5-hydroxy-2-formamidophenyl-2'-thiazolylketone | 197512-22-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hydroxy-2-formamidophenyl-2'-thiazolylketone
• 英文别名: N-[4-hydroxy-2-(1,3-thiazole-2-carbonyl)phenyl]formamide
• CAS: 197512-22-4
• 化学式: C₁₁H₈N₂O₃S
• 分子量: 248.262
• InChiKey: OUCSINCULLASQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2-formamidophenyl-2'-thiazolylketone 在 吡啶 、 盐酸 、 titanium(III) chloride 、 锌 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.5h， 生成 5-hydroxycamalexin
  参考文献：
  名称：

  Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani

  摘要：

  The unusual metabolism of the cruciferous phytoalexin camalexin by virulent and weakly virulent isolates of the root rot fungus Rhizoctonia solani Kuhn is reported. This biotransformation proceeded via 5-hydroxycamalexin, which was further biotransformed into more polar metabolites. Importantly, the metabolites resulting from transformation of camalexin were significantly less toxic to the pathogen than camalexin. Thus, it was concluded that R. solani can detoxify camalexin through oxidation of the indole ring. The chemistry involved in the structure determination of the intermediates of this pathway, their synthesis as well as antifungal activity is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00479-3
• 作为产物：
  描述：

  2-nitro-5-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde 在 palladium on activated charcoal 盐酸 、 重铬酸吡啶 、 正丁基锂 、 氢气 、 乙酸酐 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 17.75h， 生成 5-hydroxy-2-formamidophenyl-2'-thiazolylketone
  参考文献：
  名称：

  Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani

  摘要：

  The unusual metabolism of the cruciferous phytoalexin camalexin by virulent and weakly virulent isolates of the root rot fungus Rhizoctonia solani Kuhn is reported. This biotransformation proceeded via 5-hydroxycamalexin, which was further biotransformed into more polar metabolites. Importantly, the metabolites resulting from transformation of camalexin were significantly less toxic to the pathogen than camalexin. Thus, it was concluded that R. solani can detoxify camalexin through oxidation of the indole ring. The chemistry involved in the structure determination of the intermediates of this pathway, their synthesis as well as antifungal activity is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00479-3

文献信息

• Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani
  作者：M.Soledade C. Pedras、Abdul Q. Khan

  DOI：10.1016/s0031-9422(99)00479-3

  日期：2000.1

  The unusual metabolism of the cruciferous phytoalexin camalexin by virulent and weakly virulent isolates of the root rot fungus Rhizoctonia solani Kuhn is reported. This biotransformation proceeded via 5-hydroxycamalexin, which was further biotransformed into more polar metabolites. Importantly, the metabolites resulting from transformation of camalexin were significantly less toxic to the pathogen than camalexin. Thus, it was concluded that R. solani can detoxify camalexin through oxidation of the indole ring. The chemistry involved in the structure determination of the intermediates of this pathway, their synthesis as well as antifungal activity is described. (C) 2000 Elsevier Science Ltd. All rights reserved.