Ethyl 2-(1,3-benzoxazol-2-ylamino)-4,5-dimethylthiophene-3-carboxylate | 159852-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: Ethyl 2-(1,3-benzoxazol-2-ylamino)-4,5-dimethylthiophene-3-carboxylate
• CAS: 159852-76-3
• 化学式: C₁₆H₁₆N₂O₃S
• 分子量: 316.381
• InChiKey: QWFKWBOHTYSGFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(1,3-benzoxazol-2-ylamino)-4,5-dimethylthiophene-3-carboxylate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以82%的产率得到3-(2-hydroxyphenyl)-4,5-dimethyl-1H,3H-thieno<2,3-d>pyrimido-2,4-dione
  参考文献：
  名称：

  Synthesis of new thienopyrimidobenzothiazoles and thienopyrimidobenzoxazoles with analgesic and antiinflammatory properties

  摘要：

  As an extension of research on analgesic and antiinflammatory compounds, a series of substituted analogues based on the novel 4H-thieno[2',3':4,5]pyrimido[2,1-b]benzothiazole and 4H-thieno[2',3':4,5]pyrimido[2,1-b]benzoxazole ring systems was synthesized. The compounds were obtained by reaction of 2 amino-3-carbethoxy-4,5-disubstituted thiophenes with 2-chlorobenzothiazole and 2-chlorobenzoxazole, respectively. Starting from 2-carbomethoxy-3-aminothiophene, 11H-thieno[3',2':4,5]pyrimido[2,1-b]benzothiazol-11-one and 11H-thieno[3',2':4,5]pyrimido[2,1-b]benzoxazol-11-one were prepared in the same way. Synthesized compounds were evaluated for their potential analgesic activity in phenylquinone-induced writhing test in mice and fdr their potential antiinflammatory activity in carrageenan-induced rat-paw oedema test, in acetic-acid peritonitis assay and in croton oil-induced mouse-ear oedema test. 9,10,11,12-Tetrahydro-12H-benzothieno[2',3':4,5]pyrimido[2,1-b]benzoxazol-12-one 12 was the most active derivative in the series in all performed tests. It showed remarkable analgesic and antiinflammatory activities associated with an excellent gastric tolerance.

  DOI：

  10.1016/0223-5234(94)90149-x
• 作为产物：
  描述：

  2-氯苯并恶唑 、 2-氨基-4,5-二甲基噻吩-3-羧酸乙酯 反应 0.08h， 以45%的产率得到Ethyl 2-(1,3-benzoxazol-2-ylamino)-4,5-dimethylthiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis of new thienopyrimidobenzothiazoles and thienopyrimidobenzoxazoles with analgesic and antiinflammatory properties

  摘要：

  As an extension of research on analgesic and antiinflammatory compounds, a series of substituted analogues based on the novel 4H-thieno[2',3':4,5]pyrimido[2,1-b]benzothiazole and 4H-thieno[2',3':4,5]pyrimido[2,1-b]benzoxazole ring systems was synthesized. The compounds were obtained by reaction of 2 amino-3-carbethoxy-4,5-disubstituted thiophenes with 2-chlorobenzothiazole and 2-chlorobenzoxazole, respectively. Starting from 2-carbomethoxy-3-aminothiophene, 11H-thieno[3',2':4,5]pyrimido[2,1-b]benzothiazol-11-one and 11H-thieno[3',2':4,5]pyrimido[2,1-b]benzoxazol-11-one were prepared in the same way. Synthesized compounds were evaluated for their potential analgesic activity in phenylquinone-induced writhing test in mice and fdr their potential antiinflammatory activity in carrageenan-induced rat-paw oedema test, in acetic-acid peritonitis assay and in croton oil-induced mouse-ear oedema test. 9,10,11,12-Tetrahydro-12H-benzothieno[2',3':4,5]pyrimido[2,1-b]benzoxazol-12-one 12 was the most active derivative in the series in all performed tests. It showed remarkable analgesic and antiinflammatory activities associated with an excellent gastric tolerance.

  DOI：

  10.1016/0223-5234(94)90149-x