({2-[4-(2-guanidinoethyl)[1,2,3]triazol-1-yl]acetyl}phenylamino)-acetic acid hydrochloride | 1243153-84-5

• 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: ({2-[4-(2-guanidinoethyl)[1,2,3]triazol-1-yl]acetyl}phenylamino)-acetic acid hydrochloride
• 英文别名: 2-(N-[2-[4-[2-(diaminomethylideneamino)ethyl]triazol-1-yl]acetyl]anilino)acetic acid;hydrochloride
• CAS: 1243153-84-5
• 化学式: C₁₅H₁₉N₇O₃*ClH
• 分子量: 381.822
• InChiKey: QRJJXGXBJSYGKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  153
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 反应 16.0h， 生成 ({2-[4-(2-guanidinoethyl)[1,2,3]triazol-1-yl]acetyl}phenylamino)-acetic acid hydrochloride
  参考文献：
  名称：

  Click-Chemistry-Derived Triazole Ligands of Arginine−Glycine−Aspartate (RGD) Integrins with a Broad Capacity To Inhibit Adhesion of Melanoma Cells and Both in Vitro and in Vivo Angiogenesis

  摘要：

  A click chemistry approach was applied for the discovery of triazole-based arginine-glycine-aspartate (RGD) mimetics by Cu(1)-catalyzed 1,3-dipolar alkyne azide coupling reaction, which showed binding all properties toward alpha(v)beta(3)/alpha(v)beta(5) integrins. Biological assays showed compound 18 capable of binding alpha(v)beta(3) integrin with nanomolar affinity according, to a two-sites model, and molecular modeling studies revealed a peculiar pi-stacking interaction between the triazole ring and Tyr178 side chain. Accordingly, compound 18 inhibited the adhesion of integrin-expressing human melanoma cells to RGD-containing proteins of the extracellular matrix, such as vitronectin, fibronectin, and osteopontin. and also angiogenesis in in vitro and in vivo experimental models. The relevant biological effects exerted by compound 18 suggest its potential application as an antiangiogenic agent in the diagnosis and therapy of tumors where alpha(v)beta(3) integrin expression is up-regulated.

  DOI：

  10.1021/jm100754z