2-(5-(3,5-dimethoxyphenyl)-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-(3,5-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)naphthalen-1-ol
• 英文别名: 2-[5-(3,5-dimethoxyphenyl)-pyrazolin-3-yl]naphthalen-1-ol；2-[5-(3,5-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]naphthalen-1-ol
• 化学式: C₂₁H₂₀N₂O₃
• 分子量: 348.401
• InChiKey: GBMFIEKYKLAQDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(5-(3,5-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)naphthalen-1-ol 、 异氰酸2-甲氧苯酯 以 乙醇 为溶剂， 反应 2.0h， 生成 3-(1-hydroxynaphthalen-2-yl)-5-(3,5-dimethoxyphenyl)-N-(2-methoxyphenyl)-pyrazoline-1-carbothioamide
  参考文献：
  名称：

  带有吡唑啉-1-碳硫酰胺基团的18种新型聚甲氧基萘萘的1H和13C NMR光谱分配。

  摘要：

  DOI：

  10.1002/mrc.4217
• 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 为溶剂， 生成 2-(5-(3,5-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

文献信息

• 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.
• 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
• 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.