MICROWAVE-ASSISTED SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF SOME PYRAZOLE DERIVATIVES
Abstract
Reaction of 3-[4-(dimethylamino)phenyl]-(1-methyl/phenyl)prop-2-en-1-one (Chalcones) was carried out with hydrazine hydrate, phenyl hydrazine, isoniazide, nicotinic hydrazide and thiosemicarbezide (corresponding hydrazides) in ethanol containing a few drops of glacial acetic acid under microwave irradiation giving N, N-dimethylaniline containing pyrazole derivatives. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR and 1H NMR. All the synthesized compounds have been screened for their antibacterial and antifungal activities.
Keywords:
3-[4-(dimethylamino) phenyl]-(1-methyl/phenyl)prop-2-en-1-one, Antimicrobial activity, Microwave irradiationDOI
https://doi.org/10.25004/IJPSDR.2014.060306References
1. Taylor EC, Patel H, Kuma H. Synthesis of pyrazolo 3,4-dpyrimidine analogues of the potent agent N-4-2-2-amino-43H-oxo-7H-pyrrolo2,3-dpyrimidin-5-yl ethylbenzoyl-L-glutamic acid(LY231514). Tetrahedron 1992; 48: 8089-8100.
2. Abdel-Rahman AAH, Abdel-Megied AES, Hawata MAM, Kasem ER, Shabaan MT. Synthesis and antimicrobial of some chalcones and their derived pyrazoles, pyrazolines, isoxzolines and 5,6-dihydropyrimidine-2-(1H)-thiones. Monatsh Chem 2007; 138: 889-897.
3. Sharshira EM, Hamada NM. Synthesis and in vitro antimicrobial activity of some pyrazolyl-1-carboxamide derivatives. Molecules 2011; 16: 7736–7745.
4. Rashad AE, Shamroukh AH, Hegab MI, Awad HM. Synthesis of some biologically active pyrazoles and C-nucleosides. Acta Chim Slov 2005; 52: 429-434.
5. Rashad AE, Hegab MI, Abdel-Megeid RE, Micky JA, Abdel-Megeid FME. Synthesis and antiviral evaluation of some new pyrazole and fused pyrazolopyrimidine derivatives. Bioorg Med Chem 2008; 16: 7102-7106.
6. Bhat BA, Dhar KL, Saxena AK, Shanmugavel M. Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agent. Bioorg Med Chem 2005; 15: 3177-3180.
7. Michael LE, David MS, Prasad SS. Chalcones: A new class of antimitotic agents. J Med Chem 1990; 33: 1948-1954.
8. Kalirajan R, Sivakumar SU, Jubie S, Gowramma B, Suresh B. Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. Int. J ChemTech Res 2009; 1: 27-34.
9. Holla BS, Akberali PM, Sivanada MK. Studies on arylfuran derivatives: Part X. Synthesis and antibacterial properties of arylfuryl-Δ2-pyrazolines. Farmaco 2000; 55: 256-263.
10. Maggio B, Daidone G, Raffa D, Plescia S, Mantione L, Cutuli VMC, Mangano NG, Caruso A. Synthesis and pharmacological study of ethyl 1-methyl-5-(substituted-3,4-dihydro-4-oxoquinazolin-3-yl)-1H-pyrazole-4-acetates. Eur J Med Chem 2001; 36: 737-742.
11. Vibhute YB, Basser MA. Synthesis and activities of a new series of chalcones as antibacterial agents. Ind. J. Chem. 2003; 42B: 202-205.
12. Clinton RO, Manson AJ, Stonner FW, Beyler AL, Potts GO, Arnold A. Steroidal [3,2-c] pyrazoles. J Am Chem Soc 1959; 81: 1513-1514.
13. Kalirajan R, Palanivelu M, Rajamanickam V, Vinothapooshan G, Andarajagopal K. Synthesis and biological evaluation of some heterocyclic derivatives chalcones. Int J Chem Sci 2007; 5: 73-80.
14. Urmila G, Vineeta S, Vineeta K, Sanjana C. Synthesis and antifungal activity of new fluorine containing 4-(substituted phenylazo) pyrazoles and isoxazoles. Indian J Heterocycl Chem 2005; 14: 265-266.
15. Stephen AF, Philip DP. Reexamination of the Claisen-Schmidt condensation of phenylacetone with aromatic aldehydes. J Org Chem 1973; 38: 1747-1749.
16. Azarifar D, Shaabanzadeh M. Synthesis and characterization of new 3,5-dinaphthyl substituted 2-pyrazolines and study of their antimicrobial activity. Molecules 2002; 7: 885-895.
17. Padmaia A, Payani T, Reddy GD, Padmavathi V. Synthesis, antimicrobial and antioxidant activities of substituted pyrazoles, isoxazoles, pyrimidine and thioxopyrimidine derivatives. Eur J Med Chem 2009; 44, 4557-4566.
18. Yale HL, Lose K, Martins J, Holing M, Perry FM, Bernstein J. Chemotherapy of experimental tuberculosis. VIII. The synthesis of acid hydrazides, their derivatives and related compounds. J Am Chem Soc 1953; 75: 1933-1942.
19. National Committee for Clinical Laboratory Standard. Reference method for broth dilution antifungal susceptibility testing of yeasts Approved standard M27A. NCCLS, Wayne, PA (1997).
2. Abdel-Rahman AAH, Abdel-Megied AES, Hawata MAM, Kasem ER, Shabaan MT. Synthesis and antimicrobial of some chalcones and their derived pyrazoles, pyrazolines, isoxzolines and 5,6-dihydropyrimidine-2-(1H)-thiones. Monatsh Chem 2007; 138: 889-897.
3. Sharshira EM, Hamada NM. Synthesis and in vitro antimicrobial activity of some pyrazolyl-1-carboxamide derivatives. Molecules 2011; 16: 7736–7745.
4. Rashad AE, Shamroukh AH, Hegab MI, Awad HM. Synthesis of some biologically active pyrazoles and C-nucleosides. Acta Chim Slov 2005; 52: 429-434.
5. Rashad AE, Hegab MI, Abdel-Megeid RE, Micky JA, Abdel-Megeid FME. Synthesis and antiviral evaluation of some new pyrazole and fused pyrazolopyrimidine derivatives. Bioorg Med Chem 2008; 16: 7102-7106.
6. Bhat BA, Dhar KL, Saxena AK, Shanmugavel M. Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agent. Bioorg Med Chem 2005; 15: 3177-3180.
7. Michael LE, David MS, Prasad SS. Chalcones: A new class of antimitotic agents. J Med Chem 1990; 33: 1948-1954.
8. Kalirajan R, Sivakumar SU, Jubie S, Gowramma B, Suresh B. Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. Int. J ChemTech Res 2009; 1: 27-34.
9. Holla BS, Akberali PM, Sivanada MK. Studies on arylfuran derivatives: Part X. Synthesis and antibacterial properties of arylfuryl-Δ2-pyrazolines. Farmaco 2000; 55: 256-263.
10. Maggio B, Daidone G, Raffa D, Plescia S, Mantione L, Cutuli VMC, Mangano NG, Caruso A. Synthesis and pharmacological study of ethyl 1-methyl-5-(substituted-3,4-dihydro-4-oxoquinazolin-3-yl)-1H-pyrazole-4-acetates. Eur J Med Chem 2001; 36: 737-742.
11. Vibhute YB, Basser MA. Synthesis and activities of a new series of chalcones as antibacterial agents. Ind. J. Chem. 2003; 42B: 202-205.
12. Clinton RO, Manson AJ, Stonner FW, Beyler AL, Potts GO, Arnold A. Steroidal [3,2-c] pyrazoles. J Am Chem Soc 1959; 81: 1513-1514.
13. Kalirajan R, Palanivelu M, Rajamanickam V, Vinothapooshan G, Andarajagopal K. Synthesis and biological evaluation of some heterocyclic derivatives chalcones. Int J Chem Sci 2007; 5: 73-80.
14. Urmila G, Vineeta S, Vineeta K, Sanjana C. Synthesis and antifungal activity of new fluorine containing 4-(substituted phenylazo) pyrazoles and isoxazoles. Indian J Heterocycl Chem 2005; 14: 265-266.
15. Stephen AF, Philip DP. Reexamination of the Claisen-Schmidt condensation of phenylacetone with aromatic aldehydes. J Org Chem 1973; 38: 1747-1749.
16. Azarifar D, Shaabanzadeh M. Synthesis and characterization of new 3,5-dinaphthyl substituted 2-pyrazolines and study of their antimicrobial activity. Molecules 2002; 7: 885-895.
17. Padmaia A, Payani T, Reddy GD, Padmavathi V. Synthesis, antimicrobial and antioxidant activities of substituted pyrazoles, isoxazoles, pyrimidine and thioxopyrimidine derivatives. Eur J Med Chem 2009; 44, 4557-4566.
18. Yale HL, Lose K, Martins J, Holing M, Perry FM, Bernstein J. Chemotherapy of experimental tuberculosis. VIII. The synthesis of acid hydrazides, their derivatives and related compounds. J Am Chem Soc 1953; 75: 1933-1942.
19. National Committee for Clinical Laboratory Standard. Reference method for broth dilution antifungal susceptibility testing of yeasts Approved standard M27A. NCCLS, Wayne, PA (1997).
Published
01-07-2014
Statistics
Abstract Display: 616 
PDF Downloads: 638
Dimension Badge
How to Cite
“MICROWAVE-ASSISTED SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF SOME PYRAZOLE DERIVATIVES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 6, no. 3, July 2014, pp. 200-3, https://doi.org/10.25004/IJPSDR.2014.060306.
Issue
Section
Research Article
How to Cite
“MICROWAVE-ASSISTED SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF SOME PYRAZOLE DERIVATIVES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 6, no. 3, July 2014, pp. 200-3, https://doi.org/10.25004/IJPSDR.2014.060306.
