5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid (4-chlorobenzylidene)hydrazide | 957760-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid (4-chlorobenzylidene)hydrazide
• 英文别名: N-[(4-chlorophenyl)methylideneamino]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamide
• CAS: 957760-04-2
• 化学式: C₁₅H₁₅ClN₄O
• 分子量: 302.763
• InChiKey: VJKWLKXHNMJQOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid hydrazide 、 4-氯苯甲醛 以 乙醇 为溶剂， 以84%的产率得到5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid (4-chlorobenzylidene)hydrazide
  参考文献：
  名称：

  Synthesis and the selective antifungal activity of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine derivatives

  摘要：

  Even though there are new classes of compounds now frequently used in treatment of fungal infections, the density of deeply invasive candidiasis has increased at least 10-fold during the past decade. Furthermore, many infections due to Candida species are actually refractory to antifungal therapy. In this present study, it was aimed to synthesize, new hydrazide derivatives of tetrahydroimidazo[1,2-a]pyridine and evaluate their anticandidal activity and cytotoxicity in vitro. The reaction of tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid hydrazides with various benzaldehydes gave tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid benzylidene hydrazide derivatives. The chemical structures of the compounds were elucidated and confirmed by IR, H-1 NMR, MS-FAB(+) spectroscopy and elemental analyses. Eight new tetrahydroimidazo[1,2-a]pyridine derivatives were synthesized and screened for their antifungal effects against a panel of ten human pathogenic Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, Candida tropicalis, Candida utilis, and Candida zeylanoides using agar diffusion and broth microdilution assays, respectively. Furthermore, their cytotoxicity was tested against six mammalian cell lines. Among the analogues, the compound 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid-(4-cyanobenzylidene) showed very strong inhibitory activity (up to MIC 0.016 mg/mL) against the screened Candida species. The same compound showed no in vitro toxicity up to 25 mu g/mL concentration suggesting that its antifungal activity (MICs 0.016-1 mg/mL) is selective. (C) 2009 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2009.12.023

文献信息

• Synthesis and the selective antifungal activity of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine derivatives
  作者：Ahmet Özdemir、Gülhan Turan-Zitouni、Zafer Asım Kaplancıklı、Gökalp İşcan、Shabana Khan、Fatih Demirci

  DOI：10.1016/j.ejmech.2009.12.023

  日期：2010.5

  Even though there are new classes of compounds now frequently used in treatment of fungal infections, the density of deeply invasive candidiasis has increased at least 10-fold during the past decade. Furthermore, many infections due to Candida species are actually refractory to antifungal therapy. In this present study, it was aimed to synthesize, new hydrazide derivatives of tetrahydroimidazo[1,2-a]pyridine and evaluate their anticandidal activity and cytotoxicity in vitro. The reaction of tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid hydrazides with various benzaldehydes gave tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid benzylidene hydrazide derivatives. The chemical structures of the compounds were elucidated and confirmed by IR, H-1 NMR, MS-FAB(+) spectroscopy and elemental analyses. Eight new tetrahydroimidazo[1,2-a]pyridine derivatives were synthesized and screened for their antifungal effects against a panel of ten human pathogenic Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, Candida tropicalis, Candida utilis, and Candida zeylanoides using agar diffusion and broth microdilution assays, respectively. Furthermore, their cytotoxicity was tested against six mammalian cell lines. Among the analogues, the compound 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid-(4-cyanobenzylidene) showed very strong inhibitory activity (up to MIC 0.016 mg/mL) against the screened Candida species. The same compound showed no in vitro toxicity up to 25 mu g/mL concentration suggesting that its antifungal activity (MICs 0.016-1 mg/mL) is selective. (C) 2009 Published by Elsevier Masson SAS.