SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF FUSED ISOXAZOLE DERIVATIVES USING GRINDING METHOD

Authors

  • Mohamed G. Badrey Chemistry Department; Faculty of Science; Fayoum University, El-Fayoum, 63514, Egypt,
  • Sobhi M. Gomha Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt.

Keywords:

Isoxazolone derivative, Pyrazoloisoxazole derivatives, Hydrazino and hydrazides compounds, Grinding and antimicrobial activity

Abstract

Objective: A facile and efficient synthesis of new pyrazoloisoxazole, isoxazolopyridine and isoxazolopyrimidine derivatives is discribed through interaction of isoxazolone derivative with different nitrogen nucleophiles. Nine of the newly synthesized compounds were tested for antibacterial activities.

Methods: Interaction of isoxazolone derivative with different nitrogen nucleophiles under grinding conditions.

Results: New pyrazoloisoxazole, isoxazolopyridine and isoxazolopyrimidine derivatives were synthesized and the structures of the prepared compounds were elucidated from spectral data.

Conclusion: 4-(4-Chlorobenzylidene)-3-phenylisoxazol-5(4H)-one was utilized as key intermediate for the synthesis of some new heterocycles, namely pyrazoloisoxazole, isoxazolopyridine and isoxazolopyrimidine derivatives under grinding conditions. Most of the newly synthesized products revealed moderate activity against Gram-negative and Gram-positive bacteria.

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References

Badrey MG, Gomha SM. 3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d]pyrimidine:An effecient key precursor for novel synthesis of some interesting triazines and triazepines as potential anti-tumor agents. Molecules (Basel, Switzerland) 2012;17(10):11538-53.

Gomha SM, Khalil KD. A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity. Molecules (Basel, Switzerland). 2012;17(8):9335-47.

Gomha SM, Riyadh SM, Abbas IM, Bauomi MA. Synthetic utility of ethylidenethio-semicarbazide:Synthesis and anti-cancer activity of 1,3-thiazines and thiazoles with imidazole moiety. Heterocycles 2013;87:341-56.

Abdel-Aziz HM, Gomha SM, Synthesis and in vitro anti-breast cancer activity of some novel 1,4-dihydropyridine derivatives. Int J Pharm Pharm Sci

Gomha SM, Abdel-Aziz HA. Synthesis of new heterocycles derived from 3-(3-methyl-1H-indol-2-yl)-3-oxopropanenitrile as potent antifungal agents. J Bull Korean Chem Soc 2012;33:2985-90.

Gomha SM, Abdel-aziz HM, An efficient synthesis of functionalized 2-(heteroaryl)-3H-benzo[f]chromen-3-ones and antibacterial evaluation. J Chem Res 2013; 2: 298–303.

Gomha SM, Riyadh SM. Synthesis under microwave irradiation of [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazoles and other diazoles bearing indole moieties and their antimicrobial evaluation. Molecules (Basel, Switzerland) 2011;16(10):8244-56.

Gomha, SM. A facile one-pot synthesis of 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones. J Monatsh Chem 2009;140:213-220.

Gomha SM, Efficient catalytic synthesis, characterization and antimicrobial evaluation of 1,4-bis(6-substituted-7-(2-aryl hydrazono)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl) benzene derivatives using chitosan. Int J Pharm Pharm Sci 2013; 5: 42-45.

Farghaly TA, Gomha SM, Abbas EMH, Abdalla MM. Hydrazonoyl halides as precursors for new fused heterocycles of 5α-reductase inhibitors. Archiv der Pharmazie, 2012; 345: 117–122.

Dabholkar, VV, Ansari, FY. Synthesis and characterization of selected fused isoxazole and pyrazole derivatives and their antimicrobial activity. J Serb Chem Soc 2009;74:1219-28.

Ramana, PV, Reddy, AR. Synthesis of dihydro oxazoylarylisoxazoles by conventional and under microwave conditions. Eur J of Chem 2011;2:300-7.

Kane JL, Hirth BH, Liang B, Gourlie BB, Nahill S, Barsomian G. Ureas of 5-aminopyrazole and 2-aminothiazole inhibit growth of gram-positive bacteria. Bioorg Med Chem Lett 2003;13(24):4463-6.

Brown, D J. Comprehensive Heterocyclic Chemistry edited by A R Katritzky & C W Rees (Pergamon Press, Oxford) 1984;443.

Roth, B;Cheng C. Progress in Medicinal Chemistry edited by G B Ellisand G E West, (Elsevier Biomedical Press, New York) 1982;19:267.

El-Gaby MSA, Abdel-Hamide SG, Ghorab MM, El-Sayed SM. Synthesis and anticancer activity in vitro of some new pyrimidines. Acta Pharm 1999;49:149-58.

Petrie CR, Cottam HB, McKernan PA, Robins RK, Revankar GR. Synthesis and biological activity of 6-azacadeguomycin and certain 3,4,6-trisubstituted pyrazolo[3,4-d]pyrimidine ribonucleosides. J Med Chem 1985;28(8):1010-6.

Baraldi PG, Pavani MG, Nuñez MdC, Brigidi P, Vitali B, Gambari R, et al. Antimicrobial and antitumor activity of N-heteroimmine-1,2,3-dithiazoles and their transformation in triazolo-, imidazo-, and pyrazolopirimidines. Bioorg Med Chem 2002;10(2):449-56.

Sondhi SM, Johar M, Rajvanshi S, Dastidar SG, Shukla R, Rag-hubir R, et al. Anticancer, anti-inflammatory and analgesic activity evaluation of heterocyclic compounds synthesized by the reaction of 4-isothiocyanato-4-methylpentan-2-one with substituted o-phenylenediamines, o-diaminopyridine and (un)substituted o-diaminopyrimidines. Australian J Chem2001;54:69-74.

Sakya, SM, Rast, B. Efficient synthesis of 5-alkyl amino and thioether substituted pyrazoles. Tetrahedron Lett 2003;44:7629-7632.

Sugiura S, Ohno S, Ohtani O, Izumi K, Kitamikado T, Asai H, et al. Synthesis and antiinflammatory and hypnotic activity of 5-alkoxy-3-(N-substituted carbamoyl)-1-phenylpyrazoles. J Med Chem 1977;20(1):80-5.

Goda FE, Maarouf AR, Bendary ER, EL-Synthesis and antimicrobial evaluation of new isoxazole and pyrazole derivatives. Saudi Pharm J 2003;11:111-7.

Lee HT, Kay EP. Regulatory role of cAMP on expression of Cdk4 and p27(Kip1) by inhibiting phosphatidylinositol 3-kinase in corneal endothelial cells. J Invest Ophthalmol Vis Sci 2003;44(9):3816-25.

Peruncheralathan S, Yadav AK, Ila H, Junjappa H. Highly regioselective synthesis of 1-aryl-3 (or 5)-alkyl/aryl-5 (or 3)-(N-cycloamino)pyrazoles. J Org Chem 2005;70(23):9644-7.

Xue CB, Roderick J, Mousa S, Olson RE, De Grado WF. Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists. Bioorg Med Chem Lett 1998;8(24):3499-504.

Kang YK, Shin KJ, Yoo KH, Seo KJ, Hong CY, Lee CS, et al. Synthesis and antibacterial activity of new carbapenems containing isoxazole moiety. Bioorg Med Chem Lett 2000;10(2):95-9.

Petkevich SK, Potkin VI, Kaberdin RV. Synthesis of Substituted Isoxazoles and Pyrazoles Based on 1-Aryl-3,4,4-trichloro-3-buten-1-ones. Russ J Org Chem 2004;40:1146-50.

Maczynski M, Zimeck M, Ryng S, The M. A new class of isoxazole derivatives:series of compounds eithimmunotropic activity. Acta pol-pharm 2008; 65: 241-244.

Mauro FAA, Vivekananda RK, Donato D, Piero SF, Tomas T. Three multicomponent reactions of 3, 5-dimethyl-4-nitroisoxazoles. Acta pol-pharm 2008; 65: 241-244. 2007;63:9741-5.

Ablajan K, Xiamuxi H. The convenient synthesis of 4-arylmethylidene-4,5-dihydro-3-phenylisoxazol-5-ones. Chinese Chem Lett 2011;22:151-4.

Smania, A, Monache, FD, Smania, EFA, Cuneo, RS. Antibacterial activity of steroidal compounds isolated from Ganoderma applanatum (Pers.) Pat. (Aphyllophoromycetideae) fruit body. Int J Med Mushrooms 1999;1:325-30.

Published

01-07-2014

How to Cite

Badrey, M. G., and S. M. Gomha. “SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF FUSED ISOXAZOLE DERIVATIVES USING GRINDING METHOD”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 6, no. 7, July 2014, pp. 236-9, https://www.innovareacademics.in/journals/index.php/ijpps/article/view/2001.

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