5-ethyl-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-propyl-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione | 847951-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-ethyl-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-propyl-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione
• 英文别名: 1-Ethyl-3-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-5-propyl-1,3,5-triazinane-2,4,6-trione
• CAS: 847951-95-5
• 化学式: C₂₅H₃₁N₅O₄
• 分子量: 465.552
• InChiKey: IYZPYTBIHKGMGH-UHFFFAOYSA-N

物化性质

• 沸点：
  650.4±55.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-ethyl-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-propyl-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione 在 氢溴酸 、 sodium hexamethyldisilazane 、 sodium hydrogensulfite 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.17h， 生成 1-[4-[4-[4-[[(2R,4S)-2-(2,4-difluorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-3-ethyl-5-propyl-1,3,5-triazinane-2,4,6-trione
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Structure−Activity Relationships of Novel Antifungal Triazoles for Dermatology

  摘要：

  In search for new compounds with potential for clinical use as antifungal agents in dermatology, a series of 12 azole compounds were synthesized stereospecifically and investigated specifically for their activity against dermatophyte fungal infections in animal models. This panel of azoles was studied in vitro and compared with itraconazole and terbinafine for their antifungal activity using a panel of 24 Candida spp. and 182 dermatophyte isolates. Three azoles (1c, 2c, and 4c) showed in vitro antifungal potency equivalent to itraconazole, but superior to terbinafine, against a panel of 24 Candida spp. with comparable or lower activity than that of itraconazole and terbinafine against 182 dermatophyte isolates and only rare activity against other pathogenic fungi. However, in vivo 1c and 4c, both given orally, demonstrated antifungal activity at least three times greater than itraconazole and were superior compared to terbinafine in M. cants infected guinea pigs. In a mouse model infected by T mentagrophytes, again 4c, but not 1c, showed 5-fold superior activity over itraconazole and terbinafine. Compound 2c was effective in both models but less effective than itraconazole in these models. On the basis of these promising results, 4c is currently being clinically investigated for its potential as a novel antifungal agent against dermatophytosis.

  DOI：

  10.1021/jm0494772
• 作为产物：
  描述：

  1-(4-氨基苯基)-4-(4-甲氧基苯基)哌嗪 在 氢氧化钾 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-ethyl-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-propyl-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Structure−Activity Relationships of Novel Antifungal Triazoles for Dermatology

  摘要：

  In search for new compounds with potential for clinical use as antifungal agents in dermatology, a series of 12 azole compounds were synthesized stereospecifically and investigated specifically for their activity against dermatophyte fungal infections in animal models. This panel of azoles was studied in vitro and compared with itraconazole and terbinafine for their antifungal activity using a panel of 24 Candida spp. and 182 dermatophyte isolates. Three azoles (1c, 2c, and 4c) showed in vitro antifungal potency equivalent to itraconazole, but superior to terbinafine, against a panel of 24 Candida spp. with comparable or lower activity than that of itraconazole and terbinafine against 182 dermatophyte isolates and only rare activity against other pathogenic fungi. However, in vivo 1c and 4c, both given orally, demonstrated antifungal activity at least three times greater than itraconazole and were superior compared to terbinafine in M. cants infected guinea pigs. In a mouse model infected by T mentagrophytes, again 4c, but not 1c, showed 5-fold superior activity over itraconazole and terbinafine. Compound 2c was effective in both models but less effective than itraconazole in these models. On the basis of these promising results, 4c is currently being clinically investigated for its potential as a novel antifungal agent against dermatophytosis.

  DOI：

  10.1021/jm0494772