(S)-t-butyl 3-(3-(2-(2-(2-(2-(2-(2-(2-(t-butoxycarbonyl)aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)acetamido)-4-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy)phenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propanoate | 1197191-85-7

• 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)-t-butyl 3-(3-(2-(2-(2-(2-(2-(2-(2-(t-butoxycarbonyl)aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)acetamido)-4-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy)phenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propanoate
• 英文别名: tert-butyl (2S)-3-[3-(20-([(tert-butoxy)carbonyl]amino)-3,6,9,12,15,18-hexaoxaicosanamido)-4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy]phenyl]-2-([3-(trifluoromethyl)benzene]sulfonamido)propanoate；tert-butyl (2S)-3-[3-[[2-[2-[2-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl]amino]-4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy]phenyl]-2-[[3-(trifluoromethyl)phenyl]sulfonylamino]propanoate
• CAS: 1197191-85-7
• 化学式: C₅₀H₇₂F₃N₅O₁₄S
• 分子量: 1056.21
• InChiKey: KROVCBIHZCSUHC-WBCKFURZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  73
• 可旋转键数：
  36
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  238
• 氢给体数：
  4
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  (S)-t-butyl 3-(3-(2-(2-(2-(2-(2-(2-(2-(t-butoxycarbonyl)aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)acetamido)-4-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy)phenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propanoate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 4.0h， 以100%的产率得到bis(2,2,2-trifluoroacetate); 2-{3-[2-(20-azaniumyl-3,6,9,12,15,18-hexaoxaicosanamido)-4-[(2S)-2-carboxy-2-{[3 (trifluoromethyl)benzene]sulfonamido}ethyl]phenoxy]propyl}-5,6,7,8-tetrahydro-1,8-naphthyridin 1-ium
  参考文献：
  名称：

  Ultrasmall particle of iron oxide—RGD peptidomimetic conjugate: synthesis and characterisation

  摘要：

  Ultrasmall particles of iron oxide (USPIOs) coated with 3,3'-bis(phosphonate) propionic acid were covalently coupled to a home-made Arg-Gly-Asp (RGD) peptidomimetic molecule via a short oligoethyleneglycol (OEG) spacer. The conjugation rate was measured by X-ray photoelectron spectroscopy (XPS). The particle size and magnetic characteristics were kept. Our novel conjugate targeted efficiently Jurkat cells (increase of 229% vs the control). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.150
• 作为产物：
  描述：

  叔丁氧羰基六聚乙二醇乙酸 、 tert-butyl (2S)-3-(3-amino-4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy]phenyl)-2-([3-(trifluoromethyl)benzene]sulfonamido)propanoate 在 (benzotriazo-1-yloxy)tris(dimethylamino)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 15.0h， 以33%的产率得到(S)-t-butyl 3-(3-(2-(2-(2-(2-(2-(2-(2-(t-butoxycarbonyl)aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)acetamido)-4-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy)phenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propanoate
  参考文献：
  名称：

  Ultrasmall particle of iron oxide—RGD peptidomimetic conjugate: synthesis and characterisation

  摘要：

  Ultrasmall particles of iron oxide (USPIOs) coated with 3,3'-bis(phosphonate) propionic acid were covalently coupled to a home-made Arg-Gly-Asp (RGD) peptidomimetic molecule via a short oligoethyleneglycol (OEG) spacer. The conjugation rate was measured by X-ray photoelectron spectroscopy (XPS). The particle size and magnetic characteristics were kept. Our novel conjugate targeted efficiently Jurkat cells (increase of 229% vs the control). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.150

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.
• Ultrasmall particle of iron oxide—RGD peptidomimetic conjugate: synthesis and characterisation
  作者：Vincent Rerat、Sophie Laurent、Carmen Burtéa、Benoît Driesschaert、Vincent Pourcelle、Luce Vander Elst、Robert N. Muller、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.bmcl.2010.01.150

  日期：2010.3

  Ultrasmall particles of iron oxide (USPIOs) coated with 3,3'-bis(phosphonate) propionic acid were covalently coupled to a home-made Arg-Gly-Asp (RGD) peptidomimetic molecule via a short oligoethyleneglycol (OEG) spacer. The conjugation rate was measured by X-ray photoelectron spectroscopy (XPS). The particle size and magnetic characteristics were kept. Our novel conjugate targeted efficiently Jurkat cells (increase of 229% vs the control). (C) 2010 Elsevier Ltd. All rights reserved.