99933-65-0Relevant academic research and scientific papers
Synthesis and structure-activity relationship study of 1-phenyl-1-(quinazolin-4-yl)ethanols as anticancer agents
Kuroiwa, Kenta,Ishii, Hirosuke,Matsuno, Kenji,Asai, Akira,Suzuki, Yumiko
, p. 287 - 291 (2015/03/30)
A quinazoline derivative PVHD121 (1a) was shown to have strong antiproliferative activity against various tumor-derived cell lines, including A549 (lung), NCI-H460 (lung), HCT116 (colon), MCF7 (breast), PC3 (prostate), and HeLa (cervical) cells with IC50 values from 0.1 to 0.3 M. A structure-activity relationship (SAR) study at the 2- and 4-position of the quinazoline core lead to the discovery of more potent anticancer agents (14, 16, 17, 19, 24, and 31). The results of an in vitro tubulin polymerization assay and fluorescent-based colchicine site competition assay with purified tubulin indicated that 1a inhibits tubulin polymerization by binding to the colchicine site.
Reaction of 4-Aroylquinazolines with Sodium Hydroxide: Aryl Migration to Give 4-Aryl-3,4-dihydro-4-quinazolinecarboxylic Acids and Formation of Quinazoline and Aroic Acids
Higashino, Takeo,Takemoto, Masumi,Hayashi, Eisaku
, p. 1351 - 1359 (2007/10/02)
4-Aroylquinazolines (3) were prepared in good yields by alkaline hydrolysis of α-aryl-4-quinazolinylmethyl benzoates (15), followed by oxidation.The reaction of 3 with sodium hydroxide in dimethyl sulfoxide(DMSO) was found to proceed in two ways.One path is the aryl migration to lead to 4-aryl-3,4-dihydro-4-quinazolinecarboxylic acids (4), and the other is the fission of the C4-CO bond to yield quinazoline (5) and aroic acids (6). Potassium ferricyanide oxidized the carboxylic acids 4 to the corresponding 4-arylquinazolines (14) with elimination of carbon dioxide. Reaction of 4-benzoylquinazoline (3a) with methylmagnesium iodide did not result in the migration, but instead yielded of α-methyl-α-phenyl-4-quinazolinemethanol (18) and 3,4-dihydro-α,4-dimethyl-α-phenyl-4-quinazolinemethanol (19).
