4-methoxy-2-nitro-1H-phenalen-1-one | 1181778-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 4-methoxy-2-nitro-1H-phenalen-1-one
• 英文别名: 2-nitro-4-methoxyperinaphthenone；4-methoxy-2-nitrophenalen-1-one
• CAS: 1181778-63-1
• 化学式: C₁₄H₉NO₄
• 分子量: 255.23
• InChiKey: KCFXCWMGRGYAIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-methoxy-1H-phenalen-1-one 在 硝酸 、 溶剂黄146 作用下， 反应 3.0h， 以33%的产率得到4-methoxy-2-nitro-1H-phenalen-1-one
  参考文献：
  名称：

  Structure−Activity Relationship in the Interaction of Substituted Perinaphthenones with Mycosphaerella fijiensis

  摘要：

  The levels of native fungitoxic perinaphthenone phytoalexins in susceptible Musa varieties (banana), which are commercially grown in large plantations, are too low to provide plants with long-lasting protection against highly pathogenic fungi. Novel strategies for plant protection are necessary to reduce crop losses and to prevent the development of resistant fungal strains. The synthesis of novel fungicides based on the structures of perinaphthenone natural products is considered to be a promising strategy. Thirteen substituted, perinaphthenones, among them two known natural products (1, 2) and 11 synthetics (3-13), were evaluated for their activity against Mycosphaerella fijiensis, and their half-maximal inhibitory concentrations (IC50) were calculated to establish structure-activity relationships (SAR). A SAR trend was hypothesized, leading to the design of a new compound, 4-methoxy-2-nitro-1H-phenalen-1-one (14); the new compound displayed significantly enhanced in vitro activity against M. fijiensis compared to other perinaphthenone derivatives. The activity of 14 was comparable to that of two commercial fungicides.

  DOI：

  10.1021/jf901052e

文献信息

• Structure−Activity Relationship in the Interaction of Substituted Perinaphthenones with Mycosphaerella fijiensis
  作者：William Hidalgo、Luisa Duque、Jairo Saez、Rafael Arango、Jesús Gil、Benjamín Rojano、Bernd Schneider、Felipe Otálvaro

  DOI：10.1021/jf901052e

  日期：2009.8.26

  The levels of native fungitoxic perinaphthenone phytoalexins in susceptible Musa varieties (banana), which are commercially grown in large plantations, are too low to provide plants with long-lasting protection against highly pathogenic fungi. Novel strategies for plant protection are necessary to reduce crop losses and to prevent the development of resistant fungal strains. The synthesis of novel fungicides based on the structures of perinaphthenone natural products is considered to be a promising strategy. Thirteen substituted, perinaphthenones, among them two known natural products (1, 2) and 11 synthetics (3-13), were evaluated for their activity against Mycosphaerella fijiensis, and their half-maximal inhibitory concentrations (IC50) were calculated to establish structure-activity relationships (SAR). A SAR trend was hypothesized, leading to the design of a new compound, 4-methoxy-2-nitro-1H-phenalen-1-one (14); the new compound displayed significantly enhanced in vitro activity against M. fijiensis compared to other perinaphthenone derivatives. The activity of 14 was comparable to that of two commercial fungicides.