N'-[(1E)-(2,5-dihydroxyphenyl)methylidene]quinoline-4-carbohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N'-[(1E)-(2,5-dihydroxyphenyl)methylidene]quinoline-4-carbohydrazide
• 英文别名: N-[(E)-(2,5-dihydroxyphenyl)methylideneamino]quinoline-4-carboxamide
• 化学式: C₁₇H₁₃N₃O₃
• 分子量: 307.309
• InChiKey: HXENVYIAYXAPIR-VXLYETTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯甲醛 、 1-苯基哌嗪-2-酮 在 溶剂黄146 作用下， 以 水 为溶剂， 以62%的产率得到N'-[(1E)-(2,5-dihydroxyphenyl)methylidene]quinoline-4-carbohydrazide
  参考文献：
  名称：

  Synthesis, leishmanicidal, trypanocidal and cytotoxic activity of quinoline-hydrazone hybrids

  摘要：

  Cutaneous leishmaniasis and Chagas disease are vector-borne parasitic disease causing serious risks to million people living in poverty-stricken areas. Both diseases are a major health problem in Latin America, and currently drugs for the effective treatment of these diseases have important concerns related with efficacy or toxicity than need to be addressed.We report herein the synthesis and biological activities (cytotoxicity, leishmanicidal and trypanocidal activities) of ten quinolone-hydrazone hybrids. The structure of the products was elucidated by spectrometric analyses. The synthesized compounds were evaluated against amastigotes forms of L. (V) panamensis which is the most prevalent Leishmania species in Colombia and Trypanosoma cruzi that is the major pathogenic species to humans; in turn, cytotoxicity was evaluated against human U-937 macrophages.Compounds 6b, 6c and 8 showed activity against L (V) panamensis with EC50 of 6.5 +/- 0.8 mu g/mL (21.2 mu M), 0.8 +/- 0.0 mu g/mL (2.6 mu M) and 3.4 +/- 0.6 mu g/mL (11.1 mu M), respectively, while compounds 6a and 6c had activity against T cruzi. with EC50 values of 1.4 +/- 0.3 mu g/mL (4.8 mu M) and 6.6 +/- 0.3 mu g/mL (4.6 mu M), respectively. Even compound 6a showed better activity against T cruzi than the standard drug benznidazole with EC50 = 10.5 +/- 1.8 mu g/mL (40.3 mu M).Analysis of the results obtained against leishmaniasis indicates that antiparasite activity is related to the presence of 2-substituted quinoline (isoquinolinic core) and the hydroxyl group in positions 3 and 4 of the aromatic ring. Although the majority of these compounds were highly cytotoxic, the antiparasite activity was higher than cytotoxicity and therefore, they still have potential to be considered as hit molecules for leishmanicidal and trypanocidal drug development. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.018

文献信息

• Synthesis, leishmanicidal, trypanocidal and cytotoxic activity of quinoline-hydrazone hybrids
  作者：Juan Carlos Coa、Wilson Castrillón、Wilson Cardona、Miguel Carda、Victoria Ospina、July Andrea Muñoz、Iván D. Vélez、Sara M. Robledo

  DOI：10.1016/j.ejmech.2015.07.018

  日期：2015.8

  Cutaneous leishmaniasis and Chagas disease are vector-borne parasitic disease causing serious risks to million people living in poverty-stricken areas. Both diseases are a major health problem in Latin America, and currently drugs for the effective treatment of these diseases have important concerns related with efficacy or toxicity than need to be addressed.We report herein the synthesis and biological activities (cytotoxicity, leishmanicidal and trypanocidal activities) of ten quinolone-hydrazone hybrids. The structure of the products was elucidated by spectrometric analyses. The synthesized compounds were evaluated against amastigotes forms of L. (V) panamensis which is the most prevalent Leishmania species in Colombia and Trypanosoma cruzi that is the major pathogenic species to humans; in turn, cytotoxicity was evaluated against human U-937 macrophages.Compounds 6b, 6c and 8 showed activity against L (V) panamensis with EC50 of 6.5 +/- 0.8 mu g/mL (21.2 mu M), 0.8 +/- 0.0 mu g/mL (2.6 mu M) and 3.4 +/- 0.6 mu g/mL (11.1 mu M), respectively, while compounds 6a and 6c had activity against T cruzi. with EC50 values of 1.4 +/- 0.3 mu g/mL (4.8 mu M) and 6.6 +/- 0.3 mu g/mL (4.6 mu M), respectively. Even compound 6a showed better activity against T cruzi than the standard drug benznidazole with EC50 = 10.5 +/- 1.8 mu g/mL (40.3 mu M).Analysis of the results obtained against leishmaniasis indicates that antiparasite activity is related to the presence of 2-substituted quinoline (isoquinolinic core) and the hydroxyl group in positions 3 and 4 of the aromatic ring. Although the majority of these compounds were highly cytotoxic, the antiparasite activity was higher than cytotoxicity and therefore, they still have potential to be considered as hit molecules for leishmanicidal and trypanocidal drug development. (C) 2015 Elsevier Masson SAS. All rights reserved.