2-(3,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one

• 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-(3,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-(3,5-dimethoxyphenyl)-2,3-dihydro-1H-quinazolin-4-one
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: MHXRDNZDXBPECV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 2-氨基苯甲酰胺 在 1-isopropyl 1,2,4-triazolium trifluoromethanesulfonate 作用下， 以 水 为溶剂， 反应 0.02h， 以95%的产率得到2-(3,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  在温和条件下一锅合成2,3-二氢喹唑啉-4（1 H）-一的离子液体催化可重复使用方案

  摘要：

  已经开发了一种有效的方案，用于通过离子液体催化的环化反应由邻氨基苯甲酰胺和醛或酮合成2，3-二氢喹唑啉酮化合物。该反应具有效率高，反应时间短，反应条件温和和试剂便宜的特点。回收催化剂并重新使用。离子液体的可回收性导致了优异的产品收率，而没有任何催化活性的损失。

  DOI：

  10.1039/c5nj01545f

文献信息

• An ionic liquid catalyzed reusable protocol for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one under mild conditions
  作者：S. Nagarajan、Tanveer Mahamadali Shaikh、Elango Kandasamy

  DOI：10.1039/c5nj01545f

  日期：——

  protocol has been developed for the synthesis of 2,3-dihydroquinazolinone compounds from anthranilamide and aldehydes or ketones via ionic liquid catalyzed cyclization reaction. The reaction features high efficiency, shorter reaction duration, mild reaction conditions and inexpensive reagents. The catalyst was recovered and reused. The recyclability of ionic liquid resulted in excellent yields of products

  已经开发了一种有效的方案，用于通过离子液体催化的环化反应由邻氨基苯甲酰胺和醛或酮合成2，3-二氢喹唑啉酮化合物。该反应具有效率高，反应时间短，反应条件温和和试剂便宜的特点。回收催化剂并重新使用。离子液体的可回收性导致了优异的产品收率，而没有任何催化活性的损失。
• 6-Alkylamino- and 2,3-Dihydro-3‘-methoxy-2-phenyl-4-quinazolinones and Related Compounds:  Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization
  作者：Mann-Jen Hour、Li-Jiau Huang、Sheng-Chu Kuo、Yi Xia、Kenneth Bastow、Yuka Nakanishi、Ernest Hamel、Kuo-Hsiung Lee

  DOI：10.1021/jm000151c

  日期：2000.11.1

  As part of our continuing search for potential anticancer candidates among 2-phenyl-4-quinolones and 2-phenyl-4-quinazolinones, two series of 6,7,2',3',4',5'-substituted 2-phenyl-4-quinazolinones and 6,2',3',4',5'-substituted 2,3-dihydro-2-phenyl-4-quinazolinones were synthesized and evaluated for cytotoxicity and as inhibitors of tubulin polymerization. In general, a good correlation was found between the two activities. Five of the 6-substituted heterocyclic 2-phenyl-4-quinozolinones (37-51) showed significant cytotoxicity against a panel of human tumor cell lines with EC50 values in the low micromolar to nanomolar concentration ranges. Compound 38 was the most potent of these compounds, as well as the most potent inhibitor of tubulin polymerization in this series. The activity of 38 was in the same range as those of the antimitotic natural products, colchicine, podophyllotoxin, and combretastatin A-4. Substituted 2-phenyl-4-quinazolinones and 2,3-dihydro-2-phenyl-4-quinazolinones also displayed highly selective cytotoxicity against the ovarian cancer 1A9 and P-gp resistant KB-VIN cell lines.
• US6479499B1
  申请人：——

  公开号：US6479499B1

  公开（公告）日：2002-11-12
• Self-Assembled Nanoliposomes of Phosphatidylcholine: Bridging the Gap between Organic and Aqueous Media for a Green Synthesis of Hydroquinazolinones
  作者：Fatemeh Tamaddon、MohammadTaghi KazemiVarnamkhasti

  DOI：10.1055/s-0035-1562604

  日期：——

  Self-assembly of phosphatidylcholine in water creates liposomal nanoreactors for environmentally friendly synthesis of hydroquinazolinones by two- or three-component reactions, without the use of an extra catalyst or solvent. Recycling of the reaction medium and the absence of a need for other organic reagents are further advantages of this protocol.