7,9-dihydroxy-2-methyl-6H-benzo[c]chromen-6-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7,9-dihydroxy-2-methyl-6H-benzo[c]chromen-6-one
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: RGFSUSDJJWZKMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.67
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-溴-4,6-二甲氧基苯甲醛 在 sodium chlorite 、 sodium dihydrogenphosphate 、 四(三苯基膦)钯 、 三溴化硼 、 potassium carbonate 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 7,9-dihydroxy-2-methyl-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  The Fungal Phytotoxin Alternariol 9-Methyl Ether and Some of Its Synthetic Analogues Inhibit the Photosynthetic Electron Transport Chain

  摘要：

  Alternariol and monomethylalternariol are natural phytotoxins produced by some fungal strains, such as Nimbya and Alternaria. These substances confer virulence to phytopathogens, yet no information is available concerning their mode of action. Here we show that in the micromolar range alternariol 9-methyl ether is able to inhibit the electron transport chain (IC50 = 29.1 +/- 6.5 mu M) in isolated spinach chloroplasts. Since its effectiveness is limited by poor solubility in water, several alternariol analogues were synthesized using different aromatic aldehydes. The synthesized 6H-benzo[c]cromen-6-ones, 5H-chromene[4,3-b]pyridin-5-one, and 5H-chromene[4,3-c]pyridin-5-one also showed inhibitory properties, and three 6H-benzo[c]cromen-6-ones were more effective (IC50 =12.8-22.8 mu M) than the lead compound. Their addition to the culture medium of a cyanobacterial model strain was found to inhibit algal growth, with a relative effectiveness that was consistent with their activity in vitro. In contrast, the growth of a nonphotosynthetic plant cell culture was poorly affected. These compounds may represent a novel lead for the development of new active principles targeting photosynthesis.

  DOI：

  10.1021/np4005882

文献信息

• The Fungal Phytotoxin Alternariol 9-Methyl Ether and Some of Its Synthetic Analogues Inhibit the Photosynthetic Electron Transport Chain
  作者：Antonio Jacinto Demuner、Luiz Cláudio Almeida Barbosa、Ana Cristina Mendes Miranda、Guilherme Carvalho Geraldo、Cleiton Moreira da Silva、Samuele Giberti、Michele Bertazzini、Giuseppe Forlani

  DOI：10.1021/np4005882

  日期：2013.12.27

  Alternariol and monomethylalternariol are natural phytotoxins produced by some fungal strains, such as Nimbya and Alternaria. These substances confer virulence to phytopathogens, yet no information is available concerning their mode of action. Here we show that in the micromolar range alternariol 9-methyl ether is able to inhibit the electron transport chain (IC50 = 29.1 +/- 6.5 mu M) in isolated spinach chloroplasts. Since its effectiveness is limited by poor solubility in water, several alternariol analogues were synthesized using different aromatic aldehydes. The synthesized 6H-benzo[c]cromen-6-ones, 5H-chromene[4,3-b]pyridin-5-one, and 5H-chromene[4,3-c]pyridin-5-one also showed inhibitory properties, and three 6H-benzo[c]cromen-6-ones were more effective (IC50 =12.8-22.8 mu M) than the lead compound. Their addition to the culture medium of a cyanobacterial model strain was found to inhibit algal growth, with a relative effectiveness that was consistent with their activity in vitro. In contrast, the growth of a nonphotosynthetic plant cell culture was poorly affected. These compounds may represent a novel lead for the development of new active principles targeting photosynthesis.