6-Chloro-2-(3-methoxy-phenyl)-3H-quinazolin-4-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: 6-Chloro-2-(3-methoxy-phenyl)-3H-quinazolin-4-one
• 英文别名: 6-chloro-2-(3-methoxyphenyl)-3H-quinazolin-4-one
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: GEPNISACABGZJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲氧基苯甲醛 、 2-氨基-5-氯苯甲酰胺 在 sodium hydrogensulfite 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 以94%的产率得到6-Chloro-2-(3-methoxy-phenyl)-3H-quinazolin-4-one
  参考文献：
  名称：

  6-Alkylamino- and 2,3-Dihydro-3‘-methoxy-2-phenyl-4-quinazolinones and Related Compounds:  Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization

  摘要：

  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.

  DOI：

  10.1021/jm000151c

文献信息

• <i>ortho</i>-Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3<i>H</i>)-ones: a convergent synthetic route to bouchardatine and sildenafil
  作者：Kyeongha Kim、Hun Young Kim、Kyungsoo Oh

  DOI：10.1039/d0ra06820a

  日期：——

  A facile access to fused pyrimidin-4(3H)-one derivatives has been established by using the metal-free ortho-naphthoquinone-catalyzed aerobic cross-coupling reactions of amines. The utilization of two readily available amines allowed a direct coupling strategy to quinazolinone natural product, bouchardatine, as well as sildenafil (Viagra™) in a highly convergent manner.

  通过使用无金属邻萘醌催化的胺有氧交叉偶联反应，已经建立了一种容易获得稠合 pyrimidin-4(3 H )-one 衍生物的方法。利用两种容易获得的胺，可以以高度收敛的方式直接偶联喹唑啉酮天然产物布沙达汀和西地那非 (Viagra™)。
• 2-phenyl-4-quinazolinone compounds, 2-phenyl-4-alkoxy-quinazoline compounds and their pharmaceutical compositions
  申请人：National Science Council

  公开号：US06479499B1

  公开（公告）日：2002-11-12

  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 are synthesized and evaluated for cytotoxicity against a panel of human tumor cell lines, such as epidermoid carcinoma of the nasopharynx (KB), lung carcinoma (A-549), ileocecal carcinoma (HCT-8), breast cancer (MCF-7), melanoma (SKMEL-2), ovarian cancer (1A9), glioblastoma (U-87-MG), bone (HOS), P-gp-expressing epidermoid carcinoma of the nasopharynx (KB-VIN), and prostate cancer (PC3) cell lines, and some of the compounds are found potent. The present invention also synthesizes 2-phenyl-4-alkoxy-quinazoline compounds, wherein some of the compounds exhibit antiplatelet activity.

  合成了两系列6,7,2′,3′,4′,5′-取代的2-苯基-4-喹唑啉酮和6,2′,3′,4′,5′-取代的2,3-二氢-2-苯基-4-喹唑啉酮，并对它们进行了细胞毒性评估，针对人类肿瘤细胞系，如鼻咽癌表皮样癌（KB）、肺癌（A-549）、回肠癌（HCT-8）、乳腺癌（MCF-7）、黑色素瘤（SKMEL-2）、卵巢癌（1A9）、胶质母细胞瘤（U-87-MG）、骨癌（HOS）、表达P-gp的鼻咽癌表皮样癌（KB-VIN）和前列腺癌（PC3）细胞系，其中一些化合物显示出潜在的细胞毒性。本发明还合成了2-苯基-4-烷氧基-喹唑啉化合物，其中一些化合物表现出抗血小板活性。
• US6479499B1
  申请人：——

  公开号：US6479499B1

  公开（公告）日：2002-11-12
• 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.