3,4,5-trihydroxy-N-[(6-hydroxy-4-oxochromen-3-yl)methylideneamino]benzamide

• 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: 3,4,5-trihydroxy-N-[(6-hydroxy-4-oxochromen-3-yl)methylideneamino]benzamide
• 化学式: C₁₇H₁₂N₂O₇
• 分子量: 356.291
• InChiKey: MXXNDZPKDOSPNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  152.59
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  6-羟基-4-氧代-4H-色烯-3-甲醛 、 3,4,5-三羟基苯甲酰肼 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 3,4,5-trihydroxy-N-[(6-hydroxy-4-oxochromen-3-yl)methylideneamino]benzamide
  参考文献：
  名称：

  Activity of some 3-formylchromone derivatives on the induction of chloroplast-free mutants in Euglena gracilis

  摘要：

  The hereditary bleaching test on Euglena gracilis was used for detecting extranuclear mutations. The highest bleaching activity (induction of the chloroplast-free mutants) was shown by the 6-R-3-formylchromones. On the other hand, bleaching-inactive 6-R-3-formylchromone acylhydrazones (derived from gallic and salicylic acids), added at sufficient concentrations in the case of chloroplast mutagenesis in E. gracilis, act as a potent antimutagen. This effect appeared to be a unique feature of chromone derivatives, but was dependent on the type of mutagen. These substances were very effective against the bleaching activity of acridine orange, and were less effective against N-methyl-N'-nitro-N-nitrosoguanidine. The genotoxic effects of these mutagens was reduced, especially during the first stages of induction of this specific cytoplasmic mutation. The experimental study of mutagenicity and antimutagenicty of 3-formylchromone hydrazones was reinforced by data obtained by the semi-empirical AM1 method and lipophilicity values. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00114-7

文献信息

• Synthesis, antimicrobial activity and bleaching effect of some reaction products of 4-oxo-4H-benzopyran-3-carboxaldehydes with aminobenzothiazoles and hydrazides
  作者：Hafez M. El-Shaaer、Pavlína Foltínová、Margita Lácová、Jarmila Chovancová、Henrieta Stankovičová

  DOI：10.1016/s0014-827x(98)00015-9

  日期：1998.3

  The synthesis of the biologically active novel systems derived from reaction of 3-formylchromones with three types of amino derivatives, 6-R-2-2-aminobenzothiazoles, 6-amino-2-R-3-thiobenzothiazoles and hydrazide derivatives (derived from cyanoacetic, isonicotine, salicylic and gallic acids) was carried out. The structures of the prepared compounds have been proved by elemental analysis, H-1 NMR and IR spectra. Antimicrobial activity was studied against the following microorganisms-bacteria G(+) (Staphylococcus aureus 29/58, Bacillus subtilis 18/66), G(-) (Escherichia coli 326/71, Pseudomonas aeruginosa); yeasts: Candida albicans, Saccharomyces cerevisiae; moulds: Microsporum gypseum, Aspergillus niger, Scopulariopsis brevicaulis; and against typical and atypical mycobacteria: Mycobacterium tuberculosis (H37Rv), Mycobacterium kansasii (PFG8), Mycobacterium avium (My 80/72), Mycobacterium fortuitum (1021). The hereditary bleaching effect on the plastid system of Euglena gracilis, a unique phenomenon of the biological activity of chromone derivatives, is reported. The bleaching test on E. gracilis is used for detecting extranuclear mutations. (C) 1998 Elsevier Science S.A. All rights reserved.
• Activity of some 3-formylchromone derivatives on the induction of chloroplast-free mutants in Euglena gracilis
  作者：Pavlı́na Foltı́nová、Margita Lácová、Dušan Loos

  DOI：10.1016/s0014-827x(99)00114-7

  日期：2000.1

  The hereditary bleaching test on Euglena gracilis was used for detecting extranuclear mutations. The highest bleaching activity (induction of the chloroplast-free mutants) was shown by the 6-R-3-formylchromones. On the other hand, bleaching-inactive 6-R-3-formylchromone acylhydrazones (derived from gallic and salicylic acids), added at sufficient concentrations in the case of chloroplast mutagenesis in E. gracilis, act as a potent antimutagen. This effect appeared to be a unique feature of chromone derivatives, but was dependent on the type of mutagen. These substances were very effective against the bleaching activity of acridine orange, and were less effective against N-methyl-N'-nitro-N-nitrosoguanidine. The genotoxic effects of these mutagens was reduced, especially during the first stages of induction of this specific cytoplasmic mutation. The experimental study of mutagenicity and antimutagenicty of 3-formylchromone hydrazones was reinforced by data obtained by the semi-empirical AM1 method and lipophilicity values. (C) 2000 Elsevier Science S.A. All rights reserved.