benzo-1,2,3-thiadiazole-7-carboxylic acid 2-(2-hydroxybenzoyloxy)ethyl 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-(2-hydroxybenzoyloxy)ethyl ester
• 英文别名: benzo-1,2,3-thiadiazole-7-carboxylic acid 2-benzoyloxyethyl ester；2-(2-Hydroxybenzoyl)oxyethyl 1,2,3-benzothiadiazole-7-carboxylate
• 化学式: C₁₆H₁₂N₂O₅S
• 分子量: 344.348
• InChiKey: DBZVWHNHGMOVML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  8

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 24.0h， 生成 benzo-1,2,3-thiadiazole-7-carboxylic acid 2-(2-hydroxybenzoyloxy)ethyl 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

• Derivatives of benzothiadiazole-7-carboxylates: synthesis and biological activity
  作者：Weiping Zhu、Zhenjiang Zhao、Yufang Xu

  DOI：10.1007/s00706-008-0887-3

  日期：2008.9

  Salicylic acid (SA) and methyl jasmonate (MJ) are important plant signal molecules to cause systemic acquired resistance (SAR), while it's reported that they also have wide spectrum antitumor activities. Benzothiadiazole-7-carboxylates are plant activators which can cause SAR just like SA and MJ. To investigate whether the benzothiadiazole-7-carboxylate family is endowed with anticancer activities, several benzothiadiazole-7-carboxylate derivatives are synthesized and their inhibition to P388 murine leukemia cell and A549 human lung cancer cell compared with MJ are evaluated. The data indicated that benzo-1,2,3-thiadiazole-7-carboxylic acid 2-benzoyloxyethyl ester has a higher inhibition ability to the cancer cell P388 and A549, compared with MJ.
• Novel Benzo-1,2,3-thiadiazole-7-carboxylate Derivatives As Plant Activators and the Development of Their Agricultural Applications
  作者：Qingshan Du、Weiping Zhu、Zhenjiang Zhao、Xuhong Qian、Yufang Xu

  DOI：10.1021/jf203974p

  日期：2012.1.11

  Plant activators are a novel kind of agrochemicals that could induce resistance in many plants against a broad spectrum of diseases. To date, only few plant activators have been commercialized. In order to develop novel plant activators, a series of benzo-1,2,3-thiadiazole-7-carboxylate derivatives were synthesized, and the structures were characterized by H-1 NMR, IR, elemental analyses, and HRMS or MS. Their potential systemic acquired resistance as plant activators was evaluated as well. Most of them showed good activity, especially, fluoro-containing compounds 3d and 3e, which displayed excellent SAR-inducing activity against cucumber Erysiphe cichoracearum and Colletotrichum lagenarium in assay screening. Field test results illustrated that compounds 3d and 3e were more potent than the commercial plant activator, S-methyl benzo[1,2,3]thiadiazole-7-carbothioate (BTH) toward these pathogens. Further, the preparation of compound 3d is more facile than BTH with lower cost, which will be helpful for further applications in agricultural plant protection.
• 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.