Synthesis and Biological Activity of a New Schiff Base Ligand Pyridazine Based

محورهای موضوعی :

M. H. Fekri ¹ , M. Darvishpour ² , H. Khanmohammadi ³ , M. Rashidipour ⁴

1 -
2 -
3 -
4 -

تاریخ دریافت : 1392/12/03 تاریخ پذیرش : 1397/08/07 تاریخ انتشار : 1392/09/10

کلید واژه: antibiotic, Schiff base, Di-azo compound, Pyridazine, O-vanilin,

چکیده مقاله :

In this work 3, 6-bis (2-[2-sulfanyl-ethylimino)-methyl]-4-(4-nitro-phenylazo)-3-metoxy-phenol) pyridazine (2) was prepared and its antibacterial properties have studied. The structures of all the newly synthesized compounds have been comfirmed by elemental analysis, IR, 1H-NMR. Anti bacterial effects of compounds (1 and 2) have been studied. Following concentrations of materials were used: a=0.005 g/ml and b=0.01 M. Study was done on two strains of S.aureus and E.coli that experiments were done in Trypticase Soy Broth (TSB) and Nutrien Agar (TSB; Difco Laboratory). It is likely that these synthetic materials exert higher antibacterial effect on gram positive bacteria in comparison with gram negative.

منابع و مأخذ:

1. Venturini A., Gonzalez J., 2002. Theoretical Studies on the Mechanisms of [2+2] Cycloaddition Reactions, Journal of Organic Chemistry 67, 9089-9092.
2. Taggi A., Hafez A., Wack M. H., Young B., Ferraris D., Lectka T., 2002. The Development of the First Catalyzed Reaction of Ketenes and Imines: Catalytic, Asymmetric Synthesis of â-Lactams, Journal of the American Chemical Society, 124, 6626-6635.
3. Delpiccolo C., M., L., Mata E., G., 2002. Stereoselective solid-phase synthesis of 3,4-substituted β-lactam antibiotics and enzyme inhibitors, Tetrahedron
4. Asymmetry 13, 905-910.
5. More P., G., Bhalvankar R., B., Pattar S. , C., J., 2001. Synthesis and biological activities of Schiff bases of aminothiazoles , Indian Chemical Society, 78, 474-475.
6. Pandeya S. , N., Sriram D., Nath G., 1999. Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine, De Clercq Edition II Farmaco, 54, 624-628.
7. Baseer M., A., Jadhav V., D., Phule R., M., Archana Y., V., Vibhute Y., B., 2000. Synthesis and antimicrobial activity of some new Schiff bases, Oriental Journal of Chemistry, 16, 553-556.
8. El-Masry A., H., Fahmy H., H., Abdelwahed S., H. A., 2000. Synthesis and Antimicrobial Activity of Some New Benzimidazole Derivatives, Molecules. 5, 1429-1438.
9. Karia F., D., Parsania P., H., 1999. Synthesis and Spectroscopic Studies of New Schiff Bases, Asian Journal of chemistry, 11, 991-995.
10. Kabeer A., S., Baseer M., A., Mote N., A., 2001. Synthesis and antimicrobial activity of some Schiff bases from benzothiazoles,ââ‚‌ Asian Journal of Chemistry, Asian Journal of chemistry, 13, 496-500.
11. Singh W., M., Dash B., C., 1988. Synthesis of some new schiff bases containing thiazole and oxazole nuclei and their fungicidal activity Pesticides, Pesticides 22, 33-37.
12. Wang P., H., Keck J., G., Lien E., J., Lai M., M., C., 1990. Design, synthesis, testing, and quantitative structure-activity relationship analysis of substituted salicylaldehyde Schiff bases of 1-amino-3-hydroxyguanidine tosylate as new antiviral agents against coronavirus, Journal of Medicinal Chemistry, 33, 608-614.
13. Das A., Trousdale M., D., Ren S., Lien E., J., 1999. Inhibition of herpes simplex virus type 1 and adenovirus type 5 by heterocyclic Schiff bases of amino hydroxy guanidine tosylate, Antiviral Research, 44, 201-208.
14. Desai S., B., Desai P., B., Desai K., R., 2001. Synthesis of some Schiff bases, thiazollidones, and azetidinones derived from 2,6-diaminobenzo[1,2-d:4,5-d,]
15. bisthiazole and their anticancer activities,Hetrocyclic Communications, 7, 83-90.
16. Pathak P., Jolly V., S., Sharma K., P., 2000. Synthesis and biological activities of some new substituted arylazo Schiff bases, Oriental Journal of Chemistry, 16, 161-162.
17. Kuzmin V., E., Lozitsky V., P., Kamalov G., L., Lozitskaya R., N., Zheltvay A., I., Fedtchouk A., S., Kryzhanovsky D., N., 2000. The analysis of ââ‚‌œstructureââ‚‌”anticancer activityââ‚‌ relationship in a set of macrocyclic 2,6-bis (2- and 4-formylaryloxymethyl) pyridines Schiff bases , Acta Biochimca Polonica 47, 867-875.
18. Phatak P., Jolly V., S., Sharma K., P., 2000. Schiff base and their derivatives as potential anticancer agents, Oriental Journal of Chemistry, 16, 493-494.
19. Das, B.P., D.N. Chowdhury, B. Chowdry, G.K. Das and T. Roy-Choudhury, 1996. Studies of some alkaloids for toxicity on the larvae of Culex quinquefasciatus, Indian Journal of Environmental Health, 38, 8 1-85.
20. Samadhiya S., Halve A., 2001. Synthetic utility of Schiff bases as potential herbicidal agents, Oriental Journal of Chemistry, 17, 119-122.
21. Jarrahpour A. A., Motamedifar M., Pakshir K., Hadi N., Zarei M., 2004. Synthesis of Novel Azo Schiff Bases and Their Antibacterial and Antifungal Activities, Molecules, 9, 815-824.
22. Hlve A., Goyal A., 1996. Synthesis and crystal structure of 2-(2, 3, 4-trimethoxy-6-methylbenzyl ideneamino) phenol, Oriental Journal of Chemistry, 12, 87-88.
23. Song H., Chen K., Wu D., Tian H., 2004. Synthesis and absorption properties of some new azo-metal chelates and their ligands, Dyes and pigments 60, 111-119.
24. Tanaka K., Matsuo K., Nakanishi A., Jo M., Shiota H., Yamaguchi M., Yoshino S., Kawaguchi K., 1984. Synthesis and Antimicrobial Activities of Five-Membered Heterocycles Having a Phenylazo Substituent, Chemical and Pharmaceutical Bulletin, 8, 3291-3298.
25. Hartman H., Schulze M., 1991. Nucleophilic Substitution in Arylazo Phenols - A Simple Route for Preparing Chlorosubstituted Azobenzenes, Dyes and pigments 15, 255-262.
26. Peters A., T., Chisowa E., 1993. Colour-Constitution Relationships in 2-acylamino -4-N, N-diethyl amino azobenzene Disperse Dyes, Dyes and pigments 22, 223-238.
27. Brooker S., 2002.Some Copper and Cobalt Complexes of Schiff-base Macrocycles Containing Pyridazine Head Units, European Journal of Inorganic Chemistry, Journal of Inorganic Chemistry, 2535-2547.
28. Brandet C., D., Plieger P., G., Kell R., J., Geest D., J., Kennepohl D., K., Iremonger S., S., Brooker S., 2004. Dinickel(II), dizinc(II) and dilead(II) complexes of a pyridazine-containing Schiff-base macrocycle, Inorganica Chemica Acta, 357, 4265-4272.
29. Figueiredo H., Silva B., Raposo M., M., M., Fonseca A., M., Neves I., C., Quintelas C., Tavares T., 2008. Immobilization of Fe(III) Complexes of Pyradizine Derivatives prepared from Biosorbents supported on Zeolites, Microporous and Mesopours Materials 109, 163-171.
30. Khanmohammadi H., Darvishpour M., 2009. New azo ligands containing azomethine groups in the pyridazine-based chain: Synthesis and characterization, Dyes and Pigments 81, 167-173.
31. Dinçaple H., Toke F., Durucasu I., Avcibasi N., Icli S., 2007. New thiophene-based azo ligands containing azo methine group in the main chain for the determination of copper(II) ions,Dyes and Pigments 75, 11-24.
32. Botros R., 1977 US Patent 4, 119-166.
33. Thrupp L., D., Susceptibility Testing of Antibiotic in Liquid Media. 1986. Antibiotics in Laboratory Medicine 2nd Edition, Victor Lorian, Williams and Wilkins Baltimore 93-150
34. Besty McCaughy Unnecessary Deaths. The Human and Financial Costs of Hospital Infections. 2nd Edition Copyright, All Rights Reserved. Park Avenue New York, 2006.
35. Farr B., M., Salgado C., D., Karchmer T., B., Sherers R., J., 2001. Can antibutic-resistant nosocomial infections be controlled? Lancet Infect Dis,