2-(3,4-dioxymethylenphenyl)-2-(4-methylpiperazin-1-yl) acetonitrile | 93476-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(3,4-dioxymethylenphenyl)-2-(4-methylpiperazin-1-yl) acetonitrile
• 英文别名: α-(N'-Methylpiperazino)-piperonylnitril；benzo[1,3]dioxol-5-yl-(4-methyl-piperazin-1-yl)-acetonitrile；1,3-benzodioxol-5-yl(4-methyl-1-piperazinyl)acetonitrile；2-(1,3-Benzodioxol-5-yl)-2-(4-methylpiperazin-1-yl)acetonitrile
• CAS: 93476-70-1
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: QJNKDAPKWVOYBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,4-dioxymethylenphenyl)-2-(4-methylpiperazin-1-yl) acetonitrile 在 二异丁基氢化铝 、 Glauber's salt 作用下， 以 甲苯 、 乙醚 为溶剂， 生成 F2189-0334
  参考文献：
  名称：

  [EN] CALCILYTIC COMPOUNDS
  [FR] COMPOSÉS CALCILYTIQUE

  摘要：

  提供了新型钙受体拮抗剂化合物、药物组合物、合成方法和使用方法。

  公开号：

  WO2010039911A1
• 作为产物：
  描述：

  N-甲基哌嗪 、 胡椒醛 、 丙酮氰醇 在 sulfuric acid supported on silica gel 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以71%的产率得到2-(3,4-dioxymethylenphenyl)-2-(4-methylpiperazin-1-yl) acetonitrile
  参考文献：
  名称：

  Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever

  摘要：

  Girgensohnine alkaloid was used as a natural model in the design and generation of new alkaloid-like alpha-aminonitrile series that was completed by the use of SSA-catalyzed Strecker reaction between commercial and inexpensive substituted benzaldehydes, piperidine (pyrrolidine, morpholine and N-methylpiperazine) and acetone cyanohydrin. Calculated ADMETox parameters of the designed analogs revealed their good pharmacokinetic profiles indicating lipophilic characteristics. In vitro AChE enzyme test showed that obtained alpha-aminonitriles could be considered as AChEIs with micromolar IC50 values ranging from 42.0 to 478.0 mu M (10.3-124.0 mu g/mL). Among this series, the best AChE inhibitor was the Pyrrolidine alpha-aminonitrile 3 (IC50 = 42 mu M) followed by the piperidine alpha-aminonitriles 2 and 6 (IC50 = 45 mu M and IC50 = 51 mu M, respectively), and the compound 7 (IC50 = 51 mu M). In vivo insecticidal activity of more active AChEIs against Aedes aegypti larvae was also performed showing a good larvicidal activity at concentrations less than 140 ppm, highlighting products 2 and 7 that could serve as lead compounds to develop new potent and selective insecticides. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.067

文献信息

• Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever
  作者：Aurora L. Carreño Otero、Leonor Y. Vargas Méndez、Jonny E. Duque L.、Vladimir V. Kouznetsov

  DOI：10.1016/j.ejmech.2014.03.067

  日期：2014.5

  Girgensohnine alkaloid was used as a natural model in the design and generation of new alkaloid-like alpha-aminonitrile series that was completed by the use of SSA-catalyzed Strecker reaction between commercial and inexpensive substituted benzaldehydes, piperidine (pyrrolidine, morpholine and N-methylpiperazine) and acetone cyanohydrin. Calculated ADMETox parameters of the designed analogs revealed their good pharmacokinetic profiles indicating lipophilic characteristics. In vitro AChE enzyme test showed that obtained alpha-aminonitriles could be considered as AChEIs with micromolar IC50 values ranging from 42.0 to 478.0 mu M (10.3-124.0 mu g/mL). Among this series, the best AChE inhibitor was the Pyrrolidine alpha-aminonitrile 3 (IC50 = 42 mu M) followed by the piperidine alpha-aminonitriles 2 and 6 (IC50 = 45 mu M and IC50 = 51 mu M, respectively), and the compound 7 (IC50 = 51 mu M). In vivo insecticidal activity of more active AChEIs against Aedes aegypti larvae was also performed showing a good larvicidal activity at concentrations less than 140 ppm, highlighting products 2 and 7 that could serve as lead compounds to develop new potent and selective insecticides. (C) 2014 Elsevier Masson SAS. All rights reserved.
• [EN] CALCILYTIC COMPOUNDS<br/>[FR] COMPOSÉS CALCILYTIQUE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2010039911A1

  公开（公告）日：2010-04-08

  Novel calcilytic compounds, pharmaceutical compositions, methods of synthesis and methods of using them are provided.

  提供了新型钙受体拮抗剂化合物、药物组合物、合成方法和使用方法。