85094-66-2Relevant articles and documents
Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives
Bui, Hue Thi Buu,Do, Kiep Minh,Nguyen, Huy Tran Duc,Mai, Hieu Van,Danh, Thanh La Duc,Tran, De Quang,Morita, Hiroyuki
, (2021/09/08)
Twenty 2,3-disubstituted quinazolin-4(3H)-one derivatives 1–20 were successfully synthesized in moderate to good yields (25–82%). Their syntheses were based on a one pot tandem ring opening procedure followed by iodine-catalyzed oxidative cyclization of isatoic anhydride with aldehydes, using water as the only solvent under both classical and microwave irradiation conditions. Cytotoxicity assays of the prepared compounds against three human cancer cell lines (HeLa, MCF-7, and A549) indicated that 2, 3, and 20 possessed moderate activities against MCF-7 cells (IC50 = 47.2 μM, 43.9 μM, and 44.9 μM, respectively). Good cytotoxic activities against A549 cells were observed for 3 and 8 with IC50 values of 30.7 μM and 29.8 μM, respectively, which were comparable to the positive control, 5-fluorouracil (5-FU, IC50 = 27.9 μM). Furthermore, compound 4 exhibited slightly stronger activity (IC50 = 23.6 μM) than the positive control 5-FU against the A549 cell line.
Cu/Pd-catalyzed C-2-H arylation of quinazolin-4(3H)-ones with (hetero)aryl halides
Godeau, Julien,Harari, Marine,Laclef, Sylvain,Deau, Emmanuel,Fruit, Corinne,Besson, Thierry
, p. 7705 - 7717 (2015/12/31)
The regiospecific C-2-H arylation of N-3-substituted quinazolin-4(3H)-ones with a wide range of aryl or (hetero)aryl halides under microwave irradiation was studied. A ligand-dependent palladium/copper bicatalytic system was developed and allowed direct c
Rapid assembly of quinazolinone scaffold via copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia: Application to the synthesis of the alkaloid tryptanthrin
Guo, Shenghai,Li, Yan,Tao, Li,Zhang, Wenwen,Fan, Xuesen
, p. 59289 - 59296 (2015/02/19)
An efficient and practical procedure for the preparation of 2-substituted and 2,3-disubstituted quinazolinones was achieved through copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia under air. Control experimental results indicated that this tandem reaction is triggered by a copper-catalyzed direct amination of 2-bromobenzamides with aqueous ammonia, followed by cyclocondensation and oxidative aromatization. As an application, this novel methodology provides a concise and practical one-pot route to the synthesis of alkaloid tryptanthrin. This journal is