1-(2,5-dideoxy-5-O-tosyl-β-D-threo-pentofuranosyl)thymine | 37085-55-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2,5-dideoxy-5-O-tosyl-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-(2-deoxy-5-O-tosyl-β-D-threo-pentofuranosyl)thymine；1-(5-O-tosyl-2-deoxy-β-D-threopentofuranosyl)thymine；5'-O-[(4-Methylphenylsulphonyl)thymidine；[(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 37085-55-5
• 化学式: C₁₇H₂₀N₂O₇S
• 分子量: 396.421
• InChiKey: RSEWNGNFIIXLHN-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2,5-dideoxy-5-O-tosyl-β-D-threo-pentofuranosyl)thymine 在 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 硫化氢 、 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 四甲基胍 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 1-(2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranosyl)-2-thiothymine
  参考文献：
  名称：

  Thiated derivatives of 2′,3′-dideoxy-3′-fluorothymidine: Synthesis, in vitro anti-HIV-1 activity and interaction with recombinant drug resistant HIV-1 reverse transcriptase forms

  摘要：

  Various thiated analogues of thymine 2',3'-dideoxy-3'-fluoronucleoside (FLT) and their 5'-monophosphates and 5'-triphosphates were prepared with the use of modified multistep procedures. The thiated analogues of FLT and FLTMP were evaluated against the wild type and drug- and multidrug-resistant strains of HIV-1, using the replicative phenotyping format of the deCIPhR assay, and showed potent inhibition of drug-resistant HIV-1 strains at low cytotoxicity. Additionally, inhibition of recombinant drug resistant forms of reverse transcriptase from single and multiple HIV-1 mutants by the synthesized 5'-triphosphates was investigated. The strongest inhibition was observed for K103N and Delta 67 mutants and the most potent anti-HIV-1 activity against drug resistant strains and the lowest cytotoxicity was exerted by S(4)FLTMP and FLTMP which may be regarded as potential anti-HIV/AIDS agents. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.antiviral.2011.05.012

文献信息

• METHOD FOR PREPARING NANOPARTICLES BASED ON FUNCTIONAL AMPHIPHILIC MOLECULES OR MACROMOLECULES, AND THE USE THEREOF
  申请人：UNIVERSITE VICTOR SEGALEN BORDEAUX 2

  公开号：US20140308343A1

  公开（公告）日：2014-10-16

  The invention relates to a method for preparing nanoparticles based on functional amphiphilic molecules or macromolecules, optionally in the presence of at least one colipide, enabling the encapsulation of therapeutic agents, especially anti-tumoral agents, and the use thereof for the transport and vectorization of therapeutic agents, especially anti-tumoral agents.

  本发明涉及一种基于功能性两亲分子或大分子的纳米粒子制备方法，可选地在至少一种胆固醇类物质的存在下，使治疗剂，特别是抗肿瘤剂封装，并用于治疗剂，特别是抗肿瘤剂的输送和载荷。
• Urjasz, Wojciech; Celewicz, Lech; Golankiewicz, Krzysztof, Organic Preparations and Procedures International, 1995, vol. 27, # 1, p. 109 - 113
  作者：Urjasz, Wojciech、Celewicz, Lech、Golankiewicz, Krzysztof

  DOI：——

  日期：——
• Synthesis of New 5″-Sulfonylamido Derivatives of 3″-Azido-3″-Deoxythymidine (AZT)
  作者：Wojciech Urjasz、Lech Celewicz、Krzysztof Golankiewicz

  DOI：10.1080/07328319608007387

  日期：1996.6

  A series of 5'-N-methanesulfonyl derivatives of 3'-azido-5'-(alkylamino)-3',5'-dideoxythymidine was synthesised. The first step of the synthesis involved the reaction of 1-(2,5-dideoxy-5-O-tosyl-beta-D-threo-pentofuranosyl)thymine 1 with an appropriate amine to give 1-[5-(alkylamino)-2,5-dideoxy-beta-D-threo-pentofuranosyl]thymine 2a-e and 1-(2,5-dideoxy-beta-threo-pent-4-enofuranosyl)thymine 3 as a by-product. Compounds 2a-e were treated with an excess of methanesulfonyl chloride to yield intermediates 1-[5-(dimethylamino)-3-O-methanesulfonyl-2,3,5-trideoxy-beta-D-threo-pentofuranosyl]thymine 4a and 1-[5-(N-alkyl-N-methanesulfonyl)-3-O-methanesulfonyl-2,3,5-trideoxy-beta-D-threo-penfuranosyl]thymines 4b-e. The reaction of 4a-e with lithium azide in dimethylformamide afforded the final compounds 1-[3-azido-5-(N-methyl-N-methanesulfonyl)-2,3,5-trideoxy-beta-D-erythro-penofuranosyl]thymine 5a and 1-[3-azido-5-(N-alkyl-N-methanesulfonyl)-2,3,5-trideoxy-beta-D-erythro-penofuranosyl]thymines 5b-e. The independent synthesis of 4',5'-unsaturated product 3 was also described.
• US3975374A
  申请人：——

  公开号：US3975374A

  公开（公告）日：1976-08-17
• US9050268B2
  申请人：——

  公开号：US9050268B2

  公开（公告）日：2015-06-09