10-(3-methoxybenzyl)acridin-9(10H)-one | 1073142-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-(3-methoxybenzyl)acridin-9(10H)-one
• 英文别名: 10-[(3-Methoxyphenyl)methyl]acridin-9-one
• CAS: 1073142-65-0
• 化学式: C₂₁H₁₇NO₂
• 分子量: 315.371
• InChiKey: CJNVUMOHFIPJHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 10-(3-methoxybenzyl)acridin-9(10H)-one
  参考文献：
  名称：

  Synthesis and Evaluation of N-Benzyl-Acridinone Derivatives Induced Apoptosis in Human Liver Cancer Cell-Lines

  摘要：

  一系列N-苄基-9(10H)-吖啶酮被合成并测试了它们对HepG2细胞的体外抗肿瘤活性。基于HepG2细胞系的抗增殖活性研究揭示，几种化合物对细胞毒性具有显著效果，其中化合物5h被发现是最活性的化合物，使用MTT assay测得的IC50值约为1.33 μM。化合物5h的抗肿瘤效应被认为是通过诱导凋亡实现的，这一结论通过Hoechst 33258荧光染色、琼脂糖凝胶电泳和使用流式细胞术的Annexin VFITC/PI染色 assay进一步证实。总之，化合物5h可能是一种有潜力的抗癌药物，值得进一步研究。

  DOI：

  10.2174/157018011796235176

文献信息

• SULFONIUM SALT, HEAT- OR PHOTO-ACID GENERATOR, HEAT- OR PHOTO-CURABLE COMPOSITION, AND CURED PRODUCT THEREOF
  申请人：SAN APRO LTD.

  公开号：US20190284134A1

  公开（公告）日：2019-09-19

  The sulfonium salt does not contain a toxic metal and exhibits higher cationic polymerization performance and crosslinking performance than a tetrakis(pentafluorophenyl)borate salt. The heat- or photo-acid generator contains the sulfonium salt. The sulfonium salt is formed of a sulfonium cation selected from a group represented by general formulas (1), (9), (10) and (11) described below and a gallate anion represented by formula (a). The heat- or photo-acid generator contains the sulfonium salt. The heat- or energy ray-curable composition contains the acid generator and a cationically polymerizable compound. A cured product can be obtained by curing the same.

  硫铵盐不含有毒金属，表现出比四(五氟苯基)硼酸盐更高的阳离子聚合性能和交联性能。热或光酸发生剂含有硫铵盐。硫铵盐由下面描述的通用公式(1)、(9)、(10)和(11)所代表的一组硫铵阳离子和由公式(a)代表的镓酸根阴离子形成。热或光酸发生剂含有硫铵盐。热或能量射线固化组合物含有酸发生剂和阳离子聚合性化合物。通过固化可以获得固化产品。
• Sulfonium salt, heat- or photo-acid generator, heat- or photo-curable composition, and cured product thereof
  申请人：SAN APRO LTD.

  公开号：US11370751B2

  公开（公告）日：2022-06-28

  The sulfonium salt does not contain a toxic metal and exhibits higher cationic polymerization performance and crosslinking performance than a tetrakis(pentafluorophenyl)borate salt. The heat- or photo-acid generator contains the sulfonium salt. The sulfonium salt is formed of a sulfonium cation selected from a group represented by general formulas (1), (9), (10) and (11) described below and a gallate anion represented by formula (a). The heat- or photo-acid generator contains the sulfonium salt. The heat- or energy ray-curable composition contains the acid generator and a cationically polymerizable compound. A cured product can be obtained by curing the same.

  锍盐不含有毒金属，与四(五氟苯基)硼酸盐相比，具有更高的阳离子聚合性能和交联性能。热酸或光酸发生器中含有锍盐。锍盐由选自下述通式 (1)、(9)、(10) 和 (11) 所代表的锍阳离子和由式 (a) 所代表的没食子酸阴离子组成。热或光固化酸发生器含有锍盐。热固化或能量射线固化组合物包含酸发生器和阳离子可聚合化合物。通过固化可得到固化产品。
• Synthesis and potent antileukemic activities of 10-benzyl-9(10H)-acridinones
  作者：Chunmei Gao、Yuyang Jiang、Chunyan Tan、Xuyu Zu、Huachen Liu、Derong Cao

  DOI：10.1016/j.bmc.2008.07.086

  日期：2008.9

  A novel series of 10-benzyl-9(10H)-acridinones and 1-benzyl-4-piperidones were synthesized and tested for their in vitro antitumor activities against CCRF-CEM cells. Assay-based antiproliferative activity study using CCRF-CEM cell lines revealed that the acridone group and the substitution pattern on the benzene unit had significant effect on cytotoxicity of this series of compounds, among which 10-(3,5-dimethoxy) benzyl-9(10H)-acridinone (3b) was found to be the most active compound with IC(50) at about 0.7 mu M. Compound 3b was also found to have antiproliferative activity against two other human leukemic cell lines K562 and HL60 using the MTT assay. The antitumor effect of 3b is believed to be due to the induction of apoptosis, which is further confirmed by PI ( Propidium iodide) staining and Annexin V-FITC/PI staining assay using flow cytometry analysis. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and Evaluation of N-Benzyl-Acridinone Derivatives Induced Apoptosis in Human Liver Cancer Cell-Lines
  作者：Xian-Feng Huang、Yulan-Zhu、Hai-Liang Zhu

  DOI：10.2174/157018011796235176

  日期：2011.8.1

  A series of N-benzyl-9(10H)-acridinones were synthesized and tested for their antitumor activities in vitro against HepG2 cells.Assay-based antiproliferative activity study using HepG2 cell lines revealed that several compounds had significant effects on cytotoxicity, among which compound 5h was found to be the most active compound with IC50 at about 1.33 μM using the MTT assay. The antitumor effect of compound 5h is believed to be due to the induction of apoptosis, which was further confirmed by Hoechst 33258 fluorescence staining, agarose gel electrophoresis and Annexin VFITC/ PI staining assay using flow cytometry analysis. Above all, compound 5h would be a potential anticancer agent which deserves further research.

  一系列N-苄基-9(10H)-吖啶酮被合成并测试了它们对HepG2细胞的体外抗肿瘤活性。基于HepG2细胞系的抗增殖活性研究揭示，几种化合物对细胞毒性具有显著效果，其中化合物5h被发现是最活性的化合物，使用MTT assay测得的IC50值约为1.33 μM。化合物5h的抗肿瘤效应被认为是通过诱导凋亡实现的，这一结论通过Hoechst 33258荧光染色、琼脂糖凝胶电泳和使用流式细胞术的Annexin VFITC/PI染色 assay进一步证实。总之，化合物5h可能是一种有潜力的抗癌药物，值得进一步研究。