1-Isopropyl-5-phenylamino-2,3,9,9b-tetraaza-cyclopenta[a]naphthalene-4-carboxylic acid diethylamide | 848820-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-Isopropyl-5-phenylamino-2,3,9,9b-tetraaza-cyclopenta[a]naphthalene-4-carboxylic acid diethylamide
• 英文别名: 5-anilino-N,N-diethyl-9-propan-2-yl-[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide
• CAS: 848820-49-5
• 化学式: C₂₃H₂₆N₆O
• 分子量: 402.499
• InChiKey: LRAGENYHZMBSJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 1-Isopropyl-5-phenylamino-2,3,9,9b-tetraaza-cyclopenta[a]naphthalene-4-carboxylic acid diethylamide 在 氢氧化钾 、 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 1.0h， 以58%的产率得到1-Isopropyl-5-(methyl-phenyl-amino)-2,3,9,9b-tetraaza-cyclopenta[a]naphthalene-4-carboxylic acid diethylamide
  参考文献：
  名称：

  1,8-Naphthyridines V. Novel N-substituted 5-amino-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-a] [1,8]naphthyridine-6-carboxamides, as potent anti-inflammatory and/or analgesic agents completely devoid of acute gastrolesivity

  摘要：

  Most N,N-disubstituted 5-amino-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-alpha] [1,8]naphthyridine-6-carboxamides 9 (compounds 9a, c-i) and the N-monosubstituted one 8c were obtained by treating with excess amine the corresponding 5-chloroderivative 7a, which was in turn prepared by cyclocondensation of the 2,4-dichloro-N,N-diethyl-1,8-naphthyridine-3-carboxamide (4a) with isobutyrohydrazide. Compounds 8a,b and 9b,j-m were obtained according with the methods shown in Scheme 1. The above now synthesized compounds, along with the previously described 8d and 8e, were tested for their anti-inflammatory, analgesic and antipyretic properties, and most compounds also for their effect on spontaneous mice locomotor activity and their acute gastrolesivity in rats. Several compounds showed potent anti-inflammatory and/or analgesic activities, and all the compounds tested proved to be completely lacking in acute gastrolesivity. In many cases compounds 8 and 9 produced hypothermic effect, usually at high doses. On the whole, the N-monosubstituted 5-aminoderivatives 8 appeared to be more potent anti-inflammatory agents than the corresponding N,N-disubstituted 9, whereas these latter compounds exhibited higher analgesic activity. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.09.022
• 作为产物：
  描述：

  2,4-dichloro-N,N-diethyl-1,8-naphthyridine-3-carboxamide 在 diphenyl ether-biphenyl eutectic 作用下， 以 乙二醇 为溶剂， 反应 24.33h， 生成 1-Isopropyl-5-phenylamino-2,3,9,9b-tetraaza-cyclopenta[a]naphthalene-4-carboxylic acid diethylamide
  参考文献：
  名称：

  1,8-Naphthyridines V. Novel N-substituted 5-amino-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-a] [1,8]naphthyridine-6-carboxamides, as potent anti-inflammatory and/or analgesic agents completely devoid of acute gastrolesivity

  摘要：

  Most N,N-disubstituted 5-amino-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-alpha] [1,8]naphthyridine-6-carboxamides 9 (compounds 9a, c-i) and the N-monosubstituted one 8c were obtained by treating with excess amine the corresponding 5-chloroderivative 7a, which was in turn prepared by cyclocondensation of the 2,4-dichloro-N,N-diethyl-1,8-naphthyridine-3-carboxamide (4a) with isobutyrohydrazide. Compounds 8a,b and 9b,j-m were obtained according with the methods shown in Scheme 1. The above now synthesized compounds, along with the previously described 8d and 8e, were tested for their anti-inflammatory, analgesic and antipyretic properties, and most compounds also for their effect on spontaneous mice locomotor activity and their acute gastrolesivity in rats. Several compounds showed potent anti-inflammatory and/or analgesic activities, and all the compounds tested proved to be completely lacking in acute gastrolesivity. In many cases compounds 8 and 9 produced hypothermic effect, usually at high doses. On the whole, the N-monosubstituted 5-aminoderivatives 8 appeared to be more potent anti-inflammatory agents than the corresponding N,N-disubstituted 9, whereas these latter compounds exhibited higher analgesic activity. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.09.022

文献信息

• 1,8-Naphthyridines V. Novel N-substituted 5-amino-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-a] [1,8]naphthyridine-6-carboxamides, as potent anti-inflammatory and/or analgesic agents completely devoid of acute gastrolesivity
  作者：Giancarlo Grossi、Mario Di Braccio、Giorgio Roma、Vigilio Ballabeni、Massimiliano Tognolini、Elisabetta Barocelli

  DOI：10.1016/j.ejmech.2004.09.022

  日期：2005.2

  Most N,N-disubstituted 5-amino-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-alpha] [1,8]naphthyridine-6-carboxamides 9 (compounds 9a, c-i) and the N-monosubstituted one 8c were obtained by treating with excess amine the corresponding 5-chloroderivative 7a, which was in turn prepared by cyclocondensation of the 2,4-dichloro-N,N-diethyl-1,8-naphthyridine-3-carboxamide (4a) with isobutyrohydrazide. Compounds 8a,b and 9b,j-m were obtained according with the methods shown in Scheme 1. The above now synthesized compounds, along with the previously described 8d and 8e, were tested for their anti-inflammatory, analgesic and antipyretic properties, and most compounds also for their effect on spontaneous mice locomotor activity and their acute gastrolesivity in rats. Several compounds showed potent anti-inflammatory and/or analgesic activities, and all the compounds tested proved to be completely lacking in acute gastrolesivity. In many cases compounds 8 and 9 produced hypothermic effect, usually at high doses. On the whole, the N-monosubstituted 5-aminoderivatives 8 appeared to be more potent anti-inflammatory agents than the corresponding N,N-disubstituted 9, whereas these latter compounds exhibited higher analgesic activity. (C) 2004 Elsevier SAS. All rights reserved.