2-(4-hydroxyphenyl)-1H-indole-3-carbaldehyde

• 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: 2-(4-hydroxyphenyl)-1H-indole-3-carbaldehyde
• 英文别名: 2-(4-hydroxyphenyl)-1H-indole-3-carboxaldehyde
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: RDWXPWLANYTDNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 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：

  2-(4-hydroxyphenyl)-1H-indole-3-carbaldehyde 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以90%的产率得到2-(4-hydroxyphenyl)-1H-indole-3-carboxaldehyde oxime
  参考文献：
  名称：

  Synthesis, molecular docking study and antitumor activity of novel 2-phenylindole derivatives

  摘要：

  The starting material, 4-(1-indol-2-yl)phenol 1 was obtained via Fischer synthesis. Vilsmeir Haack's formylation of 1 gave the carboxaldehyde derivative 2 which was subjected to different reactions affording the 3-substituted compounds 3-10. Compound 1 reacted with halo esters to give 11 and 12a,b. The reaction of 12a with various amino derivatives gave compounds 13-16. The hydrazide derivative 15a reacted with 1,3-diketones, ethyl acetoacetate and aromatic carboxylic acid derivatives to give 17a,b, 18 and 19a-e, respectively. Antitumor activity of target compounds were tested against breast cancer cell lines (MCF-7) and (MDA-MB-231). The most potent compound was 3e with IC50 = 1.60 nM against (MCF-7). Docking was performed on colchicine binding site of tubulin to study the binding mode of the designed compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.007
• 作为产物：
  描述：

  对羟基苯乙酮 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2-(4-hydroxyphenyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  新型细胞毒性吲哚-氨基硫脲衍生物的设计与合成：生物学评价与对接研究

  摘要：

  在这项工作中，与作为参考药物的依托泊苷和秋水仙碱相比，设计、合成了两个新系列的吲哚-缩氨基硫脲衍生物，并评估了它们对 MCF-7、A-549 和 Hep-G2 细胞系的细胞毒活性。一般来说，合成的化合物对 A-549 和 Hep-G2 显示出比 MCF-7 更好的细胞毒性。其中，(2E)-2-{[2-(4-氯苯基)-1H-吲哚-3-基]亚甲基}-N-(4-甲氧基苯基)肼碳硫酰胺(8l)被发现是最有效的化合物A-549 和 Hep-G2，至少比依托泊苷强三倍。通过吖啶橙/溴化乙锭双染色试验和流式细胞术分析的形态学分析表明，化合物8l诱导A-549细胞凋亡。而且，

  DOI：

  10.1002/cbdv.201800470

文献信息

• Design and Synthesis of Novel Cytotoxic Indole‐Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study
  作者：Zohreh Bakherad、Maliheh Safavi、Afshin Fassihi、Hojjat Sadeghi‐Aliabadi、Mohammad Bakherad、Hossein Rastegar、Mina Saeedi、Jahan B Ghasemi、Lotfollah Saghaie、Mohammad Mahdavi

  DOI：10.1002/cbdv.201800470

  日期：2019.4

  In this work, two novel series of indole‐thiosemicarbazone derivatives were designed, synthesized, and evaluated for their cytotoxic activity against MCF‐7, A‐549, and Hep‐G2 cell lines in comparison to etoposide and colchicine as the reference drugs. Generally, the synthesized compounds showed better cytotoxicity towards A‐549 and Hep‐G2 than MCF‐7. Among them, (2E)‐2‐[2‐(4‐chlorophenyl)‐1H‐indo

  在这项工作中，与作为参考药物的依托泊苷和秋水仙碱相比，设计、合成了两个新系列的吲哚-缩氨基硫脲衍生物，并评估了它们对 MCF-7、A-549 和 Hep-G2 细胞系的细胞毒活性。一般来说，合成的化合物对 A-549 和 Hep-G2 显示出比 MCF-7 更好的细胞毒性。其中，(2E)-2-[2-(4-氯苯基)-1H-吲哚-3-基]亚甲基}-N-(4-甲氧基苯基)肼碳硫酰胺(8l)被发现是最有效的化合物A-549 和 Hep-G2，至少比依托泊苷强三倍。通过吖啶橙/溴化乙锭双染色试验和流式细胞术分析的形态学分析表明，化合物8l诱导A-549细胞凋亡。而且，
• Preparation of some novel imidazopyridine derivatives of indole as anticancer agents: one-pot multicomponent synthesis, biological evaluation and docking studies
  作者：Zohreh Bakherad、Maliheh Safavi、Saghi Sepehri、Afshin Fassihi、Hojjat Sadeghi-Aliabadi、Mohammad Bakherad、Hossein Rastegar、Bagher Larijani、Lotfollah Saghaie、Mohammad Mahdavi

  DOI：10.1007/s11164-019-03915-z

  日期：2019.10

  A series of novel imidazopyridine derivatives of indole has been synthesized. All the synthesized derivatives were evaluated for their antiproliferative activity against A-549, T-47D, Hep-G2 and MCF-7 human cancer cell lines. The results demonstrated that some of these derivatives exhibited moderate to excellent cytotoxic activities. Compounds 7a having a cyclohexyl ring substituted to the second amine

  合成了一系列新的吲哚咪唑并吡啶衍生物。评价所有合成的衍生物对A-549，T-47D，Hep-G2和MCF-7人癌细胞系的抗增殖活性。结果表明，这些衍生物中的一些表现出中等至优异的细胞毒性活性。具有在C 2吲哚环的咪唑并吡啶基部分的第二胺和苯基环上取代的环己基环的化合物 7a 和 在同一位置具有 对 甲基苯环的 7f ， 对具有IC 50的A-594细胞系表现出最高的活性分别为11.48μM和10.66μM。结果表明化合物 7a 和 7f 与依托泊苷相比，对癌细胞系的细胞毒性更高。此外，化合物 7d 和 7j 对Hep-G2的活性最高，相当于依托泊苷为标准药物。同样，大多数化合物对T-47D和MCF-7细胞系也没有活性。通过cr啶橙/溴化乙锭双染色试验和流式细胞术分析的形态分析表明，化合物 7a 和 7f 诱导了A-549细胞的凋亡。此外，合成化合物的计算机和体外结果显示出良好的相关性。 7a
• Synthesis, molecular docking study and antitumor activity of novel 2-phenylindole derivatives
  作者：Sally S. El-Nakkady、Mona M. Hanna、Hanaa M. Roaiah、Iman A.Y. Ghannam

  DOI：10.1016/j.ejmech.2011.11.007

  日期：2012.1

  The starting material, 4-(1-indol-2-yl)phenol 1 was obtained via Fischer synthesis. Vilsmeir Haack's formylation of 1 gave the carboxaldehyde derivative 2 which was subjected to different reactions affording the 3-substituted compounds 3-10. Compound 1 reacted with halo esters to give 11 and 12a,b. The reaction of 12a with various amino derivatives gave compounds 13-16. The hydrazide derivative 15a reacted with 1,3-diketones, ethyl acetoacetate and aromatic carboxylic acid derivatives to give 17a,b, 18 and 19a-e, respectively. Antitumor activity of target compounds were tested against breast cancer cell lines (MCF-7) and (MDA-MB-231). The most potent compound was 3e with IC50 = 1.60 nM against (MCF-7). Docking was performed on colchicine binding site of tubulin to study the binding mode of the designed compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Anti-cancer, anti-oxidant and molecular docking studies of thiosemicarbazone indole-based derivatives
  作者：Zohreh Bakherad、Maliheh Safavi、Afshin Fassihi、Hojjat Sadeghi-Aliabadi、Mohammad Bakherad、Hossein Rastegar、Jahan B. Ghasemi、Saghi Sepehri、Lotfollah Saghaie、Mohammad Mahdavi

  DOI：10.1007/s11164-019-03765-9

  日期：2019.5

  Based on the structural elements of bioactive 3-substituted indoles, a new series of indole–thiosemicarbazone hybrid derivatives were designed, synthesized, and well-characterized using different spectral techniques. The intended scaffolds were screened for their in vitro anti-proliferative activities against breast cancer (MCF-7), lung cancer (A-549), and liver cancer (Hep-G2) cell lines, as well as their anti-oxidant properties. Cytotoxicity studies revealed that compound 6n was the most potent, at least threefold more potent than the commercially available reference drug etoposide, against A-549. In addition, morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis confirmed induction of apoptosis in the A-549 cells by compound 6n. In order to validate the experimental results, molecular studies were performed to achieve the possible binding interactions of the most potent compound (6n) and colchicine with tubulin as well as ANP with ATPase domain of topoisomerase IIα active sites. Moreover, the radical scavenging potential of the final derivatives was found to be excellent with the range of 0.015–0.630 µM, comparable to the standard ascorbic acid (0.655 µM).

  基于生物活性3-取代吲哚的结构元素，设计、合成了新一系列吲哚-缩氨硫脲杂化衍生物，并利用不同光谱技术对其进行了很好的表征。对这些预期的支架结构进行了体外抗增殖活性筛选，针对乳腺癌（MCF-7）、肺癌（A-549）和肝癌（Hep-G2）细胞系，以及它们的抗氧化性能。细胞毒性研究表明，化合物6n对A-549的活性最强，至少是市售参考药物依托泊苷的三倍。此外，通过吖啶橙/溴化乙锭双重染色试验和流式细胞术分析，确认化合物6n诱导A-549细胞凋亡。为了验证实验结果，进行了分子研究，以实现最强化合物（6n）和秋水仙碱与微管蛋白的可能结合相互作用，以及ANP与拓扑异构酶IIα的ATP酶域活性位点的相互作用。此外，最终衍生物的自由基清除潜力非常出色，范围为0.015-0.630 µM，与标准抗坏血酸（0.655 µM）相当。