N,N-diethyl-5-(4-ethyl-1-piperazinyl)-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N,N-diethyl-5-(4-ethyl-1-piperazinyl)-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide
• 英文别名: N,N-diethyl-5-(4-ethylpiperazin-1-yl)-9-propan-2-yl-[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide
• 化学式: C₂₃H₃₃N₇O
• 分子量: 423.561
• InChiKey: VALBCSHJUXQBQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-乙基哌嗪 、 5-chloro-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-a] [1,8]naphthyridine-6-carboxamide 以 二甲基亚砜 为溶剂， 反应 2.0h， 以81%的产率得到N,N-diethyl-5-(4-ethyl-1-piperazinyl)-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide
  参考文献：
  名称：

  1,8-Naphthyridines IX. Potent anti-inflammatory and/or analgesic activity of a new group of substituted 5-amino[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides, of some their Mannich base derivatives and of one novel substituted 5-amino-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6-carboxamide derivative

  摘要：

  A new group of 5-(alkylamino)-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine derivatives bearing a CONHR group at the 6-position (1c-g), designed to obtain new effective analgesic and/or anti-inflammatory agents, were synthesized and tested along with three new 9-alkyl-5-(4-alkyl-1-piperazinyl)-N,N-diethyl [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides (2b-d). Besides, a new class of analogues of compounds 1 and 2, bearing a Mannich base moiety at the 9-position (12a-d), as well as the novel N,N-diethyl-5-(isobutylamino)-8-methyl-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6-carboxamide (15) were prepared and tested. Compounds 1c-g exhibited very interesting anti-inflammatory properties in rats, whereas compounds 2b-d and 15 proved to be endowed with prevalent analgesic activity frequently associated with sedative effects in mice. On the contrary, the Mannich bases 12a-d resulted inactive. The most effective (80% inhibition of oedema) and potent (threshold dose 1.6 mg kg(-1) with 31% inhibition of oedema) anti-inflammatory compound 1d did not show gastrolesive effects following 100 mg kg(-1) oral administration in rats. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.069

文献信息

• 1,8-Naphthyridines IX. Potent anti-inflammatory and/or analgesic activity of a new group of substituted 5-amino[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides, of some their Mannich base derivatives and of one novel substituted 5-amino-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6-carboxamide derivative
  作者：Mario Di Braccio、Giancarlo Grossi、Silvana Alfei、Vigilio Ballabeni、Massimiliano Tognolini、Lisa Flammini、Carmine Giorgio、Simona Bertoni、Elisabetta Barocelli

  DOI：10.1016/j.ejmech.2014.08.069

  日期：2014.10

  A new group of 5-(alkylamino)-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine derivatives bearing a CONHR group at the 6-position (1c-g), designed to obtain new effective analgesic and/or anti-inflammatory agents, were synthesized and tested along with three new 9-alkyl-5-(4-alkyl-1-piperazinyl)-N,N-diethyl [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides (2b-d). Besides, a new class of analogues of compounds 1 and 2, bearing a Mannich base moiety at the 9-position (12a-d), as well as the novel N,N-diethyl-5-(isobutylamino)-8-methyl-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6-carboxamide (15) were prepared and tested. Compounds 1c-g exhibited very interesting anti-inflammatory properties in rats, whereas compounds 2b-d and 15 proved to be endowed with prevalent analgesic activity frequently associated with sedative effects in mice. On the contrary, the Mannich bases 12a-d resulted inactive. The most effective (80% inhibition of oedema) and potent (threshold dose 1.6 mg kg(-1) with 31% inhibition of oedema) anti-inflammatory compound 1d did not show gastrolesive effects following 100 mg kg(-1) oral administration in rats. (C) 2014 Elsevier Masson SAS. All rights reserved.