2-chloro-4-(cyclopropylamino)-N,N-diethyl-1,8-naphthyridine-3-carboxamide | 126567-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-chloro-4-(cyclopropylamino)-N,N-diethyl-1,8-naphthyridine-3-carboxamide
• CAS: 126567-84-8
• 化学式: C₁₆H₁₉ClN₄O
• 分子量: 318.806
• InChiKey: AJBABTXDBVMKLA-UHFFFAOYSA-N

物化性质

• 熔点：
  189-190 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  537.9±50.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.12
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-chloro-4-(cyclopropylamino)-N,N-diethyl-1,8-naphthyridine-3-carboxamide 在 氢氧化钾 、 diphenyl ether-biphenyl eutectic 、 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 1.33h， 生成 5-(Cyclopropyl-methyl-amino)-1-isopropyl-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：

  ethyl 3-(diethylamino)-3-oxopropanoate 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 28.5h， 生成 2-chloro-4-(cyclopropylamino)-N,N-diethyl-1,8-naphthyridine-3-carboxamide
  参考文献：
  名称：

  Di Braccio; Roma; Balbi, Il Farmaco, 1989, vol. 44, # 9, p. 865 - 881

  摘要：

  DOI：

文献信息

• 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.
• DI, BRACCIO M.;ROMA, G.;BALBI, A.;SOTTOFATTORI, E.;CARAZZONE, M., FARMACO, 44,(1989) N, C. 865-881
  作者：DI, BRACCIO M.、ROMA, G.、BALBI, A.、SOTTOFATTORI, E.、CARAZZONE, M.

  DOI：——

  日期：——