7-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-isopropyl-N-(pyridin-2-yl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-isopropyl-N-(pyridin-2-yl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
• 英文别名: 7-[3-(4-fluorophenyl)-1-phenyl-pyrazol-4-yl]-5-isopropyl-N-(2-pyridyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide；7-[3-(4-fluorophenyl)-1-phenylpyrazol-4-yl]-5-propan-2-yl-N-pyridin-2-yl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
• 化学式: C₂₉H₂₅FN₈O
• 分子量: 520.569
• InChiKey: AKTSEJDWHDEFEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(1-(4-fluorophenyl)ethylidene)-2-phenylhydrazine 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 7-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-isopropyl-N-(pyridin-2-yl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Pyrazole clubbed triazolo[1,5-a]pyrimidine hybrids as an anti-tubercular agents: Synthesis, in vitro screening and molecular docking study

  摘要：

  A series of novel pyrazole linked triazolo-pyrimidine hybrids were synthesized and evaluated for their anti-tuberculosis activity against M.tb H37Rv strain. Some of the screened entities rendered promising anti-tb activity (MIC: 0.39 mu g/mL) and were found non toxic against Vero cells (IC50: >= 20 mu g/mL). Further, the docking study against wild type InhA enzyme of Mycobacterium tuberculosis using Glide reproduced the most active inhibitors (J21 and J27) with lowest binding energies and highest Glide XP scores demonstrating efficient binding to the active pocket. Additionally, the enzyme inhibition assay and ADME prediction of the active proved to be an attest to the possibility of developing compound J27 as a potent anti-tubercular lead. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.018

文献信息

• Microwave Assisted Synthesis of Pyrimidines in Ionic Liquid and Their Potency as Non-Classical Malarial Antifolates
  作者：Jaimin D. Bhatt、Chaitanya J. Chudasama、Kanuprasad D. Patel

  DOI：10.1002/ardp.201600148

  日期：2016.10

  Synthesis of pyrazole‐linked triazolo‐pyrimidine hybrids was achieved by employing Biginelli‐type reaction methodology in an ionic liquid (triethylammonium acetate) under microwave irradiation. This method proved to be highly efficient and the ionic liquid employed was found recyclable for up to five consecutive cycles. The synthesized molecules were further screened for their antimalarial efficacy

  在微波辐射下，通过在离子液体（醋酸三乙铵）中采用 Biginelli 型反应方法合成吡唑连接的三唑并嘧啶杂化物。该方法被证明是高效的，并且发现所使用的离子液体最多可连续循环五个循环。进一步筛选合成分子的抗疟功效，筛选出活性支架 J15、J18、J21、J24、J27 和 J30。在针对活性恶性疟原虫二氢叶酸还原酶 (Pf-DHFR) 的酶抑制研究中，通过计算和体外评估了活性分子，证明了它们作为 DHFR 抑制剂的效力。还通过在计算机中预测 ADME 特性来研究活性实体的口服生物利用度，表明其具有良好的生物利用度。