(1E,4E)-1-(dimethylamino)-5-(2,6,6-trimethylcyclohex-2-en-1-yl)penta-1,4-dien-3-one | 883971-29-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1E,4E)-1-(dimethylamino)-5-(2,6,6-trimethylcyclohex-2-en-1-yl)penta-1,4-dien-3-one
• CAS: 883971-29-7
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: GHOFEKRAKPBOOX-CDKJVOIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1-(dimethylamino)-5-(2,6,6-trimethylcyclohex-2-en-1-yl)penta-1,4-dien-3-one 、 3-甲基-2-丁烯酸乙酯 在 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.25h， 以90%的产率得到(E)-1-(2-hydroxy-4-methylphenyl)-3-(2,6,6-trimethylcyclohex-2-en-1-yl)prop-2-en-1-one
  参考文献：
  名称：

  New syntheses and potential antimalarial activities of new ‘retinoid-like chalcones’

  摘要：

  A series of 'retinoid-like chalcones' and diverse derivatives relative to licochalcone A were synthesized from a new enaminone synthon. These syntheses occurred via a new aromatic annelation. These new derivatives have been tested in vitro as potential antimalarial agents. The 4-hydroxy-chalcone-like (compound 6a, derived from beta-ionone) exhibits a good and reproducible inhibitory effect on the in vitro culture of Plasmodium falciparum, with an IC 50 lower than 10 mu M for inhibition of 3 H-hypoxanthine uptake by parasites (respectively, 4.93 and 8.47 mu M for strains K1 and Thai). (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.05.008
• 作为产物：
  描述：

  alpha-ionone 、 N,N-二甲基甲酰胺二甲基缩醛 以95%的产率得到(1E,4E)-1-(dimethylamino)-5-(2,6,6-trimethylcyclohex-2-en-1-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  New syntheses and potential antimalarial activities of new ‘retinoid-like chalcones’

  摘要：

  A series of 'retinoid-like chalcones' and diverse derivatives relative to licochalcone A were synthesized from a new enaminone synthon. These syntheses occurred via a new aromatic annelation. These new derivatives have been tested in vitro as potential antimalarial agents. The 4-hydroxy-chalcone-like (compound 6a, derived from beta-ionone) exhibits a good and reproducible inhibitory effect on the in vitro culture of Plasmodium falciparum, with an IC 50 lower than 10 mu M for inhibition of 3 H-hypoxanthine uptake by parasites (respectively, 4.93 and 8.47 mu M for strains K1 and Thai). (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.05.008

文献信息

• New syntheses and potential antimalarial activities of new ‘retinoid-like chalcones’
  作者：A VALLA、B VALLA、D CARTIER、R LEGUILLOU、R LABIA、L FLORENT、S CHARNEAU、J SCHREVEL、P POTIER

  DOI：10.1016/j.ejmech.2005.05.008

  日期：2006.1

  A series of 'retinoid-like chalcones' and diverse derivatives relative to licochalcone A were synthesized from a new enaminone synthon. These syntheses occurred via a new aromatic annelation. These new derivatives have been tested in vitro as potential antimalarial agents. The 4-hydroxy-chalcone-like (compound 6a, derived from beta-ionone) exhibits a good and reproducible inhibitory effect on the in vitro culture of Plasmodium falciparum, with an IC 50 lower than 10 mu M for inhibition of 3 H-hypoxanthine uptake by parasites (respectively, 4.93 and 8.47 mu M for strains K1 and Thai). (c) 2005 Elsevier SAS. All rights reserved.