2-<<3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenol>-1,2,4-thiadiazol-5-yl>methyl>-1H-isoindole-1,3(2H)-dione | 143429-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-<<3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenol>-1,2,4-thiadiazol-5-yl>methyl>-1H-isoindole-1,3(2H)-dione
• CAS: 143429-81-6
• 化学式: C₂₅H₂₇N₃O₃S
• 分子量: 449.574
• InChiKey: ITEQKGQHNHYHSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.39
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-<<3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenol>-1,2,4-thiadiazol-5-yl>methyl>-1H-isoindole-1,3(2H)-dione 在 肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 4-(5-Aminomethyl-[1,2,4]thiadiazol-3-yl)-2,6-di-tert-butyl-phenol
  参考文献：
  名称：

  Novel 1,2,4-oxadiazoles and 1,2,4-thiadiazoles as dual 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A series of 1,2,4-oxadiazoles and 1,2,4-thiadiazoles containing a 2,6-di-tert-butylphenol substituent were prepared and evaluated as dual inhibitors of 5-lipoxygenase and cyclooxygenase in rat basophilic leukemia (RBL-1) cells. Several of these compounds show oral efficacy in the rat carageenan footpad edema (CFE) and mycobacterium footpad edema (MFE) antiinflammatory models, without concomitant gastric ulceration. Structure-activity relationships are discussed. The best compounds (ID40 values in MFE of 3-8 mg/kg po) contain guanidine-derived substituents on the heterocyclic ring.

  DOI：

  10.1021/jm00098a015
• 作为产物：
  描述：

  ethyl 3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>-1,2,4-thiadiazole-5-carboxylate 在 sodium tetrahydroborate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 32.0h， 生成 2-<<3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenol>-1,2,4-thiadiazol-5-yl>methyl>-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Novel 1,2,4-oxadiazoles and 1,2,4-thiadiazoles as dual 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A series of 1,2,4-oxadiazoles and 1,2,4-thiadiazoles containing a 2,6-di-tert-butylphenol substituent were prepared and evaluated as dual inhibitors of 5-lipoxygenase and cyclooxygenase in rat basophilic leukemia (RBL-1) cells. Several of these compounds show oral efficacy in the rat carageenan footpad edema (CFE) and mycobacterium footpad edema (MFE) antiinflammatory models, without concomitant gastric ulceration. Structure-activity relationships are discussed. The best compounds (ID40 values in MFE of 3-8 mg/kg po) contain guanidine-derived substituents on the heterocyclic ring.

  DOI：

  10.1021/jm00098a015