3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>-1,2,4-thiadiazole-5-methanol | 143429-78-1

• 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: 3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>-1,2,4-thiadiazole-5-methanol
• 英文别名: 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-hydroxymethyl-1,2,4-thiadiazole；2,6-Ditert-butyl-4-[5-(hydroxymethyl)-1,2,4-thiadiazol-3-yl]phenol
• CAS: 143429-78-1
• 化学式: C₁₇H₂₄N₂O₂S
• 分子量: 320.456
• InChiKey: BOVBFSGGRHSSQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>-1,2,4-thiadiazole-5-methanol 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 以0.14 g的产率得到3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-formyl-1,2,4-thiadiazole
  参考文献：
  名称：

  Heteroarylnitrones as Drugs for Neurodegenerative Diseases: Synthesis, Neuroprotective Properties, and Free Radical Scavenger Properties

  摘要：

  New 1,2,4-thiadiazolylnitrones and furoxanylnitrones were developed and evaluated as neuroprotective agents on a human neuroblastoma (SH-SY5Y) cells model. They inhibited at low micromolar concentrations the oxidative damage and the death induced by exposure to hydrogen peroxide. These heteroarylnitrones showed excellent peroxyl free radical absorbance capacities, analyzed by oxygen radical absorbance capacity (ORAC) assay with fluorescein as the fluorescent probe, ranging from 1.5- to 16.5-fold the value of the reference nitrone, alpha-phenyl-N-tert-butylnitrone (PBN). The electron spin resonance spectroscopy (ESR) demonstrated the ability of these derivatives to directly trap and stabilize oxygen, carbon, and sulfur-centered free radicals. These results demonstrated the potential use of these heteroarylnitrones as neuroprotective agents in preventing the death of cells exposed to enhanced oxidative stress and damage.

  DOI：

  10.1021/jm8006432
• 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 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以78%的产率得到3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>-1,2,4-thiadiazole-5-methanol
  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