1-(3-iodo-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine | 14260-82-3

• 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-(3-iodo-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine
• 英文别名: 3'-deoxy-3'-iodothymidine；3'-iodo-3'-deoxythymidine；3'-iodo-3'-deoxy-thymidine；3'-Deoxy-3'-iodothymidin；1-[(2R,4S,5R)-5-(hydroxymethyl)-4-iodooxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 14260-82-3
• 化学式: C₁₀H₁₃IN₂O₄
• 分子量: 352.129
• InChiKey: RHYWJBFVIQZQQA-XLPZGREQSA-N

物化性质

• 熔点：
  165.5-166 °C(Solv: water (7732-18-5))
• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -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-(3-iodo-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 cobalt(II) chloride 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of (3′R)-3′-deoxy-3′-C-nitromethylthymidine

  摘要：

  DOI：

  10.1016/0008-6215(95)00003-c
• 作为产物：
  描述：

  1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine 在 水 、 溶剂黄146 作用下， 反应 0.5h， 生成 1-(3-iodo-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine
  参考文献：
  名称：

  3′-Bromo Analogues of Pyrimidine Nucleosides as a New Class of Potent Inhibitors ofMycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) is a major health problem worldwide. We herein report a new class of pyrimidine nucleosides as potent inhibitors of Mycobacterium tuberculosis (M. tuberculosis). Various 2'- or 3'-halogeno derivatives of pyrimidine nucleosides containing uracil, 5-fluorouracil, and thymine bases were synthesized and evaluated for antimycobacterial activities. Among the compounds tested, 3'-bromo-3'-deoxy-arabinofuranosylthymine (3') was the most effective antituberculosis agent in the in vitro assays against wild-type M. tuberculosis strain (H37Ra) (MIC50 = 1 mu g/mL) as well as drug-resistant (H37Rv) (rifampicin-resistant and isoniazid-resistant) strains of M. tuberculosis (MIC50 = 1-2 mu g/mL). Compound 3' also inhibited intracellular M. tuberculosis in a human monocytic cell line infected with H37Ra, demonstrating higher activity against intramacrophagic mycobacteria (80% reduction at 10 mu g/mL concentration) than extracellular mycobacteria (75% reduction at 10 mu g/mL concentration). In contrast, pyrimidine nucleosides possessing 5-fluorouracil base were weak inhibitors of M. tuberculosis. No cytotoxicity was found up to the highest concentration of compounds tested (CC50 > 100-200 mu g/mL) against a human cell line. Overall, these encouraging results substantiate the potential of this new class of compounds as promising antituberculosis agents.

  DOI：

  10.1021/jm100165w

文献信息

• STABILISATION OF RADIOPHARMACEUTICAL PRECURSORS
  申请人：Kvaale Svein

  公开号：US20100015052A1

  公开（公告）日：2010-01-21

  The invention relates to a method for improving stability of radiopharmaceutical precursors, and in particular non radiolabelled nucleoside derivatives which are used as precursors for production of radiolabelled nucleoside derivatives for use in in vivo imaging procedures such as positron emission tomography (PET). The invention further includes formulations of radiopharmaceutical precursors, and cassettes for automated synthesis apparatus comprising the same.

  本发明涉及一种改进放射性药物前体稳定性的方法，特别是用作放射性核素标记核苷衍生物的前体的非放射性核苷衍生物，用于生产用于体内成像程序（如正电子发射断层扫描（PET））的放射性核苷衍生物。本发明还包括放射性药物前体的配方以及包含其的自动合成设备的卡式盒。
• Oligonucleotides having chiral phosphorus linkages
  申请人：——

  公开号：US20010008936A1

  公开（公告）日：2001-07-19

  Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphonate, chiral Rp alkylphosphonate, chiral Sp phosphoamidate, chiral Rp phosphoamidate, chiral Sp phosphotriester, and chiral Rp phosphotriester linkages. The novel oligonucleotides are prepared via a stereospecific SN 2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate anion on the 3′ position of a xylonucleotide. The reaction proceeds via inversion at the 3′ position of the xylo reactant species, resulting in the incorporation of phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate linked ribofuranosyl sugar moieties into the oligonucleotide.

  本发明提供了具有高度纯的手性Sp磷酸硫酯、手性Rp磷酸硫酯、手性Sp烷基膦酸酯、手性Rp烷基膦酸酯、手性Sp磷酰胺酸酯、手性Rp磷酰胺酸酯、手性Sp磷酸三酯和手性Rp磷酸三酯键的序列特异性寡核苷酸。新型寡核苷酸通过对木糖核苷酸的3'位置进行立体特异性的SN2亲核攻击制备而成，反应通过在木糖反应物种的3'位置进行反转，从而将磷酸二酯、磷酸硫酯、磷酸胺酯、磷酸三酯或烷基膦酸酯连接的核糖核苷糖基团并入寡核苷酸中。
• Stabilisation of fluorothymidine precursors
  申请人：GE HEALTHCARE AS

  公开号：EP2368580A1

  公开（公告）日：2011-09-28

  The invention relates to a method for improving stability of radiopharmaceutical precursors, and in particular non radiolabelled nucleoside derivatives which are used as precursors for production of radiolabelled nucleoside derivatives for use in in vivo imaging procedures such as positron emission tomography (PET). The invention further includes formulations of radiopharmaceutical precursors, and cassettes for automated synthesis apparatus comprising the same.

  本发明涉及一种提高放射性药物前体稳定性的方法，特别是非放射性标记核苷衍生物的稳定性，该衍生物用作生产放射性标记核苷衍生物的前体，用于正电子发射断层扫描（PET）等体内成像程序。本发明还包括放射性药物前体的制剂，以及包含这些前体的自动合成装置盒。
• OLIGONUCLEOTIDES HAVING CHIRAL PHOSPHORUS LINKAGES
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0655088B1

  公开（公告）日：2002-07-24
• Cell culture medium
  申请人：Genetix Limited

  公开号：EP1818392B1

  公开（公告）日：2010-08-25