2-(3,4-dimethoxy-styryl)-3H-quinazolin-4-one | 72756-61-7

• 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: 2-(3,4-dimethoxy-styryl)-3H-quinazolin-4-one
• 英文别名: 2-(3,4-dimethoxy-trans-styryl)-3H-quinazolin-4-one；2-(3,4-Dimethoxy-trans-styryl)-3H-chinazolin-4-on；2-[2-(3,4-dimethoxyphenyl)vinyl]-4(3H)-quinazolinone；2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-3H-quinazolin-4-one
• CAS: 72756-61-7
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: HCRGAVLYPBSJQE-CSKARUKUSA-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：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxy-styryl)-3H-quinazolin-4-one 在 sodium amalgam 、 乙醇 作用下， 生成 2-<2-(3,4-dimethoxyphenyl)ethyl>quinazolin-4(3H)-one
  参考文献：
  名称：

  Researches on Quinazolines. XXXIX. The Synthesis of Quinazoline Derivatives Structurally Analogous to the Angostura Alkaloids Galiopine and Galipine¹

  摘要：

  DOI：

  10.1021/ja01307a041
• 作为产物：
  描述：

  2-氨基苯甲酰胺 在 溶剂黄146 作用下， 反应 12.5h， 生成 2-(3,4-dimethoxy-styryl)-3H-quinazolin-4-one
  参考文献：
  名称：

  2-Styryl-4-aminoquinazoline derivatives as potent DNA-cleavage, p53-activation and in vivo effective anticancer agents

  摘要：

  Forty-eight analogues of CP-31398, an antitumor agent modulated the mutant p53 gene were synthesized and their cytotoxicities against four cancer cell lines with different p-53 status including bladder cell 724 (w-p53), gastric cell MGC-803 (m-p53), prostate cell DU145 (m-p53), prostate cell PC-3 (null-p53), lung cell A549 (w-p53) and normal liver cell line HL-7702 (w-p53) were examined. (E)-2-(4-Nitrostyryl)-4-(3-dimethylaminopropyl)-aminoquinazoline (10ah) was identified as the most potent compound in anti-proliferation against MGC-803 cells, with IC50 lowed to 1.73 mu M, far potency than that of CP-31398.Molecular mechanism study revealed that 10ah and CP-31398 differ greatly in mechanism to exert their antitumor properties. 10ah could intercalate into DNA and resulted in significant DNA double-strand break 10ah-treatment in MGC-803 cells increased the expression of p53, phosphorylated p53 (p-p53), CDK4, p21 to cause cell cycle arrest at G2/M phase, significantly up-regulated the levels of pro-apoptosis proteins Bak, Bax, Bim while down-regulated the anti-apoptosis proteins Bcl-2, Bcl-xL and the levels of cyclin B1, fluctuated the intracellular reactive oxygen species (ROS), Ca2+ and mitochondria! membrane potential, activated Caspase-9 and Caspase-3 to induce apoptosis. 10ah also displayed potent anticancer efficiency against MGC-803 xenograft tumors models, with tumor growth inhibition (TGI) up to 61.8% at 20 mg/kg without obvious toxicity. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111851

文献信息

• ABCA-1 elevating compounds
  申请人：——

  公开号：US20030220356A1

  公开（公告）日：2003-11-27

  The present invention provides compounds that elevate cellular expression of the ABCA-1 gene, promoting cholesterol efflux from cells and increasing HDL levels in the plasma of a mammal, in particular humans. The compounds are useful for treating coronary artery disease.

  本发明提供了一种能够提高ABCA-1基因细胞表达的化合物，促进胆固醇从细胞中流出并增加哺乳动物（尤其是人类）血浆中的高密度脂蛋白水平。这些化合物可用于治疗冠心病。
• Kovalenko, Sergey; Belenichev, Igor; Nikitin, Vladislav, Acta poloniae pharmaceutica, 2003, vol. 60, # 4, p. 275 - 279
  作者：Kovalenko, Sergey、Belenichev, Igor、Nikitin, Vladislav、Karpenko, Aleksandr

  DOI：——

  日期：——
• MAHMOUD M.; EL-HASHASH M., REV. ROUM. CHIM., 1979, 24, NO 6, 849-858
  作者：MAHMOUD M.、 EL-HASHASH M.

  DOI：——

  日期：——
• COMPOUNDS FOR INCREASING ABCA-1 EXPRESSION USEFUL FOR TREATING CORONARY ARTERY DISEASE AND ATHEROSCLEROSIS
  申请人：CV THERAPEUTICS, INC.

  公开号：EP1513534A2

  公开（公告）日：2005-03-16
• US6900219B2
  申请人：——

  公开号：US6900219B2

  公开（公告）日：2005-05-31