2'-O-propargylthymidine | 860640-50-2

• 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: 2'-O-propargylthymidine
• 英文别名: 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-prop-2-ynoxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 860640-50-2
• 化学式: C₁₃H₁₆N₂O₆
• 分子量: 296.28
• InChiKey: BSRONJSLOYHEHY-DNRKLUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-O-propargylthymidine 、 1,4-二甲苯二叠氮化 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 5.0h， 以48%的产率得到1-[(2R,3R,4R,5R)-4-hydroxy-3-[[1-[[4-[[4-[[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]phenyl]methyl]triazol-4-yl]methoxy]-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Cross-Linked DNA: Propargylated Ribonucleosides as “Click” Ligation Sites for Bifunctional Azides

  摘要：

  2'-O or 3'-O-propargylated adenosines and ribothymidines were used as click targets for cross-linking of oligonucleotides with aliphatic and aromatic azides. The cross-link generates a sugar modification at the 2'-O-ligation site. Inexpensive ribonucleosides were used as starting materials. Cross-linking of oligonucleotides was performed at internal or terminal positions. Hybridization of homodimers with two complementary single strands resulted in stable ligated DNA duplexes.

  DOI：

  10.1021/jo300421p

文献信息

• Novel bicyclonucleoside analogues
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20040143114A1

  公开（公告）日：2004-07-22

  Bicyclonucleoside analogues which exhibit anti-AIDS activity and intermediates to produce oligonucleotide analogues which have anti-sense or anti-gene activity as well as in vivo stability. Compounds of the following formula (1) or their pharmaceutically acceptable salts. 1 wherein R 1 represents a hydrogen atom or a protecting group for a hydroxy group, R 2 represents an azido group or an optionally protected amino group or the like, B represents a purin-9-yl or a 2-oxo-1,2-dihydropyrimidin-1-yl group, which are optionally substituted with substituents selected from the group consisting of a halogen atom, an alkyl group having 1-6 carbon atoms, a hydroxy group, a mercapto group and an amino group.

  具有抗艾滋病活性的双环核苷类似物，以及生产具有抗义或抗基因活性和体内稳定性的寡核苷酸类似物的中间体。下式(1)化合物或其药学上可接受的盐类。 1 其中 R 1 代表氢原子或羟基的保护基团，R 2 B 代表嘌呤-9-基或 2-氧代-1,2-二氢嘧啶-1-基，它们可选择被选自卤素原子、具有 1-6 个碳原子的烷基、羟基、巯基和氨基的取代基取代。
• Novel nucleoside and oligonucleotide analogues
  申请人：SANKYO COMPANY LIMITED

  公开号：US20030207841A1

  公开（公告）日：2003-11-06

  A compound of the formula (1): 1 wherein R 1 and R 2 are the same or different and represent a hydrogen atom, a hydroxyl protecting group, a phosphate group, or —P(R 3 )R 4 , wherein R 3 and R 4 are the same or different and represent a hydroxyl group, an amino group, an alkoxy group having from 1 to 4 carbon atoms, a cyanoalkoxy group having from 1 to 5 carbon atoms or an amino group substituted by an alkyl group having from 1 to 4 carbon atoms; A represents an alkylene group having from 1 to 4 carbon atoms and B represents a purin-9-yl group, a 2-oxo-pyrimidin-1-yl group, a substituted purin-9-yl group or a substituted 2-oxo-pyrimidin-1-yl group having a substituent &agr; selected from the group consisting of a hydroxyl group which may be protected, an alkoxy group having from 1 to 4 carbon atoms, a mercapto group which may be protected, an alkylthio group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an amino group which may be protected, a mono- or di-alkylamino group which may be substituted by an alkyl group having from 1 to 4 carbon atoms, an alkyl group having from 1 to 4 carbon atoms and a halogen atom; or a salt thereof.
• Oligonucleotide analogues and methods utilizing the same
  申请人：Kaneko Masakatsu

  公开号：US20090149404A1

  公开（公告）日：2009-06-11

  A method for the prevention or treatment in a mammal of a disease preventable or treatable by the pharmacologically useful antisense or antigene activity of an oligonucleotide analogue or a pharmacologically acceptable salt thereof in the body of said mammal, which method comprises administering to said mammal in need of such prevention or treatment a pharmaceutically effective amount of an oligonucleotide analogue comprising two or more nucleoside units, wherein at least one of said nucleoside units is a structure of the formula (2): wherein A is methylene; and B is an unsubstituted purin-9-yl, an unsubstituted 2-oxo-pyrimidin-1-yl or a substituted purin-9-yl; or a pharmacologically acceptable salt thereof.
• US7217805B2
  申请人：——

  公开号：US7217805B2

  公开（公告）日：2007-05-15
• US7314923B2
  申请人：——

  公开号：US7314923B2

  公开（公告）日：2008-01-01