6-formyl-9-oxo-9H-xanthene-1,3-diyl diacetate | 1025879-60-0

• 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: 6-formyl-9-oxo-9H-xanthene-1,3-diyl diacetate
• 英文别名: (1-Acetyloxy-6-formyl-9-oxoxanthen-3-yl) acetate
• CAS: 1025879-60-0
• 化学式: C₁₈H₁₂O₇
• 分子量: 340.289
• InChiKey: FJPQDNOOBNOUCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-formyl-9-oxo-9H-xanthene-1,3-diyl diacetate 在 碳酸氢钠 、 溶剂黄146 作用下， 以 丙醇 、 乙醇 为溶剂， 反应 0.5h， 生成 6-[(E)-[(3-chlorophenyl)hydrazinylidene]methyl]-1,3-dihydroxyxanthen-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
• 作为产物：
  描述：

  4-甲基水杨酸 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 tetra(n-butyl)ammonium dichromate(VI) 、 甲烷磺酸 、 phosphorus pentoxide 、 过氧化苯甲酰 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 6-formyl-9-oxo-9H-xanthene-1,3-diyl diacetate
  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

• Synthesis and antiproliferative activity of aryl- and heteroaryl-hydrazones derived from xanthone carbaldehydes
  作者：Martine Varache-Lembège、Stéphane Moreau、Stéphane Larrouture、Danièle Montaudon、Jacques Robert、Alain Nuhrich

  DOI：10.1016/j.ejmech.2007.09.003

  日期：2008.6

  In order to explore the antiproliferative effect associated with the xanthone framework, several arylhydrazonomethyl derivatives were synthesized from various isomeric 1,3-dihydroxyxanthone carbaldehydes. Variation in the position of the aldehydic function led to three sets of compounds, bearing the hydrazonomethyl chain at positions 5, 6 or 7 on the xanthone nucleus, respectively.The antiproliferative effect of the compounds was evaluated in vitro using the MTT colorimetric method against two human cancer cell lines (MCF-7, breast adenocarcinoma, and KB 3.1, squamous, cell oral carcinoma) for two time periods (24 h and 72 h).Among the series, four compounds exhibited interesting growth inhibitory effects against both the cell lines, with IC(50) values in the micromolar concentration range. When compared with doxorubicin, the xanthone derivatives showed moderate cytotoxic effects. Surprisingly, unlike doxorubicin, these compounds displayed no significant time-dependent change in the concentration causing 50% inhibitory effect in proliferation.This unusual cytotoxicity profile led to the hypothesis that these molecules could be endowed with a mechanism of action distinct to that of doxorubicin. (c) 2007 Elsevier Masson SAS. All rights reserved.
• (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.