Schiff Bases of 3-formylchromones as antibacterial, antifungal, and phytotoxic agents

Letters in Drug Design and Discovery

Volumn 6, Issue 5, 2009, Pages 363-373

  Khan, Khalid Mohammed ^a   Ahmad, Aqeel ^a   Ambreen, Nida ^a   Amyn, Afroze ^a   Perveen, Shahnaz ^b   Khan, Shakeel Ahmed ^a   Choudhary, Muhammad Iqbal ^a  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b PCSIR LABORATORIES COMPLEX   (Pakistan)

Author keywords

3 Formylchromone; 3 methyl 7 hydroxychromone; Antibacterial; Antifungal; Phytotoxic activity; Schiff Bases

Indexed keywords

2 [[(4 OXO 4H CHROMEN 3 YL)METHYLIDENE]AMINO]BENZOIC ACID; 3 [(PHENYLIMINO)METHYL] 4H CHROMEN 4 ONE; 3 [[(2 BENZOYL 4 CHLOROPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(2 METHOXY 4 NITROPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(2 METHOXY 5 NITROPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(2 METHYL 6 NITROPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(2,3 DIMETHYLPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(2,4 DICHLOROPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(2,4 DIMETHYLPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(2,6 DIMETHYLPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(3 HYDROXY 2 PYRIDINYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(3 METHYLPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[(3,5 DIMETHYLPHENYL)IMINO]METHYL] 4H CHROMEN 4 ONE; 3 [[[2 [(4 OXO 4H CHROMEN 3 YL)METHYLIDENE]AMINO]ETHYL]IMINO]METHYL] 4H CHROMEN 4 ONE; 4 METHYL N' [(4 OXO 4H CHROMEN 3YL)METHYLIDENE]BENZENESULFONOHYDRAZIDE; 4 OXO 4H CHROMENE 3 CARBALDEHYDE; 7 HYDROXY 3 METHYL 4H CHROMEN 4 ONE; AMPICILLIN; CHROMONE DERIVATIVE; N HYDROXY N OXO 4 [[2 [(4 OXO 4H CHROMEN 3 YL)METHYLIDENE]HYDRAZINO]CARBONYL]BENZENAMINIUM; N' [(4 OXO 4H CHROMEN 3 YL)METHYLENE] 2,2 DIPHENYLACETOHYDRAZIDE; N' [(4 OXO 4H CHROMEN 3 YL)METHYLENE]HEPTANOHYDRAZIDE; N' [(4 OXO 4H CHROMEN 3 YL)METHYLIDENE]BENZOHYDRAZIDE; N' [(4 OXO 4H CHROMEN 3 YL)METHYLIDENE]BUTANOHYDRAZIDE; N' [(4 OXO 4H CHROMEN 3 YL)METHYLIDENE]NICOTINOHYDRAZIDE; N' [(4 OXO 4H CHROMEN 3 YL)METHYLIDENE]NONANOHYDRAZIDE; N' [(4 OXO 4H CHROMEN 3 YL)METHYLIDENE]PROPANOHYDRAZIDE; SCHIFF BASE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGAL STRAIN; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HERBICIDAL ACTIVITY; IN VITRO STUDY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY;

EID: 67650561624     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570180810906050363     Document Type: Article

References (27)

1. Gibbons, A. Exploring new strategies to fight drug-resistant microbes. Science, 1992, 25, 1036-1038.
2. Scholar, E.M.; Pratt, W.B. Antimicrobial Drugs; 2nd ed., Oxford University Press, London. 2000.
3. Gibbon, S. Anti-staphylococcal plant natural products. Nat. Prod. Rep., 2004, 21, 263-277.
4. Tereschuk, M.L.; Riera, M.V.Q.; Castro, G.R.; Abdala, L.R. Antimicrobial activity of flavonoids from leaves of Tagetes minuta J. Ethnopharmacol., 1997, 56, 227-232. (Pubitemid 27271818)
5. Walsh, C. Antibiotics: Actions, Origins, Resistance; ASM Press: Washington, 2003.
6. Copp, B.R. Antimycobacterial natural products. Nat. Prod. Rep., 2003, 20, 535-537.
7. Cowan, M.M. Plant products as antimicrobial agents. Clin. Microbiol. Rev., 1999, 12(4): 564-582.
8. Wang, Y.; Hamburger, M.; Gueho, J.; Hostettmann, K. Antimicrobial flavonoids from Psiadia trinervia and their methylated and acetylated derivatives. Phytochemistry, 1989, 28, 2323-2327.
9. Ellis, G.P. In Chromenes, Chromanones and Chromones; Weissberger, A.; Taylor, E.C. Eds.; John Wiley and Sons: New York, 1977; pp. 1-10.
10. Kumar, R.; Yousuf, M. Chromones and bischromones: An account of photo induced reactions. ARKIVOC, 2006, 9, 239-264.
11. Athanasellis, G.; Melagraki, G.; Afantitis, A.; Makridima, K.; Igglessi-Markopoulou, O.A simple synthesis of functionalized 2-amino-3-cyano-4-chromones by application of the N-hydroxybenzotriazole methodology. ARKIVOC, 2006, 10, 28-34.
12. Singh, G.R.; Singh, N.K.; Girdhar, M.P.; Ishar, S.A versatile rout to 2-Alkyl-/aryl-amino-3-formyl and hetero annelated chromones through a facile nucleophilic substitution at C-2 in 2-(N-methylanilino)-3-formylchromones Tetrahedron, 2002, 58, 2471-2478 and references quoted therein.
13. Piao, L.Z.; Park, H.R.; Park, Y.K.; Lee, S.K.; Park, J.H.; Park, M.K. Mushroom tyrosinase inhibition activity of some chromones. Chem. Pharm. Bull., 2002, 50, 309-311.
14. Harnisch, H. Chromone-3-carboxaldehyde. Liebigs Ann. Chem., 1972, 765, 8-11.
15. Kubicova, L.; Pour, M.; Lacova, M.; Kralova, K.; Chovancova, J.; Kaustova, J. Synthesis and biological activity of 2-(4H-4-oxobenzopyran-3-yl)-3- phenyl-1,2-dihydroquinazolin-4(3H)-ones. Sixth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-6), http://www.mdpi.org/ecsoc- 6, 1-30 September 2002.
16. Foltínová, P.; Lácová, M.; Loos, D. Activity of some 3-formylchromone derivatives on the induction of chloroplast-free mutants in Euglena gracilis. Farmaco, 2000, 55, 21-26. (Pubitemid 30155684)
17. a) Khan, K.M.; Saify, Z.S.; Khan, M.Z.; Perveen, S.; Choudhary, M.I. Synthesis and antimicrobial studies on various morpholine derivatives. J. Chem. Soc. Pak., 2006, 28, 161-164.
18. b) Khan, K.M.; Zia-Ullah; Maharvi, G.M.; Shahzad, S.A.; Miana, G.A.; Perveen, S.; Haider, S.M.; Choudhary, M.I.; Atta-ur-Rahman, Selected biological evaluation of synthesized iridoids. J. Chem. Soc. Pak., 2004, 26, 340-347.
19. Iqbal, R.; Zareef, M.; Ahmed, S.; Zaidi, J.H.; Khan, K.M.; Arfan, M.; Shafique, M.; Shahzad, S.A. A convenient syntheses and antibacterial activities of symmetrical and unsymmetrical 2,5-disubstitutded-1,3,4-oxadiazoles. J. Chem. Soc. Pak., 2006, 28, 165-168.
20. b) Khan, K.M.; Saify, Z.S.; Hayat, S.; Khan, M.Z.; Noor, F.; Choudhary, M.I.; Zia-Ullah; Perveen, S. Synthesis and antioxidant and insecticidal activities of coumarin derivatives. J. Chem. Soc. Pak., 2002, 24, 226-231.
21. Margita, L.; Dusan, L.; Mikulas, F.; Maria, M.; Elshaaer, H.M. Synthesis and reactions of new 4-oxo-4H-benzopyran-3-carboxaldehydes containing hydroxy groups or 2-oxopyran cycles. Molecules, 1998, 3, 149-163.
22. Bauer, A.W.; Kirby, W.M.M.; Sherris, J.C.; Turk, M. Antibiotic susceptibility testing by a standardized single disk method. Am. J. Clin. Pathol., 1966, 45, 493.
23. Kalyoncuoglu, N.; Rollas, S.; Sür-Altiner, D. et al. 1-(p-Benzoylamino) benzoyl)-4-substituted thisemicarbazides: Synthesis and antibacterial and antifungal activities. Pharmazie, 1992, 47, 796-797.
24. a) Khan, K.M.; Saify, Z.S.; Zeeshan; Khan, A.; Ahmed, M.; Saeed, M.; Schick, M.; Kohlbau, H.-J.; Voelter, W. Synthesis and cytotoxic antimicrobial, antifungal anf cardiovascular activity of new quinoline derivatives. Arzneim-Forsch./Drug Res., 2000, 50, 915-919.
25. b) Khan, K.A.; Khan, S.A.; Khalid, S.M.; Siddiqui, B.S.; Saleem, R.; Siddiqui, S.; Faizi, S. In vitro Studies of the antibacterial and antifungal activity of oxine and its derivatives. Arzneim-Forsch/Drug Res., 1994, 44, 972-975.
26. McLaughlin, J.L.; Chang, C.J.; Smith, D.L. Bench-top bioassays for the discovery of products: Structure and chemistry. In Studies in natural products chemistry, (Part-B); Atta-ur-Rahman, Ed.; Elsevier Science Publishers B. V.: Netherlands, 1991, Vol.9, 383.
27. Khan, K.M.; Ambreen, N.; Hussain, S.; Perveen, S.; Choudhary, M.I. Schiff Bases of 3-formylchromone as thymidine phosphorylase inhibitors. Accepted for publication in Biorg. Med. Chem., 2009.