3-[(2-hydroxybenzoyl)sulfanylmethyl]-5-phenyl-12(pyrrolidin-1-yl)-1,2,5,6,8,9,10,11,12,12a-decahydropyrimido[4',5':4,5]pyrimido[1,6-a]azepine-1,6-dione | 1272379-76-6

• 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-[(2-hydroxybenzoyl)sulfanylmethyl]-5-phenyl-12(pyrrolidin-1-yl)-1,2,5,6,8,9,10,11,12,12a-decahydropyrimido[4',5':4,5]pyrimido[1,6-a]azepine-1,6-dione
• 英文别名: 3-[(2-Hydroxybenzoyl)sulfanylmethyl]-5-phenyl-12(pyrrolidin-1-yl)-1,2,5,6,8,9,10,11,12,12a-decahydropyrimido[4',5':4,5]pyrimido[1,6-a]azepine-1,6-dione；S-[(3,9-dioxo-8-phenyl-15-pyrrolidin-1-yl-4,6,8,10-tetrazatricyclo[8.5.0.02,7]pentadeca-2(7),5-dien-5-yl)methyl] 2-hydroxybenzenecarbothioate
• CAS: 1272379-76-6
• 化学式: C₂₉H₃₁N₅O₄S
• 分子量: 545.662
• InChiKey: BHQBUGSRECSWIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-amino-1-oxo-2-phenyl-5-(pyrrolidin-1-yl)-1,2,4a,5,6,7,8,9-octahydropyrimido[1,6-a]azepine-4-carbonitrile 在 三乙胺 、 硫脲 作用下， 以 乙醇 、 苯 为溶剂， 反应 9.0h， 生成 3-[(2-hydroxybenzoyl)sulfanylmethyl]-5-phenyl-12(pyrrolidin-1-yl)-1,2,5,6,8,9,10,11,12,12a-decahydropyrimido[4',5':4,5]pyrimido[1,6-a]azepine-1,6-dione
  参考文献：
  名称：

  Potential anti-inflammatory activity and ulcerogenicity study of some novel pyrimido[4′,5′:4,5]pyrimido[1,6-a]azepine derivatives

  摘要：

  A series of novel tricyclic pyrimido[4',5':4,5]pyrimido[1,6-a]azepine derivatives were synthesized using the starting compound 3-amino-1-oxo-2-phenyl-5-(pyrrolidin-1-yl)-1,2,4a,5,6,7,8,9-octahydropyrimido[1,6-a]azepine-4-carbonitrile 4. This series includes the 3-aryl derivatives 6a, b, the 3-cycloaminoalkyl derivatives 8a-f, the 3-mercaptomethyl derivatives 10 and 11a, b, the 2-cycloaminomethyl derivatives 13a-c, the 1-cycloamino derivatives 15a-c and the 1-amino derivative 16. The structures of the newly synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR, mass spectroscopy and elemental analyses. The anti-inflammatory activity of all newly synthesized compounds was evaluated using the carrageenan-induced paw oedema test in rats using diclofenac sodium as the reference drug. Ulcer indices for the most active compounds were calculated. The 3-mercaptomethylacetic acid derivative 10 was the most active compound, showing activity comparable to diclofenac sodium with minimal ulcerogenic effect while the rest of the tested compound exhibited moderate anti-inflammatory activity.

  DOI：

  10.1007/s00044-010-9545-5

文献信息

• Potential anti-inflammatory activity and ulcerogenicity study of some novel pyrimido[4′,5′:4,5]pyrimido[1,6-a]azepine derivatives
  作者：Nehad A. El-Sayed、Fadi M. Awadallah、Nashwa A. Ibrahim、Mohamed T. El-Saadi

  DOI：10.1007/s00044-010-9545-5

  日期：2012.3

  A series of novel tricyclic pyrimido[4',5':4,5]pyrimido[1,6-a]azepine derivatives were synthesized using the starting compound 3-amino-1-oxo-2-phenyl-5-(pyrrolidin-1-yl)-1,2,4a,5,6,7,8,9-octahydropyrimido[1,6-a]azepine-4-carbonitrile 4. This series includes the 3-aryl derivatives 6a, b, the 3-cycloaminoalkyl derivatives 8a-f, the 3-mercaptomethyl derivatives 10 and 11a, b, the 2-cycloaminomethyl derivatives 13a-c, the 1-cycloamino derivatives 15a-c and the 1-amino derivative 16. The structures of the newly synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR, mass spectroscopy and elemental analyses. The anti-inflammatory activity of all newly synthesized compounds was evaluated using the carrageenan-induced paw oedema test in rats using diclofenac sodium as the reference drug. Ulcer indices for the most active compounds were calculated. The 3-mercaptomethylacetic acid derivative 10 was the most active compound, showing activity comparable to diclofenac sodium with minimal ulcerogenic effect while the rest of the tested compound exhibited moderate anti-inflammatory activity.