2-Cyano-N-cyclobutyl-acetamide | 1064448-86-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Cyano-N-cyclobutyl-acetamide
• 英文别名: 2-cyano-N-cyclobutylacetamide
• CAS: 1064448-86-7
• 化学式: C₇H₁₀N₂O
• 分子量: 138.169
• InChiKey: WYSOIFLPUNNWOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  365.8±21.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Cyano-N-cyclobutyl-acetamide 在 盐酸 、 aluminum (III) chloride 、 四(三苯基膦)钯 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 甲苯 为溶剂， 生成 4-amino-N-cyclobutyl-8-(2,5-dimethoxyphenyl)cinnoline-3-carboxamide
  参考文献：
  名称：

  Development and SAR of functionally selective allosteric modulators of GABAA receptors

  摘要：

  Positive modulators at the benzodiazepine site of alpha 2- and alpha 3-containing GABA(A) receptors are believed to be anxiolytic. Through oocyte voltage clamp studies, we have discovered two series of compounds that are positive modulators at alpha 2-/alpha 3-containing GABA(A) receptors and that show no functional activity at alpha 1-containing GABAA receptors. We report studies to improve this functional selectivity and ultimately deliver clinical candidates. The functional SAR of cinnolines and quinolines that are positive allosteric modulators of the alpha 2- and alpha 3-containing GABA(A) receptors, while simultaneously neutral antagonists at alpha 1-containing GABAA receptors, is described. Such functionally selective modulators of GABA(A) receptors are expected to be useful in the treatment of anxiety and other psychiatric illnesses. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.035
• 作为产物：
  描述：

  环丁基胺 、 氰乙酰胺 在 N-甲基哌嗪 作用下， 反应 4.0h， 生成 2-Cyano-N-cyclobutyl-acetamide
  参考文献：
  名称：

  Synthesis of resveratrol acrylamides derivatives and biological evaluation of their anti-proliferative effect on cancer cell lines

  摘要：

  设计、合成并评价了一系列白藜芦醇丙烯酰胺胺衍生物对三种癌细胞株的抗增殖活性，包括人慢性髓细胞白血病细胞K562、人肝癌HuH-7和人肺癌A549。与母体白藜芦醇相比，大多数化合物对三种细胞株表现出更强的活性。C13对HuH-7细胞株具有最佳的抗肿瘤活性，其IC50为4.5 μmol/L; C16对K562细胞株具有最佳的抗肿瘤活性，其IC50为2.9 μmol/L；C18对A549细胞株具有最佳的抗肿瘤活性，其IC50为3.8 μmol/L。通过分析实验数据可以发现，芳香胺衍生物的活性优于脂肪胺衍生物。

  DOI：

  10.2174/15701808113109990057

文献信息

• Aminoisoxazole derivatives active as kinase inhibitors
  申请人：Cavicchioli Marcello

  公开号：US20050059657A1

  公开（公告）日：2005-03-17

  Compounds (I) which are aminoisoxazole derivatives or pharmaceutically acceptable salts thereof, together with pharmaceutical compositions comprising them are disclosed; these compounds or compositions are useful in the treatment of diseases caused by and/or associated with an altered protein kinase activity such as cancer, cell proliferative disorders, Alzheimer's disease, viral infections, auto-immune diseases and neurodegenerative disorders.

  本发明涉及氨基异噁唑衍生物(I)或其药学上可接受的盐，以及包含它们的药物组合物。这些化合物或组合物在治疗由蛋白激酶活性改变引起和/或相关的疾病方面具有用途，例如癌症、细胞增殖性疾病、阿尔茨海默病、病毒感染、自身免疫性疾病和神经退行性疾病。
• AMINOISOXAZOLE DERIVATIVES ACTIVE AS KINASE INHIBITORS
  申请人：Pharmacia Italia S.p.A.

  公开号：EP1435948A1

  公开（公告）日：2004-07-14
• [EN] AMINOISOXAZOLE DERIVATIVES ACTIVE AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS D'AMINOISOXAZOLE AGISSANT COMME INHIBITEURS DE LA KINASE
  申请人：PHARMACIA ITALIA SPA

  公开号：WO2003013517A1

  公开（公告）日：2003-02-20

  Compounds (I) which are aminoisoxazole derivatives or pharmaceutically acceptable salts thereof, together with pharmaceutical compositions comprising them are disclosed; these compounds or compositions are useful in the treatment of diseases caused by and/or associated with an altered protein kinase activity such as cancer, cell proliferative disorders, Alzheimer's disease, viral infections, auto-immune diseases and neurodegenerative disorders.
• Synthesis of resveratrol acrylamides derivatives and biological evaluation of their anti-proliferative effect on cancer cell lines
  作者：Ban-Feng Ruan、Si-Qi Wang、Xiao-Lin Ge、Ri-Sheng Yao

  DOI：10.2174/15701808113109990057

  日期：2013.11

  A new series of resveratrol acrylamides amine derivatives was designed, synthesized, and evaluated for their anti-proliferative activity against three cancer cell lines including human chronic myelocytic leukemia cell K562, human hepatoma HuH-7 and human lung carcinoma A549. Most of the compounds showed superior activity against three cell lines when compared to parent resveratrol. C13 had the best anti-tumor activity against the HuH-7 cell line and its IC50 was 4.5 μmol/L; C16 had the best anti-tumor activity against the K562 cell line and its IC50 was 2.9 μmol/L; C18 had the best anti-tumor activity against the A549 cell line and its IC50 was 3.8 μmol/L. It could be seen that the activity of the aromatic amine derivatives was better than the fatty amine derivatives by analyzing the experimental data.

  设计、合成并评价了一系列白藜芦醇丙烯酰胺胺衍生物对三种癌细胞株的抗增殖活性，包括人慢性髓细胞白血病细胞K562、人肝癌HuH-7和人肺癌A549。与母体白藜芦醇相比，大多数化合物对三种细胞株表现出更强的活性。C13对HuH-7细胞株具有最佳的抗肿瘤活性，其IC50为4.5 μmol/L; C16对K562细胞株具有最佳的抗肿瘤活性，其IC50为2.9 μmol/L；C18对A549细胞株具有最佳的抗肿瘤活性，其IC50为3.8 μmol/L。通过分析实验数据可以发现，芳香胺衍生物的活性优于脂肪胺衍生物。
• Development and SAR of functionally selective allosteric modulators of GABAA receptors
  作者：Cristobal Alhambra、Chris Becker、Timothy Blake、Amy (Hui-Fang) Chang、James R. Damewood、Thalia Daniels、Bruce T. Dembofsky、David A. Gurley、James E. Hall、Keith J. Herzog、Carey L. Horchler、Cyrus J. Ohnmacht、Richard Jon Schmiesing、Adam Dudley、Maria D. Ribadeneira、Katherine S. Knappenberger、Carla Maciag、Mark M. Stein、Maninder Chopra、Xiaodong F. Liu、Edward P. Christian、Jeffrey L. Arriza、Marc J. Chapdelaine

  DOI：10.1016/j.bmc.2011.03.035

  日期：2011.5

  Positive modulators at the benzodiazepine site of alpha 2- and alpha 3-containing GABA(A) receptors are believed to be anxiolytic. Through oocyte voltage clamp studies, we have discovered two series of compounds that are positive modulators at alpha 2-/alpha 3-containing GABA(A) receptors and that show no functional activity at alpha 1-containing GABAA receptors. We report studies to improve this functional selectivity and ultimately deliver clinical candidates. The functional SAR of cinnolines and quinolines that are positive allosteric modulators of the alpha 2- and alpha 3-containing GABA(A) receptors, while simultaneously neutral antagonists at alpha 1-containing GABAA receptors, is described. Such functionally selective modulators of GABA(A) receptors are expected to be useful in the treatment of anxiety and other psychiatric illnesses. (C) 2011 Elsevier Ltd. All rights reserved.