3-benzyl-6-[4-(2-fluorophenyl)piperazin-1-yl]quinazolin-4(3H)-one | 1619257-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-benzyl-6-[4-(2-fluorophenyl)piperazin-1-yl]quinazolin-4(3H)-one
• 英文别名: 3-Benzyl-6-[4-(2-fluorophenyl)piperazin-1-yl]-3h-quinazolin-4-one；3-benzyl-6-[4-(2-fluorophenyl)piperazin-1-yl]quinazolin-4-one
• CAS: 1619257-96-3
• 化学式: C₂₅H₂₃FN₄O
• 分子量: 414.482
• InChiKey: PEDIVRULQIIGRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴靛红酸酐 在 aluminum potassium sulfate dodecahydrate 、 potassium tert-butylate 、 palladium diacetate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 24.5h， 生成 3-benzyl-6-[4-(2-fluorophenyl)piperazin-1-yl]quinazolin-4(3H)-one
  参考文献：
  名称：

  某些氨基和硫烷基-3 H-喹唑啉-4-酮衍生物的合成及生物学评价

  摘要：

  摘要在Buchwald–Hartwig型反应条件下，在Pd（OAc）2 / Xantphos体系存在下，通过6-溴喹唑啉酮与芳基或烷基胺和硫醇的反应，制备了一系列6-取代喹唑啉酮衍生物。通过5-溴氨基苯甲酸酐，原甲酸三乙酯和适当的胺的三组分反应获得6-溴喹唑啉酮。对合成化合物对HT29和HCT116细胞系以及对淋巴细胞的潜在细胞毒性的生物学筛选显示，喹唑啉酮的某些衍生物具有显着的抗癌活性。报告了详细的合成，光谱数据和生物学分析。 图形概要

  DOI：

  10.1007/s00706-015-1508-6

文献信息

• Substituted benzoquinazolinones. Part 1: Synthesis of 6-aminobenzo[h]quinazolinones via Buchwald–Hartwig amination from 6-bromobenzo[h]quinazolinones
  作者：Monika Nowak、Zbigniew Malinowski、Andrzej Jóźwiak、Emilia Fornal、Alina Błaszczyk、Renata Kontek

  DOI：10.1016/j.tet.2014.05.117

  日期：2014.8

  6-(Morpholin-4-yl)benzothlquinazolin-4(3H)-one derivatives 18a,b were prepared under Buchwald-Hartwig conditions by reacting 6-bromobenzo[h]quinazolin-4(3H)-ones 13a,b with morpholine in the presence of a Pd(OAc)(2)/XantPhos system in 1,4-dioxane as solvent. The starting 6-bromobenzo[h] quinazolin-4(3H)-ones 13 were synthesized via condensation of the ethyl 1-amino-4-bromonaphthalene-2-carboxylate (11) with formamide (Niementowski reaction), and then reaction of the obtained benzoquinazolinone 9 with appropriates benzyl bromides. Compound 11 was prepared using a three-step procedure involving (a) metalation of the N-Boc- or N-Piv-protected 1-aminonaphthalenes with t-BuLi, followed by reaction with ethyl chloroformate, (b) bromination of the naphthalene ring of ester 3 using NBS, and next (c) deprotecion of the amine group with TFA or HCI. Biological screening of the potential cytotoxicity of compounds 8, 9, 18b on A549 and HT29 cell lines, as well as on the lymphocytes showed that compound 18b has interesting anticancer activities. The detailed synthesis, spectroscopic data, and biological assays were reported. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of some amino- and sulfanyl-3H-quinazolin-4-one derivatives as potential anticancer agents
  作者：Zbigniew Malinowski、Emilia Fornal、Monika Nowak、Renata Kontek、Gabriela Gajek、Bartłomiej Borek

  DOI：10.1007/s00706-015-1508-6

  日期：2015.10

  5-bromoisatoic anhydride, triethyl orthoformate and an appropriate amine. Biological screening of the potential cytotoxicity of synthesized compounds on HT29 and HCT116 cell lines, as well as on the lymphocytes, showed that some derivatives of quinazolinone have significant anticancer activities. The detailed synthesis, spectroscopic data, and biological assays were reported. Graphical abstract

  摘要在Buchwald–Hartwig型反应条件下，在Pd（OAc）2 / Xantphos体系存在下，通过6-溴喹唑啉酮与芳基或烷基胺和硫醇的反应，制备了一系列6-取代喹唑啉酮衍生物。通过5-溴氨基苯甲酸酐，原甲酸三乙酯和适当的胺的三组分反应获得6-溴喹唑啉酮。对合成化合物对HT29和HCT116细胞系以及对淋巴细胞的潜在细胞毒性的生物学筛选显示，喹唑啉酮的某些衍生物具有显着的抗癌活性。报告了详细的合成，光谱数据和生物学分析。 图形概要