2',3',5'-tri-O-acetyl-2-iodoinosine | 115952-29-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3',5'-tri-O-acetyl-2-iodoinosine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-iodo-6-oxo-3H-purin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 115952-29-9
• 化学式: C₁₆H₁₇IN₄O₈
• 分子量: 520.237
• InChiKey: YAQIMBZTFSDCSB-SDBHATRESA-N

物化性质

• 密度：
  2.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  151.7
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-2-iodoinosine 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 四乙基氯化铵 、 氨 、 N,N-二甲基苯胺 、 三乙胺 、 三氯氧磷 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 [(6aR,8R,9R,9aR)-8-[6-amino-2-(4-butylanilino)purin-9-yl]-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Tomikawa, Aki; Seno, Masaki; Sato-Kiyotaki, Kunie, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 487 - 501

  摘要：

  DOI：
• 作为产物：
  描述：

  2',3',5'-tri-O-acetyl-2-iodoadenosine 在 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 以84.9%的产率得到2',3',5'-tri-O-acetyl-2-iodoinosine
  参考文献：
  名称：

  Tomikawa, Aki; Seno, Masaki; Sato-Kiyotaki, Kunie, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 487 - 501

  摘要：

  DOI：

文献信息

• Impdh As A Biological Probe For Rna Antiviral Drug Discovery: Synthesis, Enzymology, Molecular Docking, And Antiviral Activity Of New Ribonucleosides With Surrogate Bases
  作者：Vasu Nair、Xiaohui Ma、Qingning Shu、Fan Zhang、Vinod Uchil、Govardhan R. Cherukupalli

  DOI：10.1080/15257770701490506

  日期：2007.11.26

  Our interest in the discovery of molecules with antiviral activity against RNA viruses led us to the design of ribonucleosides with surrogate bases with the intent Of using inhibition of inosine monophosphate dehydrogenase (IMPDH) as a probe for antiviral drug discovery. A general methodology for the preparation of these compounds is discussed. Kinetic parameters of the inhibition studies with IMPDH, which were carried out spectrophotometrically by monitoring the formation of NADH, are given. Antiviral information and correlation of activity with IMPDH inhibition are discussed.
• Synthesis and Biological Activities of Sugar-Modified 2-(p-n-Butylanilino)-2'-deoxyadenosine Analogues
  作者：Toyofumi Yamaguchi、Kunie Sato、Mineo Saneyoshi

  DOI：10.1080/15257779508012419

  日期：1995.5.1

  Several sugar-modified 2-(p-n-butylanilino)-2'-deoxyadenosine analogues, including arabino and 2'(R)-azido-2'-deoxy analogues and their 5'-triphosphates were synthesized. These nucleosides thus obtained exhibited moderate cytotoxicity against P-388 leukemic cells in culture (IC50 = 13-24 mu M). In contrast to above results, the 5'-triphosphates have been shown to exert strong and selective inhibitory effects on mammalian DNA polymerase alpha (Ki=0.02-0.04 mu M).