1-(4"-hydroxy phenyl)-3-(1'H-indol-3'-yl)-prop-2-en-1-one | 224818-98-8

• 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: 1-(4"-hydroxy phenyl)-3-(1'H-indol-3'-yl)-prop-2-en-1-one
• 英文别名: 1-(4''-hydroxyphenyl)-3-(1'H-indol-3'-yl)prop-2-en-1-one；1-(4-hydroxyphenyl)-3-(1H-indol-3-yl)-2-propen-1-one；1-(4-hydroxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
• CAS: 224818-98-8
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: DUFRKBZXGNZLSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.09
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4"-hydroxy phenyl)-3-(1'H-indol-3'-yl)-prop-2-en-1-one 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 苯 为溶剂， 生成 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-(4-trimethyl-silylmethylenoxyphenyl)propan-1-ol
  参考文献：
  名称：

  Foeldeak, Sandor; Hegyes, Peter; Dombi, Gyoergy, Acta Chimica Hungarica, 1988, vol. 125, # 2, p. 275 - 280

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吲哚甲醛 、 对羟基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(4"-hydroxy phenyl)-3-(1'H-indol-3'-yl)-prop-2-en-1-one
  参考文献：
  名称：

  新型吡唑啉-吲哚衍生物的合成和抗癌活性：用于鉴定新型 EGFR 抑制剂的药效相互作用和对接研究

  摘要：

  合成了新设计的一系列含有吲哚的吡唑类似物，吡唑啉吲哚，并根据1 H NMR 的光谱数据确认了它们的结构，13C NMR 和 HR-MS 分析。初步抗癌活性测试由美国国家癌症研究所 (NCI, USA) 进行。化合物 HD02、HD05 和 HD12 对九种基于癌症类型的细胞系组显示出显着的细胞毒活性，这些细胞系包括白血病、结肠癌、乳腺癌、黑色素瘤、肺癌、肾癌、前列腺癌、CNS 和卵巢癌细胞系。化合物 HD02 [1-(5-(1-H-indol-3-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl) 表现出最高的细胞毒性作用-2-苯乙酮]，HD05 [1-(3-(4-氯苯基)-5-(1H-吲哚-3-基)-4,5-二氢-1H-吡唑-1-基)-2-苯氧基乙酮] , 和 HD12 [(3-(4-chlorophenyl)-5-(1H-indol-3-yl)-4

  DOI：

  10.3390/ijms23126548

文献信息

• Solvent Effect Profiles of Absorbance and Fluorescence Spectra of Some Indole Based Chalcones
  作者：Manju Kumari Saroj、Neera Sharma、Ramesh C. Rastogi

  DOI：10.1007/s10895-011-0926-z

  日期：2011.11

  The photophysical properties of a series of 3-(1′H-Indol-3′-yl)-1-phenylprop-2-en-1-one and its derivatives (indole chalcones) were studied in different solvents. Solvent effects on the absorption and fluorescence spectra were quantified using Reichardt’s and bulk solvent polarity parameters and were complemented by the results of the Kamlet-Taft treatment. The observed excited state dipole moment

  在不同溶剂中研究了一系列 3-(1' H -Indol-3'-yl)-1-phenylprop-2-en-1-one 及其衍生物（吲哚查尔酮）的光物理性质。溶剂对吸收和荧光光谱的影响使用 Reichardt 和本体溶剂极性参数量化，并由 Kamlet-Taft 处理的结果补充。发现观察到的激发态偶极矩大于这些查耳酮的基态偶极矩。发现溶剂化变色斯托克斯位移与微观溶剂极性参数 ( \( E_T^N \) ) 的相关性优于使用本体溶剂极性函数获得的相关性。
• Investigation of indole chalcones encapsulation in β-cyclodextrin: determination of stoichiometry, binding constants and thermodynamic parameters
  作者：Manju K. Saroj、Ritu Payal、Sapan K. Jain、Neera Sharma、Ramesh C. Rastogi

  DOI：10.1007/s10847-018-0782-4

  日期：2018.4

  with increase in the concentration of β-CD in the aqueous solution. The stoichiometries and binding constants (Kin) of these complexes have been investigated by monitoring their absorbance and fluorescence spectral profiles. The data are analyzed by Benesi–Hildebrand plots as well as Job’s method, which indicate 1:1 stoichiometry of IC:β-CD complexes. Fluorescence measurements are also used to investigate

  该研究的重点是吲哚查尔酮 (IC) 衍生物与 β-环糊精 (β-CD) 的包合物的形成，涉及吸收和稳态荧光光谱。包合物的形成通过其吸光度和荧光强度的增加以及随着水溶液中 β-CD 浓度增加的蓝移而得到证实。这些复合物的化学计量和结合常数 (Kin) 已通过监测它们的吸光度和荧光光谱图进行了研究。数据通过 Benesi-Hildebrand 图和 Job 方法进行分析，表明 IC:β-CD 复合物的化学计量为 1:1。荧光测量还用于研究温度对包合物稳定性的影响。IC的稳定性：β-CD 复合物受苯环上取代基和温度变化的显着影响。观察到包合物的稳定性随着温度的升高而降低；Kin(293 K) > Kin(298 K) > Kin(308 K) > Kin(318 K)。使用PM3半经验方法获得的所有实验结果和几何数据说明了β-CD腔中苯环侧的IC衍生物部分包含。发现 IC 衍生物与 β-CD 的
• Radiation and Quantum Chemical Studies of Chalcone Derivatives
  作者：P. Gaikwad、K. I. Priyadarsini、S. Naumov、B. S. M. Rao

  DOI：10.1021/jp103382x

  日期：2010.8.5

  barrierless. The stability and lack of dehydration of the •OH adducts arise from two factors: strong frontier orbital interaction due to the low energy gap between interacting orbitals and the negligible Coulombic repulsion due to small absolute values of Mulliken charges. The transient absorption spectrum measured in the •OH radical reaction with all the indole chalcone derivatives exhibited a maximum

  通过辐射和量子化学方法研究了氧化自由基（• OH，Br 2 •-和SO 4 •-）与-OH -，- CH 3-或-NH 2取代的吲哚查耳酮和羟基苯甲酚查耳酮的反应。 。的• OH自由基，发现通过加入在扩散控制的速率（反应ķ = 1.1-1.7×10 10分米3摩尔-1小号-1），但溴2 • -自由基反应2个数量级的降低。在理论上B3LYP / 6-31 + G（d，p）的量子化学计算表明（C2-OH）•，（C11-OH）•和（C10-OH）•吲哚查耳酮的加合物以及（C7-OH）•和（C8-OH）•羟基苯甲酰查耳酮的加合物在ΔH = −39时更稳定至-28kcal mol -1和ΔG＝ -32至-19kcal mol -1。这表明• α，β-不饱和键中的OH加成是两种查耳酮中的主要反应通道，并且是无障碍的。稳定性和缺乏的脱水•OH加合物的产生有两个原因：相互作用轨道之间的能隙低，导致强烈的轨
• Synthesis and biological evaluation of indolyl chalcones as antitumor agents
  作者：Dalip Kumar、N. Maruthi Kumar、Kanako Akamatsu、Eriko Kusaka、Hiroshi Harada、Takeo Ito

  DOI：10.1016/j.bmcl.2010.05.016

  日期：2010.7

  A series of indolyl chalcones were synthesized and evaluated in vitro for their anticancer activity against three human cancer cell lines. Compounds 3b-d, 3h, 3j, 3l, 3m, 4g, and 4j showed significant cytotoxicity, particularly, indolyl chalcones 3l and 3m were identified as the most potent and selective anticancer agents with IC50 values 0.03 and 0.09 mu M, against PaCa-2 cell line, respectively. (c) 2010 Elsevier Ltd. All rights reserved.
• First‐in‐class pyrido[2,3‐ <i>d</i> ]pyrimidine‐2,4(1 <i>H</i> ,3 <i>H</i> )‐diones against leishmaniasis and tuberculosis: Rationale, in vitro, ex vivo studies and mechanistic insights
  作者：Deepthi Ramesh、Deblina Sarkar、Annu Joji、Monica Singh、Amaresh K. Mohanty、Balaji G. Vijayakumar、Mitali Chatterjee、Dharmarajan Sriram、Suresh K. Muthuvel、Tharanikkarasu Kannan

  DOI：10.1002/ardp.202100440

  日期：2022.4

  AbstractPyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones were synthesized, for the first time, from indole chalcones and 6‐aminouracil, and their ability to inhibit leishmaniasis and tuberculosis (Tb) infections was evaluated. The in vitro antileishmanial activity against promastigotes of Leishmania donovani revealed exceptional activities of compounds 3, 12 and 13, with IC50 values ranging from 10.23 ± 1.50 to 15.58 ± 1.67 µg/ml, which is better than the IC50 value of the standard drug pentostam of 500 μg/ml. The selectivity of the compounds towards Leishmania parasites was evaluated via ex vivo studies in Swiss albino mice. The efficiency of these compounds against Tb infection was then evaluated using the in vitro anti‐Tb microplate Alamar Blue assay. Five compounds, 3, 7, 8, 9 and 12, showed MIC100 values against the Mycobacterium tuberculosis H37Rv strain at 25 µg/ml, and compound 20 yielded an MIC100 value of 50 µg/ml. Molecular modelling of these compounds highlighted interactions with binding sites of dihydrofolate reductase, pteridine reductase and thymidylate kinase, thus establishing the rationale of their pharmacological activity against both pathogens, which is consistent with the in vitro results. From the above results, it is clear that compounds 3 and 12 are promising lead candidates for Leishmania and Mycobacterium infections and may be promising for coinfections.