2-(4-isopropoxyphenyl)-2-(4-toluidino)acetonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-isopropoxyphenyl)-2-(4-toluidino)acetonitrile
• 英文别名: 2-(4-methylanilino)-2-(4-propan-2-yloxyphenyl)acetonitrile
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: VPXAFRJEKLJHPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-isopropoxyphenyl)-2-(4-toluidino)acetonitrile 在 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 4.0h， 生成 2-(4-isopropxyphenyl)-5-oxo-1-(4-tolyl)pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  Anti-human immunodeficiency activity of novel 2-arylpyrrolidine analogs

  摘要：

  A series of 26 new compounds were synthesized and screened for their anti-human immunodeficiency virus-1 and cytotoxicity activity. Of these, 14 were found to be inhibitors of human immunodeficiency virus replications in primary human lymphocytes with 50 % effective concentration values < 20 A mu M. Moreover, most of the compounds were cytotoxic to human lymphocytes, CEM, and Vero cells. Our structure activity relationship study identified different patterns. Compounds 2g-j and 4 (whose structure is closer to the loviride structure) were very potent. Comparing the activity of the compounds containing the 2-aryl substituents, we observed that compounds with benzyloxyphenyl groups were more potent. Compounds in which the 1-aryl moiety contained methyl group in 4- or 3,5-positions also showed high activity. In the series of compounds containing the nitrile, amine, and amide groups, we observed a decrease in activity with CN > NH2 > C(O)NH2. The difference of activity between the 5-membered and 4-membered rings compounds was not significant. This initial information could be used to design improved anti-human immunodeficiency virus compounds in this class.

  DOI：

  10.1007/s00044-016-1731-7
• 作为产物：
  描述：

  sodium cyanide 、 乙烷,三氯氟- 、 4-异丙氧基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以80%的产率得到2-(4-isopropoxyphenyl)-2-(4-toluidino)acetonitrile
  参考文献：
  名称：

  Anti-human immunodeficiency activity of novel 2-arylpyrrolidine analogs

  摘要：

  A series of 26 new compounds were synthesized and screened for their anti-human immunodeficiency virus-1 and cytotoxicity activity. Of these, 14 were found to be inhibitors of human immunodeficiency virus replications in primary human lymphocytes with 50 % effective concentration values < 20 A mu M. Moreover, most of the compounds were cytotoxic to human lymphocytes, CEM, and Vero cells. Our structure activity relationship study identified different patterns. Compounds 2g-j and 4 (whose structure is closer to the loviride structure) were very potent. Comparing the activity of the compounds containing the 2-aryl substituents, we observed that compounds with benzyloxyphenyl groups were more potent. Compounds in which the 1-aryl moiety contained methyl group in 4- or 3,5-positions also showed high activity. In the series of compounds containing the nitrile, amine, and amide groups, we observed a decrease in activity with CN > NH2 > C(O)NH2. The difference of activity between the 5-membered and 4-membered rings compounds was not significant. This initial information could be used to design improved anti-human immunodeficiency virus compounds in this class.

  DOI：

  10.1007/s00044-016-1731-7

文献信息

• 10.1134/s1070363224050037
  作者：Aleksanyan、Harutyunyan、Gasparyan

  DOI：10.1134/s1070363224050037

  日期：——

  arylacetic acid chlorides and subsequent intramolecular cyclization in the presence of potassium hydroxide. Similarly, 1-allyl-4-amino-3,5-diphe­nyl-1,5-dihydro-2H-pyrrol-2-one was formed from 2-(allylamino)-2-phenylacetonitrile with a β-ethylene bond. 2-Phenyl-1-(2-phenylacetyl)pyrro­lidine-2-carbonitrile was synthesized by acylation of 2-(3-chloropropylamino)-2-phenylacetonitrile with phe­nylacetic acid

   抽象的 通过用芳基乙酰氯酰化 α-芳基氨基腈并随后在氢氧化钾存在下进行分子内环化，合成了 4-氨基-1,3,5-三芳基-1H-吡咯-2(5H)-酮的新衍生物。类似地，1-烯丙基-4-氨基-3,5-二苯基-1,5-二氢-2H-吡咯-2-酮由2-(烯丙基氨基)-2-苯基乙腈与β-乙烯键形成。 2-苯基-1-(2-苯乙酰基)吡咯烷-2-甲腈是通过2-(3-氯丙氨基)-2-苯基乙腈与苯乙酰氯的酰化和随后的分子内环化合成的。在氢氧化钾存在下，N-(3-氯丙基)-N-(氰基(苯基)甲基-2-苯基乙酰胺发生分子内环化时，反应进行时同时闭合第二个环并形成双环产品 – 1-氨基-2,7a-二苯基-5,6,7,7a-四氢-3H-吡咯嗪-3-酮。
• Anti-human immunodeficiency activity of novel 2-arylpyrrolidine analogs
  作者：Ashot H. Martirosyan、Sahak P. Gasparyan、Marina V. Alexanyan、Gohar K. Harutyunyan、Henry A. Panosyan、Raymond F. Schinazi

  DOI：10.1007/s00044-016-1731-7

  日期：2017.1

  A series of 26 new compounds were synthesized and screened for their anti-human immunodeficiency virus-1 and cytotoxicity activity. Of these, 14 were found to be inhibitors of human immunodeficiency virus replications in primary human lymphocytes with 50 % effective concentration values < 20 A mu M. Moreover, most of the compounds were cytotoxic to human lymphocytes, CEM, and Vero cells. Our structure activity relationship study identified different patterns. Compounds 2g-j and 4 (whose structure is closer to the loviride structure) were very potent. Comparing the activity of the compounds containing the 2-aryl substituents, we observed that compounds with benzyloxyphenyl groups were more potent. Compounds in which the 1-aryl moiety contained methyl group in 4- or 3,5-positions also showed high activity. In the series of compounds containing the nitrile, amine, and amide groups, we observed a decrease in activity with CN > NH2 > C(O)NH2. The difference of activity between the 5-membered and 4-membered rings compounds was not significant. This initial information could be used to design improved anti-human immunodeficiency virus compounds in this class.