benzo-1,2,3-thiadiazole-7-carboxylic acid 2,3,4,5,6-pentafluorobenzyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzo-1,2,3-thiadiazole-7-carboxylic acid 2,3,4,5,6-pentafluorobenzyl ester
• 英文别名: (2,3,4,5,6-Pentafluorophenyl)methyl 1,2,3-benzothiadiazole-7-carboxylate
• 化学式: C₁₄H₅F₅N₂O₂S
• 分子量: 360.264
• InChiKey: XHUNAWLEZATUOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  阿拉酸式苯 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 benzo-1,2,3-thiadiazole-7-carboxylic acid 2,3,4,5,6-pentafluorobenzyl ester
  参考文献：
  名称：

  Novel, Unnatural Benzo-1,2,3-thiadiazole-7-carboxylate Elicitors of Taxoid Biosynthesis

  摘要：

  In order to establish the chemical biological technology for production of valuable secondary metabolites, a novel family of unnatural elicitors derived from the plant activator benzo-1,2,3-thiadiazole-7-carboxylic acid were designed and synthesized. New synthetic elicitors that showed powerful eliciting activities upon taxoid biosynthesis by Taxus chinensis suspension cells were obtained. For example, benzo-1,2,3-thiadiazole-7-carboxylic acid 2-(2-hydroxybenzoxyl) ethyl ester was more effective and resulted in nearly 40% increase in taxuyunnanine C content and production in comparison with methyl jasmonate, which was previously reported as the most powerful chemical elicitor for taxoid biosynthesis. The novel class of elicitors was found to induce plant defense responses, including promotion of H2O2 levels originating from oxidative burst and activation of phenylalanine ammonia lyase. Interestingly the plant defense responses induced corresponded well to the superior stimulating activity in T. chinensis cell cultures. The work indicates that the newly synthesized benzothiadiazoles can act as a new family of elicitors for taxoid biosynthesis in plant cells.

  DOI：

  10.1021/jf0618574

文献信息

• Novel, Unnatural Benzo-1,2,3-thiadiazole-7-carboxylate Elicitors of Taxoid Biosynthesis
  作者：Yufang Xu、Zhengjiang Zhao、Xuhong Qian、Zhigang Qian、Wenhong Tian、Jianjiang Zhong

  DOI：10.1021/jf0618574

  日期：2006.11.1

  In order to establish the chemical biological technology for production of valuable secondary metabolites, a novel family of unnatural elicitors derived from the plant activator benzo-1,2,3-thiadiazole-7-carboxylic acid were designed and synthesized. New synthetic elicitors that showed powerful eliciting activities upon taxoid biosynthesis by Taxus chinensis suspension cells were obtained. For example, benzo-1,2,3-thiadiazole-7-carboxylic acid 2-(2-hydroxybenzoxyl) ethyl ester was more effective and resulted in nearly 40% increase in taxuyunnanine C content and production in comparison with methyl jasmonate, which was previously reported as the most powerful chemical elicitor for taxoid biosynthesis. The novel class of elicitors was found to induce plant defense responses, including promotion of H2O2 levels originating from oxidative burst and activation of phenylalanine ammonia lyase. Interestingly the plant defense responses induced corresponded well to the superior stimulating activity in T. chinensis cell cultures. The work indicates that the newly synthesized benzothiadiazoles can act as a new family of elicitors for taxoid biosynthesis in plant cells.