Asian Journal of Research in Chemistry

Open Access Open Access  Restricted Access Subscription Access
Open Access Open Access Open Access  Restricted Access Restricted Access Subscription Access

Synthesis of 1, 3, 5-Trisubstituted Pyrazoline Nucleus Containing Compounds and Screening for Anti-Inflammatory Activity


Affiliations
1 Department of Chemistry, Faculty of Science & IT, Madhyanchal Professional University, Ratibad-462042, Bhopal, Madhya Pradesh, India., India
     

   Subscribe/Renew Journal


In this study, a novel series of heterocyclic compounds containing pyrazoline nucleus has been synthesized. The compounds were synthesized in two steps. Chalcone was synthesized in the first step by Claisen-Schmidt reaction, using 1-acetylnaphthalene and p-nitrobenzaldehyde as reactants. In the second step, the chalcone was cyclized in an acidic medium with some hydrazine derivatives to form pyrazolines. All the compounds were characterized by physical, chromatographic, spectroscopic, and elemental analysis and evaluated in vitro for antimicrobial activity against nine microorganisms by cup plate method. The minimum inhibitory concentration of all the compounds was determined by tube dilution method. All the compounds exhibited higher antibacterial activity as compared to the antifungal activity. Compound 5g (3-Naphthalen-1-yl-1-(2-nitro-phenyl)-5-(4-nitrophenyl)-4, 5-dihydro-1H-pyrazole)exhibited maximum antibacterial and antifungal activity and may be designated as the most potent member of the series, with 2-nitrophenyl group at N-1 position of the 2-pyrazoline ring.

Keywords

Pyrazoline, Chalcone, Antimicrobial activity, Claisen-Schmidt reaction
Subscription Login to verify subscription
User
Notifications
Font Size


  • Azarifar D. Ghasemnejad H. Microwave-assisted synthesis of some 3, 5-arylated 2-pyrazolines. Molecules. 2003; 8(8):642-648.

  • Ozdemir A. Zitouni GT. Kaplancikli ZA. Synthesis and antimicrobial activity of 1-(4-aryl-2-thiazolyl)-5-aryl-2pyrazolinederivatives. Eur J Med Chem. 2007a; 42(3):403-409.

  • Azarifar D. Shaebanzadeh M. Synthesis and characterization of new 3, 5-dinaphthyl substituted 2-pyrazolines and study of their antimicrobial activity. Molecules. 2002; 7(12):885-895.

  • Ashok M. Holla BS. Convenient synthesis of some 3, 5-arylated2-pyrazolines carrying 4-methylthiophenyl moiety and evaluation of their antimicrobial activity. J Pharmacol Toxicol 2006; 1:464470.

  • Kumar V. Aggarwal R. Tyagi P. Singh SP. Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-4-phenyl3-trifluoromethylpyrazoles. Eur J Med Chem. 2005; 40(9):922927.

  • Abunada NM. Hassaneen HM. Kandile NG. Mieldad OA. Synthesis and biological activity of some new pyrazoline and pyrrolo[3,4-c]pyrazole-4,6-dione derivatives: reaction of nitrilimines with some dipolarophiles. Molecules. 2008; 13:10111024.

  • Abdel-Wahab BF. Abdel-Aziz HA. Ahmed EM. Synthesis and antimicrobial evaluation of 1-(benzofuran-2-yl)-4-nitro-3arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-dihydro-5-aryl-1-[4(aryl)-1,3-thiazol-2-yl]-1H-pyrazoles. Eur J Med Chem. 2009; 44(6): 2632-2635.

  • Rai NP. Narayanaswamy VK. Shashikanth S. Arunachalam PN. Synthesis, characterization and antibacterial activity of 2-[1-(5chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-5(substituted-phenyl)-[1, 3, 4] oxadiazoles. Eur J Med Chem. 2009; 44(11):4522-4527.

  • Prakash O. Kumar R. Sehrawat R. Synthesis and antibacterial activity of some new 2, 3-dimethoxy-3-hydroxy-2-(1-phenyl-3aryl-4-pyrazolyl) chromanones. Eur J Med Chem. 2009; 44(4):1763-1767.

  • Sahu SK. Banerjee M. Samantray A. Behera C. Azam MA. Synthesis, analgesic, anti-inflammatory and antimicrobial activities of some novel pyrazoline derivatives. Trop J Pharm Res.2008; 7(2):961-968.

  • Venkataraman S. Jain S. Shah K. Upmanyu N. Synthesis and biological activity of some novel pyrazolines. Acta Pol Pharm. 2010; 67(4):361-366.

  • Girisha KS. Kalluraya B. Narayana V. Padmashree. Synthesis and pharmacological study of 1-acetyl/propyl-3-aryl-5-(5-chloro-3methyl-1-phenyl-1H-pyrazol-4-yl)-2-pyrazoline. Eur J Med Chem.2010; 45(10):4640-4644.

  • Bashir R. Ovais S. Yaseen S. Hamid H. Alam MS. Samim M.Singh S. Javed K. Synthesis of some new 1, 3, 5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and antiinflammatory agents. Bioorg Med Chem Lett. 2011; 21(14):43014305.

  • Kaplancikli ZA. Turan-Zitouni G. Ozdemir A. Can O. Chevallet P. Synthesis and antinociceptive activities of some pyrazoline derivatives. Eur J Med Chem. 2009; 44(6):2606-2610.

  • Ozdemir Z. Kandilci HB. Gu¨mu¨s¸el B. Calis U. Bilgin AA. Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur J Med Chem. 2007b; 42(3):373-379.

  • Bhat AR. Athar F. Azam A. Bis-pyrazolines: synthesis, characterization and antiamoebic activity as inhibitors of growth of Entamoeba histolytica. Eur J Med Chem. 2009; 44(1):426-431.

  • Furniss BS. Hannaford AJ. Smith PWG. Tatchell AR. Vogel’s textbook of practical organic chemistry. Pearson education, Quezon City, 2007; 1034.

  • Gautam V. Chawla V. Sonar PK. Saraf SK. Syntheses, characterization and antimicrobial evaluation of some 1,3,5trisubustitutedpyrazole derivatives. E–J Chem. 2010; 7(4):11901195.

  • Havrylyuk D, Zimenkovsky B, Vasylenko O, Zaprutko L, Gzella A, Lesyk R Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity. Eur J Med Chem. 2009; 44(4):1396-1404.

  • Havrylyuk D, Kovach N, Zimenkovsky B, Vasylenko O, Lesyk R Synthesis and anticancer activity of isatin-based pyrazolines and thiazolidines conjugates. Arch Pharm (Weinheim) 2011. doi:10.1002/ardp.201100055

  • Khode S, Maddi V, Aragade P, Palkar M, Ronad PK, Mamledesai S, Thippeswamy AH, Satyanarayana D. Synthesis and pharmacological evaluation of a novel series of 5-(substituted) aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel antiinflammatory and analgesic agents. Eur J Med Chem. 2009;

  • (4):1682-1688.

  • Pandey V, Chawla V, Saraf SK. Comparative study of conventional and microwave-assisted synthesis of some Schiff bases and their potential as antimicrobial agents. Med Chem Res. 2011; doi: 10.1007/s00044-011-9592-6.

  • Rostom SA, Badr MH, Abd El Razik HA, Ashour HM, Abdel Wahab AE. Synthesis of some pyrazolines and pyrimidines derived from polymethoxychalcones as anticancer and antimicrobial agents. Arch Pharm (Weinheim). 2011; doi:10.1002/ardp.201100077.


Abstract Views: 116

PDF Views: 0




  • Synthesis of 1, 3, 5-Trisubstituted Pyrazoline Nucleus Containing Compounds and Screening for Anti-Inflammatory Activity

Abstract Views: 116  |  PDF Views: 0

Authors

Suneeti Rajput
Department of Chemistry, Faculty of Science & IT, Madhyanchal Professional University, Ratibad-462042, Bhopal, Madhya Pradesh, India., India

Abstract


In this study, a novel series of heterocyclic compounds containing pyrazoline nucleus has been synthesized. The compounds were synthesized in two steps. Chalcone was synthesized in the first step by Claisen-Schmidt reaction, using 1-acetylnaphthalene and p-nitrobenzaldehyde as reactants. In the second step, the chalcone was cyclized in an acidic medium with some hydrazine derivatives to form pyrazolines. All the compounds were characterized by physical, chromatographic, spectroscopic, and elemental analysis and evaluated in vitro for antimicrobial activity against nine microorganisms by cup plate method. The minimum inhibitory concentration of all the compounds was determined by tube dilution method. All the compounds exhibited higher antibacterial activity as compared to the antifungal activity. Compound 5g (3-Naphthalen-1-yl-1-(2-nitro-phenyl)-5-(4-nitrophenyl)-4, 5-dihydro-1H-pyrazole)exhibited maximum antibacterial and antifungal activity and may be designated as the most potent member of the series, with 2-nitrophenyl group at N-1 position of the 2-pyrazoline ring.

Keywords


Pyrazoline, Chalcone, Antimicrobial activity, Claisen-Schmidt reaction

References