Synthesis and antimicrobial activity of chalcones and pyrazolines

Racha Umadevi

Abstract


Chalcones are 1,3-diphenyl-2-propene-1-one,  in  which  two  aromatic  rings are  linked by  a  three  carbon  α,β-unsaturated  carbonyl  system. They have displayed a broad spectrum of biological activities. In this view it was proposed to synthesize some novel pyrazolines from chalcones. Chalcones are prepared by treating 2-acetyl-5-bromothiophene with different aromatic compounds. These chalcones on condensation with phenyl hydrazine HCl. pyridine as a catalyst gave 3-(5-bromothiphene-2yl)-1-phenyl-1H-pyrazole derivatives. The synthesized compounds have been characterized by their melting point, TLC, IR and 1H NMR spectral data. They have been screened for their antibacterial activity against Gram positive bacteria B.subtillis & B.pumilus and Gram negative bacteria E. coli & P.vulgaris and antifungal against A.niger & p.crysogenium.


Keywords


Pyrazolines, Chalcones, 2-acetyl-5-bromothiophene, 3-(5-bromothiphene-2yl)-1-phenyl-1H-pyrazole

Full Text:

PDF

References


. Rajendra Prasad, Y., Ravi Kumar, P., Asha Deepthi, Ch. and Venkata Ramana, M., Synthesis and Antidepressant Activity of Some 3-(3''-Coumarinyl)-1,5-diphenyl-2-pyrazolines and 3-(2''- hydroxy naphthalen-1''-yl)-1,5-diphenyl-2-pyrazolines. Asian J. Chem., 2007;

(6): 4799-4798.

. Nielsen, S.F., Thomas, B., Larsen, M., Kristian, S. and Kromann, H., Antibacterial chalcones--bioisosteric replacement of the 4'-hydroxy group. Bioorg. Med. Chem., 2004; 12(11):3047-54.

. Boeck, P., Leal, P.C., Yunes, R.A. and Zacchino, S., Antifungal activity and studies on mode of action of novel xanthoxyline-derived chalcones. Archiv der Pharmazie 2005; 338: 87-95.

. Shah, A.K., Ahmed, B. and Tanveer, A., Synthesis and antihepatotoxic activity of some new chalcones containing 1, 4-dioxane ring system. Pak. J. Pharm. Sci., 2006; 19:290.

. Tewtrakul S, Subhadhirasakul S, Puripattanavong J, Panphadung T. HIV-1 protease inhibitory substances from the rhizomes of Boesenbergia pandurata Holtt. Songklanakarin J Sci Technol. 2003; 25(6).

. Algar, J. and Flynn, J.P., Proc. Roy. Irish. Acad., 42B, 1 (1937).

. Frölich S, Schubert C, Bienzle U, Jenett-Siems K. In vitro antiplasmodial activity of prenylated chalcone derivatives of hops (Humulus lupulus) and their interaction with haemin. Journal of Antimicrobial Chemotherapy. 2005 Apr 11; 55(6):883-7.

. Narender T, Gupta S. A convenient and biogenetic type synthesis of few naturally occurring chromeno dihydrochalcones and their in vitro antileishmanial activity. Bioorganic & medicinal chemistry letters. 2004 Aug 2; 14(15):3913-6.

. Sivakumar PM, Priya S, Doble M. Synthesis, biological evaluation, mechanism of action and quantitative structure–activity relationship studies of chalcones as antibacterial agents. Chemical biology & drug design. 2009 Apr 1;73(4):403-15.

. Nagaraj, A. and Sanjeev Reddy, C., J. Iran. Chem. Soc., 2008; 5:262-267.

. Kalirajan R, Sivakumar SU, Jubie S, Gowramma B, Suresh B. Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. International Journal of ChemTech Research. 2009 Jan; 1(1):27-34.

. Li ming, Z., Hai Shan, J., Liang Peng, S., Hu Ri, P. and Zhe Shan, Q., Bioorg. Med. Chem. Lett., 2005; 15: 5027.

. Francesco E, Salvatore G, Luigi M, Massimo C. Synthesis of some novel chalcones of phthalimidoester possessing good antiinflammatory and antimicrobial activity. Phytochemistry. 2007; 68:939-53.

. Ducki, S., Forrest, R., Hadfield, J.A., Kendall, A., Lawrence, N.J., Mc Gown, A.T. and Rennison, D., Biorg. Med. Chem. Lett., 1998; 8: 1051.

. Komazawa, Y., Takeda, S., Hosaka, K., Mitsuhashi, H. and Watanabe, T., PCT Int. Appl., 256 (1988).

. Satyanarayana M, Tiwari P, Tripathi BK, Srivastava AK, Pratap R. Synthesis and antihyperglycemic activity of chalcone based aryloxypropanolamines. Bioorganic & medicinal chemistry. 2004 Mar 1; 12(5):883-9.

. Barfod L, Kemp K, Hansen M, Kharazmi A. Chalcones from Chinese liquorice inhibit proliferation of T cells and production of cytokines. International immunopharmacology. 2002 Mar 31;2(4):545-55.

. Zwaagstra ME, Zhang M, Timmerman H, Onogi K, Tamura M, Toma T, Wada Y, inventors; Kowa Co., Ltd., assignee. Chalcone derivatives and drugs containing the same. United States patent US 6,046,212. 2000 Apr 4.

. Onyilagha JC, Malhotra B, Elder M, French CJ, Towers GN. Comparative studies of inhibitory activities of chalcones on tomato ringspot virus (ToRSV). Canadian Journal of Plant Pathology. 1997 Jun 1; 19(2):133-7.

. Deshpande AM, Argade NP, Natu AA, Eckman J. Synthesis and screening of a combinatorial library of naphthalene substituted chalcones: inhibitors of leukotriene B 4. Bioorganic & medicinal chemistry. 1999 Jun 30; 7(6):1237-40.

. Hsu, K.K. and Shi, J.Y., Taiwan Kexue, 29, 32 (1975).

. Maradufu A, Ouma JH. A new chalcone as a natural molluscicide from Polygonum senegalense. Phytochemistry. 1978 Jan 1; 17(4):823-4.

. Maayan, S., Ohad, N. and Soliman, K., Bioorg. Med. Chem., 13, 433 (2005).

. Nowakowska Z. A review of anti-infective and anti-inflammatory chalcones. European Journal of Medicinal Chemistry. 2007 Feb 28; 42(2):125-37.

. Makrandi JK, Kumar S. An efficient synthesis of 2'-Hydroxychalcones. Asian Journal of Chemistry. 2004 Apr 1; 16(2):1189.

. Powers DG, Casebier DS, Fokas D, Ryan WJ, Troth JR, Coffen DL. Automated parallel synthesis of chalcone-based screening libraries. Tetrahedron. 1998 Apr 16; 54(16):4085-96.

. Reichel L, Müller K. Ber. deutsch. chem. Ges. 1941; 74:1741.

. Saravanamurugan S, Palanichamy M, Arabindoo B, Murugesan V. Solvent free synthesis of chalcone and flavanone over zinc oxide supported metal oxide catalysts. Catalysis Communications. 2005 Jun 30; 6(6):399-403.

. Anjaneyulu AS, Murthy YL. Synthesis and characterization of some new chalcones and flavanones. Indian J Heterocycl Chem. 1994; 4(1):9-14.

. Elizabeth, P.R., Rosa, M.M., Casal, B., Carlos, J., Willma, N., Zhang, X.F. and Yeung, K.L., Catalysis Today, 96 (2006).




DOI: http://dx.doi.org/10.7439/ijpc.v7i8.4348

Article Metrics

Metrics Loading ...

Metrics powered by PLOS ALM

Refbacks

  • There are currently no refbacks.


Copyright (c) 2017 International Journal of Pharmaceutical Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.