tert-cutyl ({1-[2-(diisopropylamino)-2-oxoethyl]-1H-1,2,3-triazol-4-yl}methyl)carbamate | 1491137-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-cutyl ({1-[2-(diisopropylamino)-2-oxoethyl]-1H-1,2,3-triazol-4-yl}methyl)carbamate
• CAS: 1491137-18-8
• 化学式: C₁₆H₂₉N₅O₃
• 分子量: 339.438
• InChiKey: INOVEPVYZUOBIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  89.35
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-cutyl ({1-[2-(diisopropylamino)-2-oxoethyl]-1H-1,2,3-triazol-4-yl}methyl)carbamate 在 盐酸 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-(4-{[(7-chloroquinolin-4-yl)amino]methyl}-1H-1,2,3-triazol-1-yl)-N,N-diisopropylacetamide
  参考文献：
  名称：

  In vitro antimalarial activity, β-haematin inhibition and structure–activity relationships in a series of quinoline triazoles

  摘要：

  A novel series of quinoline triazole amide analogues (38-51) has been synthesized. Analogues 38-44 had a Cl substituent at the 7-position of the quinoline ring, while 45-51 had a CN substituent at this position. Compounds 40,45 and 49 were found to be the most active in the series against the Plasmodium falciparum chloroquine-sensitive D10 strain, with IC50 values in the range of 349-1247 nM, with 40 and 45, but not 49 also exhibiting similar activity against the chloroquine-resistant 1(1 strain of parasite. Quinoline triazoles 40 and 44 were the most active beta-haematin inhibitors, with 50% inhibitory concentrations of 14.7 and 8.9 1tM respectively. In vitro antimalarial activity of the 7-C1 bearing analogues 38 -44 exhibited a strong linear dependence of log(1/IC50) on log P. Thus, the more lipophilic, the more active it was found be. The 7-CN series 45-51 showed no such dependence. The resistance index (IC50 K1 /IC50 D10) also exhibited a linear dependence on log P, with a substantially steeper slope in the case of the 7-CI series. The findings demonstrate the feasibility of producing hydrophilic analogues with strong activity and low cross-resistance with chloroquine. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.046
• 作为产物：
  描述：

  二异丙胺 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 tert-cutyl ({1-[2-(diisopropylamino)-2-oxoethyl]-1H-1,2,3-triazol-4-yl}methyl)carbamate
  参考文献：
  名称：

  In vitro antimalarial activity, β-haematin inhibition and structure–activity relationships in a series of quinoline triazoles

  摘要：

  A novel series of quinoline triazole amide analogues (38-51) has been synthesized. Analogues 38-44 had a Cl substituent at the 7-position of the quinoline ring, while 45-51 had a CN substituent at this position. Compounds 40,45 and 49 were found to be the most active in the series against the Plasmodium falciparum chloroquine-sensitive D10 strain, with IC50 values in the range of 349-1247 nM, with 40 and 45, but not 49 also exhibiting similar activity against the chloroquine-resistant 1(1 strain of parasite. Quinoline triazoles 40 and 44 were the most active beta-haematin inhibitors, with 50% inhibitory concentrations of 14.7 and 8.9 1tM respectively. In vitro antimalarial activity of the 7-C1 bearing analogues 38 -44 exhibited a strong linear dependence of log(1/IC50) on log P. Thus, the more lipophilic, the more active it was found be. The 7-CN series 45-51 showed no such dependence. The resistance index (IC50 K1 /IC50 D10) also exhibited a linear dependence on log P, with a substantially steeper slope in the case of the 7-CI series. The findings demonstrate the feasibility of producing hydrophilic analogues with strong activity and low cross-resistance with chloroquine. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.046