(E)-1-(3-hydroxyphenyl)-3-(3-pyridinyl)prop-2-en-1-one | 952577-78-5

• 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)-1-(3-hydroxyphenyl)-3-(3-pyridinyl)prop-2-en-1-one
• 英文别名: (E)-1-(3-hydroxyphenyl)-3-pyridin-3-ylprop-2-en-1-one
• CAS: 952577-78-5
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: QSMSQDPZHFLUOL-VOTSOKGWSA-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：

  (E)-1-(3-hydroxyphenyl)-3-(3-pyridinyl)prop-2-en-1-one 在 Lindlar's catalyst 4-二甲氨基吡啶 、 氢气 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 (+)-二异松蒎基氯硼烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -20.0~20.0 ℃ 、275.79 kPa 条件下， 反应 22.25h， 生成 (1R)-1-[3-(carboxymethoxy)phenyl]-3-(3-pyridinyl)-1-propanyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate trifluoroacetic salt
  参考文献：
  名称：

  Synthesis and activity of bivalent FKBP12 ligands for the regulated dimerization of proteins

  摘要：

  The total synthesis and in vitro activities of a series of chemical inducers of dimerization (CIDs) is described. The use of small-molecule CIDs to control the dimerization of engineered FKBP12-containing fusion proteins has been demonstrated to have broad utility in biological research as well as potential medical applications in gene and cell therapies. The facility and flexibility of preparation make this new class of wholly synthetic compounds exceptionally versatile tools for the study of intracellular signaling events mediated by protein-protein interactions or protein localization. While some congeners possess potency comparable to or better than the first generation natural product-derived CID, FK1012, structure-activity relationships are complex and underscore the need for application-specific compound optimizations. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00125-4
• 作为产物：
  描述：

  3-吡啶甲醛 、 3-羟基苯乙酮 在 lithium hydroxide monohydrate 作用下， 以 1,4-二氧六环 为溶剂， 以55%的产率得到(E)-1-(3-hydroxyphenyl)-3-(3-pyridinyl)prop-2-en-1-one
  参考文献：
  名称：

  新型吡啶基查耳酮的合成及抗胰酶活性

  摘要：

  合成了一个新颖的吡啶查酮的文库，并进行了罗氏锥虫的筛选。八显示出具有良好的活性与最有效的8具有IC 50 0.29μM的值。用人KB细胞进行的细胞毒性测试表明该化合物具有良好的选择性，选择性指数为47。当该库针对利什曼原虫donovani进行测试时，几乎没有活性。总之，吡啶基查耳酮是开发用于治疗人类非洲锥虫病（HAT）的新型化合物的有希望的先导。

  DOI：

  10.1016/j.ejmech.2017.01.027

文献信息

• 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.