拉米夫定相关化合物(Α-TROXACITABINE) | 145416-37-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: 拉米夫定相关化合物(Α-TROXACITABINE)
• 英文名称: (-)-L-α-dioxolane-cytosine
• 英文别名: (+) BCH-203；4-amino-1-[(2S,4R)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]pyrimidin-2-one
• CAS: 145416-37-1
• 化学式: C₈H₁₁N₃O₄
• 分子量: 213.193
• InChiKey: RXRGZNYSEHTMHC-RQJHMYQMSA-N

物化性质

• 沸点：
  422.5±55.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [(2S,4R)-4-(4-Acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-dioxolan-2-yl]methyl benzoate 在 氨 作用下， 以 甲醇 为溶剂， 生成 拉米夫定相关化合物(Α-TROXACITABINE)
  参考文献：
  名称：

  Potent anti-HIV and anti-HBV activities of (−)-L-β-dioxolane-C and (+)-L-β-dioxolane-T and their asymmetric syntheses.

  摘要：

  The asymmetric syntheses of (+)-L-beta-dioxolane-T and (-)-L-beta-dioxolane-C were accomplished starting from 1,6-anhydro-L-beta-gulopyranose, and their anti-HIV and anti-HBV activities were evaluated in human PBM cells, CEM cells and 2.2.15 cells, respectively.

  DOI：

  10.1016/s0040-4039(00)60890-0

文献信息

• L-.beta.-(2S,4S)- and L-.alpha.-(2S,4R)-dioxolanyl nucleosides as potential anti-HIV agents: asymmetric synthesis and structure-activity relationships
  作者：Hea O. Kim、Raymond F. Schinazi、Kirupathevy Shanmuganathan、Lak S. Jeong、J. Warren Beach、Satyanarayana Nampalli、Deborah L. Cannon、Chung K. Chu

  DOI：10.1021/jm00057a001

  日期：1993.3

  In order to study the structure-activity relationships of L-(2S,4S)- and L-(2S,4R)-dioxolanyl nucleoside as potential anti-HIV agents, various enantiomerically pure L-(2S,4S)- and (2S,4R)-dioxolanylpyrimidine and -purine nucleosides have been synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells. The enantiomerically pure key intermediate 8 has been synthesized in

  为了研究L-（2S，4S）-和L-（2S，4R）-二氧戊环核苷作为潜在抗HIV药物的构效关系，各种对映体纯的L-（2S，4S）-和（2S合成了（4R）-二氧戊环基嘧啶和-嘌呤核苷，并对人外周血单核（PBM）细胞中的HIV-1进行了评估。对映体纯的关键中间体8是由1,6-脱水β-L-古洛糖（2）六步合成的，化合物8与5-取代的嘧啶，6-氯嘌呤和2,6-二取代的嘌呤缩合分别获得各种二氧戊环基嘧啶和-嘌呤核苷。在合成的化合物中，发现5-氟胞嘧啶衍生物29尽管具有毒性（IC50 = 10.0 microM），却显示出最有效的抗HIV活性（EC50 = 0.0012 microM）。嘧啶类似物的抗HIV效能的顺序如下：5-氟胞嘧啶（β-异构体）>胞嘧啶（β-异构体）> 5-氟胞嘧啶（α-异构体）> 5-碘胞嘧啶（β-异构体）>胞嘧啶（ （α-异构体）> 5-溴胞嘧啶（β-异构体）>胸腺嘧啶（β-异构体）>
• Oxidative degradation of L-ascorbic acid acetals to 2′,3′-dideoxy-3′-oxaribofuranosides. Synthesis of enantiomerically pure 2′,3′-dideoxy-3′-oxacytidine stereoisomers as potential antiviral agents
  作者：Bernard R. Belleau、Colleen A. Evans、H.L.Allan Tse、Haolun Jin、Dilip M. Dixit、Tarek S. Mansour

  DOI：10.1016/s0040-4039(00)60903-6

  日期：1992.11

  Enantiomerically pure 2′,3′-dideoxy-3′-oxacytidine nucleoside analogues were synthesized from L-ascorbic acid in eight steps and good overall yield.

  对映体纯的2'，3'-二脱氧-3'-氧代胞苷核苷类似物是由L-抗坏血酸分八步合成的，具有良好的总收率。
• Processes for preparing 1,3-dioxolane nucleosides
  申请人：——

  公开号：US20040087806A1

  公开（公告）日：2004-05-06

  Disclosed are novel processes for preparing 1,3-dioxolane nucleosides of general formula I and II: 1 wherein B is a purine or pyrimidine base or an analog or derivative thereof. The invention also provides intermediates for use in the preparation of these compounds.

  本发明涉及制备一般式I和II的1,3-二氧杂环己烷核苷的新型工艺：其中B是嘌呤或嘧啶碱基或其类似物或衍生物。该发明还提供了用于制备这些化合物的中间体。
• Structure-Activity Relationships Among a New Class of Antiviral Heterosubstituted 2',3'-Dideoxynucleoside Analogues
  作者：Tarek Mansour、Haolun Jin、Wei Wang、Dilip Dixit、Colleen Evans、H. L. Allan Tse、Bernard Belleau、John Gillard、Elizabeth Hooker、Claire Ashman、Nick Cammack、Horacio Salomon、Antonietta Belmonte、Mark Wainberg

  DOI：10.1080/15257779508012439

  日期：1995.5.1

  3'-Oxa-4'-thiocytidine nucleoside analogues 14-17 were prepared from oxathiolanes 10 and 11, and evaluated for activity against HIV-1 and HBV in vitro. The nucleoside analogues were found to possess potent activities against HIV-1 in a panel of cell lines. Compound 16 is moderately active against HBV in 2.2.15 cells.
• PROCESSES FOR PREPARING 1,3-DIOXOLANE NUCLEOSIDES
  申请人：Pharmasset, Inc.

  公开号：EP1534255B1

  公开（公告）日：2011-01-19