(S)-t-butyl 3-(3-(2-(2-(2-(2-(t-butoxycarbonyl)aminoethoxy)ethoxy)ethoxy)acetamido)-4-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy)phenyl)-2-(3(trifluoromethyl)phenylsulfonamido)propanoate | 1197191-81-3

• 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-(t-butoxycarbonyl)aminoethoxy)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-[[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]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: 1197191-81-3
• 化学式: C₄₄H₆₀F₃N₅O₁₁S
• 分子量: 924.049
• InChiKey: BGSYWQFAILUCIL-BHVANESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  64
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  210
• 氢给体数：
  4
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (S)-t-butyl 3-(3-(2-(2-(2-(2-(t-butoxycarbonyl)aminoethoxy)ethoxy)ethoxy)acetamido)-4-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy)phenyl)-2-(3(trifluoromethyl)phenylsulfonamido)propanoate 在 硫酸 作用下， 以47%的产率得到
  参考文献：
  名称：

  与 RGD-肽模拟物缀合的四硫三芳基甲基自由基

  摘要：

  四硫三芳基甲基 (TAM) 自由基是电子顺磁共振成像 (EPRI) 中最受欢迎的自旋标记。在这项工作中，我们报告了与已知是细胞靶向剂的 Arg-Gly-Asp (RGD)-肽模拟物结合的新 TAM 自由基的直接合成。这些新自由基在溶液中稳定，对氧敏感，它们的实验 EPR 数据与密度泛函理论 (DFT) 计算一致。

  DOI：

  10.1002/ejoc.201403049
• 作为产物：
  描述：

  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 、 2-[2-[2-[2-(BOC-氨基)乙氧基]乙氧基]乙氧基]乙酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以37%的产率得到(S)-t-butyl 3-(3-(2-(2-(2-(2-(t-butoxycarbonyl)aminoethoxy)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：

  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.
• Tetrathiatriarylmethyl Radicals Conjugated to an RGD-Peptidomimetic
  作者：Benoît Driesschaert、Philippe Levêque、Bernard Gallez、Jacqueline Marchand-Brynaert

  DOI：10.1002/ejoc.201403049

  日期：2014.12

  Tetrathiatriarylmethyl (TAM) radicals are favourite spin labels for electron paramagnetic resonance imaging (EPRI). In this work, we report a straightforward synthesis of new TAM radicals bound to an Arg-Gly-Asp (RGD)-peptido-mimetic known to be a cell-targeting agent. These new radicals are stable in solution, and sensitive to oxygen, and their experimental EPR data is consistent with density functional

  四硫三芳基甲基 (TAM) 自由基是电子顺磁共振成像 (EPRI) 中最受欢迎的自旋标记。在这项工作中，我们报告了与已知是细胞靶向剂的 Arg-Gly-Asp (RGD)-肽模拟物结合的新 TAM 自由基的直接合成。这些新自由基在溶液中稳定，对氧敏感，它们的实验 EPR 数据与密度泛函理论 (DFT) 计算一致。