1-(2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine | 94892-66-7

• 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: 1-(2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-(2,5-dideoxy-5-iodo-beta-D-threo-pentofuranosyl)thymine；1-[(2R,4R,5S)-4-hydroxy-5-(iodomethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 94892-66-7
• 化学式: C₁₀H₁₃IN₂O₄
• 分子量: 352.129
• InChiKey: LEQXAJKTJWCXEC-BWZBUEFSSA-N

物化性质

• 熔点：
  151-153 °C
• 密度：
  1.871±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine 在 silver(I) acetate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 反应 3.0h， 生成 1-<2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine
  参考文献：
  名称：

  Action of nucleophiles on 2,3′-anhydrothymidine: side-reactions involving the possible intermediacy of 2,5′-anhydro-1-(2-deoxy---Threo-pentofuranosyl) thymine

  摘要：

  2,3'-Anhydrothymidine (1) reacts with the sodium salt of propane-2-thiol and with sodium phenyl selenide to give 5'-substituted products [(3b) and (3c), respectively] in addition to the expected 3'-substituted 2',3'-dideoxynucleoside derivatives [(2b) and (2c)].

  DOI：

  10.1016/s0040-4039(00)74215-8
• 作为产物：
  描述：

  3',4'-anhydrothymidine 在 sodium iodide 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以85%的产率得到1-(2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Nucleophilic Substitution at the 4‘-Position of Nucleosides: New Access to a Promising Anti-HIV Agent 2‘,3‘-Didehydro-3‘-deoxy-4‘-ethynylthymidine

  摘要：

  For the synthesis of 2',3'-didehydro-3'-deoxy-4'-ethynylthymidine (8: 4'-Ed4T), a recently reported promising anti-HIV agent, a new approach was developed. Since treatment of 1-(2,5-dideoxy-beta-L-glyceropent4- enofuranosyl) thymine with Pb(OBz) 4 allowed the introduction of the 4'-benzoyloxy leaving group, nucleophilic substitution at the 4'-position became feasible for the first time. Thus, reaction between the 4'-benzoyloxy derivative (14) and Me3SiC CAl(Et) Cl as a nucleophile led to the isolation of the desired 4'-"down"-ethynyl derivative (18) stereoselectively in 62% yield. As an application of this approach, other 4'-substituted nucleosides, such as the 4'-allyl (24a) and 4'-cyano (26a) derivatives, were synthesized using organosilicon reagents. In these instances, pretreatment of 14 with MeAlCl2 was necessary.

  DOI：

  10.1021/jo060194m

文献信息

• Nucleotide mimics and their prodrugs
  申请人：——

  公开号：US20040059104A1

  公开（公告）日：2004-03-25

  The present invention relates to nucleoside diphosphate mimics and nucleoside triphosphate mimics, which contain diphosphate or triphosphate moiety mimics and optionally sugar-modifications and/or base-modifications. The nucleotide mimics of the present invention, in a form of a pharmaceutically acceptable salt, a pharmaceutically acceptable prodrug, or a pharmaceutical formulation, are useful as antiviral, antimicrobial, and anticancer agents. The present invention provides a method for the treatment of viral infections, microbial infections, and proliferative disorders. The present invention also relates to pharmaceutical compositions comprising the compounds of the present invention optionally in combination with other pharmaceutically active agents.

  本发明涉及核苷二磷酸模拟物和核苷三磷酸模拟物，其中包含二磷酸或三磷酸基团模拟物，以及可选的糖修饰和/或碱基修饰。本发明的核苷酸模拟物，以药学上可接受的盐、药学上可接受的前药或药物配方的形式，可用作抗病毒、抗微生物和抗癌剂。本发明提供了一种治疗病毒感染、微生物感染和增生性疾病的方法。本发明还涉及包含本发明化合物的药物组合物，可选地与其他药理活性剂结合。
• Anti-viral nucleoside analogs and methods for treating viral infections, especially HIV infections
  申请人：Cheng Yung-chi

  公开号：US09126971B2

  公开（公告）日：2015-09-08

  The present invention relates to novel compounds according to the general formulas I, II, III, IV or V: wherein B is nucleoside base according to the structure: and the remaining variables as defined in the specification, and pharmaceutical compositions comprising the compounds. The compounds are useful interalia as anti-viral agents in viral therapy.

  本发明涉及根据一般式I、II、III、IV或V的新化合物： 其中B是根据以下结构的核苷酸碱基： 以及规范中定义的其余变量，以及包含这些化合物的药物组合物。这些化合物可用作抗病毒剂，用于病毒治疗。
• Ozonolysis of 6-N-benzoyl-9-(5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranosyl)adenine and related compounds
  作者：Bhalchandra V. Joshi、Colin B. Reese

  DOI：10.1016/s0040-4039(00)73866-4

  日期：1993.9

  The nucleoside 4',5'-olefins 3, 5, 7 and 9 are readily converted into the corresponding lactones 4, 6, 8 and 10, respectively, by ozonolysis in dichloromethane solution at -78-degrees-C.
• Matulic-Adamic, Jasenka; Pavela-Vrancic, Maja; Skaric, Vinko, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2681 - 2686
  作者：Matulic-Adamic, Jasenka、Pavela-Vrancic, Maja、Skaric, Vinko

  DOI：——

  日期：——
• Synthesis of 5'-Triphosphate Mimics (P3Ms) of 3'-Azido-3',5'-Dideoxythymidine and 3',5'-Dideoxy-5'-Difluoromethylenethymidine as HIV-1 Reverse Transcriptase Inhibitors
  作者：Vivek Rajwanshi、Marija Prhavc、Patrick Fagan、Jennifer Brooks、Tiffany Hurd、P. Dan Cook、Guangyi Wang

  DOI：10.1081/ncn-200055707

  日期：2005.3.1

  3'-Azido-3,5-dideoxythymidine 5-phosphonate and 3',5-dideoxy-5-difluoromethylenethymidine 5'-phosphonate were prepared by multistep syntheses. The nucleoside 5-phosphonates were converted to their triphosphates and triphosphate mimics (P3Ms) containing beta,gamma-difluoromethylene, beta,gamma-dichloromethylene, or beta,gamma-imodo by condensation with pyrophosphate or Pyrophosphate mimics, respectively. Inhibition of HIV-1 reverse transcriptase by the nucleoside P3Ms is briefly discussed.