tert-butyl (2S)-3-[4-[3-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]propoxy]-3-nitrophenyl]-2-[[3-(trifluoromethyl)phenyl]sulfonylamino]propanoate | 1197191-47-1

• 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: tert-butyl (2S)-3-[4-[3-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]propoxy]-3-nitrophenyl]-2-[[3-(trifluoromethyl)phenyl]sulfonylamino]propanoate
• CAS: 1197191-47-1
• 化学式: C₃₄H₄₆F₃N₅O₁₁S
• 分子量: 789.827
• InChiKey: OCDGXPZARNXNNJ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  225
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-3-[4-[3-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]propoxy]-3-nitrophenyl]-2-[[3-(trifluoromethyl)phenyl]sulfonylamino]propanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 18.0h， 以88%的产率得到tert-butyl (2S)-3-[3-amino-4-[3-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]propoxy]phenyl]-2-[[3-(trifluoromethyl)phenyl]sulfonylamino]propanoate
  参考文献：
  名称：

  α_vβ₃ Integrin-Targeting Arg-Gly-Asp (RGD) Peptidomimetics Containing Oligoethylene Glycol (OEG) Spacers

  摘要：

  RGD peptides are used in biomaterials science for surface modifications with a view to elicit selective cellular responses. Our objective is to replace peptides by small peptidomimetics acting similarly. We designed novel molecules targeting alpha(v)beta(3) integrin and featuring spacer-arms (for surface grafting), which do not disturb the biological activity, from (L) N-(3-(trifluoromethyl)benzenesulfonyl) tyrosine used as scaffold. Various Arg-mimics were fixed on the phenol function, and the ortho position was used for the Coupling of OEG spacers. All peptidomimetics were active in the nM range in a binding test toward human alpha(v)beta(3) integrin (IC50 = 0.1 to 1.7 nM) and selective versus platelet integrin alpha(IIb)beta(3) Selected compounds revealed excellent ability to inhibit bone cells adhesion on vitronectin. Modeling and docking studies were performed for comparing the most active RGD peptidomimetic to cilengitide, i.e., cyclo-[RGDfN(Me)V]-. Lastly, the adhesion of endothelial cells on a cultivation support grafted with RGD peptidomimetics was significantly improved.

  DOI：

  10.1021/jm901133z
• 作为产物：
  描述：

  (S)-t-butyl 3-(4-(3-aminopropoxy)-3-nitrophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propanoate 、 N,N′-二-Boc-硫脲 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以66%的产率得到tert-butyl (2S)-3-[4-[3-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]propoxy]-3-nitrophenyl]-2-[[3-(trifluoromethyl)phenyl]sulfonylamino]propanoate
  参考文献：
  名称：

  α_vβ₃ Integrin-Targeting Arg-Gly-Asp (RGD) Peptidomimetics Containing Oligoethylene Glycol (OEG) Spacers

  摘要：

  RGD peptides are used in biomaterials science for surface modifications with a view to elicit selective cellular responses. Our objective is to replace peptides by small peptidomimetics acting similarly. We designed novel molecules targeting alpha(v)beta(3) integrin and featuring spacer-arms (for surface grafting), which do not disturb the biological activity, from (L) N-(3-(trifluoromethyl)benzenesulfonyl) tyrosine used as scaffold. Various Arg-mimics were fixed on the phenol function, and the ortho position was used for the Coupling of OEG spacers. All peptidomimetics were active in the nM range in a binding test toward human alpha(v)beta(3) integrin (IC50 = 0.1 to 1.7 nM) and selective versus platelet integrin alpha(IIb)beta(3) Selected compounds revealed excellent ability to inhibit bone cells adhesion on vitronectin. Modeling and docking studies were performed for comparing the most active RGD peptidomimetic to cilengitide, i.e., cyclo-[RGDfN(Me)V]-. Lastly, the adhesion of endothelial cells on a cultivation support grafted with RGD peptidomimetics was significantly improved.

  DOI：

  10.1021/jm901133z

文献信息

• α_vβ₃ Integrin-Targeting Arg-Gly-Asp (RGD) Peptidomimetics Containing Oligoethylene Glycol (OEG) Spacers
  作者：Vincent Rerat、Georges Dive、Alex A. Cordi、Gordon C. Tucker、Reine Bareille、Joëlle Amédée、Laurence Bordenave、Jacqueline Marchand-Brynaert

  DOI：10.1021/jm901133z

  日期：2009.11.26

  RGD peptides are used in biomaterials science for surface modifications with a view to elicit selective cellular responses. Our objective is to replace peptides by small peptidomimetics acting similarly. We designed novel molecules targeting alpha(v)beta(3) integrin and featuring spacer-arms (for surface grafting), which do not disturb the biological activity, from (L) N-(3-(trifluoromethyl)benzenesulfonyl) tyrosine used as scaffold. Various Arg-mimics were fixed on the phenol function, and the ortho position was used for the Coupling of OEG spacers. All peptidomimetics were active in the nM range in a binding test toward human alpha(v)beta(3) integrin (IC50 = 0.1 to 1.7 nM) and selective versus platelet integrin alpha(IIb)beta(3) Selected compounds revealed excellent ability to inhibit bone cells adhesion on vitronectin. Modeling and docking studies were performed for comparing the most active RGD peptidomimetic to cilengitide, i.e., cyclo-[RGDfN(Me)V]-. Lastly, the adhesion of endothelial cells on a cultivation support grafted with RGD peptidomimetics was significantly improved.