1-(4-chlorophenyl)-3-(4-(6,7-dichloro-4-((3-(dimethylamino)propyl)amino)thieno[3,2-d]pyrimidin-2-yl)phenyl)urea

• 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-(4-chlorophenyl)-3-(4-(6,7-dichloro-4-((3-(dimethylamino)propyl)amino)thieno[3,2-d]pyrimidin-2-yl)phenyl)urea
• 英文别名: 1-[4-[4-[[3-dimethylaminopropyl]amino]-6,7-dichlorothieno[3,2-d]pyrimidin-2-yl]phenyl]-3-(4-chlorophenyl)urea；1-(4-Chlorophenyl)-3-[4-[6,7-dichloro-4-[3-(dimethylamino)propylamino]thieno[3,2-d]pyrimidin-2-yl]phenyl]urea；1-(4-chlorophenyl)-3-[4-[6,7-dichloro-4-[3-(dimethylamino)propylamino]thieno[3,2-d]pyrimidin-2-yl]phenyl]urea
• 化学式: C₂₄H₂₃Cl₃N₆OS
• 分子量: 549.911
• InChiKey: GHUUAKQOTNDSDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(乙酰基氨基)-2-噻吩羧酸甲酯 在 ammonium hydroxide 、 磺酰氯 、 硫酸 、 铁粉 、 氯化铵 、 三乙胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 氯仿 、 异丙醇 为溶剂， 反应 41.0h， 生成 1-(4-chlorophenyl)-3-(4-(6,7-dichloro-4-((3-(dimethylamino)propyl)amino)thieno[3,2-d]pyrimidin-2-yl)phenyl)urea
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel thieno[3,2-d]pyrimidine derivatives containing diaryl urea moiety as potent antitumor agents

  摘要：

  Two series of thieno[3,2-d]pyrimidine derivatives containing diaryl urea moiety were designed, synthesized and evaluated for their biological activity. The preliminary investigation showed that most compounds displayed good to excellent potency against four tested cancer cell lines as compared with GDC-0941 and sorafenib. In particular, the most promising compound 29a showed the most potent antitumor activities with IC50 values of 0.081 mu M, 0.058 mu M, 0.18 mu M, and 0.23 mu M against H460, HT-29, MKN-45 and MDA-MB-231 cell lines, respectively. The SAR analyses indicated that compounds with mono-halogen groups at 4-position on the terminal phenyl ring were more active than those with double-halogen groups or methyl groups. In addition, the introduction of chlorine atoms into 6,7-position of thieno[3,2-d]pyrimidine moiety led to a slight decline, but more selective activity against H460 and HT-29 cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.099

文献信息

• Design, synthesis and biological evaluation of novel thieno[3,2-d]pyrimidine derivatives containing diaryl urea moiety as potent antitumor agents
  作者：Zijian Liu、Yu Wang、Huafang Lin、Dazhuang Zuo、Lihui Wang、Yanfang Zhao、Ping Gong

  DOI：10.1016/j.ejmech.2014.07.099

  日期：2014.10

  Two series of thieno[3,2-d]pyrimidine derivatives containing diaryl urea moiety were designed, synthesized and evaluated for their biological activity. The preliminary investigation showed that most compounds displayed good to excellent potency against four tested cancer cell lines as compared with GDC-0941 and sorafenib. In particular, the most promising compound 29a showed the most potent antitumor activities with IC50 values of 0.081 mu M, 0.058 mu M, 0.18 mu M, and 0.23 mu M against H460, HT-29, MKN-45 and MDA-MB-231 cell lines, respectively. The SAR analyses indicated that compounds with mono-halogen groups at 4-position on the terminal phenyl ring were more active than those with double-halogen groups or methyl groups. In addition, the introduction of chlorine atoms into 6,7-position of thieno[3,2-d]pyrimidine moiety led to a slight decline, but more selective activity against H460 and HT-29 cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.