4,9-dichloro-7H-thieno[2',3':4,5]benzo[1,2,3-ij][2,7]naphthyridin-7-one | 1450992-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4,9-dichloro-7H-thieno[2',3':4,5]benzo[1,2,3-ij][2,7]naphthyridin-7-one
• 英文别名: 4,12-Dichloro-11-thia-2,8-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,10(14),12-heptaen-15-one；4,12-dichloro-11-thia-2,8-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,10(14),12-heptaen-15-one
• CAS: 1450992-61-6
• 化学式: C₁₃H₄Cl₂N₂OS
• 分子量: 307.16
• InChiKey: WWGBCHHIWZFUAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴-苯并[b]噻吩-4-醇 在 N-氯代丁二酰亚胺 、 碘苯二乙酸 、 碳酸氢钠 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 6.5h， 生成 4-chloro-7H-thieno[2',3':4,5]benzo[1,2,3-ij][2,7]naphthyridin-7-one 、 4,9-dichloro-7H-thieno[2',3':4,5]benzo[1,2,3-ij][2,7]naphthyridin-7-one
  参考文献：
  名称：

  Scaffold hopping of sampangine: Discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans

  摘要：

  Discovery of novel antifungal agents against Aspergillus fumigatus and Cryptococcus neoformans remains a significant challenge in current antifungal therapy. Herein the antifungal natural product sampangine was used as the lead compound for novel antifungal drug discovery. A series of D-ring scaffold hopping derivatives were designed and synthesized to improve antifungal activity and water solubility. Among them, the thiophene derivative S2 showed broad-spectrum antifungal activity, particularly for Aspergillus fumigatus and Cryptococcus neoformans. Moreover, compound S2 also revealed better water solubility than sampangine, which represents a promising antifungal lead compound for further structural optimization.

  DOI：

  10.1016/j.bmcl.2014.07.064

文献信息

• Scaffold hopping of sampangine: Discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans
  作者：Zhigan Jiang、Na Liu、Guoqiang Dong、Yan Jiang、Yang Liu、Xiaomeng He、Yahui Huang、Shipeng He、Wei Chen、Zhengang Li、Jianzhong Yao、Zhenyuan Miao、Wannian Zhang、Chunquan Sheng

  DOI：10.1016/j.bmcl.2014.07.064

  日期：2014.9

  Discovery of novel antifungal agents against Aspergillus fumigatus and Cryptococcus neoformans remains a significant challenge in current antifungal therapy. Herein the antifungal natural product sampangine was used as the lead compound for novel antifungal drug discovery. A series of D-ring scaffold hopping derivatives were designed and synthesized to improve antifungal activity and water solubility. Among them, the thiophene derivative S2 showed broad-spectrum antifungal activity, particularly for Aspergillus fumigatus and Cryptococcus neoformans. Moreover, compound S2 also revealed better water solubility than sampangine, which represents a promising antifungal lead compound for further structural optimization.