6,7-Dimethoxy-2-((E)-styryl)-3H-quinazolin-4-one | 127033-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6,7-Dimethoxy-2-((E)-styryl)-3H-quinazolin-4-one
• 英文别名: 6,7-dimethoxy-2-[(E)-2-phenylethenyl]-3H-quinazolin-4-one
• CAS: 127033-39-0
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: DJFKEBKGMQPCPW-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-Dimethoxy-2-((E)-styryl)-3H-quinazolin-4-one 在 四氯化碳 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 21.0h， 生成 (E)-(2-(1-(6,7-dimethoxy-2-styrylquinazolin-4-yl)piperidin-4-yl)ethyl)sulfamide
  参考文献：
  名称：

  新型NPP1抑制剂喹唑啉-4-哌啶磺酰胺衍生物的合成及生物学评价

  摘要：

  最近显示，胞外核苷酸焦磷酸酶/磷酸二酯酶-1（NPP1）促进主动脉瓣的矿化，因此，其抑制作用是一个重要的目标。喹唑啉-4-哌啶磺酰胺化合物（QPS1）已被描述为NPP1的特异性和非竞争性抑制剂。我们在此报告了使用QPS1作为先导化合物的新型喹唑啉-4-哌啶磺酰胺类似物的合成和体外抑制研究。在制备的26种衍生物中，发现有四种化合物 对人NPP1的K i <105 nM。

  DOI：

  10.1016/j.ejmech.2018.01.094
• 作为产物：
  描述：

  4,5-Dimethoxy-2-[(E)-(3-phenyl-acryloyl)amino]-benzoic acid 在 formamide 作用下， 反应 6.0h， 生成 6,7-Dimethoxy-2-((E)-styryl)-3H-quinazolin-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization

  摘要：

  A novel series of 2-styrylquinazolin-4(3H-ones which inhibited tubulin polymerization and the growth of L1210 murine leukemia cells was discovered. Extensive structure-activity relationship studies suggest that the entire quinazolinone structure was required, but activity was further enhanced by halide or small hydrophobic substituents at position 6. These analogues did not substantially interfere with the binding of radiolabeled colchicine, vinblastine, or GTP to tubulin and weakly stimulated GTP hydrolysis uncoupled from polymerization. Several analogues have shown in vivo tumor growth inhibitory activity in the L1210 leukemia model, with the lead compound 5o exhibiting good antitumor activity against murine solid tumors as well as human tumor xenografts.

  DOI：

  10.1021/jm00168a029

文献信息

• JIANG, J. B.;HESSON, D. P.;DUSAK, B. A.;DEXTER, D. L.;KANG, G. J.;HAMEL, +, J. MED. CHEM., 33,(1990) N, C. 1721-1728
  作者：JIANG, J. B.、HESSON, D. P.、DUSAK, B. A.、DEXTER, D. L.、KANG, G. J.、HAMEL, +

  DOI：——

  日期：——
• Synthesis and biological evaluation of novel quinazoline-4-piperidinesulfamide derivatives as inhibitors of NPP1
  作者：Elsa Forcellini、Sophie Boutin、Carole-Anne Lefebvre、Elnur Elyar Shayhidin、Marie-Chloé Boulanger、Gabrielle Rhéaume、Xavier Barbeau、Patrick Lagüe、Patrick Mathieu、Jean-François Paquin

  DOI：10.1016/j.ejmech.2018.01.094

  日期：2018.3

  A quinazoline-4-piperidine sulfamide compound (QPS1) has been described as a specific and non-competitive inhibitor of NPP1. We report herein the synthesis and in vitro inhibition studies of novel quinazoline-4-piperidine sulfamide analogues using QPS1 as the lead compound. Of the 26 derivatives prepared, four compounds were found to have Ki < 105 nM against human NPP1.

  最近显示，胞外核苷酸焦磷酸酶/磷酸二酯酶-1（NPP1）促进主动脉瓣的矿化，因此，其抑制作用是一个重要的目标。喹唑啉-4-哌啶磺酰胺化合物（QPS1）已被描述为NPP1的特异性和非竞争性抑制剂。我们在此报告了使用QPS1作为先导化合物的新型喹唑啉-4-哌啶磺酰胺类似物的合成和体外抑制研究。在制备的26种衍生物中，发现有四种化合物 对人NPP1的K i <105 nM。
• Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization
  作者：Jack B. Jiang、D. P. Hesson、B. A. Dusak、D. L. Dexter、G. J. Kang、E. Hamel

  DOI：10.1021/jm00168a029

  日期：1990.6

  A novel series of 2-styrylquinazolin-4(3H-ones which inhibited tubulin polymerization and the growth of L1210 murine leukemia cells was discovered. Extensive structure-activity relationship studies suggest that the entire quinazolinone structure was required, but activity was further enhanced by halide or small hydrophobic substituents at position 6. These analogues did not substantially interfere with the binding of radiolabeled colchicine, vinblastine, or GTP to tubulin and weakly stimulated GTP hydrolysis uncoupled from polymerization. Several analogues have shown in vivo tumor growth inhibitory activity in the L1210 leukemia model, with the lead compound 5o exhibiting good antitumor activity against murine solid tumors as well as human tumor xenografts.