N-[2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-succinamic acid | 267668-79-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N-[2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-succinamic acid
• 英文别名: Suc-aT；4-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-ylamino)-4-oxobutanoic acid；4-[[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]amino]-4-oxobutanoic acid
• CAS: 267668-79-1
• 化学式: C₁₄H₁₉N₃O₇
• 分子量: 341.321
• InChiKey: KIEIVGYLTYSSPF-IQJOONFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 N-[2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-succinamic acid
  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

文献信息

• Inhibition of ribonuclease A by nucleoside–dibasic acid conjugates
  作者：Joy Debnath、Swagata Dasgupta、Tanmaya Pathak

  DOI：10.1016/j.bmc.2009.08.018

  日期：2009.9

  We report the inhibition of the ribonucleolytic activity of ribonuclease A (RNase A) by nucleoside-dibasic acid conjugates for the first time. Agarose gel and precipitation assays show that the spacer length and the pK(a) of the carboxylic group have an important role in the inhibitory capacity. Kinetic experiments indicate a competitive mode of inhibition with inhibition constant (K-i) value of 132 +/- 3 mu M for Oxa-aT. Docking studies revealed that the carboxylic group of the most active compounds is within hydrogen bonding distance of His-12, Lys-41 and His-119. (C) 2009 Elsevier Ltd. All rights reserved.
• Amino and carboxy functionalized modified nucleosides: A potential class of inhibitors for angiogenin
  作者：Joy Debnath、Swagata Dasgupta、Tanmaya Pathak

  DOI：10.1016/j.bioorg.2013.11.005

  日期：2014.2

  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.