1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-(E)-5-(2-trimethylsilylvinyl)benzene | 333723-90-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-(E)-5-(2-trimethylsilylvinyl)benzene
• CAS: 333723-90-3
• 化学式: C₁₆H₂₂F₂O₃Si
• 分子量: 328.431
• InChiKey: JKJDTJBYLYMIMZ-JWQHCSQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-(E)-5-(2-trimethylsilylvinyl)benzene 在 三氟乙酸 作用下， 反应 0.08h， 以95%的产率得到1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-5-vinylbenzene
  参考文献：
  名称：

  SYNTHESIS OF 1-(2-DEOXY-β-D-RIBOFURANOSYL)-2,4-DIFLUORO-5-SUBSTITUTED-BENZENES^*: “THYMINE REPLACEMENT” ANALOGS OF THYMIDINE FOR EVALUATION AS ANTICANCER AND ANTIVIRAL AGENTS

  摘要：

  A group of unnatural 1-(2-deoxy-beta -D-ribofuranosyl)-2,4-difluorbenzenes having a variety of C-5 two-carbon substituents II-CC-X, X = I, Br; -Cr=CH; (E)- CH=CH-X, X = I, Br; - CH=CH(2); - CH(2)CI(1); -CH(N(3)) CH(2)Br], designed as nucleoside mimics, were synthesized for evaluation as anticancer and antiviral agents. The 5-substituted (E)-CH=CH-I and -CH(2)CH(3) compounds exhibited negligible cytotoxicity in a MTT assay (CC(50) = 10(-3) to 10(-4)M range), relative to thymidine (CC(50) 10-3 to 10(-5) M range), against a variety of cancer cell lines. In contrast, the C-5 substituted -C=C-I and -CH(N(3))CH(2)Br compounds were more cytotoxic (CC(50) = 10(-5) to 10(-6) M range). The -C=C-I and -CH(2)CH(3) compounds exhibited similar cytotoxicity against non-transfected (KBALB, 143B) and HSV-1 TK(+) gene transfected (KBALB STK, 143B-LTK) cancer cell lines expressing the herpes simplex virus type 1 (HSV-1) thymidine kinase gene (TK(+)). This observation indicates that expression of the viral TK enzyme did not provide a gene therapeutic effect. The parent group of 5-substituted compounds, that were evaluated using a wide variety of antiviral assay systems [HSV-1, HSV-2, varicella-zoster virus (VZV), vaccinia virus, vesicular stomatitis, cytomegalovirus (CMV), and human immunodeficiency (HIV-1, HIV-2) viruses], showed that this class of unnatural C-aryl nucleoside mimics are inactive and/or weakly active antiviral agents.

  DOI：

  10.1081/ncn-100001436
• 作为产物：
  描述：

  三丁基[(1E)-2-(三甲基硅烷基)乙烯基]锡烷 、 1-(2'-deoxy-β-D-ribofuranosyl)-2,4-difluoro-5-iodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以86%的产率得到1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-(E)-5-(2-trimethylsilylvinyl)benzene
  参考文献：
  名称：

  SYNTHESIS OF 1-(2-DEOXY-β-D-RIBOFURANOSYL)-2,4-DIFLUORO-5-SUBSTITUTED-BENZENES^*: “THYMINE REPLACEMENT” ANALOGS OF THYMIDINE FOR EVALUATION AS ANTICANCER AND ANTIVIRAL AGENTS

  摘要：

  A group of unnatural 1-(2-deoxy-beta -D-ribofuranosyl)-2,4-difluorbenzenes having a variety of C-5 two-carbon substituents II-CC-X, X = I, Br; -Cr=CH; (E)- CH=CH-X, X = I, Br; - CH=CH(2); - CH(2)CI(1); -CH(N(3)) CH(2)Br], designed as nucleoside mimics, were synthesized for evaluation as anticancer and antiviral agents. The 5-substituted (E)-CH=CH-I and -CH(2)CH(3) compounds exhibited negligible cytotoxicity in a MTT assay (CC(50) = 10(-3) to 10(-4)M range), relative to thymidine (CC(50) 10-3 to 10(-5) M range), against a variety of cancer cell lines. In contrast, the C-5 substituted -C=C-I and -CH(N(3))CH(2)Br compounds were more cytotoxic (CC(50) = 10(-5) to 10(-6) M range). The -C=C-I and -CH(2)CH(3) compounds exhibited similar cytotoxicity against non-transfected (KBALB, 143B) and HSV-1 TK(+) gene transfected (KBALB STK, 143B-LTK) cancer cell lines expressing the herpes simplex virus type 1 (HSV-1) thymidine kinase gene (TK(+)). This observation indicates that expression of the viral TK enzyme did not provide a gene therapeutic effect. The parent group of 5-substituted compounds, that were evaluated using a wide variety of antiviral assay systems [HSV-1, HSV-2, varicella-zoster virus (VZV), vaccinia virus, vesicular stomatitis, cytomegalovirus (CMV), and human immunodeficiency (HIV-1, HIV-2) viruses], showed that this class of unnatural C-aryl nucleoside mimics are inactive and/or weakly active antiviral agents.

  DOI：

  10.1081/ncn-100001436