4'-ethynyl-2'-deoxyguanosine | 306305-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4'-ethynyl-2'-deoxyguanosine
• 英文别名: 9-(2-Deoxy-4-C-ethynyl-beta-D-ribo-pentofuranosyl)guanine；2-amino-9-[(2R,4S,5R)-5-ethynyl-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 306305-14-6
• 化学式: C₁₂H₁₃N₅O₄
• 分子量: 291.266
• InChiKey: MPCMLKLBMSFTTJ-QRPMWFLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4'-ethynyl-2'-deoxyguanosine 在 吡啶 作用下， 以 乙酸乙酯 为溶剂， 以2 %的产率得到2'-deoxy 4'-vinylguanosine
  参考文献：
  名称：

  [EN] NUCLEOSIDE LINE-1 INHIBITORS
  [FR] INHIBITEURS NUCLÉOSIDIQUES DE LINE-1

  摘要：

  The present disclosure provides LINE-1 inhibitors and methods of treating or preventing a disease, disorder, or condition in a subject in need thereof, the methods comprising administering to the subject a therapeutically effective amount of a LINE-1 inhibitor.

  公开号：

  WO2023192491A2
• 作为产物：
  描述：

  9-(3,5-di-O-tert-butyldimethylsilyl-2-deoxy-4-C-ethynyl-ribo-pentofuranosyl)-2,6-dibenzamidopurine 生成 4'-ethynyl-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis of 4′-C-Ethynyl and 4′-C-Cyano Purine Nucleosides from Natural Nucleosides and Their Anti-HIV Activity

  摘要：

  Purine 2'-deoxynucleosides bearing an ethynyl or a cyano group at C-4' of the sugar moiety were synthesized from the corresponding 2'-deoxynucleosides. These compounds exhibited very potent anti-HIV activity, and remained active against drug resistant HIV strains.

  DOI：

  10.1081/ncn-120022678
• 作为试剂：
  描述：

  三羟甲基氨基甲烷盐酸盐 、 4'-ethynyl-2'-deoxyribofuranosyl-2,6-diaminopurine 、 腺苷 在 乙醇 、 4'-ethynyl-2'-deoxyguanosine 、 水 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4'-ethynyl-2'-deoxyguanosine
  参考文献：
  名称：

  4'-C-ethynyl pyrimidine nucleoside compounds

  摘要：

  本发明提供了4'-C-乙炔基嘧啶核苷（不包括4'-C-乙炔基胸腺嘧啶）的化合物，其化学式为[I]：其中B代表从嘧啶和其衍生物中选择的碱基；X代表氢原子或羟基；R代表氢原子或磷酸残基；以及含有上述任一化合物和药学上可接受的载体的制药组合物。优选地，该组合物用作抗HIV剂或治疗艾滋病的药物。

  公开号：

  US20020022722A1

文献信息

• 4′-C-ethynyl pyrimidine nucleosides and pharmaceutical compositions thereof
  申请人：Yamasa Corporation

  公开号：US06403568B1

  公开（公告）日：2002-06-11

  The invention provides 4′-C-ethynyl pyrimidine nucleosides (other than 4′-C-ethynylthymidine) represented by formula [I]: wherein B represents a base selected from the group consisting of pyrimidine and derivatives thereof; X represents a hydrogen atom or a hydroxyl group; and R represents a hydrogen atom or a phosphate residue; and a pharmaceutical composition containing any one of the compounds and a pharmaceutically acceptable carrier. Preferably, the composition is used as an anti-HIV agent or a drug for treating AIDS.

  本发明提供了4'-C-乙炔基嘧啶核苷（不包括4'-C-乙炔基胸腺嘧啶）的化合物，其化学式表示为[I]：其中B代表从嘧啶和其衍生物中选择的碱基；X代表氢原子或羟基；R代表氢原子或磷酸残基；以及含有任何一种化合物和药学上可接受的载体的制药组合物。优选地，该组合物用作抗HIV剂或治疗艾滋病的药物。
• 4′-C-ethynyl pyrimidine nucleoside compounds and pharmaceutical compositions
  申请人：Yamasa Corporation

  公开号：US06291670B1

  公开（公告）日：2001-09-18

  The invention provides 4′-C-ethynyl pyrimidine nucleosides (other than 4′-C-ethynylthymidine) represented by formula [I]: wherein B represents a base selected from the group consisting of pyrimidine and derivatives thereof; X represents a hydrogen atom or a hydroxyl group; and R represents a hydrogen atom or a phosphate residue; and a pharmaceutical composition containing any one of the compounds and a pharmaceutically acceptable carrier. Preferably, the composition is used as an anti-HIV agent or a drug for treating AIDS.

  本发明提供了4'-C-乙炔基嘧啶核苷类化合物（不包括4'-C-乙炔基胸腺嘧啶），其化学式为[I]：其中B代表从嘧啶及其衍生物中选择的碱基；X代表氢原子或羟基；R代表氢原子或磷酸酯基；以及含有任何一种上述化合物和药学上可接受的载体的制药组合物。优选地，该组合物用作抗HIV剂或治疗艾滋病的药物。
• 4′-C-ethynyl purine nucleoside compounds
  申请人：Yamasa Corporation

  公开号：US06333315B1

  公开（公告）日：2001-12-25

  The invention provides 4′-C-ethynyl purine nucleosides represented by formula [I]: wherein B represents a base selected from the group consisting of purine and derivatives thereof; X represents a hydrogen atom or a hydroxyl group; and R represents a hydrogen atom or a phosphate residue; and a pharmaceutical composition containing any one of the compounds and a pharmaceutically acceptable carrier. Preferably, the composition is used as an anti-HIV agent or a drug for treating AIDS.

  该发明提供了由公式[I]所表示的4'-C-乙炔基嘌呤核苷，其中B代表从嘌呤及其衍生物组成的基；X代表氢原子或羟基；R代表氢原子或磷酸残基；以及含有任何一种化合物和药学上可接受的载体的制药组合物。优选地，该组合物用作抗HIV剂或治疗艾滋病的药物。
• Syntheses of 4<i>‘</i><i>-</i><i>C</i>-Ethynyl-β-<scp>d</scp>-<i>arabino- </i>and 4‘-<i>C-</i>Ethynyl-2<i>‘</i>-deoxy-β-<scp>d</scp>-<i>ribo-</i>pentofuranosylpyrimidines and -purines and Evaluation of Their Anti-HIV Activity
  作者：Hiroshi Ohrui、Satoru Kohgo、Kenji Kitano、Shinji Sakata、Eiichi Kodama、Kazuhisa Yoshimura、Masao Matsuoka、Shiro Shigeta、Hiroaki Mitsuya

  DOI：10.1021/jm000209n

  日期：2000.11.1

  4'-C-Ethynyl-beta -D-arabino- and 4'-C-ethynyl-2'-deoxy-beta -D-ribo-pentofuranosylpyrine and -purine nucleosides were synthesized and evaluated for their in vitro anti-HIV activity. The key intermediate, 4-C-ethynyl- or 4-C-triethylsilylethynyl-D-ribo-pentofuranose, was prepared from D-glucose and glycosidated with various pyrimidine or purine bases. The arabino pyrimidine derivatives were prepared from the corresponding ribo derivatives via O-2,2'-anhydro nucleosides. The 2'-deoxy-ribo derivatives were synthesized by radical reduction of 2'-bromo or 2'- phenoxythiocarbonyloxy nucleosides. Among these 4'-C-ethynyl nucleosides, seven analogues proved to be potent against HIV-1 in vitro with EC50 values ranging from 0.0003 to 0.03 muM. These compounds also exerted activity against clinical and multi-dideoxy-nucleoside-resistant HIV-1 strains with comparable EC50 values. Three such 4'-C-ethynyl-2'-deoxypurine analogues including 4'-C-ethynyl-2'-deoxyadenosine and 4'-C-ethynyl-2,6-diamino-2'-deoxy-purine were less cytotoxic [selectivity indices (SIs): 975-2733] than three 4'-C-ethynyl-2-deoxycytidine analogues (SIs: 63-363). 4'-C-Ethynyl-5-fluoro-2'-deoxycytidine was least toxic (SI: >3333) and potent against all HIV strains tested.
• 4'-C-ETHYNYL PYRIMIDINE NUCLEOSIDES
  申请人：YAMASA CORPORATION

  公开号：EP1177201A1

  公开（公告）日：2002-02-06