5-溴-2',3'-二脱氧-胞苷 | 107036-57-7

• 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: 5-溴-2',3'-二脱氧-胞苷
• 英文名称: 2',3'-dideoxy-5-bromocytidine
• 英文别名: 5-bromo-2',3'-dideoxycytidine；4-amino-5-bromo-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 107036-57-7
• 化学式: C₉H₁₂BrN₃O₃
• 分子量: 290.117
• InChiKey: KCVDVEDJMJMYNW-CAHLUQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-溴-2',3'-二脱氧-胞苷 生成 4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-5-tritiopyrimidin-2-one
  参考文献：
  名称：

  TAYLOR, GEORGE F.;KEPLER, JOHN A., J. LABELL. COMPOUNDS AND RADIOPHARM., 27,(1989) N, C. 683-690

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二脱氧胞啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以57%的产率得到5-溴-2',3'-二脱氧-胞苷
  参考文献：
  名称：

  5-substituted-2',3'-dideoxycytidine compounds with anti-HTLV-III activity

  摘要：

  抗逆转录病毒活性强的5-取代2',3'-脱氧胞苷化合物及其一磷酸盐已被披露。5-氟和5-氮取代的2',3'-脱氧胞苷化合物已被发现对HTLV-III/LAV病毒有效。

  公开号：

  US04788181A1

文献信息

• Novel fluorophosphonate nucleotide derivatives
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0339161A1

  公开（公告）日：1989-11-02

  This invention relates to fluoromethylphosphonate derivatives of certain nucleosides, to methods for their preparation and to their use as antiviral and antitumoral agents.

  这项发明涉及某些核苷类化合物的氟甲基磷酸酯衍生物，涉及它们的制备方法以及它们作为抗病毒和抗肿瘤药物的用途。
• Determining DNA sequences by mass spectrometry
  申请人：Genomyx, Inc.

  公开号：US05003059A1

  公开（公告）日：1991-03-26

  This invention relates to the methods, apparatus, reagents and mixtures of reagents for sequencing natural or recombinant DNA and other polynucleotides. In particular, this invention relates to a method for sequencing polynucleotides based on mass spectrometry to determine which of the four bases (adenine, guanine, cytosine or thymine) is a component of the terminal nucleotide. In particular, the present invention relates to identifying the individual nucleotides by the mass of stable nuclide markers contained within either the dideoxynucleotides, the DNA primer, or the deoxynucleotide added to the primer. This invention is particularly useful in identifying specific DNA sequences in very small quantities in biological products produced by fermentation or other genetic engineering techniques. The invention is therefore useful in evaluating safety and other health concerns related to the presence of DNA in products resulting from genetic engineering techniques.

  本发明涉及用于测序自然或重组DNA和其他多核苷酸的方法、装置、试剂和试剂混合物。特别地，本发明涉及一种基于质谱法的多核苷酸测序方法，以确定四种碱基（腺嘌呤、鸟嘌呤、胞嘧啶或胸腺嘧啶）中哪一种是末端核苷酸的组成部分。具体而言，本发明涉及通过稳定核素标记的质量来识别单个核苷酸，这些标记包含在二脱氧核苷酸、DNA引物或添加到引物中的脱氧核苷酸中。本发明特别适用于在发酵或其他基因工程技术产生的生物制品中识别极小量的特定DNA序列。因此，本发明有助于评估与基因工程技术产生的产品中DNA存在相关的安全和其他健康问题。
• Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogs
  作者：Chong Ho Kim、Victor E. Marquez、Samuel Broder、Hiroaki Mitsuya、John S. Driscoll

  DOI：10.1021/jm00388a020

  日期：1987.5

  5-Substituted 2',3'-dideoxycytidine analogues have been synthesized and evaluated in vitro for their capabilities to protect T4+ lymphocytes from the cytopathic effects of the HTLV-III/LAV (HIV) virus, the causative agent of acquired immunodeficiency syndrome (AIDS). These analogues were designed to be more lipophilic than 2',3'-dideoxycytidine (ddC) in order to enhance central nervous system penetration. Earlier reports had shown that ddC is a potent protective agent. When ddC is substituted at the 5-position with either methyl or bromo substituents, activity is completely abolished. However, when the substitution is fluoro (5-F-ddC), both activity and potency are retained. 2',3'-Dideoxy-5-azacytidine is also protective but more toxic than ddC or 5-F-ddC. In a different approach, an attempt was made to utilize ddCMP, ddTMP, and ddAMP as preformed nucleotides in order to circumvent the generally low level of phosphorylation achieved with dideoxynucleosides which function as relatively poor substrates for the cellular kinases. Only ddAMP is as active as its nucleoside precursor. Because ddAMP is not more active than ddA at low concentrations, it is possible that the active agent is ddA which is generated from ddAMP prior to cell entry.
• DRISCOLL, JOHN S.;MARQUEZ, VICTOR E.;KIM, CHONG-HO;KELLEY, JAMES A.
  作者：DRISCOLL, JOHN S.、MARQUEZ, VICTOR E.、KIM, CHONG-HO、KELLEY, JAMES A.

  DOI：——

  日期：——
• US4788181A
  申请人：——

  公开号：US4788181A

  公开（公告）日：1988-11-29