA R.

  DOI：——

  日期：——
• 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.
• US4088770A
  申请人：——

  公开号：US4088770A

  公开（公告）日：1978-05-09
• US4275210A
  申请人：——

  公开号：US4275210A

  公开（公告）日：1981-06-23