1-(3,5-di-O-benzyl-4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)-5-fluorouracil | 306305-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,5-di-O-benzyl-4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)-5-fluorouracil
• 英文别名: 5-fluoro-1-[(2R,3R,4S,5R)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)-5-(2-triethylsilylethynyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 306305-16-8
• 化学式: C₃₁H₃₇FN₂O₆Si
• 分子量: 580.728
• InChiKey: FKGRXRVVSSKTCF-LBWLPYLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3,5-di-O-benzyl-4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)-5-fluorouracil 在 三氯化硼 、 吡啶 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 以51 %的产率得到1-(4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)-5-fluorouracil
  参考文献：
  名称：

  [EN] 4'-ALKYNE-2'-DEOXYCYTIDINE-BASED COMPOUNDS AND ANTI-CANCER USES THEREOF
  [FR] COMPOSÉS À BASE DE 4'-ALCYNE-2'-DÉSOXYCYTIDINE ET LEURS UTILISATIONS ANTICANCÉREUSES

  摘要：

  This invention relates, in part, to 4'-alkyne-2'-deoxycytidine-based compounds and derivatives and pharmaceutical compositions thereof for preventing or treating cancers.

  公开号：

  WO2024015916A2
• 作为产物：
  描述：

  1-(2-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)-5-fluorouracil 在 甲醇 、 三乙胺 作用下， 以77 %的产率得到1-(3,5-di-O-benzyl-4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)-5-fluorouracil
  参考文献：
  名称：

  [EN] 4'-ALKYNE-2'-DEOXYCYTIDINE-BASED COMPOUNDS AND ANTI-CANCER USES THEREOF
  [FR] COMPOSÉS À BASE DE 4'-ALCYNE-2'-DÉSOXYCYTIDINE ET LEURS UTILISATIONS ANTICANCÉREUSES

  摘要：

  This invention relates, in part, to 4'-alkyne-2'-deoxycytidine-based compounds and derivatives and pharmaceutical compositions thereof for preventing or treating cancers.

  公开号：

  WO2024015916A2

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATING DISEASE<br/>[FR] COMPOSÉS ET MÉTHODES POUR TRAITER UNE MALADIE
  申请人：[en]ROME THERAPEUTICS, INC.

  公开号：WO2023178133A1

  公开（公告）日：2023-09-21

  The invention provides compounds, compositions and methods for treating medical disorders, such as cancer, an autoimmune disorder, and/or a neurological disorder, and inhibiting LINE1 reverse transcriptase and/or HERV-K reverse transcriptase using a compound according to Formula I or a pharmaceutically acceptable salt thereof, or a related compound provided herein.
• [EN] 4'-ALKYNE-2'-DEOXYCYTIDINE-BASED COMPOUNDS AND ANTI-CANCER USES THEREOF<br/>[FR] COMPOSÉS À BASE DE 4'-ALCYNE-2'-DÉSOXYCYTIDINE ET LEURS UTILISATIONS ANTICANCÉREUSES
  申请人：[en]THOMAS JEFFERSON UNIVERSITY

  公开号：WO2024015916A2

  公开（公告）日：2024-01-18

  This invention relates, in part, to 4'-alkyne-2'-deoxycytidine-based compounds and derivatives and pharmaceutical compositions thereof for preventing or treating cancers.
• 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.