2-[(7-hydroxy-2-oxochromen-4-yl)methylsulfanyl]-1H-quinazolin-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-[(7-hydroxy-2-oxochromen-4-yl)methylsulfanyl]-1H-quinazolin-4-one
• 英文别名: 2-[(7-hydroxy-2-oxochromen-4-yl)methylsulfanyl]-3H-quinazolin-4-one
• 化学式: C₁₈H₁₂N₂O₄S
• 分子量: 352.37
• InChiKey: WJUOJTBPBKGQGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  间苯二酚 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 2-[(7-hydroxy-2-oxochromen-4-yl)methylsulfanyl]-1H-quinazolin-4-one
  参考文献：
  名称：

  Benzouracil–coumarin–arene conjugates as inhibiting agents for chikungunya virus

  摘要：

  Chikungunya virus (CHIKV) is an arbovirus that was first recognized in an epidemic form in East Africa in 1952-1953. The virus is primarily transmitted through mosquitoes and the resulting disease, chikungunya fever, is found in nearly 40 countries. Neither an effective vaccine nor a specific antiviral drug exists for treatments of chikungunya fever. Thus 22 new conjugated compounds of uracil-coumarin-arene were designed and synthesized as potential inhibiting agents. Their chemical structures were determined unambiguously by spectroscopic methods, including single-crystal X-ray diffraction crystallography. The three units in these conjugates were connected by specially designed -SCH2- and -OOSO2- joints. Five of these new conjugates were found to inhibit CHIKV in Vero cells with significant potency (ECK50 = 10.2-19.1 mu M) and showed low toxicity (CC50 = 75.2-178 mu M). The selective index values were 8.8-11.5 for three conjugates. By analysis of the data from the anti-viral assays, the structure-activity relationship is derived on the basis of the nature of the uracil, the functional groups attached to the arene, and the joints between the ring units. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.antiviral.2015.03.013