trans-α-Methyl-crotonaldehyd-dimethylhydrazon | 21083-08-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: trans-α-Methyl-crotonaldehyd-dimethylhydrazon
• 英文别名: 2-Methyl-but-2-enal-N,N-dimethyl-hydrazon；N-methyl-N-(2-methylbut-2-enylideneamino)methanamine
• CAS: 21083-08-9
• 化学式: C₇H₁₄N₂
• 分子量: 126.202
• InChiKey: OQGHKNMZJCKZBC-UHFFFAOYSA-N

物化性质

• 沸点：
  163.0±23.0 °C(Predicted)
• 密度：
  0.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-nitrobenzo[b]thiophene-4,7-dione 、 trans-α-Methyl-crotonaldehyd-dimethylhydrazon 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以28.1%的产率得到7,8-dimethyl-2-nitrothieno[2,3-g]quinoline-4,9-dione
  参考文献：
  名称：

  Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2017.10.043
• 作为产物：
  描述：

  2-Bromo-2-methyl-butyraldehyde 、 偏二甲肼 生成 trans-α-Methyl-crotonaldehyd-dimethylhydrazon
  参考文献：
  名称：

  Duhamel,L.; Valnot,J.-Y., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1978, vol. 286, p. 47 - 50

  摘要：

  DOI：

文献信息

• Ioffe,B.V.; Tsibul'skii,V.V., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 1161 - 1164
  作者：Ioffe,B.V.、Tsibul'skii,V.V.

  DOI：——

  日期：——
• Duhamel,L.; Valnot,J.-Y., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1978, vol. 286, p. 47 - 50
  作者：Duhamel,L.、Valnot,J.-Y.

  DOI：——

  日期：——
• 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.