2',3'-dideoxy-3'-L-leucylamino-thymidine | 1186588-70-4

• 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: 2',3'-dideoxy-3'-L-leucylamino-thymidine
• 英文别名: Leu-aT；(2S)-2-amino-N-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-4-methylpentanamide
• CAS: 1186588-70-4
• 化学式: C₁₆H₂₆N₄O₅
• 分子量: 354.406
• InChiKey: IHTNVOZACAWFKV-WUHRBBMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  benzyl N-[(2S)-1-[[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate 生成 2',3'-dideoxy-3'-L-leucylamino-thymidine
  参考文献：
  名称：

  MORINIERE, JEAN-LUC;FAUIQUES, MICHELLE;ROUSSEAU, CLAUDE;DANREE, BERNARD;M+

  摘要：

  DOI：

文献信息

• 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.
• Nucleoside–amino acid conjugates: An alternative route to the design of ribonuclease A inhibitors
  作者：Joy Debnath、Swagata Dasgupta、Tanmaya Pathak

  DOI：10.1016/j.bmc.2009.06.002

  日期：2009.7

  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.
• US5212161A
  申请人：——

  公开号：US5212161A

  公开（公告）日：1993-05-18