8-methylthieno[2,3-g]quinoline-4,9-dione | 1450992-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-methylthieno[2,3-g]quinoline-4,9-dione
• CAS: 1450992-69-4
• 化学式: C₁₂H₇NO₂S
• 分子量: 229.259
• InChiKey: ITGDYRYLWLAGSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-methylthieno[2,3-g]quinoline-4,9-dione 在 硫酸 、 溴 、 二甲基亚砜 、 potassium nitrate 作用下， 以 溶剂黄146 为溶剂， 反应 8.5h， 生成 2-nitro-4,9-dioxo-4,9-dihydrothieno[2,3-g]quinoline-8-carboxaldehyde
  参考文献：
  名称：

  取代噻吩并苯醌并异噁唑类化合物及其制备 方法与应用

  摘要：

  本发明涉及医药技术领域。本发明提供了一种取代噻吩并苯醌并异噁唑类化合物及其药学上可接受的盐，所述的取代芳香四环类化合物，其结构通式如下：本发明还提供上述化合物的制备方法，以及在制备抗真菌药物中的应用。

  公开号：

  CN105001235B
• 作为产物：
  描述：

  5-溴-苯并[b]噻吩-4-醇 在 碘苯二乙酸 、 碳酸氢钠 、 三氟乙酸 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 8-methylthieno[2,3-g]quinoline-4,9-dione
  参考文献：
  名称：

  取代噻吩并苯醌并异噁唑类化合物及其制备 方法与应用

  摘要：

  本发明涉及医药技术领域。本发明提供了一种取代噻吩并苯醌并异噁唑类化合物及其药学上可接受的盐，所述的取代芳香四环类化合物，其结构通式如下：本发明还提供上述化合物的制备方法，以及在制备抗真菌药物中的应用。

  公开号：

  CN105001235B

文献信息

• 取代芳香四环类抗真菌化合物及其制备方法与 应用
  申请人：中国人民解放军第二军医大学

  公开号：CN103254191B

  公开（公告）日：2016-01-27

  本发明涉及医药技术领域。本发明提供了一种取代芳香四环类化合物及其药学上可接受的盐，所述的取代芳香四环类化合物，其结构通式如下：，本发明还提供上述化合物的制备方法，以及在制备抗真菌药物中的应用。
• Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors
  作者：Na Liu、Hua Zhong、Jie Tu、Zhigan Jiang、Yanjuan Jiang、Yan Jiang、Yuanying Jiang、Jian Li、Wannian Zhang、Yan Wang、Chunquan Sheng

  DOI：10.1016/j.ejmech.2017.10.043

  日期：2018.1

  Lack of novel antifungal agents and severe drug resistance have led to high incidence and associated mortality of invasive fungal infections. To tackle the challenges, novel antifungal agents with new chemotype, fungicidal activity and anti-resistant potency are highly desirable. On the basis of our previously identified simplified analogue of antifungal natural product sampangine, systemic structure-activity relationships were clarified and two novel derivatives showed promising features as novel antifungal lead compounds. Compounds 22b and 22c showed good fungicidal activity against both fluconazole-sensitive and fluconazole-resistant Candida albicans strains. Moreover, they were proven to be potent inhibitors of Candida albicans biofilm formation and yeast-to-hypha morphological transition by down-regulating biofilm-associated genes. In a rat vaginal Candida albicans infection model, compounds 22b and 22c showed excellent therapeutic effects with low toxicity. The results highlighted the potential of sampangine derivatives to overcome fluconazole-related and biofilm-related drug resistance. (C) 2017 Elsevier Masson SAS. All rights reserved.
• 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.