1-[(2R,4S,5S)-5-(羟基甲基)-4-异氰基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮 | 123533-12-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 1-[(2R,4S,5S)-5-(羟基甲基)-4-异氰基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮
• 中文别名: D-丙氨酸,N-(N-甲基-D-丙氨酰)-(9CI)
• 英文名称: 3'-isocyano-3'-deoxythymidine
• 英文别名: 1-[(2R,4S,5S)-5-(hydroxymethyl)-4-isocyanooxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 123533-12-0
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: NQXZOJJOKDQOHV-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 1-[(2R,4S,5S)-5-(羟基甲基)-4-异氰基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮 以 二氯甲烷 为溶剂， 以90%的产率得到dichloro(3'-isocyan-3'-desoxythymidine)(η5-pentamethylcyclopentadienyl)rhodium(III)
  参考文献：
  名称：

  Pill, Thomas; Polborn, Kurt; Kleinschmidt, Andrea, Chemische Berichte, 1991, vol. 124, # 7, p. 1541 - 1548

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-胸苷 在 sodium azide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 tin(ll) chloride 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-[(2R,4S,5S)-5-(羟基甲基)-4-异氰基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  3'-取代-2'，3'-二脱氧核苷类似物的合成作为潜在的抗抑郁药

  摘要：

  3'-氨基-3'-脱氧胸苷分六个步骤制备，胸腺嘧啶核苷的总收率为67％。五个衍生品和复合他们的抗HIV活性进行了测试。

  DOI：

  10.1016/s0040-4039(00)99623-0

文献信息

• Synthesis ofN-Substituted 3′-Amino-3′-deoxythymidines and their Biological Evaluation against HIV
  作者：Mohammed S. Motawia、Erik B. Pedersen、Carsten M. Nielsen

  DOI：10.1002/ardp.19903231207

  日期：——

  with a variety of isothiocyanates led to the corresponding thioureido derivatives 3a–i. Also, conversion of 1 into 3′‐carbylamino‐3′‐deoxythymidine (7) is reported. The compounds 2, 3, and 8 were evaluated for their anti‐HIV activity in MT‐4 cells, but did not show sufficient efficacy.

  用羧酸酐处理 3'-氨基-3'-脱氧胸苷 (1) 得到相应的酰氨基衍生物 2a-f。1 与各种异硫氰酸酯反应生成相应的硫脲基衍生物 3a – i。此外，还报道了 1 转化为 3'-carbylamino-3'-deoxythymidine (7)。评估了化合物 2、3 和 8 在 MT-4 细胞中的抗 HIV 活性，但没有显示出足够的功效。
• Synthesis of 3′-Isocyano-3′-deoxythymidine
  作者：Rosmarie Karl、Peter Lemmen、Ivar Ugi

  DOI：10.1055/s-1989-27373

  日期：——

  The synthesis of 3′-isocyano-3′-deoxythymidine (3) from the corresponding 5′-protected azido derivatives 1a, b is reported.

  报道了从相应的5′-保护的叠氮衍生物1a、b合成3′-异氰基-3′-脱氧胸苷（3）的方法。
• Synthesis, antiretrovirus effects and phosphorylation kinetics of 3'-isocyano-3'-deoxythymidine and 3'-isocyano-2',3'-dideoxyuridine
  作者：Johann Hiebl、Erich Zbiral、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00164a059

  日期：1990.2

  The silylated AzddThd 5 and AzddUrd 6 prepared from 2,3'-anhydronucleoside derivatives 3 and 4 were transformed to formamides 7 and 8 by using the sequence RN3----RN = P(C6H5)----RNHCHO. Formamides 7 and 8 were dehydrated to the protected 3'-isocyano derivatives 9 and 10; deblocking gave 11 and 12. Neither 3'-isocyano-3'-deoxythymidine (11) nor 3'-isocyano-2',3'-dideoxyuridine (12) showed anti-HIV activity at noncytotoxic concentrations. ddThd derivative 11 was considerably more toxic to MT-4 cells than ddUrd derivative 12; it also had a much greater affinity (Ki) for MT-4 cell dThd kinase than ddUrd derivative 12. Both compounds appear to be linear mixed-type inhibitors of MT-4 cell dThd kinase.
• Synthesis and evaluation of new 2′,3′-dideoxynucleoside analogs as potential anti-AIDS and anti-herpes drugs
  作者：A Faraj、M Maillard、M Lemaître、S Letellier、F Frappier、JC Florent、DS Grierson、C Monneret、A Zerial

  DOI：10.1016/0223-5234(92)90102-7

  日期：1992.3

  Based on the known structure-activity relationships for the active anti-HIV, a series of 3'-deoxy-3'-N-functionalized thymidine analogs has been synthesized from thymidine. Evaluation for inhibitory activity against human immunodeficiency virus (HIV) replication in CEM cells and against herpes simplex virus in MRC-5 cells is reported.
• Synthesis of 3′-substituted-2′,3′-dideoxynucleoside analogs as potential anti-aids drugs
  作者：Michel Maillard、Abdesslem Faraj、François Frappier、Jean-Claude Florent、David S. Grierson、Claude Monneret

  DOI：10.1016/s0040-4039(00)99623-0

  日期：1989.1

  3′-Amino-3′-deoxythymidine was prepared in six steps and in 67% overall yield from thymidine. Five derivatives of and compound were tested for their anti-HIV activity.

  3'-氨基-3'-脱氧胸苷分六个步骤制备，胸腺嘧啶核苷的总收率为67％。五个衍生品和复合他们的抗HIV活性进行了测试。