2,4-Dichloro-5-[(4-chloro-phenyl)-hydrazonomethyl]-1,3-dihydroxy-xanthen-9-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,4-Dichloro-5-[(4-chloro-phenyl)-hydrazonomethyl]-1,3-dihydroxy-xanthen-9-one
• 英文别名: 2,4-dichloro-5-[(Z)-[(4-chlorophenyl)hydrazinylidene]methyl]-1,3-dihydroxyxanthen-9-one
• 化学式: C₂₀H₁₁Cl₃N₂O₄
• 分子量: 449.677
• InChiKey: YRNBNWPZINZLDF-GYRAYZOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲基水杨酸 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 磺酰氯 、 tetra(n-butyl)ammonium dichromate(VI) 、 甲烷磺酸 、 phosphorus pentoxide 、 碳酸氢钠 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 丙醇 、 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 14.33h， 生成 2,4-Dichloro-5-[(4-chloro-phenyl)-hydrazonomethyl]-1,3-dihydroxy-xanthen-9-one
  参考文献：
  名称：

  (2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species

  摘要：

  A series of arylhydrazones derived from various 6,8-diacetoxy- or 6,8-dihydroxy-9-oxo-9H-xanthene carboxaldehydes were synthesized and evaluated for their in vitro antifungal properties against two human pathogenic yeasts (Candida albicans and C. krusei) according to a diffusion method. The activity was strongly dependent from the position of the (1-arylhydrazinyl-2-ylidene)methyl chain in the xanthone molecular skeleton. Compounds having the nitrogen side chain in the 4-position, with a further halogen substitution on the terminal phenyl ring showed fungistatic effects. Within this series, the 4-fluorophenylhydrazinyl derivative 13g exhibited the highest activity, particularly against C. krusei, with a greater efficacy than that of econazole, used as reference. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01332-0

文献信息

• (2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species
  作者：Stéphane Moreau、Martine Varache-Lembège、Stéphane Larrouture、Djibril Fall、Arlette Neveu、Gérard Deffieux、Joseph Vercauteren、Alain Nuhrich

  DOI：10.1016/s0223-5234(01)01332-0

  日期：2002.3

  A series of arylhydrazones derived from various 6,8-diacetoxy- or 6,8-dihydroxy-9-oxo-9H-xanthene carboxaldehydes were synthesized and evaluated for their in vitro antifungal properties against two human pathogenic yeasts (Candida albicans and C. krusei) according to a diffusion method. The activity was strongly dependent from the position of the (1-arylhydrazinyl-2-ylidene)methyl chain in the xanthone molecular skeleton. Compounds having the nitrogen side chain in the 4-position, with a further halogen substitution on the terminal phenyl ring showed fungistatic effects. Within this series, the 4-fluorophenylhydrazinyl derivative 13g exhibited the highest activity, particularly against C. krusei, with a greater efficacy than that of econazole, used as reference. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.