| Summary: | 碩士 === 文化大學 === 應用化學系 === 85 === The objective of thesis is to invettigate the synthesis of
4-substituted-quinazoline derivatives.Because the derivatives of
4-substituted quinazoline are able to be as tyrosine kinases
inhibitors.In the study, it consists of four synthetic proesses.
Firstly, the starting materials, 4- and 5-nitroanthranilic acid
reacted with formamide in high temperature and refluxed to give
7- and 6-nitro-4-hydroxyquinazoline products. Secondly, 7- and
6-nitro-4-hydroxyquinazoline products were carried out a
chlorination reaction with phosphorus oxychloride(POCl3) and
phosphorus pentachloride(PCl5). Then, the chlorination products
reacted with 3-ethynylaniline to form 3-ethynylphenyl-(7-nitro
and 6-nitro)quinazolin-4-yl)-amine hydrochloride, the yield
percentage are 61% and 49% respectively. Finally,3-
ethynylphenyl-(7-nitro and 6-nitro quinazoline-4-yl)-amine
hydrochloride reacted with sodium thiosulfate in formic acid
under room temperature,then added sodium bica rbonate, and
purified to obtain the target compound,(6-amino-quinazoline-4-
yl)-(3-ethynylphenyl)-amine. The yield percentage is 34%. The
biological bioassay of the target compounds were carried out
with cyto toxicity test of cell lines, such as: hunan
nasalpharyngeal carcinoma(KB); human hepatoma(HEPT-3B); human
cervix carcinoma(HELA); human colon carcinoma(COLO-205).The data
of the results shiwed that (3-ethynylphenyl)-(6-nitro
quinazoline-4-yl)-amine hydrochloride and (6-amino-
quinazoline-4-yl)-(3-ethynylphenyl)-amine possess KB and HELA
biologicalactivities respectively.
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