1-[5-(4-Ethoxyanilino)-1,2,4-thiadiazol-3-yl]propan-2-one | 579495-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[5-(4-Ethoxyanilino)-1,2,4-thiadiazol-3-yl]propan-2-one
• CAS: 579495-28-6
• 化学式: C₁₃H₁₅N₃O₂S
• 分子量: 277.347
• InChiKey: ZHNGTJTZGUYXNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[5-(4-Ethoxyanilino)-1,2,4-thiadiazol-3-yl]propan-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-[5-(4-ethoxyphenylamino)-1,2,4-thiadiazol-3-yl]-propan-2-ol
  参考文献：
  名称：

  Novel 1,2,4-Thiadiazole Derivatives as Potent Neuroprotectors: Approach to Creation of Bioavailable Drugs

  摘要：

  Novel 1,2,4-thiadiazole derivatives as potent neuroprotectors were synthesized and identified. Their ability to inhibit the glutamate stimulated Ca uptake was measured. Permeation experiments on the phospholipid membranes were conducted, and the apparent permeability coefficients were obtained. The partition coefficients in n-octanol/buffer (pH 7.4) and n-hexane/buffer (pH 7.4) immiscible phases (as model systems for characterizing gastrointestinal tract membranes and BBB) were determined. A classification of the studied compounds from the standpoint of "permeability-activity" properties was proposed.

  DOI：

  10.1021/mp300011r
• 作为产物：
  描述：

  5-甲基-3-异噁唑基异硫氰酸 、 对乙氧基苯胺 以 乙腈 为溶剂， 生成 1-[5-(4-Ethoxyanilino)-1,2,4-thiadiazol-3-yl]propan-2-one
  参考文献：
  名称：

  Novel 1,2,4-Thiadiazole Derivatives as Potent Neuroprotectors: Approach to Creation of Bioavailable Drugs

  摘要：

  Novel 1,2,4-thiadiazole derivatives as potent neuroprotectors were synthesized and identified. Their ability to inhibit the glutamate stimulated Ca uptake was measured. Permeation experiments on the phospholipid membranes were conducted, and the apparent permeability coefficients were obtained. The partition coefficients in n-octanol/buffer (pH 7.4) and n-hexane/buffer (pH 7.4) immiscible phases (as model systems for characterizing gastrointestinal tract membranes and BBB) were determined. A classification of the studied compounds from the standpoint of "permeability-activity" properties was proposed.

  DOI：

  10.1021/mp300011r

文献信息

• Synthesis of polyazaheterocycles containing linearly bound 1,2,4-thiadiazole using enaminones
  作者：Kh. S. Shikhaliev、P. S. Romanov、A. S. Shestakov、N. V. Stolpovskaya、M. Yu. Krysin、A. Yu. Potapov、A. N. Proshin

  DOI：10.1007/s11172-016-1404-1

  日期：2016.4

  A reaction of N-substituted 5-amino-3-(2-oxopropyl)-1,2,4-thiadiazoles with dimethylformamide dimethyl acetal gave 3-(5-amino-1,2,4-thiadiazol-3-yl)-4-(dimethylamino)but-3en-2-ones, whose cyclization with hydrazine, guanidine, 1H-pyrazol-5-amines and 6-aminopyrimidin-4(3H)-ones led to 3-methyl-1H-pyrazole, 4-methylpyrimidin-2-amine, 5-methyl3-arylpyrazolo[1,5-a]pyrimidines, and 5-methyl-2-R-pyrido[2

  N-取代的 5-氨基-3-(2-氧代丙基)-1,2,4-噻二唑与二甲基甲酰胺二甲基乙缩醛反应得到 3-(5-氨基-1,2,4-噻二唑-3-基)- 4-(二甲氨基)but-3en-2-ones，其与肼、胍、1H-pyrazol-5-amines 和 6-aminopyrimidin-4(3H)-ones 环化生成 3-methyl-1H-pyrazole, 4-甲基嘧啶-2-胺、5-甲基3-芳基吡唑并[1,5-a]嘧啶和含有5-氨基的5-甲基-2-R-吡啶并[2,3-d]嘧啶-4(3H)-酮-1,2,4-噻二唑片段在位置 3 处线性结合。