3-(4-chlorophenyl)-7a-methyl-7,7a-dihydrofuran[3,2-d][1,2]oxathin-5,5-dioxide-2(4H)-one | 1589532-63-7

• 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-chlorophenyl)-7a-methyl-7,7a-dihydrofuran[3,2-d][1,2]oxathin-5,5-dioxide-2(4H)-one
• 英文别名: 3-(4-Chlorophenyl)-7a-methyl-5,5-dioxo-4,7-dihydrofuro[3,2-d]oxathiin-2-one；3-(4-chlorophenyl)-7a-methyl-5,5-dioxo-4,7-dihydrofuro[3,2-d]oxathiin-2-one
• CAS: 1589532-63-7
• 化学式: C₁₃H₁₁ClO₅S
• 分子量: 314.746
• InChiKey: MXVBRFUHXOACAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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-difluorophenyl)-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-chlorophenyl)-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

• Antiviral Activity of 3D, a Butene Lactone Derivative Against Influenza A Virus In Vitro and In Vivo
  作者：Zhenya Wang、Jieyu Fang、Jiao Luo、Duoduo Hou、Yayun Tan、Zichen Gu、Yongzhuang Ge、Lu Mao、Luyang Liu、Hongmin Liu、Zhanyong Wei、Haiwei Xu

  DOI：10.3390/v13020278

  日期：——

  Influenza A virus is a highly variable and contagious respiratory pathogen that can cause annual epidemics and it poses an enormous threat to public health. Therefore, there is an urgent need for a new generation of antiviral drugs to combat the emergence of drug-resistant strains of the influenza virus. A novel series of butene lactone derivatives were screened and the compound 3D was selected, as

  甲型流感病毒是一种高度可变且具有传染性的呼吸道病原体，可引起年度流行病，并对公众健康构成巨大威胁。因此，迫切需要新一代抗病毒药物来对抗流感病毒耐药株的出现。筛选了一系列新的丁烯内酯衍生物并选择了化合物 3D，因为它在体外表现出潜在的抗 A/Weiss/43 H1N1 病毒的低毒抗病毒活性。此外，3D 剂量依赖性地抑制病毒复制、病毒 mRNA 和病毒蛋白的表达。3D 在体外对 A/Virginia/ATCC2/2009 H1N1 和 A/California/2/2014 H3N2 产生抑制作用。添加时间分析表明 3D 在其生命周期的早期阶段抑制了 H1N1。A/Weiss/43 H1N1 诱导的 A549 细胞凋亡通过线粒体凋亡途径通过 3D 减少。3D 可以减少 H1N1 诱导的促炎细胞因子的产生，这些细胞因子在体外和体内由 H1N1 诱导。3D 的给药减少了体内肺部病变和病毒载量。这些结果表明，3D
• 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.