1-[(2R,4S,5S)-5-(羟基甲基)-4-甲基氨基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮 | 141039-00-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 1-[(2R,4S,5S)-5-(羟基甲基)-4-甲基氨基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮
• 中文别名: 4-(1H-咪唑-1-基)丁酸
• 英文名称: 3'-N-methylamino-3'-deoxythymidine
• 英文别名: 3'-Methylamino-2',3'-dideoxyribosylthymine；1-[(2R,4S,5S)-5-(hydroxymethyl)-4-(methylamino)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 141039-00-1
• 化学式: C₁₁H₁₇N₃O₄
• 分子量: 255.274
• InChiKey: LDZKBUFNIZADPS-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  90.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5S)-5-(羟基甲基)-4-甲基氨基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮 在 三正丁胺 、 三丁基焦磷酸铵 、 三氯氧磷 作用下， 生成 3'-N-methylamino-3'-deoxythymidine 5'-triphosphate ammonium salt
  参考文献：
  名称：

  Synthesis, Molecular and Crystal Structure of 3′-N-Alkylamino-3′-deoxythymidines and Some Biochemical Properties of Their Phosphorous Esters

  摘要：

  Two approaches for tile synthesis of 3'-N-alkylated 3'-amino-3'deoxythymidines were developed, including both tile reaction of 3'-amino-3'deoxythymidine with aldehydes followed by tile sodium borohydride reduction and preparation of tile triphenylphosphinimine derivative and subsequent reaction with alkyl iodide. 5'-Triphosphates of tile synthesized compounds were shown to be terminating substrates for human immunodeficiency virus and avian myeloblastosis virus reverse transcriptases as well as for DNA polymerase beta from rat liver. At the same time these compounds did not demonstrate tile properties of a terminating substrate ill DNA synthesis catalyzed by human DNA polymerases alpha, epsilon, and 1 from E. coli.

  DOI：

  10.1080/15257779508014650
• 作为产物：
  描述：

  3'-叠氮基-3'-脱氧-5'-O-三苯甲基胸苷 在 sodium tetrahydroborate 、 Dowex 50Wx₂ (H⁺) 、 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 、 异丙醇 为溶剂， 反应 14.08h， 生成 1-[(2R,4S,5S)-5-(羟基甲基)-4-甲基氨基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Synthesis of 3′-N-Substituted 3′-Amino-3′-Deoxythymidine Derivatives

  摘要：

  A series of 3'-N-substituted 3'-amino-3'-deoxythymidine derivatives with alkyl, alkenyl and alkylaryl substituents was synthesized by two methods. The first method involved the reaction of 1-(2,3-dideoxy-3-O-mesyl-5-O-trityl-beta-D-threo-pentofuranosyl)thymine with an appropriate amine. In the second method, 3'-amino-5'-O-trityl-3'-deoxy-thymidine served as a synthetic precursor which was reacted with an appropiate aldehyde or ketone followed by sodium borohydride reduction. An improved synthesis of 3'-amino-3'-deoxythymidine from 3'-azido-5'-O-trityl-3'-deoxythymidine using sodium borohydride was also described.

  DOI：

  10.1080/07328319308018565

文献信息

• Synthesis of 3′-N-Substituted 3′-Amino-3′-Deoxythymidine Derivatives
  作者：Lech Celewicz、Wojciech Urjasz、Krzysztof Golankiewicz

  DOI：10.1080/07328319308018565

  日期：1993.11

  A series of 3'-N-substituted 3'-amino-3'-deoxythymidine derivatives with alkyl, alkenyl and alkylaryl substituents was synthesized by two methods. The first method involved the reaction of 1-(2,3-dideoxy-3-O-mesyl-5-O-trityl-beta-D-threo-pentofuranosyl)thymine with an appropriate amine. In the second method, 3'-amino-5'-O-trityl-3'-deoxy-thymidine served as a synthetic precursor which was reacted with an appropiate aldehyde or ketone followed by sodium borohydride reduction. An improved synthesis of 3'-amino-3'-deoxythymidine from 3'-azido-5'-O-trityl-3'-deoxythymidine using sodium borohydride was also described.
• Synthesis, Molecular and Crystal Structure of 3′-N-Alkylamino-3′-deoxythymidines and Some Biochemical Properties of Their Phosphorous Esters
  作者：Maxim V. Jasko、lvati I. Fedorov、Alexey M. Atrazhev、Diriiitry Yu. Mozzherin、Nicolay A. Novicov、Alexey V. Bochkarev、Gnliiia V. Gurskaya、Alexander A. Krayevsky

  DOI：10.1080/15257779508014650

  日期：1995.2

  Two approaches for tile synthesis of 3'-N-alkylated 3'-amino-3'deoxythymidines were developed, including both tile reaction of 3'-amino-3'deoxythymidine with aldehydes followed by tile sodium borohydride reduction and preparation of tile triphenylphosphinimine derivative and subsequent reaction with alkyl iodide. 5'-Triphosphates of tile synthesized compounds were shown to be terminating substrates for human immunodeficiency virus and avian myeloblastosis virus reverse transcriptases as well as for DNA polymerase beta from rat liver. At the same time these compounds did not demonstrate tile properties of a terminating substrate ill DNA synthesis catalyzed by human DNA polymerases alpha, epsilon, and 1 from E. coli.