5'-N-methyl,N-(2-hydroxyethyl)-5'-deoxy-5'-aminothymidine | 174827-61-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 5'-N-methyl,N-(2-hydroxyethyl)-5'-deoxy-5'-aminothymidine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-[[2-hydroxyethyl(methyl)amino]methyl]tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-[[2-hydroxyethyl(methyl)amino]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 174827-61-3
• 化学式: C₁₃H₂₁N₃O₅
• 分子量: 299.327
• InChiKey: FWYNPYUVXGJIAJ-HBNTYKKESA-N

物化性质

• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 5'-N-methyl,N-(2-hydroxyethyl)-5'-deoxy-5'-aminothymidine 在 吡啶 作用下， 反应 8.0h， 以75%的产率得到1-[(2R,4S,5R)-5-[[2-[bis(4-methoxyphenyl)-phenylmethoxy]ethyl-methylamino]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Oligodeoxynucleotides with extended zwitter-ionic internucleotide linkage

  摘要：

  Two non-natural nucleoside analogues, N-(2-hydroxyethyl)-2',5'-dideoxy-5'-aminothymidine (dT(NH)) and N-(2-hydroxyethyl)N-methyl-2,5'-dideoxy-5'-aminothymidine (dT(NMe)), have been prepared and used in the synthesis of oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides, modified at internucleotide linkages. Both modified oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides have been shown to form zwitter-ionic phosphate-amine pairs as evidenced by their decreased electrophoretic mobility in denaturing polyacrylamide gel. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01034-1
• 作为产物：
  描述：

  N-甲基-2-羟基乙胺 、 5-O-(4-甲基苯基磺酰基)胸腺嘧啶脱氧核苷 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以67%的产率得到5'-N-methyl,N-(2-hydroxyethyl)-5'-deoxy-5'-aminothymidine
  参考文献：
  名称：

  Oligodeoxynucleotides with extended zwitter-ionic internucleotide linkage

  摘要：

  Two non-natural nucleoside analogues, N-(2-hydroxyethyl)-2',5'-dideoxy-5'-aminothymidine (dT(NH)) and N-(2-hydroxyethyl)N-methyl-2,5'-dideoxy-5'-aminothymidine (dT(NMe)), have been prepared and used in the synthesis of oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides, modified at internucleotide linkages. Both modified oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides have been shown to form zwitter-ionic phosphate-amine pairs as evidenced by their decreased electrophoretic mobility in denaturing polyacrylamide gel. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01034-1

文献信息

• Synthesis and Evaluation of Novel Thymidine Analogs as Antitumor and Antiviral Agents
  作者：Xiannong Chen、Kenneth Bastow、Barry Goz、Louis S. Kucera、Susan L. Morris-Natschke、Khalid S. Ishaq

  DOI：10.1021/jm9601260

  日期：1996.1.1

  Two series of thymidine analogs with a hydroxyalkylammonium(amine) moiety have been synthesized and evaluated for antitumor and antiviral activities. The hydroxyalkylammonium-(amine) group was introduced at the 5' position of the 2'-deoxyribose residue of thymidine or at a corresponding position in acyclic thymidine analogs. In order to increase the lipophilicity of these compounds and potentially

  已经合成了具有羟烷基铵（胺）部分的两个系列的胸苷类似物，并评估了其抗肿瘤和抗病毒活性。将羟烷基铵-（胺）基团引入胸苷的2'-脱氧核糖残基的5'位置或无环胸苷类似物中的相应位置。为了增加这些化合物的亲脂性并可能使它们穿过细胞膜，游离羟基也被长烃链酯化了。十六烷酰基类似物（化合物1c，1d，7c和7d）显示出对SV-28和KB细胞系的中等抗肿瘤细胞毒性（IC50约为20 microM）。化合物1d显示中等抗HIV活性（EC50 = 6.8 microM），而化合物5显示弱抗HIV活性（EC50 = 55 microM）。
• Oligodeoxynucleotides with extended zwitter-ionic internucleotide linkage
  作者：Svetlana V Kochetkova、Edward N Timofeev、Ekaterina A Korobeinikova、Natalia A Kolganova、Vladimir L Florentiev

  DOI：10.1016/s0040-4020(01)01034-1

  日期：2001.12

  Two non-natural nucleoside analogues, N-(2-hydroxyethyl)-2',5'-dideoxy-5'-aminothymidine (dT(NH)) and N-(2-hydroxyethyl)N-methyl-2,5'-dideoxy-5'-aminothymidine (dT(NMe)), have been prepared and used in the synthesis of oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides, modified at internucleotide linkages. Both modified oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides have been shown to form zwitter-ionic phosphate-amine pairs as evidenced by their decreased electrophoretic mobility in denaturing polyacrylamide gel. (C) 2001 Elsevier Science Ltd. All rights reserved.