threothymidine | 16053-52-4

• 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: threothymidine
• 英文别名: 1-(2-deoxy-β-D-threo-pentofuranosyl)thymine；thymidine；2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-threo-pentofuranosyl)-5-methyl-；1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 16053-52-4
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 242.232
• InChiKey: IQFYYKKMVGJFEH-BWZBUEFSSA-N

物化性质

• 熔点：
  172-173 °C
• 密度：
  1.452±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基甲酰胺、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 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：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

制备方法与用途

1-(2-脱氧-β-D-苏基五呋喃基)胸腺嘧啶是一种胸苷类似物，具有在复制的DNA中插入的活性。这类化合物可用于标记细胞并追踪DNA合成过程。

反应信息

• 作为反应物：
  描述：

  threothymidine 在 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 3’-脱氧-3-氟胸苷
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Novel Fluorinated 2′,3′‐Dideoxynucleosides

  摘要：

  A series of 5-(trifluoroethoxymethyl)-2',3'-dideoxyuridines and 5-[bis(trifluorroethoxy)-methyl]-2', 3'-dideoxyuri dines have been prepared and screened for antiviral activity. The conformations of these compounds are discussed on the bases of NOE studies and the MO calculations. Modelling and NOE studies suggest both syn- and anti conformations for these 5-(2,2,2-trifluoroethoxymethyl)- and 5-[bis(2,2,2-trifluoroethoxy)-methyl]- derivatives. The NOE parameters are also suggested to be more attributable to the nature of the fluorine atom than to structural or conformational changes. Compounds 17, 26 and 30 showed some activity in anti-HIV-1 and anti-HIV-2 assays, but the compounds were devoid of activity against HSV and human rhinovirus. The compounds tested exhibited low cytotoxicity and were inactive against a bank of cancer cells in vitro.

  DOI：

  10.1081/ncn-120027814
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 threothymidine
  参考文献：
  名称：

  An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2-diols

  摘要：

  Reaction between suitably protected furanoid glycals 1b-4b, readily obtained from furanoid 1,2-diols (1a-4a), and different silylated pyrimidine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'-deoxy-2'-iodo-beta-D-xylo-pentofuranosyl 5-10 and beta-D-gluco-hexofuranosyl 11 nucleosides, respectively. Compound 5 has been transformed into its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereoselectivity of the reaction is discussed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00332-7

文献信息

• Selective Cleavage of O-(Dimethoxytrityl) Protecting Group with Sodium Periodate
  作者：Dominik Rejman、Šárka Králíková、Zdeněk Točík、Radek Liboska、Ivan Rosenberg

  DOI：10.1135/cccc20020502

  日期：——

  Sodium periodate in aqueous organic solvents selectively removes, under mild reaction conditions, the O-(dimethoxytrityl) protecting group. Selectivity of the cleavage was studied using the nucleoside derivatives protected by various types of groups commonly used in nucleoside and nucleotide chemistry.

  在水有机溶剂中，过碘酸钠在温和的反应条件下选择性地去除了O-(二甲氧基三苯甲基)保护基团。利用核苷衍生物进行了裂解的选择性研究，这些核苷衍生物受到核苷和核苷酸化学中常用的各种基团的保护。
• REACTIVE, LIPOPHILIC NUCLEOSIDE BUILDING BLOCKS FOR THE SYNTHESIS OF HYDROPHOBIC NUCLEIC ACIDS
  申请人：Ionovation GmbH

  公开号：US20190175633A1

  公开（公告）日：2019-06-13

  The present invention relates to a method for the isolation and/or identification of known or unknown sequences of nucleic acids (target sequences) optionally marked with reporter groups by base specific hybridation with complementary sequences using nucleolipids. The nucleolipids are prepared by lipophilizing nucleosides of formula (Ia) wherein Q represents a group having a substituted tetrahydrofuran ring and Bas represents a group having one or more heterocyclic rings having one or more heterocyclic nitrogen atoms.

  本发明涉及一种方法，用于通过碱特异性杂交与互补序列使用核苷酸脂质来分离和/或识别带有报告基团的已知或未知核酸序列（目标序列）。所述核苷酸脂质是通过使式（Ia）的核苷的亲脂化制备的， 其中，Q代表具有取代四氢呋喃环的基团，Bas代表具有一个或多个含有一个或多个杂环氮原子的杂环环的基团。
• New Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides.
  作者：Ahmed E. S. Abdel-Megied、Poul Hansen、Erik B. Pedersen、Carsten M. Nielsen、Hugh Brian Dunford、Nils Åge Frøystein、George W. Francis、Britt Karlsson

  DOI：10.3891/acta.chem.scand.45-1060

  日期：——

  The 3'-iodonucleoside 4 and the 3'-O-methylsulfonylthymidine 9 have been synthesized by condensation of silylated uracils 2 with methyl 5-O-tert-butyldiphensilyl-2,3-dideoxy-3-iodo-D-threo-pentofuran oside (3) and methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-methylsulfonyl-D-erythro- pentofuranoside (8), respectively. The nucleoside 4 and 9 produced the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides

  3'-碘核苷4和3'-O-甲基磺酰基胸苷9是通过将甲硅烷基化的尿嘧啶2与5-O-叔丁基二苯甲硅烷基-2,3-二脱氧-3-碘-D-苏-戊呋喃糖苷缩合而合成的（3）和甲基5-O-叔丁基二苯基甲硅烷基-2-脱氧-3-甲基磺酰基-D-季戊基呋喃呋喃糖苷（8）。在用甲醇钠处理的消除反应中，核苷4和9产生了相应的2'，3'-二氢-2'，3'-二脱氧核苷5。化合物5b对HIV-1没有抗病毒活性。
• Solid-Phase Synthesis of Positively Charged Deoxynucleic Guanidine (DNG) Tethering a Hoechst 33258 Analogue:  Triplex and Duplex Stabilization by Simultaneous Minor Groove Binding
  作者：Putta Mallikarjuna Reddy、Thomas C. Bruice

  DOI：10.1021/ja031557s

  日期：2004.3.1

  charged guanidine replaces the phosphodiester linkages, tethering to Hoechst 33258 fluorophore by varying lengths has been synthesized. A pentameric thymidine DNG was synthesized on solid phase in the 3' --> 5' direction that allowed stepwise incorporation of straight chain amino acid linkers and a bis-benzimidazole (Hoechst 33258) ligand at the 5'-terminus using PyBOP/HOBt chemistry. The stability

  脱氧核胍 (DNG) 是一种 DNA 类似物，其中带正电荷的胍取代了磷酸二酯键，通过不同长度与 Hoechst 33258 荧光团相连。在固相上以 3' --> 5' 方向合成了五聚体胸苷 DNG，允许使用 PyBOP/HOBt 化学在 5'-末端逐步掺入直链氨基酸接头和双苯并咪唑 (Hoechst 33258) 配体. (DNA)(2).DNG-H 三链体和 DNA.DNG-H 双链体的稳定性由 DNG 和 DNG-Hoechst 33258 (DNG-H) 偶联物​​与 30 聚体双链 (ds) DNA、d(CGCCGCGCGCGCGAAAAACCCGGCGCGCGC) 形成)/d(GCGGCGCGCGCGCTTTTTGGGCCGCGCGCG) 和单链 (ss) DNA，5'-CGCCGCGCGCGCGAAAAACCCGGCGCGCGC-3'，分别通过热熔解和荧光发射实验进行了评估。在
• 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。