1-(2-hydroxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one | 33268-88-1

• 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-(2-hydroxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
• 英文别名: 1-(2'-hydroxyphenyl)-3-(1H-indol-3-yl)-2-propen-1-one；1-(2-hydroxy-phenyl)-3-indol-3-yl-propenone
• CAS: 33268-88-1
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: BNYXDAPVMGMJTA-UHFFFAOYSA-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：

  1-(2-hydroxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 在 吡啶 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1-acetoxy-2-(5-indol-3-yl-4,5-dihydro-isoxazol-3-yl)-benzene
  参考文献：
  名称：

  Venturella; Bellino; Piozzi, Farmaco, Edizione Scientifica, 1971, vol. 26, # 7, p. 591 - 596

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吲哚甲醛 、 2'-羟基苯乙酮 在 哌啶 作用下， 生成 1-(2-hydroxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  吲哚基苯并呋喃支架作为抗菌剂和抗氧化剂的微波辅助合成和评价

  摘要：

  在微波辐射和常规条件下合成了一系列新型吲哚基苯并呋喃衍生物。根据1HNMR、13C NMR、IR和质谱数据确定了化合物的结构。评估了类似物对两种革兰氏阳性菌、两种革兰氏阴性菌和两种真菌菌株的体外抗微生物活性。针对 2,2-二苯基-1-苦基肼 (DPPH) 的体外抗氧化活性筛选了同一系列。大多数标题化合物表现出有希望的抗微生物和抗氧化活性。

  DOI：

  10.1134/s1068162016050034

文献信息

• Microwave-assisted synthesis and evaluation of indole based benzofuran scaffolds as antimicrobial and antioxidant agents
  作者：D. Ashok、G. Srinivas、A. V. Kumar、D. M. Gandhi

  DOI：10.1134/s1068162016050034

  日期：2016.9

  A novel series of indole based benzofuran derivatives has been synthesized under microwave irradiation and conventional conditions. The structures of the compounds were established on the basis of 1HNMR, 13C NMR, IR and mass spectral data. The analogues were evaluated for their in vitro antimicrobial activity against two gram-positive bacteria, two gram-negative bacteria and two fungal strains. The

  在微波辐射和常规条件下合成了一系列新型吲哚基苯并呋喃衍生物。根据1HNMR、13C NMR、IR和质谱数据确定了化合物的结构。评估了类似物对两种革兰氏阳性菌、两种革兰氏阴性菌和两种真菌菌株的体外抗微生物活性。针对 2,2-二苯基-1-苦基肼 (DPPH) 的体外抗氧化活性筛选了同一系列。大多数标题化合物表现出有希望的抗微生物和抗氧化活性。
• Photogeneration of reactive oxygen species and photoinduced plasmid DNA cleavage by novel synthetic chalcones
  作者：Y. Yesuthangam、S. Pandian、K. Venkatesan、R. Gandhidasan、R. Murugesan

  DOI：10.1016/j.jphotobiol.2010.12.004

  日期：2011.3

  This paper describes the synthesis and photodynamic properties of six different chalcone derivatives. Using N,N-dimethyl-4-nitrosoaniline (RNO) bleaching assay, the singlet oxygen generating efficiencies of these chalcones are determined relative to rose bengal (RB). Superoxide dismutase (SOD) inhibitable cytochrome c reduction assay and electron magnetic resonance (EMR) spin trapping techniques are used to determine the superoxide anion radical (O-2(center dot-)) yield upon photoirradiation. Photoinduced DNA scission studies show that O-2(center dot-) is involved in the DNA strand break. In addition, antimicrobial activity of these chalcones is also investigated. Structure activity relationship accounts for the difference in the photogeneration of reactive oxygen species (ROS) by these sensitizers. Presence of electron releasing -OCH3 groups enhances the photogeneration of ROS. Cyclic voltammetry studies indicate a correlation between enzymatic O-2(center dot-) generation efficiency and redox potential of chalcones. Both O-2(center dot-) (Type I) and O-1(2) (Type II) paths are involved in the photosensitization of chalcones. The LUMO energies obtained by molecular modeling correlate with the one-electron reduction potentials. (C) 2010 Elsevier B.V. All rights reserved.
• Venturella; Bellino; Piozzi, Farmaco, Edizione Scientifica, 1971, vol. 26, # 7, p. 591 - 596
  作者：Venturella、Bellino、Piozzi

  DOI：——

  日期：——
• Synthesis and Anti-Cancer Activity of New Pyrazolinyl-Indole Derivatives: Pharmacophoric Interactions and Docking Studies for Identifying New EGFR Inhibitors
  作者：Habibullah Khalilullah、Deepak K. Agarwal、Mohamed J. Ahsan、Surender S. Jadav、Hamdoon A. Mohammed、Masood Alam Khan、Salman A. A. Mohammed、Riaz Khan

  DOI：10.3390/ijms23126548

  日期：——

  exhibited by the compounds HD02 [1-(5-(1-H-indol-3-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-phenylethanone], HD05 [1-(3-(4-chlorophenyl)-5-(1H-indol-3-yl)-4,5-dihydro-1H-pyrazol-1-yl)-2-phenoxyethanone], and HD12 [(3-(4-chlorophenyl)-5-(1H-indol-3-yl)-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanone] against some of the 56 types of NCI-based cell lines in different panels. Compound HD05 showed

  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