3-(4-oxo-9-(phenylcarbamoyl)-4,5,6,7-tetrahydro-1Hpyrimido[5,4-a]pyrrolizin-2-yl) acrylic acid | 1214880-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: 3-(4-oxo-9-(phenylcarbamoyl)-4,5,6,7-tetrahydro-1Hpyrimido[5,4-a]pyrrolizin-2-yl) acrylic acid
• CAS: 1214880-12-2
• 化学式: C₁₉H₁₆N₄O₄
• 分子量: 364.36
• InChiKey: OECDJTZEEDKWGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  117.08
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  马来酸酐 、 6-amino-7-cyano-N-phenyl-2,3-dihydro-1H-pyrrolizine-5-carboxamide 在 溶剂黄146 作用下， 反应 3.0h， 以64%的产率得到3-(4-oxo-9-(phenylcarbamoyl)-4,5,6,7-tetrahydro-1Hpyrimido[5,4-a]pyrrolizin-2-yl) acrylic acid
  参考文献：
  名称：

  Novel substituted and fused pyrrolizine derivatives: Synthesis, anti-inflammatory and ulcerogenecity studies

  摘要：

  Synthesis of several substituted pyrrolizines 10a-f, 11a-f, 13a-c, pyrimidopyrrolizines 14a-c, 15a-c, and pyrrolizinopyrimidoisoindoles 12a-c was discussed. The starting compounds 6-amino-7-cyano-N-(4-(un)substitutedphenyl)-2,3-dihydro-1H-pyrrolizine-5-carboxamides 9a-c were reacted with different aldehydes, acid chlorides, and acid anhydrides to give the target compounds. The structures of the new compounds were characterized by spectral and elemental analyses. All compounds were tested for their anti-inflammatory activity using the carrageenan-induced rat paw oedema model and exhibited weak to good activities compared to ketorolac as the reference drug. Also, analgesic activity of selected compounds, which are the most active in the anti-inflammatory screening, was measured using the acetic acid-induced writhing model; revealing activities comparable to or higher than ketorolac. Ulcer indices for the most active compounds were calculated and some compounds showed no or minimal ulcerogenic effect compared to ketorolac. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.031