3'-O-acetyl-5'-amino-5'-deoxythymidine | 27930-49-0

• 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: 3'-O-acetyl-5'-amino-5'-deoxythymidine
• 英文别名: O^3'-acetyl-5'-amino-5'-deoxy-thymidine；5'-Amino-5'-desoxy-3'-O-acetyl-thymidin；[(2R,3S,5R)-2-(aminomethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 27930-49-0
• 化学式: C₁₂H₁₇N₃O₅
• 分子量: 283.284
• InChiKey: KIDWNDSBSZGYKG-IVZWLZJFSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-5'-amino-5'-deoxythymidine 在 吡啶 作用下， 反应 60.0h， 生成
  参考文献：
  名称：

  Synthesis of Extended Carbamate and Urea Linked Thymidine Dimers¹

  摘要：

  Thymidine dimers with extended carbamate and urea linkages were-synthesized. The length of the linker is expected to increase flexibility and improve duplex formation after incorporation into oligomer.

  DOI：

  10.1080/07328319608002452
• 作为产物：
  描述：

  5-叠氮基-5-脱氧胸腺嘧啶脱氧核苷 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 3'-O-acetyl-5'-amino-5'-deoxythymidine
  参考文献：
  名称：

  Synthesis of Extended Carbamate and Urea Linked Thymidine Dimers¹

  摘要：

  Thymidine dimers with extended carbamate and urea linkages were-synthesized. The length of the linker is expected to increase flexibility and improve duplex formation after incorporation into oligomer.

  DOI：

  10.1080/07328319608002452

文献信息

• Synthesis of new nucleoside phosphoraziridines as potential site-directed antineoplastic agents
  作者：Robert G. Breiner、William C. Rose、Joseph A. Dunn、Joan E. MacDiarmid、Thomas J. Bardos

  DOI：10.1021/jm00171a039

  日期：1990.9

  With the aim of increasing the selectivity of the 2,2-dimethylphosphoraziridine type antitumor agents toward the intracellular site of DNA synthesis, a series of new compounds was synthesized in which the reactive bis(2,2-dimethyl-1-aziridinyl)phosphinyl (2,2-DMAP) group was linked through a carbamate or amide linkage to thymidine or cytosine nucleoside moieties. The 3'- and 5'-(2,2-DMAP)carbamates

  为了提高2,2-二甲基磷杂氮杂吡啶类抗肿瘤剂对DNA合成的细胞内位点的选择性，合成了一系列新的化合物，其中反应性双（2,2-二甲基-1-叠氮基）次膦酰基（通过氨基甲酸酯或酰胺键将2，2-DMAP）基团连接至胸苷或胞嘧啶核苷部分。发现胸腺嘧啶（1和2）的3'-和5'-（2,2-DMAP）氨基甲酸酯非常不稳定，因此通过使5'-和3'反应制备相应的O-乙酰基衍生物5和6 -乙酰基胸苷分别用二氯异氰酸根合膦氧化物氧化，然后加入2，2-二甲基氮丙啶和三乙胺。胸腺嘧啶14和15的3'-和5'-（2,2-DMAP）酰胺是通过使适当的胸苷胺与bis（2，2-二甲基-1-叠氮基）次膦酰氯（17）。通过使O-过乙酰化胞嘧啶核苷的盐酸盐与三乙胺和POCl3反应，制得胞苷，2'-脱氧胞苷和胞嘧啶阿拉伯糖苷（分别为18、19和20）的N4-（2,2-DMAP）酰胺随后，用2，2-二甲基氮丙啶和三乙胺分别得到相应的N
• Modified oligodeoxyribonucleoditides
  申请人：Sankyo Company, Limited

  公开号：US05674856A1

  公开（公告）日：1997-10-07

  Compounds for the treatment or prophylaxis of a viral infection in a mammal, which may be human, are provided. The compounds are oligodeoxyribonucleic acid derivatives, and a novel route to such compounds is also provided together with intermediates of more general utility. The active compounds are of the general formula (1): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen atoms, alkyl groups, aryl groups as defined, and anthraquinonyl groups as defined; Z is carbon or silicon; or R.sub.2, R.sub.3 and Z together represent fluorenyl or xanthenyl; R.sub.4 is a hydrogen atom, an alkyl group as defined, an aryl group as defined; Y.sub.1, Y.sub.3 and Y.sub.4 are oxygen, sulfur or >NH; Y.sub.2 is oxygen, sulfur, >NH, alkylene or phenylene; X is alkylene group as defined; m and n are 0 to 10; and B is an oligodeoxyribonucleotide of chain length 3 to 9; or salts thereof.

  提供了用于治疗或预防哺乳动物（包括人类）病毒感染的化合物。这些化合物是寡聚脱氧核糖核酸衍生物，同时提供了一种新的制备这些化合物的方法以及更通用的中间体。活性化合物的一般式（1）如下：##STR1##其中R.sub.1、R.sub.2和R.sub.3是氢原子、烷基、芳基（如定义）和蒽醌基（如定义）；Z是碳或硅；或R.sub.2、R.sub.3和Z共同表示芴基或黄酮基；R.sub.4是氢原子、烷基（如定义）、芳基（如定义）；Y.sub.1、Y.sub.3和Y.sub.4是氧、硫或>NH；Y.sub.2是氧、硫、>NH、烷基或苯基；X是烷基（如定义）；m和n为0到10；B是链长为3到9的寡聚脱氧核糖核酸；或其盐。
• Composition and method for the treatment or prophylaxis of viral
  申请人：Sankyo Company, Limited

  公开号：US05807837A1

  公开（公告）日：1998-09-15

  A composition and method of treatment or prophylaxis of a viral infection in a mammal, such as a human, are provided. The compounds in the composition and which are administered in the method, are oligodeoxyribonucleic acid derivatives of the formula (1): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen atoms, alkyl groups, aryl groups, and anthraquinonyl groups; Z is carbon or silicon; or R.sub.2, R.sub.3 and Z together represent fluorenyl or xanthenyl; R.sub.4 is a hydrogen atom, an alkyl group or an aryl group; Y.sub.1, Y.sub.3 and Y.sub.4 are oxygen, sulfur or >NH; Y.sub.2 is oxygen, sulfur, >NH, alkylene or phenylene; X is an alkylene group; m and n are each 0 to 10; and B is an oligodeoxyribonucleotide of a chain length of 3 to 9, or salts thereof.

  提供了哺乳动物，如人类的病毒感染的组合物和治疗或预防方法。组合物中的化合物以及在方法中被管理的化合物是公式（1）的寡脱氧核糖核酸衍生物：##STR1##其中R.sub.1，R.sub.2和R.sub.3是氢原子，烷基，芳基和蒽醌基；Z是碳或硅；或R.sub.2，R.sub.3和Z一起代表芴基或黄酮基；R.sub.4是氢原子，烷基或芳基；Y.sub.1，Y.sub.3和Y.sub.4是氧，硫或>NH；Y.sub.2是氧，硫，>NH，烷基或苯基；X是烷基；m和n分别为0至10；B是链长为3至9的寡脱氧核糖核酸或其盐。
• Pyrrolidine PNA-DNA Chimeric Oligonucleotides with Extended Backbone
  作者：Vaijayanti A. Kumar、Meena

  DOI：10.1081/ncn-120022746

  日期：2003.10

  Cis-D-2-hydroxy-4-thymin-1-yl-pyrrolidine propionic acid unit is used to make PNA-DNA dimer block that is incorporated in DNA sequences at selected positions. Since the amide linkage is shorter than phosphodiester linkage, insertion of an extra atom in the backbone with amide linkage seems to be better accommodated for internucleotide distance-complementarity.
• Modified oligodeoxyribonucleotides, their preparation and their therapeutic use
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0611075B1

  公开（公告）日：1996-12-18