3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine | 104267-95-0

• 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: 3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine
• 英文别名: [(2R,3S,5S)-5-(5-iodo-2,4-dioxopyrimidin-1-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 104267-95-0
• 化学式: C₂₅H₂₃IN₂O₇
• 分子量: 590.371
• InChiKey: OENJVMKAWHZWNP-HBMCJLEFSA-N

物化性质

• 熔点：
  201-203 °C(Solv: ethanol (64-17-5))
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  116.69
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine 在 甲醇 、 sodium methylate 作用下， 反应 1.0h， 以92%的产率得到5-iodo-α-2'-desoxyuridine
  参考文献：
  名称：

  5-Propynylamino α-deoxyuridine promotes DNA duplex stabilization of anionic and neutral but not cationic α-oligonucleotides

  摘要：

  Incorporation of 5-propynylamino and 5-propynyl alpha-2'-deoxyuridine into alpha-oligonucleotides (a-ON) allows high-affinity targeting of complementary DNA for a-ON with anionic and neutral backbone but not for cationic a-ON, revealing clues on the role of the amino group of the propynylamino on the formation of DNA duplexes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.052
• 作为产物：
  描述：

  5-iodo-3',5'-di-O-p-toluyl-2'-deoxyuridine 在 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 41.0h， 以52%的产率得到3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine
  参考文献：
  名称：

  5-Propynylamino α-deoxyuridine promotes DNA duplex stabilization of anionic and neutral but not cationic α-oligonucleotides

  摘要：

  Incorporation of 5-propynylamino and 5-propynyl alpha-2'-deoxyuridine into alpha-oligonucleotides (a-ON) allows high-affinity targeting of complementary DNA for a-ON with anionic and neutral backbone but not for cationic a-ON, revealing clues on the role of the amino group of the propynylamino on the formation of DNA duplexes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.052

文献信息

• 5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication
  作者：P. Wigerinck、C. Pannecouque、R. Snoeck、P. Claes、E. De Clercq、P. Herdewijn

  DOI：10.1021/jm00112a011

  日期：1991.8

  2'-Deoxyuridines with a five-membered heterocyclic substituent in the 5-position were synthesized by palladium-catalyzed coupling reactions of 5-iodo-2'-deoxyuridine with the activated heteroaromatics. Further modification of the compound with the 5-thien-2-yl substituent gave 5-(5-bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothienyl-2-yl)-2'-deoxyuridine. Both compounds show potent and selective activity against herpes simplex virus type 1 and varicella-zoster virus.
• α-Oligodeoxynucleotides containing 5-propynyl analogs of α-deoxyuridine and α-deoxycytidine: Synthesis and base pairing properties
  作者：François Morvan、Joanna Zeidler、Bernard Rayner

  DOI：10.1016/s0040-4020(97)10257-5

  日期：1998.1
• FRESKOS, JOHN N., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N, C. 549-555
  作者：FRESKOS, JOHN N.

  DOI：——

  日期：——