N,N-diethyl-5-isobutylamino-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide | 327160-36-1

• 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: N,N-diethyl-5-isobutylamino-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide
• 英文别名: N,N-diethyl-5-(2-methylpropylamino)-9-propan-2-yl-[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide
• CAS: 327160-36-1
• 化学式: C₂₁H₃₀N₆O
• 分子量: 382.509
• InChiKey: CKWISBVXBWQYNM-UHFFFAOYSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  乙酸酐 、 N,N-diethyl-5-isobutylamino-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide 反应 8.0h， 以85%的产率得到5-[acetyl(2-methylpropyl)amino]-N,N-diethyl-9-propan-2-yl-[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide
  参考文献：
  名称：

  1,8-萘啶VI。5-（烷基氨基）-N，N-二乙基[1,2,4]三唑并[4,3-a] [1,8]萘啶-6-羧酰胺的合成及抗炎活性三唑环。

  摘要：

  基于9-烷基-N，N-二烷基-5-（烷基氨基）[1,2,4]三唑并[4,3-a] [1,8]萘啶-显示的良好的抗炎特性。制备并测试了6碳基乙酰胺1的一系列类似物，其中9-烷基取代基被酯或酰胺基取代（化合物3a-i）（抑制角叉菜胶诱发的爪水肿）。鼠）。还合成了两种5-（N-烷基，N-酰基氨基）衍生物（化合物4a，b），并出于相同目的对其进行了评估。尽管这些新的[1,2,4]三唑并[4,3-a] [1,8]萘啶衍生物的总体趋势是与化合物1相比活性降低，但一些新合成的化合物仍显示出良好的抗-发炎的特性。

  DOI：

  10.1016/j.ejmech.2007.04.016
• 作为产物：
  描述：

  异丁酸肼 、 2-chloro-N,N-diethyl-4-(isobutylamino)-1,8-naphthyridine-3-carboxamide 以 various solvent(s) 为溶剂， 反应 0.33h， 以64%的产率得到N,N-diethyl-5-isobutylamino-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide
  参考文献：
  名称：

  1,8-Naphthyridines IV. 9-Substituted N,N-dialkyl-5-(alkylamino or cycloalkylamino) [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides, new compounds with anti-aggressive and potent anti-inflammatory activities

  摘要：

  The title compounds (8) were synthesized through the cyclocondensation of the corresponding N-substituted 4-amino-2-chloro-1,8-naphthyridine-3-carboxamides (4) with the proper hydrazides, in order to evaluate their anti-inflammatory and antiaggressive properties. Several compounds 8 exhibited high anti-inflammatory activity (carrageenin-induced paw edema assay in the rat) along with appreciable anti-aggressive properties (isolation-induced aggressiveness test in mice). With respect to anti-inflammatory activity, the most active compounds (8n and 8c) produced a 61% edema inhibition at the 25 mg/kg dose, and 50 or 35% inhibition, respectively, at the 12.5 mg/kg dose. The structure-activity relationships are discussed. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01175-2

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.
• 1,8-Naphthyridines VI. Synthesis and anti-inflammatory activity of 5-(alkylamino)-N,N-diethyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides with a new substitution pattern on the triazole ring
  作者：Mario Di Braccio、Giancarlo Grossi、Giorgio Roma、Daniela Piras、Francesca Mattioli、Marzia Gosmar

  DOI：10.1016/j.ejmech.2007.04.016

  日期：2008.3

  in which the 9-alkyl substituent was replaced by an ester or amide group (compounds 3a-i), was prepared and tested (inhibition of carrageenan-induced paw edema in the rat). Also two 5-(N-alkyl,N-acylamino) derivatives (compounds 4a,b) were synthesized and evaluated for the same purpose. Even though the general trend for these new [1,2,4]triazolo[4,3-a][1,8]naphthyridine derivatives was a decrease

  基于9-烷基-N，N-二烷基-5-（烷基氨基）[1,2,4]三唑并[4,3-a] [1,8]萘啶-显示的良好的抗炎特性。制备并测试了6碳基乙酰胺1的一系列类似物，其中9-烷基取代基被酯或酰胺基取代（化合物3a-i）（抑制角叉菜胶诱发的爪水肿）。鼠）。还合成了两种5-（N-烷基，N-酰基氨基）衍生物（化合物4a，b），并出于相同目的对其进行了评估。尽管这些新的[1,2,4]三唑并[4,3-a] [1,8]萘啶衍生物的总体趋势是与化合物1相比活性降低，但一些新合成的化合物仍显示出良好的抗-发炎的特性。
• 1,8-Naphthyridines IV. 9-Substituted N,N-dialkyl-5-(alkylamino or cycloalkylamino) [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides, new compounds with anti-aggressive and potent anti-inflammatory activities
  作者：Giorgio Roma、Mario Di Braccio、Giancarlo Grossi、Francesca Mattioli、Marco Ghia

  DOI：10.1016/s0223-5234(00)01175-2

  日期：2000.11

  The title compounds (8) were synthesized through the cyclocondensation of the corresponding N-substituted 4-amino-2-chloro-1,8-naphthyridine-3-carboxamides (4) with the proper hydrazides, in order to evaluate their anti-inflammatory and antiaggressive properties. Several compounds 8 exhibited high anti-inflammatory activity (carrageenin-induced paw edema assay in the rat) along with appreciable anti-aggressive properties (isolation-induced aggressiveness test in mice). With respect to anti-inflammatory activity, the most active compounds (8n and 8c) produced a 61% edema inhibition at the 25 mg/kg dose, and 50 or 35% inhibition, respectively, at the 12.5 mg/kg dose. The structure-activity relationships are discussed. (C) 2000 Editions scientifiques et medicales Elsevier SAS.