N-(4-cyano-2-ethyl-1-thioxo-1,2,4a,5,6,7-hexahydropyrrolo[1,2-c]pyrimidin-3-yl) formimidic acid ethyl ester | 1198113-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(4-cyano-2-ethyl-1-thioxo-1,2,4a,5,6,7-hexahydropyrrolo[1,2-c]pyrimidin-3-yl) formimidic acid ethyl ester
• 英文别名: ethyl N-(4-cyano-2-ethyl-1-sulfanylidene-4a,5,6,7-tetrahydropyrrolo[1,2-c]pyrimidin-3-yl)methanimidate
• CAS: 1198113-96-0
• 化学式: C₁₃H₁₈N₄OS
• 分子量: 278.378
• InChiKey: AKFMTCYSMQWCFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  51.86
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  正丙胺 、 N-(4-cyano-2-ethyl-1-thioxo-1,2,4a,5,6,7-hexahydropyrrolo[1,2-c]pyrimidin-3-yl) formimidic acid ethyl ester 以 乙醇 为溶剂， 反应 3.0h， 以40%的产率得到5-ethyl-1-imino-2-propyl-6-thioxo-1,2,8,9,10,10a-hexahydro-5H-pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidine
  参考文献：
  名称：

  Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines

  摘要：

  Novel series of bicyclic pyrrolo[1,2-cipyrimidines 3a-g, 5, 6a, b, and 7a, b, tricyclic pyrimido[5,4-elpyrrolo[1,2-c]pyrimidines 8a-c, 9a-g, 13a-c, 17,18a, b, 19, 20a,b and 21 and tetracyclic condensed pyrimidines 14, 22 and 23 were synthesized through different chemical reactions. Structures of all synthesized pyrimidine derivatives were supported by spectral and elemental analyses. Analgesic activity evaluation was carried out using acetic acid-induced writhing assay, and all compounds exerted comparable activity to indomethacin. The anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema in rats, the potency of the bicyclic derivatives 3a-f and 7b revealed comparable activity to indomethacin without gastric ulceration. The tricyclic derivatives 13a and 20a exerted good activity, however, they induced gastric ulcers while 13b and 13c showed moderate activity without ulceration. In case of tetracyclic derivatives, compound 14 exhibited the highest potency and safety profile. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.028
• 作为产物：
  描述：

  2-ethyl-3-amino-1,2,4a,5,6,7-hexahydro-1-thioxopyrrolo[1,2-c]pyrimidine-4-carbonitrile 、 原甲酸三乙酯 在 溶剂黄146 作用下， 反应 3.0h， 以88%的产率得到N-(4-cyano-2-ethyl-1-thioxo-1,2,4a,5,6,7-hexahydropyrrolo[1,2-c]pyrimidin-3-yl) formimidic acid ethyl ester
  参考文献：
  名称：

  Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines

  摘要：

  Novel series of bicyclic pyrrolo[1,2-cipyrimidines 3a-g, 5, 6a, b, and 7a, b, tricyclic pyrimido[5,4-elpyrrolo[1,2-c]pyrimidines 8a-c, 9a-g, 13a-c, 17,18a, b, 19, 20a,b and 21 and tetracyclic condensed pyrimidines 14, 22 and 23 were synthesized through different chemical reactions. Structures of all synthesized pyrimidine derivatives were supported by spectral and elemental analyses. Analgesic activity evaluation was carried out using acetic acid-induced writhing assay, and all compounds exerted comparable activity to indomethacin. The anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema in rats, the potency of the bicyclic derivatives 3a-f and 7b revealed comparable activity to indomethacin without gastric ulceration. The tricyclic derivatives 13a and 20a exerted good activity, however, they induced gastric ulcers while 13b and 13c showed moderate activity without ulceration. In case of tetracyclic derivatives, compound 14 exhibited the highest potency and safety profile. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.028