Substituted benzoquinazolinones. Part 2: Synthesis of amino-, and sulfanyl-derivatives of benzo[f]- and benzo[h]quinazolinones

Radioiodination and biodistribution of newly synthesized 3-benzyl-2-([3-methoxybenzyl]thio)benzo[g]quinazolin-4-(3H)-one in tumor bearing mice

“…For instance, 3-(4-methoxybenzyl)-6-(morpholin -4-yl)benzo[ h ]quinazolin-4(3 H )-one was reported to exhibit high cytotoxic effect against human colorectal adenocarcinoma cell lined HT29 with IC 50 value of 4.12 µM in relation to cisplatin (IC 50 = 8.47 µM) (Nowak et al, 2014). This successful achieved results became an evident support to the further research on the benzo[ h ]quinazoline scaffold, thus amino-benzo[ h ]quinazoline derivatives were developed and their obtained findings demonstrated high specific cytotoxicity against HT29 and HCT116 cell lines (Nowak et al, 2015). At the same time, bromo benzo[ h ]quinazoline was emerged to exhibit potential cytotoxicity against A549 and HT29 cell lines (Nowak et al, 2015).…”

“…Benzoquinazolines, as the theme of much considerable interest research, have occupied a distinguished position in synthetic-pharmaceutical chemistry, because of their diverse range of pharmacological properties (Al-Salahi et al, 2016, Al-Salahi et al, 2017, Brullo et al, 2012). Several benzo[ h ]-,benzo[ g ]-and benzo[ f ] analogues of quinazolines were found to possess cytotoxic activities and used as tyrosine kinase inhibitors (Huijun, 2017, Nowak et al, 2014, Nowak et al, 2015, Markosyan et al, 2010, Pendergast et al, 1994, Alsaid et al, 2017, Sivalingam et al, 2017, Ghorab et al, 2016, Al-Salahi et al, 2015). For instance, 3-(4-methoxybenzyl)-6-(morpholin -4-yl)benzo[ h ]quinazolin-4(3 H )-one was reported to exhibit high cytotoxic effect against human colorectal adenocarcinoma cell lined HT29 with IC 50 value of 4.12 µM in relation to cisplatin (IC 50 = 8.47 µM) (Nowak et al, 2014).…”

Synthesis of benzoquinoline derivatives from formyl naphthylamines via Friedländer annulation under metal-free conditions

“…We began our studies from the synthesis of carbamates 2, 7 (Scheme 2) being key compounds in the construction of the benzoquinoline skeleton. Their synthesis involved the reactions of the aryllithium species, generated from 2, 7 and t-BuLi or BuLi [23][24][25], with DMF and provided to corresponding formyl derivatives 2 and 7 with 60 and 50% yields, respectively. Next, derivative 2 subjected to bromination reaction with NBS in acetonitrile used as a solvent led to bromocarbamate 3 (75%).…”

“…Previously, we have noticed that N-Boc-2-naphthylamine derivatives contrary to N-Boc-1-naphthylamine are ready for cleavage of the Boc protecting group under basic conditions [23][24][25]. This fact has prompted us to extend the presented methodology and use the carbamate 7 in the cyclization reaction, without a prior deprotection…”

An Efficient Synthesis of Pyrrolo[1,2‐a] or Pyrido[1,2‐a]benzo[4,5]imidazo[1,2‐c]quinazoline Derivatives in Ionic Liquids Catalyzed by Iodine

“…Benzimidazole is also a fused bicyclic moiety bearing two nitrogen atoms, and the noteworthy application for its family is used as the proton pump inhibitors, such as Pantoprazole and Lansoprazole (Figure ), are all the most advanced type of drugs for the treatment of peptic ulcer at present. Therefore, much attention has been devoted to searching for novel methods to synthesize benzimidazoles and quinazolines in recent years.…”