2'-deoxy-5-iodo-4'-thiouridine | 134699-95-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2'-deoxy-5-iodo-4'-thiouridine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]-5-iodo-pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-5-iodopyrimidine-2,4-dione
• CAS: 134699-95-9
• 化学式: C₉H₁₁IN₂O₄S
• 分子量: 370.168
• InChiKey: LILXFAKUXPTIFM-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-deoxy-5-iodo-4'-thiouridine 在 吡啶 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 22.0h， 生成 [(2R,3S,5R)-5-[5-ethenyl-3-(4-methylbenzoyl)-2,4-dioxopyrimidin-1-yl]-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate
  参考文献：
  名称：

  Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides

  摘要：

  A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridin (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella tester virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

  DOI：

  10.1021/jm950029r

文献信息

• Drugs for the diagnosis of tissue-reproductive activity or the treatment of proliferative diseases
  申请人：——

  公开号：US20030124054A1

  公开（公告）日：2003-07-03

  An agent which comprises, as an active ingredient, a radiolabeled compound as represented by the following formula or a pharmaceutically acceptable salt thereof: 1 wherein R 1 denotes hydrogen, or a linear- or branched-chain alkyl group having 1 - 8 carbon atoms, R 2 denotes hydrogen, hydroxyl or a halogen substituent, R 3 denotes hydrogen or fluorine substituent, R 4 denotes oxygen, sulfur, or a methylene substituent, and R 5 denotes a radioactive halogen substituent. The agent is stable in vivo, and either stays in cells or is incorporated in DNA, thus serving for diagnosis of tissue proliferation activity or treatment of proliferative disease.

  一种代理物，其作为活性成分包括以下公式所代表的放射标记化合物或其药用可接受的盐：其中R1代表氢，或者具有1-8个碳原子的线性或支链烷基基团，R2代表氢、羟基或卤素取代基，R3代表氢或氟取代基，R4代表氧、硫或亚甲基取代基，R5代表放射性卤素取代基。该代理物在体内稳定，要么停留在细胞中，要么被纳入DNA中，因此可用于诊断组织增殖活性或治疗增生性疾病。
• Antiviral pyrimidine nucleosides
  申请人：THE UNIVERSITY OF BIRMINGHAM

  公开号：EP0409575A1

  公开（公告）日：1991-01-23

  Pyrimidine 4′-thionucleosides of the formula I wherein Y is hydroxy or amino, and X is chloro, bromo, iodo, trifluoromethyl, C₂₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl or C₂₋₆ alkynyl and physiologically functional derivatives thereof. These compounds have utility as anti-viral agents.

  式 I 的嘧啶 4′-硫代核苷 其中 Y 是羟基或氨基，X 是氯、溴、碘、三氟甲基、C₂₋₆ 烷基、C₂₋₆ 烯基、C₂₋₆ 卤代烯基或 C₂₋₆ 烷基及其生理功能衍生物。这些化合物可用作抗病毒剂。
• DRUGS FOR THE DIAGNOSIS OF TISSUE-REPRODUCTIVE ACTIVITY OR THE TREATMENT OF PROLIFERATIVE DISEASES
  申请人：Nihon Medi-Physics Co., Ltd.

  公开号：EP1270017A1

  公开（公告）日：2003-01-02

  An agent which comprises, as an active ingredient, a radiolabeled compound as represented by the following formula or a pharmaceutically acceptable salt thereof: wherein R1 denotes hydrogen, or a linear- or branched-chain alkyl group having 1-8 carbon atoms, R2 denotes hydrogen, hydroxyl or a halogen substituent, R3 denotes hydrogen or fluorine substituent, R4 denotes oxygen, sulfur, or a methylene substituent, and R5 denotes a radioactive halogen substituent. The agent is stable in vivo, and either stays in cells or is incorporated in DNA, thus serving for diagnosis of tissue proliferation activity or treatment of proliferative disease.

  一种制剂，其活性成分包括下式所示的放射性标记化合物或其药学上可接受的盐： 其中 R1 表示氢或具有 1-8 个碳原子的直链或支链烷基，R2 表示氢、羟基或卤素取代基，R3 表示氢或氟取代基，R4 表示氧、硫或亚甲基取代基，R5 表示放射性卤素取代基。 该制剂在体内稳定，可留在细胞内或与 DNA 结合，因此可用于诊断组织增殖活动或治疗增殖性疾病。
• 5-IODO-4-THIO-2'-DEOXYURIDINE FOR USE AS RADIOSENSITIZER IN RADIOTHERAPY
  申请人：Uniwersytet Gdanski

  公开号：EP3632468A1

  公开（公告）日：2020-04-08

  The subject of the invention is 5-iodo-4-thio-2'-deoxyuridine for use in radiotherapy as a radiosensitizer, which increases the effectiveness of radiation treatment towards cancer cells.

  本发明的主题是 5-碘-4-硫代-2'-脱氧尿苷，可作为放射增敏剂用于放射治疗，从而提高对癌细胞的放射治疗效果。
• RADIOLABELED PYRIMIDINE NUCLEOSIDE FOR THE DIAGNOSIS OF TISSUE-REPRODUCTIVE ACTIVITY
  申请人：NIHON MEDI-PHYSICS CO., LTD.

  公开号：EP1270017B1

  公开（公告）日：2006-04-12