Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity

被引:34
作者
Abu-Hashem, Ameen Ali [1 ,2 ]
机构
[1] Natl Res Ctr, Heterocycl Unit, Photochem Dept, Dokki 2622, Gizal, Egypt
[2] Jazan Univ, Fac Sci, Chem Dept, Jazan 2097, Saudi Arabia
关键词
visnagenone; khellinone; quinazolinone; pyrimidine; thiazole; pyrazole; furane; antimicrobial activity; BIOLOGICAL-ACTIVITY; AMMI-VISNAGA; FUROCHROMONE; DNA; ANTITUMOR; DERIVATIVES; ANTICANCER; CORONARY; ANALOGS;
D O I
10.3390/molecules23112793
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Substituted-6-methyl-1-thioxo-1,2-dihydro-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-ones (5a,b) were synthesized from condensation of visnagenone (2a) or khellinone (2b) with 6-amino-thiouracil (3) in dimethylformamide or refluxing of (4a) or (4b) in dimethylformamide. Hence, compounds (5a,b) were used as the starting materials for preparing many new heterocyclic compounds such as; furo[3,2-g]pyrimido[1,6-a]quinazoline (6a,b), furo[3,2-g]thiazolo[2,3:2,3]pyrimido[1,6-a]quinazolinone (7a,b), substituted-benzylidene-furo[3,2-g]thiazolo[2,3:2,3]pyrimido[1,6-a]quinazoline-3,5-dione (8a-f), 3-oxo-furo[3,2-g]pyrimido[1,6-a]quinazoline-pentane-2,4-dione (9a,b), 1-(pyrazole)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (10a,b), 2-(oxo or thioxo)-pyrimidine-furo[3,2-g]pyrimido[1,6-a]quinazolinone (11a-d), 1-(methylthio)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (12a,b), 1-(methyl-sulfonyl)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (13a,b) and 6-methyl-1-((piperazine) or morpholino)-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-one (14a-d). The structures of the prepared compounds were elucidated on the basis of spectral data (IR, H-1-NMR, C-13-NMR, MS) and elemental analysis. Antimicrobial activity was evaluated for the synthesized compounds against Gram-positive, Gram-negative bacteria and fungi. The new compounds, furothiazolo pyrimido quinazolines 8a-f and 11a-d displayed results excellent for growth inhibition of bacteria and fungi.
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页数:20
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