4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose | 233266-81-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose
• 英文别名: 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-ethynyl-D-ribo-pentofuranose；4-C-ethynyl-1,2-di-O-acetyl-3,5-di-O-benzyl-D-ribo-pentofuranose；[(3R,4S,5R)-2-acetyloxy-5-ethynyl-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl] acetate
• CAS: 233266-81-4
• 化学式: C₂₅H₂₆O₇
• 分子量: 438.477
• InChiKey: DLSJVQLOOWHQOW-DVMHTGGUSA-N

物化性质

• 沸点：
  529.9±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose 在 吡啶 、 sodium hydroxide 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 三溴化硼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Syntheses of 4‘-C-Ethynyl-β-d-arabino- and 4‘-C-Ethynyl-2‘-deoxy-β-d-ribo-pentofuranosylpyrimidines and -purines and Evaluation of Their Anti-HIV Activity

  摘要：

  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.

  DOI：

  10.1021/jm000209n
• 作为产物：
  描述：

  (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 在 正丁基锂 、 硫酸 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose
  参考文献：
  名称：

  PRODUCTION OF BRIDGED ARTIFICIAL NUCLEOSIDES

  摘要：

  提供了一种从化合物(I)作为起始物质制备化合物(III)的方法。

  公开号：

  US20220177509A1

文献信息

• [EN] NUCLEOTIDE AND NUCLEOSIDE THERAPEUTICS COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES RENFERMANT DES NUCLÉOTIDES ET DES NUCLÉOSIDES ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2016145142A1

  公开（公告）日：2016-09-15

  This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

  这份披露涉及到核苷酸和核苷类治疗组合物，用于治疗传染病、病毒感染和癌症，其中核苷酸或核苷的碱基至少含有一个硫醇、硫醌或硫醚。
• Synthesis of 4′-<i>C</i>-Ethynyl-β-<scp>D</scp>-<i>arabino</i>- and 4′-<i>C</i>-Ethynyl-2′-deoxy-β-<scp>D</scp>-<i>ribo</i>- pentofuranosyl Pyrimidines, and Their Biological Evaluation
  作者：Satoru KOHGO、Hiroko HORIE、Hiroshi OHRUI

  DOI：10.1271/bbb.63.1146

  日期：1999.1

  4′-C-Ethynyl-β-D-arabino-pentofuranosyl thymine (14) and cytosine (16), and 4′-C-ethynyl-2′-deoxy-β-D-ribo-pentofuranosyl thymine (25) and cytosine (27) were synthesized by properly protected 4′-C-hydroxy-methyl-3,5-di-O-benzyl-α-D-ribo-pentofuranose (1) from D-glucose. Among them, 2′-deoxy derivatives 25 and 27 exhibited antiviral activity, while cytidine derivatives 16 and 27 inhibited the growth of neoplastic cells.

  4′-C-乙炔基-β-D-阿拉伯五碳呋喃糖胸腺嘧啶（14）和细胞嘧啶（16），以及4′-C-乙炔基-2′-脱氧-β-D-核糖五碳呋喃糖胸腺嘧啶（25）和细胞嘧啶（27）是通过适当保护的4′-C-羟甲基-3,5-二-O-苄基-α-D-核糖五碳呋喃糖（1）从D-葡萄糖合成的。其中，2′-脱氧衍生物25和27表现出了抗病毒活性，而胞苷衍生物16和27抑制了肿瘤细胞的生长。
• 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.

  该发明提供了由公式[I]表示的4'-C-乙炔嘧啶核苷（除了4'-C-乙炔胸腺嘧啶）：其中B代表从嘧啶及其衍生物组成的基；X代表氢原子或羟基；R代表氢原子或磷酸酯基团；以及含有任一化合物和药学上可接受的载体的药物组合物。最好，该组合物用作抗HIV药剂或治疗艾滋病的药物。
• 嘌呤核苷类化合物及其用途
  申请人：中国科学院上海药物研究所

  公开号：CN112574269A

  公开（公告）日：2021-03-30

  本公开提供了一种通式(I)所示嘌呤核苷类化合物或其药学上可接受的盐、结晶水合物或溶剂合物，包含该化合物的药物组合物及其在制备抗病毒药物中的用途。本发明提供的治疗有效量的通式(I)化合物、或其药学上可接受的盐、结晶水合物及溶剂合物或者药物组合物可单独使用，或者与其他一种或多种抗病毒药物结合，用于减轻或治疗病毒感染。本发明提供的抗病毒核苷具有显著的抗HBV活性，结构新颖，有望开发为新型核苷类乙肝的治疗药物。
• 4'-C-ethynyl pyrimidine nucleoside compounds
  申请人：——

  公开号：US20020022722A1

  公开（公告）日：2002-02-21

  The invention provides 4′-C-ethynyl pyrimidine nucleosides (other than 4′-C-ethynylthymidine) represented by formula [I]: 1 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。