Abstract
In this study, new compounds of pyrazolone heterocyclic derivatives were synthesized by reaction of 5-methyl pyrazol-3-one with appropriate substituted aromatic aldehydes to obtain various substituted 4-benzylidene-5-methyl-2,4-dihydro-3H-pyrazol-3-one (2a–j), which on treatment with benzyl chloride afforded the compound (3a–j). The synthesized compounds were evaluated for their in vitro cytotoxic activity by two models—Brine shrimp lethality bioassay and SRB assay.
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Ahmad A, Varshney H, Rauf A, Husain FM, Ahmad I (2013) Synthesis, biological screening of novel long chain derivatives of 1,3-disubstituted-1H-pyrazol-5(4H)-one and 2-substituted-3H-1,4-phthalazine-1,4-dione: Structure-activity relationship studies. J King Saud University–Science (http://dx.doi.org/10.1016/j.jksus.2013.09.003)
Anderson JE, Goetz CM, McLaughlin JL, Suffness M (1991) A blind comparison of simple bench-top bioassays and human tumour cell cytotoxicities as antitumor prescreens. Phytochem Anal 2:107–111
Chari RVJ (2008) Targeted cancer therapy: conferring specificity to cytotoxic drugs. Acc Chem Res 41:98–107
Das N, Verma A, Shrivastava PK, Shrivastava SK (2008) Synthesis and biological evaluation of some new aryl pyrazol-3-one derivatives as potential hypoglycemic agents. Indian J Chem 47B:1555–1558
Dohutia C, Kaishap PP, Chetia D (2013) Synthesis and study of analgesic, anti inflammatory activities of 3-methyl-5-pyrazolone derivatives. Int J Pharm Pharm Sci 5:86–90
Dube PN, Bule SS, Mokale SN, Kumbhare MR, Dighe PR, Ushir YV (2014) Synthesis and Biologic Evaluation of Substituted 5-methyl-2-phenyl-1H-pyrazol-3(2H)-one Derivatives as Selective COX-2 Inhibitors: Molecular Docking Study. Chem Biol Drug Des. doi:10.1111/cbdd.12324
Huang H, Yu Y, Gao Z, Zhang Y, Li C, Xu X, Jin H, Yan W, Ma R, Zhu J, Shen X, Jiang H, Chen L, Li J (2012) Discovery and optimization of 1,3,4- trisubstituted-pyrazolone derivatives as novel, potent and non-steroidal Farnesoid X Receptor (FXR) selective antagonists. J Med Chem 55:7037–7053
Jaracz S, Chen J, Kuznetsova LV, Ojima I (2005) Recent advances in tumor-targeting anticancer drug conjugates. Bioorg Med Chem 13:5043–5054
Lincoln RD, Strupinski K, Walker JM (1996) The use of Artemia naupli (Brine shrimp larvae) to detect toxic compounds from microalgal cultures. Pharm Biol 34:384–389
Loh VM, Cockcroft XL, Dillon KJ, Dixon L, Drzewiecki J, Eversley PJ, Gomez S, Hoare J, Kerrigan F, Matthews ITW, Menear KA, Martin NMB, Newton RF, Paul J, Smith GCM, Vile J, Whittle AJ (2005) Phthalazinones. Part 1: The design and synthesis of a novel series of potent inhibitors of poly (ADP- ribose) polymerase. Bioorg Med Chem Lett 15:2235–2238
Maggio B, Raffa D, Raimondi MV, Plescia F, Trincavelli ML, Martini C, Meneghetti F, Basile L, Guccione S, Daidone G (2012) Synthesis, benzodiazepine receptor binding and molecular modelling of isochromeno[4,3-c]pyrazol-5(1H)-one derivatives. Eur J Med Chem 54:709–720
Meyer BN, Ferrigni NR, Putnam JE, Jacobsen LB, Nichols DE, McLaughlin JL (1982) Brine Shrimp: a convenient general bioassay for active plant constituents. Planta Med 45:31–34
Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Langley J, Cronise P, Vaigro-Wolff A, Gray-Goodrich M, Campbell H, Boyd MR (1991) Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer 83:757–766
Ricart AD, Tolcher AW (2007) Technology insight: cytotoxic drug immunoconjugates for cancer therapy. Nat Clin Pract Oncol 4:245–255
Rubinstein LV, Shoemaker RH, Paull KD, Simon RM, Tosini S, Skehan P, Scudiero D, Monks A, Boyd MR (1990) Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J Natl Cancer 82:1113–1118
Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren J, Bokesch H, Kenney S, Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer 82:1107–1112
Varshney H, Ahmad A, Farshori NN, Ahmad A, Khan AU, Rauf A (2013) Synthesis and evaluation of in vitro antimicrobial activity of novel 2,3-disubstituted-4-thiazolidinones from fatty acid hydrazides. Med Chem Res 22:3204–3212
Xu S, Li S, Tang Y, Zhang J, Wang S, Zhou C, Li X (2013) Design, synthesis, and biological evaluation of some novel N-arylpyrazole derivatives as cytotoxic agents. Med Chem Res 22:5610–5616
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The authors are thankful to Head of the Department, Pharmaceutical Chemistry; and Principal, S.M.B.T College of Pharmacy, Nashik (MS), India for providing necessary facilities to carry out this research work.
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Dube, P.N., Bule, S.S., Ushir, Y.V. et al. Synthesis of novel 5-methyl pyrazol-3-one derivatives and their in vitro cytotoxic evaluation. Med Chem Res 24, 1070–1076 (2015). https://doi.org/10.1007/s00044-014-1201-z
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DOI: https://doi.org/10.1007/s00044-014-1201-z