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doi:10.1016/j.bmc.2004.12.006 
Copyright © 2004 Elsevier Ltd All rights reserved.
Synthesis and potent antimicrobial activity of some novel 2-phenyl or methyl-4H-1-benzopyran-4-ones carrying amidinobenzimidazoles
Received 2 April 2004;
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Abstract
Series of flavones and methyl-4H-1-benzopyran-4-ones carrying mono or diamidinobenzimidazoles at different positions were synthesized and evaluated for antibacterial and antifungal activities against E. coli, S. aureus, MRSA (methicillin-resistant S. aureus), MRSE (methicillin-resistant S. epidermidis), S. faecalis and C. albicans, C. krusei. The results showed that while all diamidines are inactive, the compounds having monoamidinobenzimidazoles at the C-6 position of the 2-phenyl-4H-1-benzopyran-4-one have potent antibacterial activities, particularly, against Gram-positive bacteria. Compounds 23 and 22 exhibited the best inhibitory activity with MIC values of 1.56 μg/mL against S. aureus, MRSA, MRSE and 3.12 μg/mL against C. albicans, respectively.
Keywords: Methicillin-resistant S. aureus; Methicillin-resistant S. epidermidis; 4H-1-Benzopyran-4-one; Amidinobenzimidazoles
Article Outline
- 1. Introduction
- 2. Chemistry
- 3. Microbiology
- 4. Conclusion
- 5. Experimental
- 5.1. 4-Bromobenzoic acid 2′-acetyl-4′-bromophenyl ester (1)
- 5.2. 1-(5-Bromo-2-hydroxyphenyl)-3-(4-bromophenyl)-1,3-propanedione (2)
- 5.3. 6-Bromo-2-(4-bromophenyl)-4H-1-benzopyran-4-one (3)
- 5.4. 6-Cyano-2-(4-cyanophenyl)-4H-1-benzopyran-4-one (4)
- 5.5. 6-(2-Imidazolinyl)-2-4-(2-imidazolinyl)phenyl-4H-1-benzopyran-4-one hydrochloride (6)
- 5.6. 6-Isopropylamidino-2-(4-isopropylamidinophenyl)-4H-1-benzopyran-4-one hydrochloride (7)
- 5.7. 4-Methylbenzoic acid 2′-acetyl-5′-methoxyphenyl ester (8)
- 5.8. 1-(2-Hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)-1,3-propanedione (9)
- 5.9. 7-Methoxy-2-(4-methylphenyl)-4H-1-benzopyran-4-one (10)
- 5.10. 2-(4-Bromomethylphenyl)-7-methoxy-4H-1-benzopyran-4-one (11)
- 5.11. 2-(4-Formylphenyl)-7-methoxy-4H-1-benzopyran-4-one (12)
- 5.12. General method for the synthesis of 14–16, 18, 20–25
- 5.12.1. 2-[4-(5(6)-Amidinobenzimidazoyl)phenyl]-4H-1-benzopyran-4-one hydrochloride (14)
- 5.12.2. 2-[4-(5(6)-Isopropylamidinobenzimidazoyl)phenyl]-4H-1-benzopyran-4-one hydrochloride (15)
- 5.12.3. 2-[4-(5(6)-Isopropylamidinobenzimidazoyl)phenyl]-7-methoxy-4H-1-benzopyran-4-one hydrochloride (16)
- 5.12.4. 2-[5-(5(6)-Isopropylamidinobenzimidazoyl)thiophenyl]-4H-1-benzopyran-4-one hydrochloride (18)
- 5.12.5. 6-[2-(5(6)-Amidinobenzimidazoyl)]-2-phenyl-4H-1-benzopyran-4-one hydrochloride (20)
- 5.12.6. 6-[2-(5(6)-Isopropylamidinobenzimidazoyl)]-2-phenyl-4H-1-benzopyran-4-one hydrochloride (21)
- 5.12.7. 6-[2-(5(6)-Butylamidinobenzimidazoyl)]-2-phenyl-4H-1-benzopyran-4-one hydrochloride (22)
- 5.12.8. 6-[2-(5(6)-Cyclohexylamidinobenzimidazoyl)]-2-phenyl-4H-1-benzopyran-4-one hydrochloride (23)
- 5.12.9. 6-[2-(5(6)-Benzylamidinobenzimidazoyl)]-2-phenyl-4H-1-benzopyran-4-one hydrochloride (24)
- 5.12.10. 2-Phenyl-6-[5(6)-(1,4,5,6-tetrahydro-pyrimidin-2yl)-1H-benzimidazol-2-yl]-4H-1-benzopyran-4-one hydrochloride (25)
- 5.13. 6-[2-(5(6)-Amidinobenzimidazoyl)]-2-[4-(5(6)-amidinobenzimidazoyl)phenyl]-4H-1-benzopyran-4-one (27)
- 5.14. 6-[2-(5(6)-Isopropylamidinobenzimidazoyl)]-2-[4-(5(6)-isopropylamidinobenzimidazoyl)phenyl]-4H-1-benzopyran-4-one hydrochloride (28)
- 5.15. 6-Bromomethyl-2-methyl-4H-1-benzopyran-4-one (31)
- 5.16. 2-Methyl-4H-1-benzopyran-4-one-6-carboxyaldehyde (32)
- 5.17. 6-[2-(5(6)-Isopropylamidinobenzimidazoyl)]-2-methyl-4H-1-benzopyran-4-one hydrochloride (33)
- 5.18. 6-[2-(5(6)-Butylamidinobenzimidazoyl)]-2-methyl-4H-1-benzopyran-4-one hydrochloride (34)
- Acknowledgements
- References
