(S)-tert-butyl 2-(2-bromoacetamido)-3-phenylpropanoate

• 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: (S)-tert-butyl 2-(2-bromoacetamido)-3-phenylpropanoate
• 英文别名: tert-butyl (2S)-2-[(2-bromoacetyl)amino]-3-phenylpropanoate
• 化学式: C₁₅H₂₀BrNO₃
• 分子量: 342.233
• InChiKey: WQSWSVVCDMUPRV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-(2-bromoacetamido)-3-phenylpropanoate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以1.31 g的产率得到(3S)-(2-azido-acetylamino)-3-phenyl-propionic acid tert-butyl ester
  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
• 作为产物：
  描述：

  L-苯基丙氨酸叔丁酯 、 溴乙酰溴 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-tert-butyl 2-(2-bromoacetamido)-3-phenylpropanoate
  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

文献信息

• Amide forming chemical ligation
  申请人：Bode W. Jeffrey

  公开号：US20070060773A1

  公开（公告）日：2007-03-15

  An amide is formed by reacting an α-ketoacid or salt thereof in a decarboxylative condensation reaction with an amine or salt thereof comprising a nitrogen covalently bound to an atom selected from oxygen, nitrogen, and sulfur. The amide bond is formed between the α-carbon of the ketoacid and the nitrogen of the amine. The α-ketoacid can be formed using a novel sulfur reagent.

  酰胺是通过将α-酮酸或其盐与含有氮原子与氧、氮、硫原子中选择的一个原子共价结合的胺或其盐在脱羧缩合反应中反应而形成的。酰胺键形成在酮酸的α-碳和胺的氮之间。α-酮酸可以使用一种新型硫试剂来形成。
• Amide Forming Chemical Ligation
  申请人：Bode Jeffrey W.

  公开号：US20090069536A1

  公开（公告）日：2009-03-12

  An amide is formed by reacting an α-ketoacid or salt thereof in a decarboxylative condensation reaction with an amine or salt thereof comprising a nitrogen covalently bound to an atom selected from oxygen, nitrogen, and sulfur. The amide bond is formed between the α-carbon of the ketoacid and the nitrogen of the amine. The α-ketoacid can be formed using a novel sulfur reagent.
• US7737293B2
  申请人：——

  公开号：US7737293B2

  公开（公告）日：2010-06-15
• US7667076B2
  申请人：——

  公开号：US7667076B2

  公开（公告）日：2010-02-23
• 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
  作者：Andrea Trabocchi、Gloria Menchi、Nicoletta Cini、Francesca Bianchini、Silvia Raspanti、Anna Bottoncetti、Alberto Pupi、Lido Calorini、Antonio Guarna

  DOI：10.1021/jm100754z

  日期：2010.10.14

  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.