1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-5-vinylbenzene | 333723-93-6

• 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-5-vinylbenzene
• 英文别名: (2R,3S,5R)-5-(2,4-difluoro-5-vinyl-phenyl)-2-(hydroxymethyl)tetrahydrofuran-3-ol；(2R,3S,5R)-5-(5-ethenyl-2,4-difluorophenyl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 333723-93-6
• 化学式: C₁₃H₁₄F₂O₃
• 分子量: 256.249
• InChiKey: ORTMIKLYRHDKIC-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-5-vinylbenzene 在 溴叠氮化物 作用下， 以 硝基甲烷 为溶剂， 反应 0.17h， 以81%的产率得到1-(2-deoxy-β-D-ribofuranosyl)-5-(1-azido-2-bromoethyl)-2,4-difluorobenzene
  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：

  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

文献信息

• SYNTHESIS OF 1-(2-DEOXY-β-<scp>D</scp>-RIBOFURANOSYL)-2,4-DIFLUORO-5-SUBSTITUTED-BENZENES^*: “THYMINE REPLACEMENT” ANALOGS OF THYMIDINE FOR EVALUATION AS ANTICANCER AND ANTIVIRAL AGENTS
  作者：Zhi-Xian Wang、Weili Duan、Leonard I. Wiebe、Jan Balzarini、Erik De Clercq、Edward E. Knaus

  DOI：10.1081/ncn-100001436

  日期：2001.2.26

  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.