t-butyl O-[2-(2-(2-(N-t-butoxycarbonyl)-2-aminoethoxy)ethoxy)ethyl]-meta-amino-N-[3-(trifluoromethyl)phenylsulfonyl]-L-tyrosinate | 798567-51-8

• 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: t-butyl O-[2-(2-(2-(N-t-butoxycarbonyl)-2-aminoethoxy)ethoxy)ethyl]-meta-amino-N-[3-(trifluoromethyl)phenylsulfonyl]-L-tyrosinate
• CAS: 798567-51-8
• 化学式: C₃₁H₄₄F₃N₃O₉S
• 分子量: 691.766
• InChiKey: NSQPKDQDJIZBMI-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  47.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  164.51
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-(N,N'-bis{[(2-methyl-2-propanyl)oxy]carbonyl}carbamimidoyl)-4-piperidinecarboxylic acid 、 t-butyl O-[2-(2-(2-(N-t-butoxycarbonyl)-2-aminoethoxy)ethoxy)ethyl]-meta-amino-N-[3-(trifluoromethyl)phenylsulfonyl]-L-tyrosinate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium 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 48.0h， 以42%的产率得到
  参考文献：
  名称：

  Novel RGD-like molecules based on the tyrosine template: design, synthesis, and biological evaluation on isolated integrins αVβ3/αIIbβ3 and in cellular adhesion tests

  摘要：

  RGD (Arg-Gly-Asp) peptidomimetics have been designed for covalent anchorage on biomaterials. The tyrosine template was thus equipped with (i) a basic side chain of various flexibility, (ii) an acidic side chain, which incorporated the XPS fluorine tag, and (iii) a spacer-arm terminated by a primary amine for surface grafting. The most active compounds showed IC50 values in the nanomolar range versus isolated human integrins alpha(v)beta(3) and alpha(IIb)beta(3). Preincubation of CaCo2 cells with soluble peptidomimetics (2 and 19a) prevented cellular adhesion on culture plates coated with vitronectin. On the other hand, peptidomimetics (19a and 19b) immobilized on a poly(ethylene)terephthalate membrane (PET) promoted CaCo2 cells adhesion. A modeling study at the ab initio level in MINI-1' basis allowed to compare the various synthetic ligands of integrins and to propose novel pharmacophore structures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.055
• 作为产物：
  描述：

  t-butyl N-[3-(trifluoromethyl)phenylsulfonyl]-L-tyrosinate 在 platinum(IV) oxide 偶氮二甲酸二异丙酯 、 氢气 、 硝酸 、 溶剂黄146 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 16.0~20.0 ℃ 、275.79 kPa 条件下， 反应 38.0h， 生成 t-butyl O-[2-(2-(2-(N-t-butoxycarbonyl)-2-aminoethoxy)ethoxy)ethyl]-meta-amino-N-[3-(trifluoromethyl)phenylsulfonyl]-L-tyrosinate
  参考文献：
  名称：

  Novel RGD-like molecules based on the tyrosine template: design, synthesis, and biological evaluation on isolated integrins αVβ3/αIIbβ3 and in cellular adhesion tests

  摘要：

  RGD (Arg-Gly-Asp) peptidomimetics have been designed for covalent anchorage on biomaterials. The tyrosine template was thus equipped with (i) a basic side chain of various flexibility, (ii) an acidic side chain, which incorporated the XPS fluorine tag, and (iii) a spacer-arm terminated by a primary amine for surface grafting. The most active compounds showed IC50 values in the nanomolar range versus isolated human integrins alpha(v)beta(3) and alpha(IIb)beta(3). Preincubation of CaCo2 cells with soluble peptidomimetics (2 and 19a) prevented cellular adhesion on culture plates coated with vitronectin. On the other hand, peptidomimetics (19a and 19b) immobilized on a poly(ethylene)terephthalate membrane (PET) promoted CaCo2 cells adhesion. A modeling study at the ab initio level in MINI-1' basis allowed to compare the various synthetic ligands of integrins and to propose novel pharmacophore structures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.055