tert-butyl4-(4-(5,6-diphenyl-1,2,4-triazin-3-yl)-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate | 1207740-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl4-(4-(5,6-diphenyl-1,2,4-triazin-3-yl)-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate
• 英文别名: Tert-butyl 4-[4-(5,6-diphenyl-1,2,4-triazin-3-yl)triazol-1-yl]piperidine-1-carboxylate
• CAS: 1207740-51-9
• 化学式: C₂₇H₂₉N₇O₂
• 分子量: 483.573
• InChiKey: MYMDRZQQRQYMTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(4-(hydrazinecarbonyl)-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate 、 联苯甲酰 在 zirconyl chloride octahydrate 、 ammonium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.67h， 以94%的产率得到tert-butyl4-(4-(5,6-diphenyl-1,2,4-triazin-3-yl)-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  One pot synthesis and SAR of some novel 3-substituted 5,6-diphenyl-1,2,4-triazines as antifungal agents

  摘要：

  An improved protocol for the synthesis of a novel series of 1,2,4-triazines possessing 1,2,3-triazole and piperidine ring using 1-(1-substituted piperidin-4-yl)-1H-1,2,3-triazole-4-carbohydrazide, benzil, ammonium acetate and ZrOCl2 center dot 8H(2)O as a catalyst in ethanol-water has been presented. The yields obtained are in the range of 87-94%. All the synthesized compounds (4a-4l) are novel and were evaluated for their in vitro antifungal activity. SAR for the series has been developed by comparing their MIC values with miconazole and fluconazole. Based on activity data SAR for the series has been developed. Compound 4c from the series was equipotent to miconazole against Candida albicans (MIC-25), Aspergillus niger (MIC-12.5) and Cryptococcus neoformans (MIC-25). Compound 4d was equipotent with miconazole against all tested organisms except Cryptococcus neoformans. Also compound 4i was equipotent with miconazole against C. albicans, A. niger and Fusarium oxysporum. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.048

文献信息

• One pot synthesis and SAR of some novel 3-substituted 5,6-diphenyl-1,2,4-triazines as antifungal agents
  作者：Jaiprakash N. Sangshetti、Devanand B. Shinde

  DOI：10.1016/j.bmcl.2009.11.048

  日期：2010.1

  An improved protocol for the synthesis of a novel series of 1,2,4-triazines possessing 1,2,3-triazole and piperidine ring using 1-(1-substituted piperidin-4-yl)-1H-1,2,3-triazole-4-carbohydrazide, benzil, ammonium acetate and ZrOCl2 center dot 8H(2)O as a catalyst in ethanol-water has been presented. The yields obtained are in the range of 87-94%. All the synthesized compounds (4a-4l) are novel and were evaluated for their in vitro antifungal activity. SAR for the series has been developed by comparing their MIC values with miconazole and fluconazole. Based on activity data SAR for the series has been developed. Compound 4c from the series was equipotent to miconazole against Candida albicans (MIC-25), Aspergillus niger (MIC-12.5) and Cryptococcus neoformans (MIC-25). Compound 4d was equipotent with miconazole against all tested organisms except Cryptococcus neoformans. Also compound 4i was equipotent with miconazole against C. albicans, A. niger and Fusarium oxysporum. (C) 2009 Elsevier Ltd. All rights reserved.