RECENT REPORTS ON PYRAZOLE-BASED BIOACTIVE COMPOUNDS AS CANDIDATE FOR ANTICANCER AGENTS


Bayu Ardiansah

Abstract


 

 Pyrazole is a five-membered heterocyclic compound containing two nitrogen atoms. Due to its biological significance, design of novel pyrazole derivatives has become an interesting research area. We report the current progress in the development of anticancer agents containing pyrazole ring covering the time span of the past few years (2013–2016). The presence of this nucleus is accompanied with some side chains, functional groups, or in combination with other nucleus such as thiazole, thiourea, glucosamine, naphthalimide, and benzofuran. Several biologically active pyrazoles synthesized by numerous researchers across the world are summarized in this paper.


Keywords


N-heterocyclic, Pyrazole, Synthetic derivatives, Anticancer agents.

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References


Srivastava M, Singh J, Singh SB, Tiwari K, Pathak KV, Singh J. Synthesis of novel fused heterocycle-oxa-aza-phenanthrene and anthracene derivatives via sequential one-pot synthesis in aqueous micellar system. Green Chem 2012;14:901-5.

Pai G, Chattopadhyay AP. N-arylation of nitrogen containing heterocycles with aryl halides using copper nanoparticle catalytic system. Tetrahedron Lett 2016;57:3140-5.

Alam R, Wahi D, Singh R, Sinha D, Tandon V, Grover A, et al. Design, synthesis, cytotoxicity, Hu Topollα inhibitory activity and molecular docking studies of pyrazole derivatives as anticancer agents. Bioorg Chem 2016;69:77-90.

Shamsuzzaman S, Siddiqui T, Alam MG, Dar AM. Synthesis, characterization and anticancer studies of new steroidal oxadiazole, pyrrole and pyrazole derivatives. J Saudi Chem Soc 2015;19:387-91.

Ismail MM, Soliman DH, Farrag AM, Sabour R. Synthesis, antitumor activity, pharmacophore modelling and QSAR studies of novel pyrazoles and pyrazolo[1,5-a]pyrimidines against breast adenocarcinoma MCF-7 cell line. Int J Pharm Pharm Sci 2016;8:434-42.

Sony JK, Ganguly S. A battle against AIDS: New pyrazole key to an older lock-reverse transcriptase. Int J Pham Pharm Sci 2016;8:75-9.

Surendra Kumar R, Arif IA, Ahamed A, Idhayadhulla A. Anti-inflammatory and antimicrobial activities of novel pyrazole analogues. Saudi J Biol Sci 2016;23:614-20.

Ningaiah S, Bhadraiah UK, Doddaramappa SD, Keshavamurthy S, Javarasetty C. Novel pyrazole integrated 1,3,4-oxadiazoles: Synthesis, characterization and antimicrobial evaluation. Bioorg Med Chem Lett 2014;24:245-8.

Bekhit AA, Hassan AM, Abd El Razik HA, El-Miligy MM, El-Agroudy EJ, Bekhit Ael-D. New heterocyclic hybrids of pyrazole and its bioisosteres: Design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents. Eur J Med Chem 2015;94:30-44.

Pathak V, Maurya HK, Sharma S, Srivastava KK, Gupta A. Synthesis and biological evaluation of substituted 4,6-diarylpyrimidines and 3,5-diphenyl-4,5-dihydro-1H-pyrazoles as anti-tubercular agents. Bioorg Med Chem Lett 2014;24:2892-6.

Kameyama T, Nabeshima T. Effects of 1,3-diphenyl-5-(2- dimethylaminopropionamide)-pyrazole[difenamizole] on a conditioned avoidance response. Neuropharmacology 1978;17:249-56.

Wyde PR, Gilbert BE, Ambrose MW. Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo. Antiviral Res 1989;11:15-26. 13. Friedrich G, Rose T, Rissler K. Determination of lonazolac and its hydroxyl and o-sulfated metabolites on-line sample preparation liquid chromatography with fluorescence detection. J Chrmatogr B 2002;786:295-305.

Pantel J, Williams SY, Mi D, Sebag J, Corbin JD, Weaver CD, et al. Development of a high throughput screen for allosteric modulators of melanocortin-4 receptor signaling using a real time cAMP assay. Eur J Pharmacol 2011;660:139-47.

Kumar KA, Jayaroopa P. Pyrazoles: Synthetic strategies and their pharmaceutical applications-an overview. Int J PharmTech Res 2013; 5(4): 1473-1486.

Parmar NJ, Pansuriya BR, Labana BM, Sutariya TR, Kant R, Gupta VK. Access to some angular aminochromeno[2,3-c]pyrazole precursor by a domino knoevenagel-hetero-diels-alder reaction. Eur J Org Chem 2012;2012:5953-64.

Ramiz MM, Hafiz IS, Reheim MA, Gaber HM. Pyrazolones as building blocks in heterocyclic synthesis: Synthesis of new pyrazolopyran, pyrazolopyridazine and pyrazole derivatives of expected antifungicidal activity. J Chin Chem Soc 2012;59:72-80.

Huang XF, Lu X, Zhang Y, Song GQ, He QL, Li QS, et al. Synthesis, biological evaluation, and molecular docking studies of N-((1,3-diphenyl-1H-pyrazol-4-yl)methyl)aniline derivatives as novel anticancer agents. Bioorg Med Chem 2012;20:4895-900.

Khan MF, Alam MM, Verma G, Akhtar W, Akhter M, Shaquiquzzaman M. The therapeutic voyage of pyrazole and its analogs: A review. Eur J Med Chem 2016;120:170-201.

Chen TC, Guh JH, Hsu HW, Chen CL, Lee CC, Wu CL, et al. Synthesis and biological evaluation of anthra[1,9-cd]pyrazol-6(2H)-one scaffold derivatives as potential anticancer agents. Arab J Chem 2015;7:914-23.

Dawood KM, Eldebss TM, El-Zahabi HS, Yousef MH, Metz P. Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents. Eur J Med Chem 2013;70:740-9.

Koca I, Özgür A, Coskun KA, Tutar Y. Synthesis and anticancer activity of acyl thioureas bearing pyrazole moiety. Bioorg Med Chem 2013;21:3859-65.

El-Gamal MI, Park YS, Chi DY, Yoo KH, Oh CH. New triarylpyrazoles as broad-spectrum anticancer agents: Design, synthesis, and biological evaluation. Eur J Med Chem 2013;65:315-22.

Kumar JA, Saidachary G, Mallesham G, Sridhar B, Jain N, Kalivendi SV, et al. Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates. Eur J Med Chem 2013;65:389-402.

Zhu SL, Wu Y, Liu CJ, Wei CY, Tao JC, Liu HM. Design and stereoselective synthesis of novel isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents. Eur J Med Chem 2013;65:70-82.

Grosse S, Mathieu V, Pillard C, Massip S, Marchivie M, Jarry C, et al. New imidazo[1,2-b]pyrazoles as anticancer agents: Synthesis, biological evaluation and structure activity relationship analysis. Eur J Med Chem 2014;84:718-30.

Kumar V, Kaur K, Karelia DN, Beniwal V, Gupta GK, Sharma AK, et al. Synthesis and biological evaluation of some 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-arylethanones: Antibacterial, DNA photocleavage, and anticancer activities. Eur J Med Chem 2014;81:267-76.

Li S, Xu S, Tang Y, Ding S, Zhang J, Wang S, et al. Synthesis, anticancer activity and DNA-binding properties of novel 4-pyrazolyl-1,8-naphtalimide derivatives. Bioorg Med Chem Lett 2014;24:586-90.

Cankara Pirol S, Çaliskan B, Durmaz I, Atalay R, Banoglu E. Synthesis and preliminary mechanistic evaluation of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid amides with potent antiproliferative activity on human cancer cell lines. Eur J Med Chem 2014;87:140-9.

Yuan JW, Wang SF, Luo ZL, Qiu HY, Wang PF, Zhang X, et al. Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents. Bioorg Med Chem Lett 2014;24:2324-8.

Abd El-Karim SS, Anwar MM, Mohamed NA, Nasr T, Elseginy SA. Design, synthesis, biological evaluation and molecular docking studies of novel benzofuran-pyrazole derivatives as anticancer agents. Bioorg Chem 2015;63:1-12.

Kamal A, Shaik AB, Jain N, Kishor C, Nagabhushana A, Supriya B, et al. Design and synthesis of pyrazole-oxindole conjugates targeting tubulin polymerization as new anticancer agents. Eur J Med Chem 2015;92:501-13.

Reddy TS, Kulhari H, Reddy VG, Bansal V, Kamal A, Shukla R. Design, synthesis and biological evaluation of 1,3-diphenyl-1H-pyrazole derivatives containing benzimidazole skeleton as potential anticancer and apoptosis inducing agents. Eur J Med Chem 2015;101:790-805.

Sankappa RU, Isloor AM, Shetty P, Pai KS, Fun HK. Synthesis and in vitro biological evaluation of new pyrazole chalcone and heterocyclic diamides as potential anticancer agents. Arab J Chem 2015;8:317-21.

Shi JB, Tang WJ, Qi XB, Li R, Liu XH. Novel pyrazole-5-carboxamide and pyrazole-pyrimidine derivatives: Synthesis and anticancer activity. Eur J Med Chem 2015;90:889-96.

Vaarla K, Kesharwani RK, Santosh K, Vedula RR, Kotamraju S, Toopurani MK. Synthesis, biological activity evaluation and molecular docking studies of novel coumarin substituted thiazolyl-3-aryl-pyrazole-4-carbaldehydes. Bioorg Med Chem Lett 2015;25:5797-803.

Dai H, Ge S, Li G, Chen J, Shi Y, Ye L, et al. Synthesis and bioactivities of novel pyrazole oxime derivatives containing a 1,2,3-thiadiazole moiety. Bioorg Med Chem Lett 2016;26:4504-7.

Hafez HN, El-Gazzar AR, Al-Hussain SA. Novel pyrazole derivatives with oxa/thiadiazolyl, pyrazolyl moieties and pyrazolo[4,3-d]-pyrimidine derivatives as potential antimicrobial and anticancer agents. Bioorg Med Chem Lett 2016;26:2428-33.

Rahmouni A, Souiei S, Belkacem MA, Romdhane A, Bouajila J, Ben Jannet H. Synthesis and biological evaluation of novel pyrazolopyrimidines derivatives as anticancer and anti-5-lipoxygenase agents. Bioorg Chem 2016;66:160-8.

Ratković Z, Muškinja J, Burmudžija A, Ranković B, Kosanić M, Bogdanović GA, et al. Dehydrozingerone based 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles: Synthesis, characterization and anticancer activity. J Mol Struct 2016;1109:82-8.

Srinivasa Reddy T, Ganga Reddy V, Kulhari H, Shukla R, Kamal A, Bansal V. Synthesis of (Z)-1-(1,3-diphenyl-1H-pyrazol-4-yl)-3-(phenylamino)prop-2-en-1-one derivatives as potential anticancer and apoptosis inducing agents. Eur J Med Chem 2016;117:157-66.

Wang FQ, Yang H, He B, Jia YK, Meng SY, Zhang C, et al. A novel domino approach for synthesis of indolyl tetrahydropyrano[4,3-c]pyrazole derivatives as anticancer agents. Tetrahedron 2016;72:5769-75.




About this article

Title

RECENT REPORTS ON PYRAZOLE-BASED BIOACTIVE COMPOUNDS AS CANDIDATE FOR ANTICANCER AGENTS

Topics

Organic Chemistry

Keywords

N-heterocyclic, Pyrazole, Synthetic derivatives, Anticancer agents.

DOI

10.22159/ajpcr.2017.v10i12.22065

Date

01-12-2017

Additional Links

Manuscript Submission

Journal

Asian Journal of Pharmaceutical and Clinical Research
Vol 10 Issue 12 December 2017 Page: 45-51

Print ISSN

0974-2441

Online ISSN

2455-3891

Statistics

148 Views | 43 Downloads

Authors & Affiliations

Bayu Ardiansah
Department of Chemistry, FMIPA, Universitas Indonesia, Kampus Depok, 16424, Depok, Jawa Barat, Indonesia
Indonesia


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