5,6-dimethyl-2'-deoxyuridine | 51432-35-0

• 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: 5,6-dimethyl-2'-deoxyuridine
• 英文别名: 5,6-Dimethyl-2'-desoxyuridin；6-methyl-thymidine；Thymidine, 6-methyl-；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5,6-dimethylpyrimidine-2,4-dione
• CAS: 51432-35-0
• 化学式: C₁₁H₁₆N₂O₅
• 分子量: 256.258
• InChiKey: SQLJDQFFUYFUQN-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,6-dimethyl-2,4-bis-O-(trimethylsilyl)uracil 在 sodium methylate 、 zinc(II) chloride 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 5,6-dimethyl-2'-deoxyuridine
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines

  摘要：

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.

  DOI：

  10.1080/15257779408013234

文献信息

• Modified 2' and 3'-nucleoside prodrugs for treating flaviridae infections
  申请人：IDENIX Pharmaceuticals, Inc.

  公开号：EP2332952A1

  公开（公告）日：2011-06-15

  2' and/or 3' prodrugs of 1', 2', 3' or 4'-branchednucleosides, and their pharmaceutically acceptable salts and derivatives are described. These prodrugs are useful in the prevention and treatment of Flaviviridae infections, including HCV infection, and other related conditions. Compounds and compositions of the prodrugs of the present invention are described. Methods and uses are also provided that include the administration of an effective amount of the prodrugs of the present invention, or their pharmaceutically acceptable salts or derivatives. These drugs may optionally be administered in combination or alteration with further anti-viral agents to prevent or treat Flaviviridae infections and other related conditions.

  描述了 1'、2'、3'或 4'-溴核苷的 2'和/或 3'原药及其药学上可接受的盐和衍生物。这些原药可用于预防和治疗弗拉维病毒科感染（包括 HCV 感染）及其他相关疾病。描述了本发明原药的化合物和组合物。还提供了包括施用有效量的本发明原药或其药学上可接受的盐或衍生物的方法和用途。这些药物可选择与其他抗病毒药物联合或改变剂量使用，以预防或治疗弗拉维病毒科感染和其他相关疾病。
• Modified 2' and 3' -nucleoside prodrugs for treating flaviridae infections
  申请人：IDENIX Pharmaceuticals, Inc.

  公开号：EP2799442A1

  公开（公告）日：2014-11-05

  2' and/or 3' prodrugs of 1', 2', 3' or 4'-branchednucleosides, and their pharmaceutically acceptable salts and derivatives are described. These prodrugs are useful in the prevention and treatment of Flaviviridae infections, including HCV infection, and other related conditions. Compounds and compositions of the prodrugs of the present invention are described. Methods and uses are also provided that include the administration of an effective amount of the prodrugs of the present invention, or their pharmaceutically acceptable salts or derivatives. These drugs may optionally be administered in combination or alteration with further anti-viral agents to prevent or treat Flaviviridae infections and other related conditions.

  描述了 1'、2'、3'或 4'-溴核苷的 2'和/或 3'原药及其药学上可接受的盐和衍生物。这些原药可用于预防和治疗弗拉维病毒科感染（包括 HCV 感染）及其他相关疾病。描述了本发明原药的化合物和组合物。还提供了包括施用有效量的本发明原药或其药学上可接受的盐或衍生物的方法和用途。这些药物可选择与其他抗病毒药物联合或改变剂量使用，以预防或治疗弗拉维病毒科感染和其他相关疾病。
• Targeting human satellite II (HSATII)
  申请人：The General Hospital Corporation

  公开号：US10301624B2

  公开（公告）日：2019-05-28

  Methods for treating cancer, e.g., cancer of epithelial origin, by specifically targeting human satellite II (HSATII) using sequence specific agents such as oligonucleotides. As shown herein, the hetero chromatic HSATII satellite repeat is silenced in normal cells, but massively over expressed in epithelial cancers and in cancer cell lines when grown as xenografts or in 3D culture. Induction of HSATII RNA, either in xenografts or using in vitro reconstitution models, suggests the appearance of complementary DNA intermediates.

  使用序列特异性制剂（如寡核苷酸）特异性靶向人类卫星 II（HSATII）治疗癌症（如上皮源性癌症）的方法。如本文所示，异色 HSATII 卫星重复序列在正常细胞中沉默，但在上皮癌中以及在异种移植或三维培养的癌细胞系中大量过度表达。无论是在异种移植中还是使用体外重组模型诱导 HSATII RNA，都表明出现了互补 DNA 中间体。
• MODIFIED 2' AND 3' -NUCLEOSIDE PRODUGS FOR TREATING FLAVIRIDAE INFECTIONS
  申请人：Idenix (Cayman) Limited

  公开号：EP1523489A2

  公开（公告）日：2005-04-20
• TARGETING HUMAN SATELLITE II (HSATII)
  申请人：The General Hospital Corporation

  公开号：EP3161159A1

  公开（公告）日：2017-05-03