trans-3-(1H-indol-3-yl)-1-(2''-hydroxyphenyl)-2-propen-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: trans-3-(1H-indol-3-yl)-1-(2''-hydroxyphenyl)-2-propen-1-one
• 英文别名: trans-3-(1H-indol-3-yl)-1-(2'-hydroxyphenyl)-2-propen-1-one；(2E)-1-(2-hydroxyphenyl)-3-(1H-indol-3-yl)-2-propen-1-one；(E)-1-(2-hydroxyphenyl)-3-(1-indol-3-yl)prop-2-en-1-one；1-(2-hydroxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one；(E)-1-(2-hydroxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: BNYXDAPVMGMJTA-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙二腈 、 trans-3-(1H-indol-3-yl)-1-(2''-hydroxyphenyl)-2-propen-1-one 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以10%的产率得到2-amino-6-(2-hydroxyphenyl)-4-(1H-indol-3-yl)nicotinonitrile
  参考文献：
  名称：

  Anti-inflammatory, analgesic and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines

  摘要：

  4,6-diaryl and 4,6-aryl-indolyl substituted 3-cyano-2-aminopyridines were synthesized and submitted to evaluation for their anti-inflammatory, analgesic and antipyretic activity. The electronegativity of the substituents and their displacement on the 4- or 6-aryl ring of the 4,6-diaryl-3-cyano-2-aminopyridine nucleus (3a-q) influenced the anti-inflammatory activity which was higher in the presence of electron-realising groups. The introduction of the indol-3-yl substituent in the 4-position of the 3-cyano-2-aminopyridine nucleus (6a-x) increased the anti-inflammatory and analgesic power, but there was no evidence of the relationship among the electronic characteristic of the substituents, their displacement on the 6-phenyl ring and the activity. Conversely, the displacement of the 2-hydroxyphenyl group in the 4-position (4a-e) and of the indol-3-yl group in the 6-position (8h-w) decreased the anti-inflammatory activity. All derivatives did not show any significative antipyretic activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80057-9
• 作为产物：
  描述：

  3-吲哚甲醛 、 2'-羟基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以55%的产率得到trans-3-(1H-indol-3-yl)-1-(2''-hydroxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Chemical synthesis, docking studies and biological effects of functionalized 1,3-diaryl-2-propen-1-ones on human colon cancer cells

  摘要：

  为了获得一种新型抗癌药物，我们合成了一系列 1，3-二芳基-2-丙烯-1-酮，其设计具有抑制结肠癌活化受体的混合特征。在计算建模和对接研究的基础上，合成了潜在的抑制剂，并对其生物活性进行了评估。新合成化合物的结构通过 1HNMR、13CNMR 和质谱进行了确认。评估了所有类似物对人结肠癌（caco-2）细胞系的体外细胞毒性。化合物 1b、1f-1h 和 2i 显示出显著的细胞毒性。查耳酮 1b、1f 和 1g 被确定为最有效的选择性抗癌剂，对 caco-2 细胞系的 IC50 值分别为 1 µg/mL 和 1.5 µg/mL。总之，这一发现证实了吲哚基查尔酮类似物适合作为进一步研究结肠癌相关疾病治疗的候选药物。

  DOI：

  10.3329/bjp.v10i1.21699

文献信息

• Synthesis, molecular modelling studies of indolyl chalcone derivatives and their antimalarial activity evaluation
  作者：Jyoti、Rashmi Gaur、Yogesh Kumar、Harveer Singh Cheema、Deepak Singh Kapkoti、Mahendra P. Darokar、Feroz Khan、Rajendra Singh Bhakuni

  DOI：10.1080/14786419.2019.1696788

  日期：2021.10.2

  of terrestrial plants, precursors for the biosynthesis of flavonoids and exhibit various biological activities. Antiplasmodial IC50 (half-maximal inhibitory concentration) activity of a compound against malaria parasites in vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was Trans-3-(1H-indol-3-yl)-1-(2’-hydroxyphenyl)-2-propen-1-one

  摘要 使用 Claisen-Schmidt 缩合合成了 21 种查尔酮衍生物，测定了它们对恶性疟原虫的抗疟活性，并建立了定量构效关系 (QSAR)。取代苯乙酮与各种芳香醛在室温下缩合得到 75-96% 产率的查耳酮。查耳酮是陆生植物的次生代谢产物，是类黄酮生物合成的前体，具有多种生物活性。化合物在体外抗疟原虫的抗疟原虫IC 50（半数最大抑制浓度）活性为鉴定该化合物的抗疟潜力提供了良好的初步筛选。最活跃的化合物是Trans-3-(1H-indol-3-yl)-1-(2'-hydroxyphenyl)-2-propen-1-one (1b)，IC 50为 2.1 µM/L。通过对活性化合物的计算机对接和 ADMET 研究探索了分子机制。
• A novel synthesis of (E)-1-(2-hydroxyphenyl)-3-(1Н-indol-3-yl)- prop-2-en-1-ones from chromone-3-carboxylic acid and indoles
  作者：Mikhail Yu. Kornev、Vladimir S. Moshkin、Vyacheslav Ya. Sosnovskikh

  DOI：10.1007/s10593-015-1786-2

  日期：2015.9

  The reaction of chromone-3-carboxylic acid with indoles in boiling ethanol proceeds as a 1,4-nucleophilic addition with successive opening of the pyrone ring and decarboxylation to afford a series of previously unknown trans-indolyl chalcones in 27-60% yields.
• Absorption and Fluorescence Properties of Chalcones Having Pyrrole or Indole Moiety
  作者：Tatsuo Arai、Yukino Shinozaki

  DOI：10.3987/com-16-s(s)62

  日期：——

  2'-Hydroxychalcone derivatives having pyrrole ring have been synthesized and their absorption and fluorescence properties have been examined in connection to intramolecular hydrogen bonding.
• Synthesis, spectral, bioactivity, and NLO properties of chalcone metal complexes
  作者：S. Sumathi、P. Tharmaraj、C.D. Sheela、R. Ebenezer

  DOI：10.1080/00958972.2011.580844

  日期：2011.5.20

  A series of metal(II) complexes ML and ML2 [where M = Cu(II), Co(II), Ni(II), Zn(II), Mn(II), Cd(II), and VO(II); L = 2-hydroxyphenyl-3-(1H-indol-3-yl)-prop-2-en-1-one (HPIP)] have been prepared and characterized by elemental analysis, magnetic susceptibility, molar conductance, IR, UV-Vis, NMR, Mass, and ESR spectral studies. Conductivity measurements reveal that the complexes are non-electrolytes, except VO(II) complex. Spectroscopy and other data show square pyramidal geometry for oxovanadium and octahedral geometry for the other complexes. Redox behavior of the copper(II) and vanadyl complexes has been studied with cyclic voltammetry. Antimicrobial activities against several microorganisms indicate that a few complexes exhibit considerable activity. The nuclease activity shows that the complexes cleave DNA. All synthesized compounds can serve as potential photoactive materials as indicated from their characteristic fluorescence properties. The second harmonic generation efficiency of the ligand is higher than that of urea and KDP.