2-(5-(2,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)naphthalen-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(5-(2,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)naphthalen-1-ol
• 英文别名: 2-[5-(2,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]naphthalen-1-ol
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: UAEDBZVIMWNWFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-(2,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)naphthalen-1-ol 、 异氰酸2-甲氧苯酯 以 乙醇 为溶剂， 以94%的产率得到3-(1-hydroxynaphthalen-2-yl)-5-(2,4,5-trimethoxyphenyl)-N-(2-methoxyphenyl)-pyrazoline-1-carbothioamide
  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 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 2-(5-(2,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)naphthalen-1-ol
  参考文献：
  名称：

  18 种新型多甲氧基化羟基萘并吡唑基查尔酮的 1H 和 13C NMR 光谱归属

  摘要：

  在通过苯丙烷途径产生的植物来源的多酚中，查耳酮是通过 4-香豆酰辅酶 A 与丙二酰辅酶 A 的组合生物合成的。查耳酮被称为查耳酮（图 1A）。它们由通过 α,β-不饱和羰基连接的两个苯环组成，它们可以靠近形成另一个环，得到具有三个环的黄酮类化合物。众所周知，查尔酮类化合物可作为钾通道阻滞剂和芳香酶抑制剂。如前所述，一些查尔酮可以很容易地转化为类黄酮（图 1B）。因此，它们的稳定性仍有待解决以开发为生物活性化合物。用吡唑啉基团（吡唑基查尔酮）取代 α,β-不饱和羰基可以阻止查尔酮向黄酮类化合物的转化（图 1C）。甲氧基化增加了许多植物来源的多酚的细胞渗透性和稳定性。我们设计了具有羟基萘基 A 环和三甲氧基化 B 环的羟基萘并吡唑基查尔酮类化合物（图 1D），并合成了 18 种衍生物。他们的核磁共振数据和质谱（MS）数据可以帮助我们识别未来新合成或从天然来源分离的植物多酚，因此，我们在此报告完整的

  DOI：

  10.1002/mrc.4225

文献信息

• ¹ H and ¹³ C NMR spectral assignments of 18 novel polymethoxylated hydroxynaphthopyrazolylchalconoids
  作者：Hyeryoung Jung、Seunghyun Ahn、Yearam Jung、Hyung Jun Noh、Seung Yu Kim、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.4225

  日期：2015.5

  (pyrazolylchalconoids) can prevent the conversion of chalconoids to flavonoids (Fig. 1C). Methoxylation increases the cell permeability and stability of many plant-derived polyphenols. We designed hydroxynaphthopyrazolylchalconoids with hydroxynaphthyl A-ring and trimethoxylated B-ring (Fig. 1D), and synthesized 18 derivatives. Their NMR data and mass spectrometric (MS) data can help us to identify plant-derived

  在通过苯丙烷途径产生的植物来源的多酚中，查耳酮是通过 4-香豆酰辅酶 A 与丙二酰辅酶 A 的组合生物合成的。查耳酮被称为查耳酮（图 1A）。它们由通过 α,β-不饱和羰基连接的两个苯环组成，它们可以靠近形成另一个环，得到具有三个环的黄酮类化合物。众所周知，查尔酮类化合物可作为钾通道阻滞剂和芳香酶抑制剂。如前所述，一些查尔酮可以很容易地转化为类黄酮（图 1B）。因此，它们的稳定性仍有待解决以开发为生物活性化合物。用吡唑啉基团（吡唑基查尔酮）取代 α,β-不饱和羰基可以阻止查尔酮向黄酮类化合物的转化（图 1C）。甲氧基化增加了许多植物来源的多酚的细胞渗透性和稳定性。我们设计了具有羟基萘基 A 环和三甲氧基化 B 环的羟基萘并吡唑基查尔酮类化合物（图 1D），并合成了 18 种衍生物。他们的核磁共振数据和质谱（MS）数据可以帮助我们识别未来新合成或从天然来源分离的植物多酚，因此，我们在此报告完整的
• Complete assignments of ¹ H and ¹³ C NMR data for 21 naphthalenyl-phenyl-pyrazoline derivatives
  作者：Doseok Hwang、Hyuk Yoon、Seunghyun Ahn、Dong-Wook Kim、Dong-Ho Bae、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.3981

  日期：2013.9

  To find potent new chemotherapy drugs, we designed and synthesized a series of naphthochalcones bearing naphthalenyl‐phenyl‐pyrazoline moieties. The complete 1H and 13C NMR data for these compounds are reported here and can be used to identify further new naphthochalcones bearing the desired pyrazoline moieties. Copyright © 2013 John Wiley & Sons, Ltd.

  为了寻找有效的新化疗药物，我们设计并合成了一系列带有萘基-苯基-吡唑啉部分的萘查耳酮。此处报告了这些化合物的完整 1H 和 13C NMR 数据，可用于进一步鉴定带有所需吡唑啉部分的新萘查耳酮。版权所有 © 2013 John Wiley & Sons, Ltd.
• 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.