(E)-3'-Hydroxy-4-azachalcone | 362589-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3'-Hydroxy-4-azachalcone
• 英文别名: (E)-1-(3-hydroxyphenyl)-3-pyridin-4-ylprop-2-en-1-one
• CAS: 362589-83-1
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: WZAWIIPNOHUNRG-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  硬脂基溴 、 (E)-3'-Hydroxy-4-azachalcone 以 乙腈 为溶剂， 反应 30.0h， 以65%的产率得到(E)-1-(3-hydroxyphenyl)-3-(1-octadecylpyridin-1-ium-4-yl)prop-2-en-1-one;bromide
  参考文献：
  名称：

  Antimicrobial activity of some N-alkyl substituted of (E)-4-azachalconium and (E)-3′-hydroxy-4-azachalconium bromides

  摘要：

  Twelve new N-substituted (E)-azachalconium bromides were synthesized and tested for antimicrobial and antifungal activities. Compounds 5c, 5d and 5h-5I showed very good antimicrobial activity against Staphylococcus aureus, Enterococcus faecalis as well as Bacillus subtilis and 5h-5j showed moderate activity against Escherichia coli. In particular, (E)-N-dodecyl-4-azachalconium bromide (5i) and (E)-N-tetradecyl-4-azachalconium bromide (5j) showed the most intensive activity against all tested microorganisms. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01230-2
• 作为产物：
  描述：

  4-吡啶甲醛 、 3-羟基苯乙酮 在 sodium hydroxide 作用下， 生成 (E)-3'-Hydroxy-4-azachalcone
  参考文献：
  名称：

  Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines

  摘要：

  Solid-phase synthesis of a parallel library of 3'-hydroxy-2,3-dihydrobenzothiazepines has been carried out through [4+3] annulation of alpha,beta-unsaturated ketones with aminothiophenol, using Wang resin as solid support. The synthesized compounds were evaluated for their potential as antibacterial, tumor inhibitors as well as acetyl- and butyrylcholinesterase inhibitors. None of the compounds showed any significant antibacterial activity. However, quite a few compounds showed significant potential as crown gall tumor inhibitors. These results reflect a strong exploratory potential in search of new benzothiazepines as source of anticancer agents. The results of the inhibition of cholinesterase revealed that benzothiazepines have a greater potential as butyrylcholinesterase inhibitors as compared to acetylcholinesterase. Moreover, the substitution of hydroxy group at C-3 in ring A led to increased activity when compared to unsubstituted- and 2'-OH substituted benzothiazepines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.009

文献信息

• Synthesis and antimicrobial properties of N-substituted derivatives of (E)-4-azachalcones
  作者：Zdzisława Nowakowska、Elżbieta Wyrzykiewicz、Bogdan Kędzia

  DOI：10.1016/s0014-827x(01)01072-2

  日期：2001.4

  Syntheses of 11 new N-bromoalkyl substituted bromides of (E)-4-azachalcone and N-o-(m- and p-) halobenzyl substituted halides of (E)-3'-hydroxy-4-azachalcone of antimicrobial activity are reported. Compounds 3d, 3e, 6b, 6c, and 6e reveal good antimicrobial activity against Staphylococcus aureus and Enterococcus faecalis as well as moderate activity against Escherichia coli and Klebsiella pneumoniae. (C) 2001 Elsevier Science S.A. All rights reserved.
• Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines
  作者：Farzana Latif Ansari、Fatima Iftikhar、Ihsan-ul-Haq、Bushra Mirza、Mohammad Baseer、Umer Rashid

  DOI：10.1016/j.bmc.2008.07.009

  日期：2008.8

  Solid-phase synthesis of a parallel library of 3'-hydroxy-2,3-dihydrobenzothiazepines has been carried out through [4+3] annulation of alpha,beta-unsaturated ketones with aminothiophenol, using Wang resin as solid support. The synthesized compounds were evaluated for their potential as antibacterial, tumor inhibitors as well as acetyl- and butyrylcholinesterase inhibitors. None of the compounds showed any significant antibacterial activity. However, quite a few compounds showed significant potential as crown gall tumor inhibitors. These results reflect a strong exploratory potential in search of new benzothiazepines as source of anticancer agents. The results of the inhibition of cholinesterase revealed that benzothiazepines have a greater potential as butyrylcholinesterase inhibitors as compared to acetylcholinesterase. Moreover, the substitution of hydroxy group at C-3 in ring A led to increased activity when compared to unsubstituted- and 2'-OH substituted benzothiazepines. (C) 2008 Elsevier Ltd. All rights reserved.
• Antimicrobial activity of some N-alkyl substituted of (E)-4-azachalconium and (E)-3′-hydroxy-4-azachalconium bromides
  作者：Zdzisława Nowakowska、Elżbieta Wyrzykiewicz、Bogdan Kędzia

  DOI：10.1016/s0014-827x(02)01230-2

  日期：2002.7

  Twelve new N-substituted (E)-azachalconium bromides were synthesized and tested for antimicrobial and antifungal activities. Compounds 5c, 5d and 5h-5I showed very good antimicrobial activity against Staphylococcus aureus, Enterococcus faecalis as well as Bacillus subtilis and 5h-5j showed moderate activity against Escherichia coli. In particular, (E)-N-dodecyl-4-azachalconium bromide (5i) and (E)-N-tetradecyl-4-azachalconium bromide (5j) showed the most intensive activity against all tested microorganisms. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.