Title:Synthesis and Antimicrobial Activity of Novel 1, 2, 4-Triazolopyrimidofuroquinazolinones from Natural Furochromones (Visnagenone and Khellinone)
Volume: 17
Issue: 7
Author(s): Ameen A. Abu-Hashem*, Hoda A.R. Hussein and Ahmed S. Aly
Affiliation:
- Photochemistry Department (Heterocyclic Unit), National Research Center, 12622 Dokki, Giza,Egypt
Keywords:
Visnagenone, khellinone, hydrazide, 1, 2, 4-triazolopyrimidine, benzylidene, furoquinazolinones, antimicrobial
activity.
Abstract:
Background: Previous and recent scientific research has shown that triazolopyrimidine
and furochromones have a wide range of pharmacological activities for the treatment of numerous
diseases, including anticancer, antiviral, anti-depressant, anti-microbial, anti-inflammatory, and
analgesic activities.
Objective: Preparation of new drugs derived from a natural furochromones as (1-hydrazinyl or
methylthio),-furopyrimidoquinazolinone, 1, 2, 4-triazolopyrimidofuroquinazolin-5-one, and quinazoline-
pyrimidofuro- quinazoline-8, 10-dione and the study of their biological activity as antimicrobial
agents.
Methods: A series of novel N’-furopyrimidoquinazoline-hydrazide; 1, 2, 4-triazolopyrimidofuroquinazolin-
5-one; furopyrimidoquinazolin-3-one and quinazoline-pyrimidofuroquinazoline-8, 10-
dione derivatives were synthesized from substituted (methylthio)-furopyrimidoquinazolinone (3ab)
and 1-hydrazinyl-furopyrimido- quinazolinone (4a-b) as the starting material.
Results: All compounds were synthesized in good yields (71-95%) in a gradually efficient system
under mild condition and some of the procedures were used such as microwave oven. The new
compounds have been confirmed by means of different spectroscopic methods such as IR, 1D and
2D -NMR techniques and mass spectrum. The in vitro antimicrobial activities were evaluated for
the prepared compounds using many types of bacteria (Gram-positive and Gram-negative) and
fungi.
Conclusion: 1, 2, 4-triazolopyrimidofuroquinazolin-5-one derivatives (10a-f, 8a-b, 7a-b and 6a-d)
showed the most efficient antimicrobial activities compared with the cefotaxime sodium and nystatin
as standard drugs.