(E)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(4-methoxy-3-(methoxymethoxy)phenyl)prop-2-en-1-one | 1430696-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(4-methoxy-3-(methoxymethoxy)phenyl)prop-2-en-1-one
• 英文别名: (E)-1-(5-methoxy-2,2-dimethylchromen-8-yl)-3-[4-methoxy-3-(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 1430696-09-5
• 化学式: C₂₄H₂₆O₆
• 分子量: 410.467
• InChiKey: GBOJNZFSABSIFI-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(4-methoxy-3-(methoxymethoxy)phenyl)prop-2-en-1-one 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以88%的产率得到(E)-3-(3-hydroxy-4-methoxyphenyl)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyranochalcone derivatives as a new class of microtubule stabilizing agents

  摘要：

  Twenty-five novel pyranochalcone derivatives were synthesized and evaluated for their in vitro and in vivo antiproliferative activities. Among them, compound 10i exhibited superior potent activity against 21 tumor cell lines including multidrug resistant phenotype with the IC50 values ranged from 0.09 to 1.30 mu M. In addition, 10i significantly induced cell cycle arrest in G2/M phase, promoted tubulin polymerization into microtubules and caused microtubule stabilization. Further studies confirmed that 10i significantly suppressed the growth of tumor volume in HepG2 xenograft tumor model. Our study demonstrated that 10i could have beneficial antitumor activity as a novel microtubule stabilizing agent. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.007
• 作为产物：
  描述：

  1-(4-methoxy-2-((2-methylbut-3-yn-2-yl)oxy)phenyl)ethanone 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 (E)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(4-methoxy-3-(methoxymethoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyranochalcone derivatives as a new class of microtubule stabilizing agents

  摘要：

  Twenty-five novel pyranochalcone derivatives were synthesized and evaluated for their in vitro and in vivo antiproliferative activities. Among them, compound 10i exhibited superior potent activity against 21 tumor cell lines including multidrug resistant phenotype with the IC50 values ranged from 0.09 to 1.30 mu M. In addition, 10i significantly induced cell cycle arrest in G2/M phase, promoted tubulin polymerization into microtubules and caused microtubule stabilization. Further studies confirmed that 10i significantly suppressed the growth of tumor volume in HepG2 xenograft tumor model. Our study demonstrated that 10i could have beneficial antitumor activity as a novel microtubule stabilizing agent. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.007

文献信息

• (E)-1-(5-METHOXY-2,2-DIMETHYL-2H-CHROMEN-8-YL)-3-(4-METHOXYPHENYL)PROP-2-EN-1-ONE AND ANALOGS THEREOF, AS WELL AS PREPARATION METHOD AND USE THEREOF
  申请人：Chen Lijuan

  公开号：US20150133659A1

  公开（公告）日：2015-05-14

  The present invention relates to millepachine ((E)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(4-methoxyphenyl)prop-2-en-1-one) and its analogues. The present invention provides methods for preparing these compounds, pharmaceutical compositions including these compounds, and methods of treating diseases utilizing pharmaceutical compositions including these compounds.

  本发明涉及米勒帕辛（（E）-1-(5-甲氧基-2,2-二甲基-2H-香豆素-8-基)-3-(4-甲氧基苯基)丙-2-烯-1-酮）及其类似物。本发明提供了制备这些化合物的方法，包括这些化合物的药物组合物，以及利用包括这些化合物的药物组合物治疗疾病的方法。
• US9394268B2
  申请人：——

  公开号：US9394268B2

  公开（公告）日：2016-07-19
• Synthesis and biological evaluation of novel pyranochalcone derivatives as a new class of microtubule stabilizing agents
  作者：Dong Cao、Xiaolei Han、Guangcheng Wang、Zhuang Yang、Fei Peng、Liang Ma、Ronghong Zhang、Haoyu Ye、Minghai Tang、Wenshuang Wu、Kai Lei、Jiaolin Wen、Jinying Chen、Jingxiang Qiu、Xiaolin Liang、Yan Ran、Yun Sang、Mingli Xiang、Aihua Peng、Lijuan Chen

  DOI：10.1016/j.ejmech.2013.01.007

  日期：2013.4

  Twenty-five novel pyranochalcone derivatives were synthesized and evaluated for their in vitro and in vivo antiproliferative activities. Among them, compound 10i exhibited superior potent activity against 21 tumor cell lines including multidrug resistant phenotype with the IC50 values ranged from 0.09 to 1.30 mu M. In addition, 10i significantly induced cell cycle arrest in G2/M phase, promoted tubulin polymerization into microtubules and caused microtubule stabilization. Further studies confirmed that 10i significantly suppressed the growth of tumor volume in HepG2 xenograft tumor model. Our study demonstrated that 10i could have beneficial antitumor activity as a novel microtubule stabilizing agent. (C) 2013 Elsevier Masson SAS. All rights reserved.