3-benzyl-6-bromobenzo[h]quinazolin-4(3H)-one | 1619257-97-4

• 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: 3-benzyl-6-bromobenzo[h]quinazolin-4(3H)-one
• 英文别名: 3-Benzyl-6-bromobenzo[h]quinazolin-4-one；3-benzyl-6-bromobenzo[h]quinazolin-4-one
• CAS: 1619257-97-4
• 化学式: C₁₉H₁₃BrN₂O
• 分子量: 365.229
• InChiKey: PITTYFNPHBXCDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-6-bromobenzo[h]quinazolin-4(3H)-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 30.0h， 生成 3-benzyl-6-(morpholin-4-yl)benzo[h]quinazolin-4(3H)-one
  参考文献：
  名称：

  酰基萘胺的合成及其在苯并喹唑啉衍生物形成中的应用

  摘要：

  a 罗兹大学，化学学院，有机化学系，Tamka 12 Str.，91-403 Lodz，波兰 b 卢布林医科大学，病理生理学系，Jaczewskiego 8b Str.，20-090 Lublin，波兰 c 罗兹大学, 生物与环境保护学院, 细胞遗传学实验室, Banacha 12/16 Str., 90-237 Lodz, 波兰 d 罗兹大学, 化学学院, 无机和分析化学系, Tamka 12 Str., 91-403 Lodz , 波兰电子邮件：[e-mail]；[e-mail]

  DOI：

  10.24820/ark.5550190.p010.739
• 作为产物：
  描述：

  ethyl 1-[(tert-butoxycarbonyl)amino]naphthalene-2-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢铵 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 24.33h， 生成 3-benzyl-6-bromobenzo[h]quinazolin-4(3H)-one
  参考文献：
  名称：

  Substituted benzoquinazolinones. Part 1: Synthesis of 6-aminobenzo[h]quinazolinones via Buchwald–Hartwig amination from 6-bromobenzo[h]quinazolinones

  摘要：

  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.

  DOI：

  10.1016/j.tet.2014.05.117

文献信息

• Substituted benzoquinazolinones. Part 2: Synthesis of amino-, and sulfanyl-derivatives of benzo[f]- and benzo[h]quinazolinones
  作者：Monika Nowak、Zbigniew Malinowski、Emilia Fornal、Andrzej Jóźwiak、Ewa Parfieniuk、Gabriela Gajek、Renata Kontek

  DOI：10.1016/j.tet.2015.10.049

  日期：2015.12

  the presence of KOt-Bu, in 1,4-dioxane as a solvent, at 90–100 °C. The 8-bromobenzo[f]quinazolin-1(2H)-one 15 was synthesized via condensation of the ethyl or tert-butyl 2-amino-8-bromonaphthalene-1-carboxylate 6, 10 with formamide, followed by reaction with 3,4-dimethoxybenzyl bromide. However, the 6-bromobenzo[h]quinazolin-4(3H)-ones 19a, 19b were prepared from ethyl 4-bromo-1-[(tert-butoxycarbo

  氨基和benzoquinazolinones的硫烷基-衍生物16A - Ç，20A - Ç和21A - ç使用bromobenzoquinazolinones钯催化的Buchwald-Hartwig偶联反应制备下15，图19A，19B和1-取代的哌嗪或硫醇。Pd（OAc）2与XantPhos的组合被证明是最有效的方法，可在90-100°C的KO t -Bu存在下，在1,4-二恶烷中作为溶剂使用。 8溴苯并[ ˚F ]喹唑啉-1（2 ħ） -酮15经由乙基的缩合或合成叔丁基2-氨基-8-溴萘-1-甲酸叔丁酯6，10与甲酰胺中，然后用3反应，4-二甲氧基苄基溴。然而，由4-溴-1-[[（叔丁氧基羰基）氨基]萘-2-羧酸乙酯（17）制备6-溴苯并[ h ]喹唑啉-4（3H）-酮19a，19b。 化合物16a，20a，20c对HT29和HCT116细胞系的潜在细胞毒性的生物学筛选显示，化合物20a具有显着的抗癌活性。
• 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 of acylnaphthylamines and their applications in the formation of benzoquinazolines
  作者：Monika Nowak、Emilia Fornal、Renata Kontek、Dariusz SroczyÅ„ski、Andrzej Jóźwiak、Ewelina Augustowska、Anna Warpas、Marta Adamczyk、Zbigniew Malinowski

  DOI：10.24820/ark.5550190.p010.739

  日期：——

  a University of Lodz, Faculty of Chemistry, Department of Organic Chemistry, Tamka 12 Str., 91-403 Lodz, Poland b Medical University of Lublin, Department of Pathophysiology, Jaczewskiego 8b Str., 20-090 Lublin, Poland c University of Lodz, Faculty of Biology and Environmental Protection, Laboratory of Cytogenetics, Banacha 12/16 Str., 90-237 Lodz, Poland d University of Lodz, Faculty of Chemistry

  a 罗兹大学，化学学院，有机化学系，Tamka 12 Str.，91-403 Lodz，波兰 b 卢布林医科大学，病理生理学系，Jaczewskiego 8b Str.，20-090 Lublin，波兰 c 罗兹大学, 生物与环境保护学院, 细胞遗传学实验室, Banacha 12/16 Str., 90-237 Lodz, 波兰 d 罗兹大学, 化学学院, 无机和分析化学系, Tamka 12 Str., 91-403 Lodz , 波兰电子邮件：[e-mail]；[e-mail]