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

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

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.

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.

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

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

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

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.
There are 19 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Peddi Srinivasan This is me

Aluru Raghavendra Guru Prasad This is me

Golla Narayana Swamy This is me

Lakshmana Rao Krishna Rao Ravindranath This is me

Publication Date March 1, 2013
Published in Issue Year 2013 Volume: 41 Issue: 1

Cite

APA Srinivasan, P., Prasad, A. R. G., Swamy, G. N., Ravindranath, L. R. K. R. (2013). Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- ones. Hacettepe Journal of Biology and Chemistry, 41(1), 73-79.
AMA Srinivasan P, Prasad ARG, Swamy GN, Ravindranath LRKR. Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- ones. HJBC. March 2013;41(1):73-79.
Chicago Srinivasan, Peddi, Aluru Raghavendra Guru Prasad, Golla Narayana Swamy, and Lakshmana Rao Krishna Rao Ravindranath. “Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- Ones”. Hacettepe Journal of Biology and Chemistry 41, no. 1 (March 2013): 73-79.
EndNote Srinivasan P, Prasad ARG, Swamy GN, Ravindranath LRKR (March 1, 2013) Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- ones. Hacettepe Journal of Biology and Chemistry 41 1 73–79.
IEEE P. Srinivasan, A. R. G. Prasad, G. N. Swamy, and L. R. K. R. Ravindranath, “Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- ones”, HJBC, vol. 41, no. 1, pp. 73–79, 2013.
ISNAD Srinivasan, Peddi et al. “Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- Ones”. Hacettepe Journal of Biology and Chemistry 41/1 (March 2013), 73-79.
JAMA Srinivasan P, Prasad ARG, Swamy GN, Ravindranath LRKR. Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- ones. HJBC. 2013;41:73–79.
MLA Srinivasan, Peddi et al. “Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- Ones”. Hacettepe Journal of Biology and Chemistry, vol. 41, no. 1, 2013, pp. 73-79.
Vancouver Srinivasan P, Prasad ARG, Swamy GN, Ravindranath LRKR. Synthesis and Characterisation of Certain Medicinally Important Novel Pyrazolin-5- ones. HJBC. 2013;41(1):73-9.

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