1-(2-methoxyphenyl)-2-aminomethyl-2-propen-1-one hydrochloride | 116218-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-methoxyphenyl)-2-aminomethyl-2-propen-1-one hydrochloride
• 英文别名: 2-[(Dimethylamino)methyl]-1-(2-methoxyphenyl)prop-2-en-1-one;hydrochloride
• CAS: 116218-19-0
• 化学式: C₁₃H₁₇NO₂*ClH
• 分子量: 255.744
• InChiKey: FTCGRADUSQULNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 盐酸二甲胺 、 1-(2-methoxyphenyl)-2-aminomethyl-2-propen-1-one hydrochloride 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 12.75h， 生成 2-(2-methoxybenzoyl)propane-1,3-diyl bis(dimethylcarbamodithioate)
  参考文献：
  名称：

  Discovery and optimization of novel dual dithiocarbamates as potent anticancer agents

  摘要：

  A series of dual dithiocarbamates were synthesized and evaluated for their in-vitro anticancer activities on human non-small cell lung cancer cell line H460. Nine compounds exhibited significant antiproliferative activities with IC50 less than I mu M. Among them, compound 14m showed the highest inhibitory activity against H460 cell and inhibited the growth of nine types of tumor cells with IC50 values less than 1 mu M. It also achieved IC50 of 54 nM and 23 nM against HepG2 and MCF-7 cell lines, respectively. Preliminary structure activity relationship study indicated that: a) when the methyl group (region A) is substituted with benzene rings, ortho substitution on the benzene ring is favored for activity; b) substitution with heterocyclic structures at region A exhibited greater impact on the anti-tumor activity of compounds, in which pyridine ring, thiazole ring, coumarin and benzo[b]thiophene are favored and quinoline ring is the most favored; c) substitution with different amines (region B) also showed marked effect on the activity of compounds and dimethylamine and morpholine are preferred to other tested amines. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.030
• 作为产物：
  描述：

  2'-甲氧基苯乙酮 、 聚合甲醛 、 盐酸二甲胺 以 溶剂黄146 为溶剂， 反应 12.0h， 生成 1-(2-methoxyphenyl)-2-aminomethyl-2-propen-1-one hydrochloride
  参考文献：
  名称：

  Discovery and optimization of novel dual dithiocarbamates as potent anticancer agents

  摘要：

  A series of dual dithiocarbamates were synthesized and evaluated for their in-vitro anticancer activities on human non-small cell lung cancer cell line H460. Nine compounds exhibited significant antiproliferative activities with IC50 less than I mu M. Among them, compound 14m showed the highest inhibitory activity against H460 cell and inhibited the growth of nine types of tumor cells with IC50 values less than 1 mu M. It also achieved IC50 of 54 nM and 23 nM against HepG2 and MCF-7 cell lines, respectively. Preliminary structure activity relationship study indicated that: a) when the methyl group (region A) is substituted with benzene rings, ortho substitution on the benzene ring is favored for activity; b) substitution with heterocyclic structures at region A exhibited greater impact on the anti-tumor activity of compounds, in which pyridine ring, thiazole ring, coumarin and benzo[b]thiophene are favored and quinoline ring is the most favored; c) substitution with different amines (region B) also showed marked effect on the activity of compounds and dimethylamine and morpholine are preferred to other tested amines. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.030

文献信息

• Structure-activity relationships of novel dithiocarbamates containing α,β-unsaturated ketone fragment as potent anticancer agents
  作者：Yuanqiang Wang、Ridong Li、Han Zhang、Zhiyong Zhang、Xin Wang、Zemei Ge、Runtao Li

  DOI：10.1007/s00044-019-02356-y

  日期：2019.7

  benzene ring or heteroaromatic rings greatly effect on the activity; (b) the presence of α,β-unsaturated ketone fragment is favorable for the activity; (c) the receptor cavity binding with amine moiety might be a relatively small hydrophobic cavity. These results will be valuable for the further development of this novel kind of dithiocarbamates.

  基于我们小组发现的新型铅化合物8的结构，进行了系统的结构修饰。合成了一系列化合物8的衍生物，并评估了其对人类非小细胞肺癌细胞H460的活性。其中，十二种化合物显示出显着的增殖抑制活性，IC 50值<1μM，而化合物12r是最有效的一种。对化合物12r的进一步研究表明，它对IC 50值<1μM的八种癌细胞系的生长具有明显的抑制作用。特别是对于细胞系A375和HCT116，IC 50值为12r分别达到63 nM和66 nM。同时，我们的研究结果还揭示了以下结构-活性关系：（a）苯环或杂芳环上的不同取代对活性有很大影响；（b）存在α，β-不饱和酮片段有利于该活性；（c）与胺部分结合的受体腔可能是相对小的疏水腔。这些结果对于这种新型的二硫代氨基甲酸酯的进一步开发将是有价值的。
• Discovery and optimization of novel dual dithiocarbamates as potent anticancer agents
  作者：Ri-Dong Li、Hui-Ling Wang、Ying-Bo Li、Zhong-Qing Wang、Xin Wang、Yi-Tao Wang、Ze-Mei Ge、Run-Tao Li

  DOI：10.1016/j.ejmech.2015.02.030

  日期：2015.3

  A series of dual dithiocarbamates were synthesized and evaluated for their in-vitro anticancer activities on human non-small cell lung cancer cell line H460. Nine compounds exhibited significant antiproliferative activities with IC50 less than I mu M. Among them, compound 14m showed the highest inhibitory activity against H460 cell and inhibited the growth of nine types of tumor cells with IC50 values less than 1 mu M. It also achieved IC50 of 54 nM and 23 nM against HepG2 and MCF-7 cell lines, respectively. Preliminary structure activity relationship study indicated that: a) when the methyl group (region A) is substituted with benzene rings, ortho substitution on the benzene ring is favored for activity; b) substitution with heterocyclic structures at region A exhibited greater impact on the anti-tumor activity of compounds, in which pyridine ring, thiazole ring, coumarin and benzo[b]thiophene are favored and quinoline ring is the most favored; c) substitution with different amines (region B) also showed marked effect on the activity of compounds and dimethylamine and morpholine are preferred to other tested amines. (C) 2015 Elsevier Masson SAS. All rights reserved.