3-(4-methylphenyl)-7a-methyl-7,7a-dihydrofuran[3,2-d][1,2]oxathin-5,5-dioxide-2(4H)-one | 1589532-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫烷类
• 英文名称: 3-(4-methylphenyl)-7a-methyl-7,7a-dihydrofuran[3,2-d][1,2]oxathin-5,5-dioxide-2(4H)-one
• 英文别名: 7a-Methyl-5,5-dioxo-3-(p-tolyl)-4,7-dihydrofuro[3,2-d]oxathiin-2-one；7a-methyl-3-(4-methylphenyl)-5,5-dioxo-4,7-dihydrofuro[3,2-d]oxathiin-2-one
• CAS: 1589532-61-5
• 化学式: C₁₄H₁₄O₅S
• 分子量: 294.328
• InChiKey: BZLODSAURQMJTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(4-methylphenyl)-5-(hydroxymethyl)-4-methoxyfuran-2(5H)-one 在 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-methylphenyl)-7a-methyl-7,7a-dihydrofuran[3,2-d][1,2]oxathin-5,5-dioxide-2(4H)-one
  参考文献：
  名称：

  Synthesis and anti-BVDV activity of novel δ-sultones in vitro: Implications for HCV therapies

  摘要：

  In this study we report the synthesis and activity against bovine viral diarrhea virus (BVDV) of a novel series of bicycle delta-sultones containing gamma-lactones. BVDV is responsible for major losses in cattle. Some of the synthesized delta-sultones showed pronounced anti-BVDV activity with EC50 values of 0.12-1.0 mu M and no significant cytotoxicity. Among them, the ortho bromosubstituted derivative 4f (EC50 = 0.12 mu M) showed better antiviral activity than other derivatives and was 10 fold more that of than positive control ribavirin (EC50 = 1.3 mu M). BVDV is also considered to be a valuable surrogate for the hepatitis C virus (HCV) in antiviral drug studies. The above results provided a novel candidate for the development of anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.012

文献信息

• Synthesis and anti-BVDV activity of novel δ-sultones in vitro: Implications for HCV therapies
  作者：Hai-Wei Xu、Ling-Jie Zhao、Huan-Fei Liu、Dan Zhao、Jiao Luo、Xiao-Ping Xie、Wen-Sheng Liu、Jia-Xin Zheng、Gui-Fu Dai、Hong-Min Liu、Long-Hua Liu、Yi-Bo Liang

  DOI：10.1016/j.bmcl.2014.03.012

  日期：2014.5

  In this study we report the synthesis and activity against bovine viral diarrhea virus (BVDV) of a novel series of bicycle delta-sultones containing gamma-lactones. BVDV is responsible for major losses in cattle. Some of the synthesized delta-sultones showed pronounced anti-BVDV activity with EC50 values of 0.12-1.0 mu M and no significant cytotoxicity. Among them, the ortho bromosubstituted derivative 4f (EC50 = 0.12 mu M) showed better antiviral activity than other derivatives and was 10 fold more that of than positive control ribavirin (EC50 = 1.3 mu M). BVDV is also considered to be a valuable surrogate for the hepatitis C virus (HCV) in antiviral drug studies. The above results provided a novel candidate for the development of anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.