Title:Heteroaromatization of Coumarin Part II: Synthesis, Reactions, and Antimicrobial Activities of Novel Pyrido[2,3-d]pyrimidine Derivatives
Volume: 22
Issue: 1
Author(s): Rita M. A. Borik, Ashraf H. F. Abd El-Wahab*, Hany M. Mohamed and Khatib S. Ismail
Affiliation:
- Department of Chemistry, Faculty of Science, Jazan University, 45142, Jazan, Kingdom of Saudi Arabia
Keywords:
3-acetyl coumarin, pyridine, Schiff base, pyridopyrimidinone, antimicrobial activities, condensation.
Abstract:
Background: Condensation of 3-acetyl coumarin (1) with 2‐(4-methoxy- benzylidene)
malononitrile (2) in ammonium acetate/acetic acid or absolute ethanol/piperidine affords
pyridine (3) and chromen-2-one (4) derivatives, respectively.
Methods: In this study, the reaction of 3 with an electrophilic reagent, namely, formic acid,
acetic anhydride and formamide afforded the pyridopyrimidinone and pyridine derivatives (6-
9). Also, treatment of 3 with different aromatic aldehydes, carbon disulfide, NaN3/NH4Cl, 2-
(4-methoxybenzylidene)malononitrile and acetophenone afforded pyridopyrimidinone, carbamodithioic
acid, tetrazol-5-yl-chromen-2-one, 2H-chromen-2-one, and pyridine derivatives
(10-14), respectively.
Results: This study synthesized coumarins with antimicrobial activity and verified the structure
and purity of the synthesized compounds using spectral data.
Conclusion: The new compounds were evaluated in vitro for their antimicrobial activity
against gram-positive bacteria (Staphylococcus aureus, Methicillin-resistant Staphylococcus
aureus) and gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), in addition
to fungus (Candida albicans). The investigated substances 3 and 14 presented good activity
against MRSA, E. coli, P. aeruginosa and C. albicans, while compounds 9, 10a-c, 11, 12 and
13 exhibited good to moderate activity.
