1-[3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-7-propynylisocarbostyril | 374695-04-2

• 分子结构分类: 有机化合物
• 英文名称: 1-[3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-7-propynylisocarbostyril
• 英文别名: [(2R,3S,5R)-3-(4-chlorobenzoyl)oxy-5-(1-oxo-4-prop-1-ynylisoquinolin-2-yl)oxolan-2-yl]methyl 4-chlorobenzoate
• CAS: 374695-04-2
• 化学式: C₃₁H₂₃Cl₂NO₆
• 分子量: 576.433
• InChiKey: DQIZHSZXXYBFFA-UPRLRBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  83.83
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-[3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-7-propynylisocarbostyril 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以90%的产率得到1-(2-deoxy-β-D-ribofuranosyl)-7-propynylisocarbostyril
  参考文献：
  名称：

  SYNTHESIS OF UNNATURAL 7-SUBSTITUTED-1-(2-DEOXY-β-D-RIBOFURANOSYL)ISOCARBOSTYRILS^†: “THYMINE REPLACEMENT” ANALOGS OF DEOXYTHYMIDINE FOR EVALUATION AS ANTIVIRAL AND ANTICANCER AGENTS

  摘要：

  A group of unnatural 1-(2-deoxy-beta -D-ribofuranosyl)isocarbostyrils having a variety of C-7 substituents [H, 4,7-(NO2)(2), I, CF3, CN, (E)-CH=CH-I, -C drop CH, -C dropC-I, -C dropC-Br, -C dropC-Me], designed as nucleoside mimics, were synthesized for evaluation as anticancer and antiviral agents. This class of compounds exhibited weak cytotoxicity in a MTT assay (CC50 = 10(-3) to 10(-5) M range) with the 4,7-dinitro derivative being the most cytotoxic, relative to thymidine (CC50=10(-3) to 10(-5) M range), against a variety of cancer cell lines. The 4,7-dinitro, 7-I and 7-C drop CH compounds exhibited similar cytotoxicity against nontransfected (KBALB, 143B), and HSV-1 TK+ gene transfected (KBALB-STK, 143B-LTK) cancer cell lines possessing the herpes simplex virus type I (HSV-1) thymidine kinase gene (TK+). This observation indicates that these compounds are not substrates for HSV type-1 TK, and are therefore unlikely to be useful in gene therapy based on the HSV gene therapy paradigm.

  DOI：

  10.1081/ncn-100105246
• 作为产物：
  描述：

  1-[3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]isocarbostyril 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 一氯化碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-[3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-7-propynylisocarbostyril
  参考文献：
  名称：

  SYNTHESIS OF UNNATURAL 7-SUBSTITUTED-1-(2-DEOXY-β-D-RIBOFURANOSYL)ISOCARBOSTYRILS^†: “THYMINE REPLACEMENT” ANALOGS OF DEOXYTHYMIDINE FOR EVALUATION AS ANTIVIRAL AND ANTICANCER AGENTS

  摘要：

  A group of unnatural 1-(2-deoxy-beta -D-ribofuranosyl)isocarbostyrils having a variety of C-7 substituents [H, 4,7-(NO2)(2), I, CF3, CN, (E)-CH=CH-I, -C drop CH, -C dropC-I, -C dropC-Br, -C dropC-Me], designed as nucleoside mimics, were synthesized for evaluation as anticancer and antiviral agents. This class of compounds exhibited weak cytotoxicity in a MTT assay (CC50 = 10(-3) to 10(-5) M range) with the 4,7-dinitro derivative being the most cytotoxic, relative to thymidine (CC50=10(-3) to 10(-5) M range), against a variety of cancer cell lines. The 4,7-dinitro, 7-I and 7-C drop CH compounds exhibited similar cytotoxicity against nontransfected (KBALB, 143B), and HSV-1 TK+ gene transfected (KBALB-STK, 143B-LTK) cancer cell lines possessing the herpes simplex virus type I (HSV-1) thymidine kinase gene (TK+). This observation indicates that these compounds are not substrates for HSV type-1 TK, and are therefore unlikely to be useful in gene therapy based on the HSV gene therapy paradigm.

  DOI：

  10.1081/ncn-100105246