3-(2,3-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one | 57822-47-6

• 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-(2,3-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
• CAS: 57822-47-6
• 化学式: C₂₁H₁₈O₄
• 分子量: 334.372
• InChiKey: CQQDEJGEKATKBY-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-(2,3-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one 在 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以53%的产率得到2-(2,3-dimethoxyphenyl)-2H-benzo[h]chromen-4(3H)-one
  参考文献：
  名称：

  세포주기 조절을 통한 항암 효과를 보이는 폴리페놀

  摘要：

  这项发明涉及通过细胞周期调节表现抗癌作用的多酚类物质。

  公开号：

  KR101524770B1
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 、 2,3-二甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 3-(2,3-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

• ¹H and¹³C NMR spectral assignments of novel naphthalenylphenylpyrazolines
  作者：Yearam Jung、Seunghyun Ahn、Hyeryoung Jung、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.4368

  日期：2016.3

  diverse biological activities, chalcones are still being derivatized. Therefore, the NMR and mass spectrometric (MS) data of the compounds we have designed and synthesized could help us identify newly synthesized derivatives or derivatives isolated from natural sources in the future. We report herein the complete H and C NMR data and high resolution MS data of 13 novel naphthalenylphenylpyrazolinyl-1-carbothioamides

  含有 pyrazolinyl-1-carbothioamide 支架的化合物（图 1A）可以作为抗癌剂、抗菌剂和单胺氧化酶抑制剂。当将 2-溴乙酸乙酯加入到 pyrazolinyl-1-carbothioamide 中时，会产生 2-pyrazolin-1-ylthiazol4(5H)-one（图 1B）。含有噻唑酮支架的化合物显示出丙型肝炎病毒抑制作用、抗结核、抗菌和抗微生物活性。我们设计了 naphthalenylphenylpyrazolinyl-1-carbothioamides（图 1C）和 naphthalenylphenyl-2-pyrazolin-1-ylthiazol-4(5H)-ones（图 1D）。已报道了 5000 种含有 pyrazolinyl-1-carbothioamide 支架的化合物和 3000 种含有 2-pyrazolin-1ylthiazol-4(5H)-one
• 신규한 벤조칼콘 유도체 및 그 화합물을 포함하는 항암 조성물
  申请人：Konkuk University Industrial Cooperation Corp 건국대학교 산학협력단(220040157648) BRN ▼206-82-07325

  公开号：KR101540033B1

  公开（公告）日：2015-07-29

  본 발명은 신규한 벤조칼콘 유도체 및 그 화합물을 포함하는 항암 조성물에 관한 것이다.

  本发明涉及一种新型苯并咔唑衍生物及其包含的抗癌组合物。
• Synthetic Naphthoflavonoids Showing Inhibitory Effects on Clonogenicity against Cisplatin-Resistant A2780/Cis Human Ovarian Cancer Cells
  作者：Yearam Jung、Soon Young Shin、Yeonjoong Yong、Hyuk Yoon、Seunghyun Ahn、Hyeryoung Jung、Dongsoo Koh、Young Han Lee、Yoongho Lim

  DOI：10.2174/1570180812666150213230949

  日期：2015.7.30

  Detecting early-stage ovarian cancer, the fourth leading cause of cancerrelated deaths in women, is difficult, and the development of novel chemotherapeutic agents is required. Since several flavonoids show anticancer activities against ovarian cancer, 35 naphthylated flavonoids including 3’,4’-naphthochalcones, 5’,6’-naphthochalcone, 7,8-nap-hthoflavones, 5,6-naphthoflavanones, 5,6-naphthoflavones, 2,3-naphthochalcone, N-phenylpyrazolyl-5’,6’-naphthocha-lcones, carbothioamidepyrazolyl-5’,6’-naphthochalcones, pyrazolyl-3’,4’-naphthochalcone, and carbothioamidepyrazolyl-3’,4’-naphthochalcone were designed and synthesized. To explore the anticancer effects of these compounds, clonogenic long-term survival assays were applied on human cisplatin-resistant A2780/Cis ovarian cancer cells. Relationships between the structural properties of 35 naphthylated flavonoids and their clonogenicities were explored using comparative molecular field analysis and hologram quantitative structure– activity relationships. As a result, several structural features that increased cell growth inhibitory activity were identified, and a compound satisfying these conditions, 5-(2,3-dimethoxyphenyl)-3-(1-hydroxynaphthalen-2-yl)-N-phenyl-4,5-dihydro-1Hpyrazole- 1-carbothioamide, was designed and synthesized. This novel compound´s half-maximal cell growth inhibitory concentration was lower than those of the 35 flavonoid derivatives tested here. Therefore, the structural features observed in this report can be used to design and develop potent chemotherapeutic agents to treat ovarian cancer cells.

  早期卵巢癌的检测难度较大，而卵巢癌是女性癌症相关死亡的第四大原因，因此需要开发新型化疗药物。由于几种类黄酮显示出对卵巢癌的抗癌活性，本研究设计并合成了35种萘基类黄酮，包括3',4'-萘酮酮、5',6'-萘酮、7,8-萘黄酮、5,6-萘黄烷酮、5,6-萘黄酮、2,3-萘酮、N-苯基吡唑基-5',6'-萘酮、碳硫酰胺吡唑基-5',6'-萘酮、吡唑基-3',4'-萘酮及碳硫酰胺吡唑基-3',4'-萘酮。为了探索这些化합物的抗癌效果，采用了克隆形成长期存活实验，对人类顺铂耐药的A2780/Cis卵巢癌细胞进行实验。使用比较分子场分析和全息量化结构-活性关系探讨了35种萘基类黄酮的结构特性与它们的克隆形成能力之间的关系。结果表明，识别出几种可以增强细胞生长抑制活性的结构特征，进一步设计并合成了满足这些条件的化合物5-(2,3-二甲氧基苯基)-3-(1-羟基萘-2-基)-N-苯基-4,5-二氢-1H-吡唑-1-碳硫酰胺。该新型化合物的半最大细胞生长抑制浓度低于本文测试的35种类黄酮衍生物。因此，本报告中观察到的结构特征可用于设计和开发有效的化疗药物以治疗卵巢癌细胞。
• Synthesis of methoxybenzoflavones and assignments of their NMR data
  作者：Doseok Hwang、Geunhyeong Jo、Jiye Hyun、Sung Dae Lee、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.3790

  日期：2012.1

  also is a potent phytotoxin. Six 7,8‐benzoflavones and eight 5,6‐benzoflavones were synthesized in this study. The NMR data for a few of these compounds have been previously reported; however, the NMR data for most of them have not been reported. For reference purposes, the complete NMR data for the 14 benzoflavones are described. Copyright © 2012 John Wiley & Sons, Ltd.

  来自 Acroptilon repens 的植物毒性根系分泌物被鉴定为 7,8-苯黄酮，一种细胞色素 P450 1A2 抑制剂和细胞色素 P450 3A4 激活剂。合成的 5,6-苯并黄酮也是一种有效的植物毒素。本研究合成了 6 种 7,8-苯并黄酮和 8 种 5,6-苯并黄酮。其中一些化合物的 NMR 数据以前已经报道过；然而，其中大部分的核磁共振数据尚未报道。出于参考目的，描述了 14 种苯黄酮的完整 NMR 数据。版权所有 © 2012 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.