tert-butyl ((S)-3-(1H-indol-3-yl)-1-(((2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)amino)-1-oxopropan-2-yl)carbamate | 1186588-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tert-butyl ((S)-3-(1H-indol-3-yl)-1-(((2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)amino)-1-oxopropan-2-yl)carbamate
• CAS: 1186588-85-1
• 化学式: C₄₅H₄₇N₅O₇
• 分子量: 769.897
• InChiKey: AYYUOSRSXFCGOE-IZSXRKQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  57.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  156.54
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((S)-3-(1H-indol-3-yl)-1-(((2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)amino)-1-oxopropan-2-yl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以47%的产率得到2',3'-dideoxy-3'-L-tryptophanylamino-thymidine
  参考文献：
  名称：

  Nucleoside–amino acid conjugates: An alternative route to the design of ribonuclease A inhibitors

  摘要：

  Nucleoside-amino acid conjugates have been employed to inhibit the ribonucleolytic activity of ribonuclease A (RNase A) and affect the protonation/deprotonation equilibrium of its active site histidine residues. Agarose gel and precipitation assays indicate inhibition of RNase A activity by these molecules with a possible role of the polar side chains of the amino acids in RNase A inhibition. Kinetic experiments demonstrated that the mode of inhibition is competitive in nature with inhibition constants (K-i) in the micromolar range. The nucleoside-serine conjugate occupies the active site of RNase A and preferential perturbs the pK(a) value of His-119 by its 'free amino group' as found from H-1 NMR studies. Docking studies revealed that the free amino groups of the most active compounds are within hydrogen bonding distance of His-119 in inhibitor-RNase A complexes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.002
• 作为产物：
  描述：

  3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine 、 N-叔丁氧羰基-L-色氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 tert-butyl ((S)-3-(1H-indol-3-yl)-1-(((2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)amino)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Amino and carboxy functionalized modified nucleosides: A potential class of inhibitors for angiogenin

  摘要：

  The 3'-amino and carboxy functionalize thymidines execute their ribonucleolytic inhibition activity for angiogenin. These modified nucleosidic molecules inhibit the ribonucleolytic activity of angiogenin in a competitive manner like the other conventional nucleotidic inhibitors, which have been confirmed from kinetic experiments. The improved inhibition constant (K-i) values 427 +/- 7, 775 +/- 6 mu M clearly indicate modified nucleosides are an obvious option for the designing of inhibitors of angiogenesis process. The chorioallantoic membrane (CAM) assay qualitatively suggests that amino functionalized nucleosides have an effective potency to inhibited angiogenin-induced angiogenesis. Docking studies further demonstrate the interaction of their polar amino group with the P-1 site residues of angiogenin, i.e., His-13 and His-114 residues. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.11.005