β-D-2',3'-dideoxy-4'-selenothymidine | 1100358-63-1

• 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: β-D-2',3'-dideoxy-4'-selenothymidine
• 英文别名: 4'-seleno-ddT；1-[(2R,5S)-5-(hydroxymethyl)selenolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1100358-63-1
• 化学式: C₁₀H₁₄N₂O₃Se
• 分子量: 289.193
• InChiKey: VELXMRXTMYIUIR-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.38
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  β-D-5'-benzoyl-2',3'-dideoxy-4'-seleno-N3-benzoylthymidine 在 氨 作用下， 以 甲醇 为溶剂， 以88%的产率得到β-D-2',3'-dideoxy-4'-selenothymidine
  参考文献：
  名称：

  Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents

  摘要：

  On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2', 3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, D-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se-2 and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.034

文献信息

• Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents
  作者：Lak Shin Jeong、Yoo Na Choi、Dilip K. Tosh、Won Jun Choi、Hea Ok Kim、Jungwon Choi

  DOI：10.1016/j.bmc.2008.10.034

  日期：2008.12

  On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2', 3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, D-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se-2 and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates. (c) 2008 Elsevier Ltd. All rights reserved.