ENVIRONMENTALLY BENIGN SYNTHESIS OF N'-SUBSTITUTED NAPHTHALENE-1-SULFONOHYDRAZIDE UNDER MICROWAVE IRRADIATION AND THEIR BIOLOGICAL EVALUATION
Keywords:
Hydrazones, Condensation, Microwave irradiation, Antimicrobial activityAbstract
Objective: Microwave synthesis provides an alternative environmentally benign method with excellent yield and shorter reaction time. The aim of this study is to synthesize some new sulfonohydrazide derivatives by conventional/microwave method and their antimicrobial evaluation.
Methods: Condensation of naphthalene-1-sulfonohydrazide with aromatic carbonyls under Conventional refluxing/microwave irradiation.
Results: A facile, rapid and eco-friendly synthetic route for the synthesis of new sulfonohydrazide derivatives by microwave irradiation method was reported. Structures of the newly synthesized compounds were elucidated by elemental analysis and spectral studies viz. IR, NMR and MS. These compounds showed good to excellent antimicrobial activity against tested microbial strains. The zone of inhibition and minimum inhibitory concentration values for tested microbial strains was in range of 10-14 mm and 6.25-25μg/ml.
Conclusion: A novel series of biologically active N′-substituted naphthalene-1-sulfonohydrazide derivatives were synthesized by green method. Most of the newly synthesized compounds showed good to excellent antimicrobial activity.
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Savini L, Massarelli P, Chiasserini L, Sega A, Pellerano C, Brazi A, et al. Chelating agents as potential antitumorals 2-quinolylhydrazones and bis-2-quinolylhydrazones. Eur J Med Chem 1995;30:547–52.
Sridhar SK, Ramesh A. Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives. Biol Pharm Bull 2001;24(10):1149-52.
Chunha AC, Tributino JLM, Miranda ALP, Fraga CAM, Barreiro EJ. Synthesis and pharmacological evaluation of novel antinociceptive N-substituted-phenylimidazolyl-4-acylhydrazone derivatives. Farmacol 2002;57(12):999-07.
Sondhi SM, Dinodia M, Kumar A. Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives. Bioorg Med Chem 2006;14(13):4657-63.
Kucukguzel SG, Rollas S, Kucukguzel I, Kiraz M. Synthesis and antimycobacterial activity of some coupling products from 4-aminobenzoic acid hydrazones. Eur J Med Chem 1999;34(12):1093-100.
Koçyiğit KB, Rollas S. Synthesis, characterization and evaluation of antituberculosis activity of some hydrazones. Farmacol 2002;57(7):595-9.
Patole J, Sandbhor U, Padhye S, Deobagkar DN, Anson CE, Powell A. Structural chemistry and in vitro antitubercular activity of acetylpyridine benzoyl hydrazone and its copper complex against Mycobacterium smegmatis. Bioorg Med Chem Lett 2003;13(1):51-5.
Maccari R, Ottana R, Vigorita MG. In vitro advanced antimycobacterial screening of isoniazid-related hydrazones, hydrazides and cyanoboranes: part 14. Bioorg Med Chem Lett 2005;15(10):2509-13.
Cocco MT, Congiu C, Onnis V, Pusceddu MC, Schivo ML, Logu A. Synthesis and antimycobacterial activity of some isonicotinoylhydrazones. Eur J Med Chem 1999;34(12):1071-6.
Karah N, Kocabalkanh A, Gursoy A, Ates O. Synthesis and antitubercular activity of 4-(3-coumarinyl)-3-cyclohexyl-4-thiazolin-2-one benzylidenehydrazones. Farmacol 2002;57(7):589-93.
Rando DG, Sato DN, Siqueira L, Malvezzi A, Leite CQF, Amaral AT, et al. Potential tuberculostatic agents. Topliss application on benzoic acid [(5-nitro-thiophen-2-yl)-methylene]-hydrazide series. Bioorg Med Chem 2002;10(3):557-60.
Cates LA, Rasheed MS. Phosphorus GABA analogues as potential prodrugs. Pharm Res 1984;1(6):271-4.
Savini L, Massarelli P, Travagli V, Pellerano C, Novellino E, Cosentino S, et al. New alpha-(N)-heterocyclichydrazones: evaluation of anticancer, anti-HIV and antimicrobial activity. Eur J Med Chem 2004;39(2):113-22.
Al-Hazmi GA, El-Asmy AA. Synthesis, spectroscopy and thermal analysis of copper(II) hydrazone complexes. J Coord Chem 2009;62(2):337-45.
Ibrahim KM, Gabr IM, Zakky RR. Synthesis and magnetic, spectral and thermal eukaryotic DNA studies of some 2-acetylpyridine-[N-(3-hydroxy-2-naphthoyl)] hydrazone complexes. J Coord Chem 2009;62(7):1100-11.
El-Behery M, El-Twigry H. Synthesis, magnetic, spectral, and antimicrobial studies of Cu(II), Ni(II) Co(II), Fe(III), and UO2(II) complexes of a new Schiff base hydrazone derived from 7-chloro-4-hydrazinoquinoline. Spectrochim Acta (A) 2007;66(1):28-36.
(a) Beraldo H, Gambino D. The wide pharmacological versatility of semicarbazones, thiosemicarba-zones and their metal complexes. Mini-Rev Med Chem 2004;4(1):31–9.
(b) Greenbaum DC, Mackey Z, Hansell E, Doyle P, Gut J, Caffrey CR, et al. Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi. J Med Chem 2004;47(12):3212–9.
(a) Costa RFF, Rebolledo AP, Matencio T, Calado HDR, Ardisson JD, Cortes ME, et al. Metal complexes of 2-benzoylpyridine semicarbazone: spectral, electrochemical and structural studies. J Coord Chem 2005;58:1307–19.
(b) Rebolledo AP, Vieites M, Gambino D, Piro OE, Castellano EE, Zani CL, et al. Palladium(II) complexes of 2-benzoylpyridine-derived thiosemicarbazones: spectral characterization, structural studies and cytotoxic activity. Inorg Biochem 2005;99(3):698–06.
Lemay M, Ogilvie WW. Mechanistic studies of hydrazide-catalyzed enantioselective Diels−Alder reactions. J Org Chem 2006;71(12):4663–6.
(b) Lemay M, Aumand L, Ogilvie WW. Design of a conformationally rigid hydrazide organic catalyst. Adv Synth Catal 2007;349(3):441–4.
(c) Lemay M, Ogilvie WW. Aqueous enantioselective organocatalytic Diels−Alder reactions employing hydrazide catalysts. A new scaffold for organic acceleration. Org Lett 2005;7(19):4141–4.
Salgm-Goksen U, Gokhan-Kelekci N, Goktas O, Koysal Y, Kilic E, et al. 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorg Med Chem 2007;15(17):5738–51.
(b) Leite ACL, de Lima RS, Moreira DRD, Cardoso VDO, de Brito ACG, dos Santos LMF, et al. Synthesis, docking, and in vitro activity of thiosemicarbazones, aminoacyl-thiosemicarbazides and acyl-thiazolidones against Trypanosoma cruzi. Bioorg Med Chem 2006;14:3749–57.
(c) Bondock S, Khalifa W, Fadda AA. Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde. Eur J Med Chem 2007;42:948–54.
(a) Banik BK, Barakat KJ, Wagle WR, Manhas MS, Bose AK. Microwave-assisted rapid and simplified hydrogenation. J Org Chem 1999;64(16):5746-53.
(b) Gadhwal S, Barauh M, Sandhu JS. Microwave induced synthesis of hydrazones and wolff-kishner reduction of carbonyl compounds. Synlett 1999;10:1573-4.
Billman JH Tai KM. Reduction of schiff bases. II. Benzhydrylamines and structurally related compounds. J Org Chem 1958;23(4):535–9.White WA,
Weingart H. A versatile new enamine synthesis. J Org Chem 1967;32(1):213–4.
Branchaud BP. Studies on the preparation and reactions of tritylsulfenimines. J Org Chem 1983;48(20):3531–8.
Chakraborti AK, Bhagat S, Rudrawar S. Magnesium perchlorate as an efficient catalyst for the synthesis of imines and phenylhydrazones. Tetrahedron Lett 2004;45(41):7641–4.
(a) Vaas RS, Dudas J, Varma RS. Solvent-free synthesis of N-sulfonylimines using microwave irradiation. Tetrahedron Lett 1999;40(27):4951–4.
(b) Landge SM, Atanassova V, Thimmaih M, Torok B. Microwave-assisted oxidative coupling of amines to imines on solid acid catalysts. Tetrahedron Lett 2007;48(29):5161–4.
Bazgir A. Microwave-assisted efficient synthesis of diimines in dry media using silica gel supported sodium hydrogen sulfate as reusable solid support. J Chem Res 2006;1:1–2.
(a) Metger JO. Solvent-free organic syntheses. Angew Chem Int Ed 1998;37(21):2975.
(b) Li CJ, Chan TH. Organic syntheses using indium-mediated and catalyzed reactions in aqueous media. Tetrahedron 1999;55(37):11149-76.
Cave GWV, Raston CL, Scott JL. Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility. Chem Commun 2001;2159-69.
Imrie C, Kleyi P, Nyamori VO, Gerber TIA, Levendis DC, et al. Further solvent-free reactions of ferrocenylaldehydes: Synthesis of 1,1′-ferrocenyldiimines and ferrocenylacrylonitriles. J Organomet Chem 2007;692(16):3443.