Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- ones

Year 2013, Volume: 41 Issue: 1, 73 - 79, 01.03.2013

Peddi Srinivasan Aluru Raghavendra Guru Prasad Golla Narayana Swamy Lakshmana Rao Krishna Rao Ravindranath

Abstract

N- Benzene sulfonyl -3-methyl-4- substistuted-arylhydrazono -pyrazolin-5-ones have been synthesized by the reaction between diazonium acetoacetic ester and benzene sulfonyl hydrazide. Pyrazolin-5-ones so obtained were characterized by elemental analysis, IR, 1H NMR and mass spectra.

Keywords

Pyrazolin-5-ones , characterization , elemental analysis , IR , 1H NMR , Mass spectral analysis

Eczacılıkta Önemli Yeni Bazı Pirazolin-5-on Bileşiklerinin Sentezi ve Karakterizasyonu

Abstract

N - benzen sülfonil -3-metil-4- substite-arilhidrazon -pirazolin-5-one bileşikleri, diazonyum asetoasetik ester ve benzen sülfonil hidrazidi reaksiyona sokmak suretiyle sentezlenmiştir. Bu şekilde elde edilen pirazolin5-on bileşikleri elementel analiz, IR, 1H NMR ve kütle spektrumları ile karakterize edilmiştir

Keywords

Pirazolin-5-on bileşikleri , karakterizasyon , elementel analiz , IR , 1H NMR ve Kütle Spektrum Analizi

References

• 1. RH. Wiley, RL. Clevenger, Aldehyde hydrazone derivatives in cancer chemotherapy, J Med Pharm Chem., 91 (1962) 1367.
• 2. HG. Garg, C. Praksh, Potential antidiabetics. 7. N 1 - (b eta-hydrox yb enz ylmethyl) -3-methyl-4- arylhydrazono-2-pyrazolin-5-ones and N1-(betahydroxybenzylmethyl)-3-methyl-4-arylazo-5-methylor –phenylpyrazoles, J. Med. Chem., 14 (1971) 175.
• 3. WCJ. Ross, GP. Warweek, Aryl-2-halogenoalkylamines. Part XVI. The preparation of derivatives of 4-[di-(2- chloroalkyl) amino] azobenzenes, J. Chem. Soc., 24 (1956) 1364.
• 4. V. Yamamoto, T. Kuwahara, K. Watanabe, K. Watanabe, Antioxidant activity of 3-methyl-1-phenyl-2-pyrazolin5-one, Redox Rep., 2 (1996) 333.
• 5. A. Gursoy, S. Demirayak, G. Capan, K. Erol, K. Vural, Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents, Eur. J. Med Chem., 7 (2000) 359.
• 6. MJ. Seo, JK. Kim, BS. Son, BG. Song, N. Zaesung, HG. Cheon, K. Kwang-Rok, YS. Sohn, HR. Kim, Novel 3-Methyl-4-(O-substituted-oximino)-pyrazolin-5- ones as a Potent Inhibitors of Cdc25B Phosphatase, Bull. Korean Chem. Soc., 25 (2004) 1121.
• 7. VS. Misra, S. Sen, N. Srivastava, HN. Verma, MS. Khan, SK. Khan, Synthesis of new 4-arylazo-1-(5-substituted benzoxazolin-2, oxyacetyl)-3-methyl-pyrazolin-5- ones and their evaluation as antiviral agents, Ind. J. Phrm. Sci., 49 (1987) 40.
• 8. M. Amir, K. Harish, SA. Khan, Synthesis and pharmacological evalution of pyrozline derivatives as new anti-inflammatory and analgesic agents, Bioorg. Med. Chem. Lett., 18 (2008) 918.
• 9. A. Gusroy, S. Demiroyak, G. Capan, K. Erol, K. Vural, Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents, Eur. J. Med. Chem., 35 (2000) 359.
• 10. A. Tantawy, H. Eisa, A. Ismail, ME. Alexandria, Synthesis of 1-(substituted) 4-arylhydrazono3-methyl-2-pyrazolin-5-ones as potential anti inflammatory agents, J. Pharm. Sci., 2 (1988) 133.
• 11. SG. Kucukguzel, S. Rollas, H. Erdeniz, M. Kiraz, AC. Ekinci, A. Vidin, Synthesis, characterization and pharmalogical properties of some 4-arylhydrazono2-pyrazoline-5-one derivatives obtained from heterocyclic amines, Eur. J. Med. Chem., 35 (2000) 761.
• 12. HS. EL-Kashef, MA. Abd-Alla, BE. Bayoumi, AAM. EL-Timawy, Synthesis and Antibacterial Activity of Some New Pyrazolone Dyes, J. of Chem. Technol. Biotechnol., 33 (1983) 294.
• 13. M. Giulia, ME, Luisa, F. Paola, S. Silvia, R. Angelo, MO. Luisa, B. Francesco, L. Roberta, M. Chiara, M. Valeria, T. Paolo Elena, Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1Hpyrazoles, Bioorg. Med. Chem., 12 (2004) 5465.
• 14. TA. Vincent, Current and future antifungal therapy: new targets for antifungal agents, J. Antimicrob. Chemotherapy, 44 (1999) 151.
• 15. A. Raghavendra Guru Prasad, V. Seshagiri, LK. Ravindranath, Polarographic Investigations of Certain Propiophenone benzoic acid hydrazones, Jordan J. Chem., 6 (2011) 51.
• 16. M. Dastagiri Reddy, A. Raghavendra Guru Prasad, Y. Spoorthy, LK. Ravindranath, Synthesis, Characterization and Antimicrobial Activity of Certain novel Aryl Hydrazone Pyrazoline-5-Ones Containing Thiazole Moiety, Adv. Pharm. Bull., 3 (2013).
• 17. L. Friedman, LL. Robert, RR. Walter, p-Toluenesulfonylhydrazide, Org. Synt., 40 (1960) 93.
• 18. SG. Kucukguzela, S. Rollas, H. Erdenizb, M. Kirazb, Synthesis, Characterization and Antimicrobial Evaluation of Ethyl 2-Arylhydrazono-3-oxobutyrates, Eur. J. Med. Chem., 34 (1999) 153.
• 19. HG. Garg, RA. Sharma, Potential antineoplastics II: 1-thiocarbamoyl-3-methyl 4-arylhydrazono-2- pyrazolin-5-ones, 2-Amino-4-phenyl-5-arylazothiazoles, and N-Phenyl-N′-2(4-phenyl-5-arylazothiazolyl) thiocarbamides, J. Pharma. Sci., 59 (1970) 348.