3-(2,4-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one | 378217-97-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(2,4-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
• CAS: 378217-97-1
• 化学式: C₂₁H₁₈O₄
• 分子量: 334.372
• InChiKey: VOPMRMGHUPBLPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,4-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-(5-(2,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)naphthalen-1-ol
  参考文献：
  名称：

  Anticancer and structure-activity relationship evaluation of 3-(naphthalen-2-yl)-N,5-diphenyl-pyrazoline-1-carbothioamide analogs of chalcone

  摘要：

  To identify new potent chemotherapeutic agents, we synthesized compounds with 3-(naphthalen-2-yl)-N,5-diphenyl-pyrazoline-1-carbothioamide (NDPC) skeletons and evaluated their cytotoxicities using a clonogenic long-term survival assay. Their half-maximal cell growth inhibitory concentrations ranged from a few hundred nanomolars to a few micromolars. Further biological experiments including flow cytometry and western blotting analysis were performed with the derivative showing the best cytotoxicity. To identify a target protein of the selected compound, an in vitro kinase assay was carried out, which revealed that aurora kinases A and B were inhibited by the test compound, and this was confirmed using western blot analysis. The molecular binding mode between the selected compound and the kinases was elucidated using in silico docking. The structural conditions required for good cytotoxicity were identified based on the quantitative relationships between the physicochemical properties of the derivatives and their cytotoxicities. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2016.08.003
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 、 2,4-二甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 3-(2,4-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  含苯并噻嗪的新型黄酮类化合物的 1H 和 13C NMR 谱图

  摘要：

  苯并噻嗪是一种含氮和硫的杂环化合物。通过改变双键和苯环的位置，可以设计出多种衍生物。2,3-Dihydro1,5-benzothiazepine（也称为 2,3-dihydro[b][1,4]thiazepine）衍生物具有多种生物活性，包括对 α-葡萄糖苷酶、脲酶、胆碱酯酶和丁酰胆碱酯酶的抑制作用，以及对瞬时受体电位锚蛋白 1 (TRPA1) 受体的激动活性（图 1（A））。当两个苯环连接在 C-2 和 C-4 位置时，可以衍生出含有 C6-C3-C6 骨架的 2,4-diphenyl2,3-dihydro-1,5-benzothiazepine（图 1（B） ）。黄酮类化合物作为次生代谢物存在于各种植物中，由 C6-C3-C6 骨架组成（图 1（C））。由于甲氧基化和萘基可以增加细胞区室化和细胞通透性，我们设计并合成了甲氧基化 4-(1-hydroxy-naphthalen-2-yl)-2-phenyl-2

  DOI：

  10.1002/mrc.4388

文献信息

• Synthesis and complete assignment of NMR data of 20 chalcones
  作者：Doseok Hwang、Jiye Hyun、Geunhyeong Jo、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.2707

  日期：2011.1

  O‐methyltransferases in plant biosynthetic pathways. Assignments of NMR peaks in the spectra of hydroxylated and/or methoxylated chalcones can help in identifying novel chalcone derivatives isolated from natural sources by referencing these data against NMR spectra obtained from known chalcones. We report here the syntheses of 20 chalcones and complete assignments of 1H and 13C NMR spectra. Copyright © 2010 John Wiley

  查耳酮是类黄酮生物合成的中间体，具有抗菌、抗增殖和抗炎特性。查耳酮含有两个苯环，羟基化和甲氧基化的类似物通常由植物生物合成途径中的羟化酶和 O-甲基转移酶产生。羟基化和/或甲氧基化查耳酮光谱中 NMR 峰的归属可以帮助通过将这些数据与从已知查耳酮获得的 NMR 谱相比较来鉴定从天然来源分离的新型查耳酮衍生物。我们在此报告了 20 种查耳酮的合成以及 1H 和 13C NMR 光谱的完整分配。版权所有 © 2010 John Wiley & Sons, Ltd.
• ¹ H and ¹³ C NMR spectral assignments of 18 novel polymethoxylated naphthochalcones bearing pyrazoline-1-carbothioamide groups
  作者：Hyeryoung Jung、Seunghyun Ahn、Mijoo Park、Hyuk Yoon、Hyung Jun Noh、Seung Yu Kim、Jin Sil Yoo、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.4217

  日期：2015.5
• ¹H and¹³C NMR spectral assignments of novel flavonoids bearing benzothiazepine
  作者：Seunghyun Ahn、Soon Young Shin、Yearam Jung、Hyeryoung Jung、Beom Soo Kim、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.4388

  日期：2016.5

  cell permeability, we designed and synthesized methoxylated 4-(1-hydroxy-naphthalen-2-yl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine derivatives (Fig. 1(D)). However, flavonoids bearing a benzothiazepine skeleton have rarely been reported, even though their design and synthesis are of interest because of their biological diversity. Furthermore, because the 1H and 13C NMR, and high resolution mass spectrometric

  苯并噻嗪是一种含氮和硫的杂环化合物。通过改变双键和苯环的位置，可以设计出多种衍生物。2,3-Dihydro1,5-benzothiazepine（也称为 2,3-dihydro[b][1,4]thiazepine）衍生物具有多种生物活性，包括对 α-葡萄糖苷酶、脲酶、胆碱酯酶和丁酰胆碱酯酶的抑制作用，以及对瞬时受体电位锚蛋白 1 (TRPA1) 受体的激动活性（图 1（A））。当两个苯环连接在 C-2 和 C-4 位置时，可以衍生出含有 C6-C3-C6 骨架的 2,4-diphenyl2,3-dihydro-1,5-benzothiazepine（图 1（B） ）。黄酮类化合物作为次生代谢物存在于各种植物中，由 C6-C3-C6 骨架组成（图 1（C））。由于甲氧基化和萘基可以增加细胞区室化和细胞通透性，我们设计并合成了甲氧基化 4-(1-hydroxy-naphthalen-2-yl)-2-phenyl-2
• Anticancer and structure-activity relationship evaluation of 3-(naphthalen-2-yl)-N,5-diphenyl-pyrazoline-1-carbothioamide analogs of chalcone
  作者：Youngshim Lee、Beom Soo Kim、Seunghyun Ahn、Dongsoo Koh、Young Han Lee、Soon Young Shin、Yoongho Lim

  DOI：10.1016/j.bioorg.2016.08.003

  日期：2016.10

  To identify new potent chemotherapeutic agents, we synthesized compounds with 3-(naphthalen-2-yl)-N,5-diphenyl-pyrazoline-1-carbothioamide (NDPC) skeletons and evaluated their cytotoxicities using a clonogenic long-term survival assay. Their half-maximal cell growth inhibitory concentrations ranged from a few hundred nanomolars to a few micromolars. Further biological experiments including flow cytometry and western blotting analysis were performed with the derivative showing the best cytotoxicity. To identify a target protein of the selected compound, an in vitro kinase assay was carried out, which revealed that aurora kinases A and B were inhibited by the test compound, and this was confirmed using western blot analysis. The molecular binding mode between the selected compound and the kinases was elucidated using in silico docking. The structural conditions required for good cytotoxicity were identified based on the quantitative relationships between the physicochemical properties of the derivatives and their cytotoxicities. (C) 2016 Elsevier Inc. All rights reserved.