1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropyl-β-D-ribofuranosyl)-5-cyanouracil | 1236160-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropyl-β-D-ribofuranosyl)-5-cyanouracil
• CAS: 1236160-95-4
• 化学式: C₁₉H₂₉N₃O₆Si
• 分子量: 423.541
• InChiKey: DPWBFDRUIPOWQR-IXYNUQLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  115.57
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropyl-β-D-ribofuranosyl)-5-cyanouracil 在 三氟乙酸 作用下， 以 水 为溶剂， 以93%的产率得到5-cyanouridine
  参考文献：
  名称：

  Structural determinants for the inhibitory ligands of orotidine-5′-monophosphate decarboxylase

  摘要：

  In recent years, orotidine-5'-monophosphate decarboxylase (ODCase) has gained renewed attention as a drug target. As a part of continuing efforts to design novel inhibitors of ODCase, we undertook a comprehensive study of potent, structurally diverse ligands of ODCase and analyzed their structural interactions in the active site of ODCase. These ligands comprise of pyrazole or pyrimidine nucleotides including the mononucleotide derivatives of pyrazofurin, barbiturate ribonucleoside, and 5-cyanouridine, as well as, in a computational approach, 1,4-dihydropyridine-based non-nucleoside inhibitors such as nifedipine and nimodipine. All these ligands bind in the active site of ODCase exhibiting distinct interactions paving the way to design novel inhibitors against this interesting enzyme. We propose an empirical model for the ligand structure for rational modi. cations in new drug design and potentially new lead structures. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.017
• 作为产物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene-5-bromouridine 、 sodium cyanide 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以96%的产率得到1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropyl-β-D-ribofuranosyl)-5-cyanouracil
  参考文献：
  名称：

  Structural determinants for the inhibitory ligands of orotidine-5′-monophosphate decarboxylase

  摘要：

  In recent years, orotidine-5'-monophosphate decarboxylase (ODCase) has gained renewed attention as a drug target. As a part of continuing efforts to design novel inhibitors of ODCase, we undertook a comprehensive study of potent, structurally diverse ligands of ODCase and analyzed their structural interactions in the active site of ODCase. These ligands comprise of pyrazole or pyrimidine nucleotides including the mononucleotide derivatives of pyrazofurin, barbiturate ribonucleoside, and 5-cyanouridine, as well as, in a computational approach, 1,4-dihydropyridine-based non-nucleoside inhibitors such as nifedipine and nimodipine. All these ligands bind in the active site of ODCase exhibiting distinct interactions paving the way to design novel inhibitors against this interesting enzyme. We propose an empirical model for the ligand structure for rational modi. cations in new drug design and potentially new lead structures. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.017