A RECENT UPDATE: ANTIMICROBIAL AGENTS CONTAINING PYRAZOLE NUCLEUS
DOI:
https://doi.org/10.22159/ajpcr.2018.v11i12.29418Keywords:
Antimicrobial, Antibacterial, Antifungal, Pyrazole, BioactiveAbstract
Objective: In this review, we report antimicrobial candidates containing pyrazole nucleus integrated with various functionalities.
Methods: research results by numerous scientists have been summarized from international journals indexed in reputed database such as Scopus and Web of Science.
Results: Pyrazole derivatives are much of interest as potent bioactive molecules. They have shown large bioactivities especially antimicrobial performance against broad spectrum of bacterial strains.
Conclusion: Several designed pyrazole derivates possessed good to superior antimicrobial activities.
Downloads
References
Raghavan S, Alagarasu K, Selvaraj P. Immunogenetics of HIV and HIV associated tuberculosis. Tuberculosis (Edinb) 2012;92:18-30.
de Oliviera DR, Tintino SR, Braga MF, Boligon AA, Athayde ML, Coutinho HD, et al. In vitro antimicrobial and modulatory activity of the natural products silymarin and silibinin. BioMed Res Int 2015;2015:7.
Phillips DJ, Harrison J, Richards SJ, Mitchell DE, Tichauer E, Hubbard AT, et al. Evaluation of the antimicrobial activity of cationic polymers against mycobacteria: Toward antitubercular macromolecules. Biomacromolecules 2017;18:1592-9.
Gabriel GJ, Som A, Madkour AE, Eren T, Tew GN. Infectious disease: Connecting innate immunity to biocidal polymers. Mater Sci Eng R Rep 2007;57:28-64.
Tuchilus CG, Nichifor M, Mocanu G, Stanciu MC. Antimicrobial activity of chemically modified dextran derivatives. Carbohydr Polym 2017;161:181-6.
Balouiri M, Sadiki M, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity: A review. J Pharm Anal 2016;6:71-9.
Pisal P, Deodhar M, Kale A, Nigade G, Pawar S. Design, synthesis, docking studies and biological evaluation of 2-phenyl-3-(substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3H)-one derivatives as antimicrobial agents. Int J Pharm Pharm Sci 2018;10:57.
Zaffiri L, Gardner J, Toledo-Pereyra LH. History of antibiotics. From salvarsan to cephalosporins. J Invest Surg 2012;25:67-77.
Abd-El Aal AM, El-Hadidy MR, El-Mashad NB, El-Sebaie AH. Antimicrobial effect of bee honey in comparison to antibiotics on organisms isolated from infected burns. Ann Burns Fire Disasters 2007;20:83-8.
Gurunanjappa P, Nagamallu R, Kariyappa AK. Synthesis and antimicrobial activity of novel fused pyrazoles. Int J Pharm Pharm Sci 2015;7:379.
Chimenti F, Carradori S, Secci D, Bolasco A, Bizzarri B, Chimenti P, et al. Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1H)-pyrazole derivatives. Eur J Med Chem 2010;45:800-4.
Peyssonnaux C, Eychène A. The raf/MEK/ERK pathway: New concepts of activation. Biol Cell 2001;93:53-62.
Khan SA, Ahmad B, Alam T. Synthesis and antihepatotoxic activity of some new chalcones containing 1, 4-dioxane ring system. Pak J Pharm Sci 2006;19:290-4.
Khalilullah H, Khan S, Ahsan MJ, Ahmed B. Synthesis and antihepatotoxic activity of 5-(2,3-dihydro-1,4-benzodioxane-6-yl)-3-substituted-phenyl-4,5-dihydro-1H-pyrazole derivatives. Bioorg Med Chem Lett 2011;21:7251-4.
dos Santos MS, Oliveira ML, Bernardino AM, de Léo RM, Amaral VF, de Carvalho FT, et al. Synthesis and antileishmanial evaluation of 1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazole derivatives. Bioorg Med Chem Lett 2011;21:7451-4.
Dardari Z, Lemrani M, Sebban A, Bahloul A, Hassar M, Kitane S, et al. Antileishmanial and antibacterial activity of a new pyrazole derivative designated 4-[2-(1-(ethylamino)-2-methyl- propyl)phenyl]-3-(4-methyphenyl)-1-phenylpyrazole. Arch Pharm (Weinheim) 2006;339:291-8.
Dos Santos MS, Gomes AO, Bernardino AM, de Souza MC, Khan MA, de Brito MA, et al. Synthesis and antileishmanial activity of new 1-aryl-1H-pyrazole-4-carboximidamides derivatives. J Braz Chem Soc 2011;22:352.
Kendre BV, Landge MG, Jadhav WN, Bhusare SR. Synthesis and bioactivities of some new 1H-pyrazole derivatives containing an aryl sulfonate moiety. Chin Chem Lett 2013;24:325.
Malladi S, Isloor AM, Shetty P, Fun HK, Telkar S, Mahmoud R, et al. Synthesis and anti-inflammatory evaluation of some new 3, 6-disubstituted-1, 2, 4-triazolo-[3, 4-b]-1, 3, 4-thiadiazoles bearing pyrazole moiety. Med Chem Res 2012;21:3272.
Tewari AK, Singh VP, Yadav P, Gupta G, Singh A, Goel RK, et al. Synthesis, biological evaluation and molecular modeling study of pyrazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents. Bioorg Chem 2014;56:8-15.
Huang YY, Wang LY, Chang CH, Kuo YK, Kaneko K, Takayama H, et al. One-pot synthesis and antiproliferative evaluation of pyrazolo[3,4-d]pyrimidine derivatives. Tetrahedron 2012;68:9658.
Sidique S, Ardecky R, Su Y, Narisawa S, Brown B, Millán JL, et al. Design and synthesis of pyrazole derivatives as potent and selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP). Bioorg Med Chem Lett 2009;19:222-5.
Sun J, Lv XH, Qiu HY, Wang YT, Du QR, Li DD, et al. Synthesis, biological evaluation and molecular docking studies of pyrazole derivatives coupling with a thiourea moiety as novel CDKs inhibitors. Eur J Med Chem 2013;68:1.
Inceler N, Yilmaz A, Baytas SN. Synthesis of ester and amide derivatives of 1-phenyl-3-(thiophen-3-yl)-1H-pyrazole-4-carboxylic acid and study of their anticancer activity. Med Chem Res 2013;22:3109.
Nitulescu GM, Draghici C, Missir AV. Synthesis of new pyrazole derivatives and their anticancer evaluation. Eur J Med Chem 2010;45:4914-9.
Prasad YR, Kumar GV, Chandrashekar SM. Synthesis and biological evaluation of novel 4,5-dihydropyrazole derivatives as potent anticancer and antimicrobial agents. Med Chem Res 2013;22:2061.
Rai U, Isloor AM, Shetty P, Pai KS, Fun HK. Synthesis and in vitro biological evaluation of new pyrazole chalcones and heterocyclic diamides as potential anticancer agents. Arabian J Chem 2015;8:317.
Chandna N, Kapoor JK, Grover J, Bairwa K, Goyal V, Jachak SM. Pyrazolylbenzyltriazoles as cyclooxygenase inhibitors: Synthesis and biological evaluation as dual anti-inflammatory and antimicrobial agents. New J Chem 2014;38:3662.
Vijesh AM, Isloor AM, Telkar S, Peethambar SK, Rai S, Isloor N, et al. Synthesis, characterization and antimicrobial studies of some new pyrazole incorporated imidazole derivatives. Eur J Med Chem 2011;46:3531-6.
Thumar NJ, Patel MP. Synthesis, characterization and biological activity of some new carbostyril bearing 1H-pyrazole moiety. Med Chem Res 2012;21:1751-61.
Ambethkar S, Padmini V, Bhuvanesh N. A green and efficient protocol for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives via a one-pot, four component reaction by grinding method. J Adv Res 2015;6:975-85.
Mardiana L, Bakri R, Septiarti A, Ardiansah B. The synthesis of 2-(5-(3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol using sodium impregnated on activated chicken eggshells catalyst. IOP Conf Ser Mater Sci Eng 2017;188:12022.
Gressler V, Moura S, Flores FC, Flores DC, Colepicolo P, Pinto E. Antioxidant and antimicrobial properties of 2-(4,5-Dihydro-1H-pyrazol-1-yl)-pyrimidine and 1-carboxamidino-1H-pyrazole derivatives. J Braz Chem Soc 2010;21:1477-83.
Sankaran M, Uvarani C, Chandraprakash K, Umamaheswari M, Mohan PS. Antioxidant and antimicrobial properties of 2-(4,5-Dihydro-1H-pyrazol-1-yl)-pyrimidine and 1-carboxamidino-1H-pyrazole derivatives. J Heterocycl Chem 2015;52:1082.
Kang Z, Wang Y, Zhou L, Zhang M, Song L, Deng H. A facile and consecutive approach to trifluoromethylated spirochromeno[2,3-c]-6H-Pyrazol-2′,5-dione derivatives. J Fluorine Chem 2016;188:131.
Gadhave AG, Uphade BK. Synthesis of some pyrazole containing chalcones and pyridine-3-carbonitirles and study of their anti-inflammatory activity. Orient J Chem 2017;33:219.
Kakarla RK, Vinnakota S, Rani BS, Swethanjali M, Golla NS. Synthesis and structural elucidation of some novel pyrazolin-5-ones. Rasayan J Chem 2016;9:227.
El-Borai MA, Rizk HF, Beltagy DM, El-Deeb IY. Microwave-assisted synthesis of some new pyrazolopyridines and their antioxidant, antitumor and antimicrobial activities. Eur J Med Chem 2013;66:415.
Gaikwad ND, Patil SV, Bobade VD. Synthesis and antimicrobial activity of novel thiazole substituted pyrazole derivatives. J Heterocycl Chem 2013;50:519-27.
Shah PJ, Patel HS, Patel BP. Synthesis, characterization and antimicrobial activity of novel sulphapiperazine containing arylazopyrazoles. J Saudi Chem Soc 2013;17:307-13.
Sharifzadeh B, Mahmoodi NO, Mamaghani M, Tabatabaeian K, Chirani AS, Nikokar I, et al. Facile regioselective synthesis of novel bioactive thiazolyl-pyrazoline derivatives via a three-component reaction and their antimicrobial activity. Bioorg Med Chem Lett 2013;23:548-51.
Vijesh AM, Isloor AM, Shetty P, Sundershan S, Fun HK. New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents. Eur J Med Chem 2013;62:410-5.
Amir M, Javed SA, Hassan MZ. Synthesis and antimicrobial activity of pyrazolinone and pyrazole analogues containing quinoline moiety. Indian J Chem 2013;52B:1493-9.
Desai NC, Rajpara KM, Joshi VV. Synthesis of pyrazole encompassing 2-pyridone derivatives as antibacterial agents. Bioorg Med Chem Lett 2013;23:2714-7.
Hassan SY. Synthesis, antibacterial and antifungal activity of some new pyrazoline and pyrazole derivatives. Molecules 2013;18:2683-711.
Siddiqui NJ, Idrees M, Khati NT, Dhonde MG. Synthesis and antimicrobial activities of some new pyrazoles, oxadiazoles and isoxazole bearing benzofuran moiety. South Afr J Chem 2013;66:248.
Aggarwal R, Masan E, Kaushik P, Kaushik D, Sharma C, Aneja KR. Synthesis and biological evaluation of 7-trifluoromethylpyrazolo [1, 5-a] pyrimidines as anti-inflammatory and antimicrobial agents. J Fluorine Chem 2014;168:16.
Kumar R, Arora J, Ruhil S, Phougat N, Chhillar AK, Prasad AK. Synthesis and antimicrobial studies of pyrimidine pyrazole heterocycles. Adv Chem 2014;2014:12.
Lavanya G, Mallikarjuna Reddy L, Padmavathi V, Padmaja A. Synthesis and antimicrobial activity of (1,4-phenylene)bis(arylsulfonylpyrazoles and isoxazoles). Eur J Med Chem 2014;73:187-94.
Malladi S, Isloor AM, Peethambar SK, Fun HK. Synthesis and biological evaluation of newer analogues of 2,5-disubstituted 1,3,4-oxadiazole containing pyrazole moiety as antimicrobial agents. Arabian J Chem 2014;7:1185.
Mehta HB, Dixit BC, Dixit RB. L-Proline catalyzed one-pot multi-component synthesis of 2-(1, 3-diphenyl-1H-pyrazol-4-yl) quinazolin-4 (3H)-one derivatives and their biological studies. Chin Chem Lett 2014;25:741.
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.
Rani M, Mohamad Y. Synthesis, studies and in vitro antibacterial activity of some 5-(thiophene-2-yl)-phenyl pyrazoline derivatives. J Saudi Chem Soc 2014;18:411-7.
Sangani CB, Makawana JA, Zhang X, Teraiya SB, Lin L, Zhu HL. Design, synthesis and molecular modeling of pyrazole–quinoline–pyridine hybrids as a new class of antimicrobial and anticancer agents. Eur J Med Chem 2014;76:549.
Mishra SK, Majumdar P, Behera RK, Behera AK. Synthesis of 3-substituted pyrazole derivatives by mixed anhydride method and study of their antibacterial activities. Synth Commun 2014;44:32.
Hafez HN, Alshammari AG, El-Gazzar AR. Facile heterocyclic synthesis and antimicrobial activity of polysubstituted and condensed pyrazolopyranopyrimidine and pyrazolopyranotriazine derivatives. Acta Pharm 2015;65:399-412.
Hamada MM, Abdo YM. Synthesis, characterization, antimicrobial screening and free-radical scavenging activity of some novel substituted pyrazoles. Molecules 2015;20:10468-86.
İskeleli NO, Alpaslan YB, Direkel Ş, Ertürk AG, Süleymanoğlu N, Ustabaş R, et al. The new schiff base 4-[(4-hydroxy-3-fluoro-5-methoxy-benzylidene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one: Experimental, DFT calculational studies and in vitro antimicrobial activity. Spectrochim Acta A Mol Biomol Spectrosc 2015;139:356-66.
Kendre BV, Landge MG, Bhusare SR. Synthesis and biological evaluation of some novel pyrazole, isoxazole, benzoxazepine, benzothiazepine and benzodiazepine derivatives bearing an aryl sulfonate moiety as antimicrobial and anti-inflammatory agents. Arabian J Chem 2015;20:30.
Li YR, Li C, Liu JC, Guo M, Zhang TY, Sun LP, et al. Synthesis and biological evaluation of 1,3-diaryl pyrazole derivatives as potential antibacterial and anti-inflammatory agents. Bioorg Med Chem Lett 2015;25:5052-7.
Miniyar PB, Barmade MA, Mahajan AA. Synthesis and biological evaluation of 1-(5-(2-chloroquinolin-3-yl)-3-phenyl-1H-pyrazol-1-yl) ethanone derivatives as potential antimicrobial agents. J Saudi Chem Soc 2015;19:655-60.
Nayak N, Ramprasad J, Dalimba U. New INH–pyrazole analogs: Design, synthesis and evaluation of antitubercular and antibacterial activity. Bioorg Med Chem Lett 2015;25:5540.
Raundal HN, Jadhav RP, Patil AA, Bobade VD. Synthesis andbiological screening of novel pyrazole and isoxazole derivatives. Indian J Chem 2015;54B:979-87.
Viveka S, Shama DP, Nagaraja GK, Ballav S, Kerkar S. Design and synthesis of some new pyrazolyl-pyrazolines as potential anti-inflammatory, analgesic and antibacterial agents. Eur J Med Chem 2015;101:442-51.
Wang JX, Zhu ZR, Bai FY, Wang XY, Zhang XX, Xing YH. Molecular design and the optimum synthetic route of the compounds with multi-pyrazole and its derivatives and the potential application in antibacterial agents Polyhedron. Polyhedron 2015;99:59.
Ahmad A, Husain A, Khan SA, Mujeeb M, Bhandari A. Synthesis, antimicrobial and antitubercular activities of some novel pyrazoline derivatives. J Saudi Chem Soc 2016;20:577-84.
Akondi AM, Kantam ML, Trivedi R, Bharatam J, Vemulapalli PB, Bhargava SK, et al. Ce/SiO2 composite as an efficient catalyst for the multicomponent one-pot synthesis of substituted pyrazolones in aqueous media and their antimicrobial activities. J Mol Catal A Chem 2016;411:325-36.
Dabholkar VV, Gavande RP. Synthesis and antimicrobial activities of novel 1,4-benzothiazine derivatives. Arabian J Chem 2016;9:S225-9.
Hafez HN, El-Gazzar BA, Al-Hussain SA. Novel pyrazole derivatives with oxa/thiadiazolyl, pyrazolyl moieties and pyrazolo [4, 3-d]-pyrimidine derivatives as potential antimicrobial and anticancer agents. Bioor Med Chem Lett 2016;26:2428-33.
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.
Nayak N, Ramprasad J, Dalimba U. Synthesis and antitubercular and antibacterial activity of some activefluorine containing quinoline–pyrazole hybrid derivatives. J Fluor Chem 2016;183:59-68.
Refat HM, Fadda AA. Synthesis and antimicrobial activity of some novel hydrazide, pyrazole, triazine, isoxazole and pyrimidine derivatives. J Heterocycl Chem 2016;53:1129-37.
Senbagam R, Vijayakumar R, Rajarajan M, Balaji S, Manikandan V, Vanangamudi G, et al. Synthesis, assessment of substituent effect and antimicrobial activities of (4E)-4-(benzylideneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one compounds. Karbala Int J Mod Sci 2016;2:56.
Ahn M, Gunasekaran P, Rajasekaran G, Kim EY, Lee SJ, Bang G, et al. Pyrazole derived ultra-short antimicrobial peptidomimetics with potent anti-biofilm activity. Eur J Med Chem 2017;125:551-64.
Allison D, Delancey E, Ramey H, Williams C, Alsharif ZA, Al-Khattabi H, et al. Synthesis and antimicrobial studies of novel derivatives of 4-(4-formyl-3-phenyl-1H-pyrazol-1-yl)benzoic acid as potent anti-Acinetobacter baumannii agents. Bioorg Med Chem Lett 2017;27:387-92.
Bhatt HB, Sharma S. Synthesis and antimicrobial activity of pyrazole nucleus containing 2-thioxothiazolidin-4-one derivatives. Arabian J Chem 2017;10:S1590-6.
Chougala BM, Samundeeswari S, Holiyachi M, Shastri LA, Dodamani S, Jalalpure S, et al. Synthesis, characterization and molecular docking studies of substituted 4-coumarinylpyrano[2,3-c]pyrazole derivatives as potent antibacterial and anti-inflammatory agents. Eur J Med Chem 2017;125:101-16.
Mehta HB, Patel PK, Dixit BC, Dixit RB. Synthesis and antimicrobial activities of new mono and bisphenyl linked bispyrazole and bispyrazolone derivatives. Arabian J Chem 2017;10:S1901-12.
Prabhudeva MG, Prabhuswamy M, Kumar AD, Lokanath NK, Naveen S, Kumar KA. Synthesis, crystal and molecular structure and antimicrobial studies of 1-(3-chlorophenyl)-3-(5-chlorothiophen-2-yl)-5-phenyl-4, 5-dihydro-1H-pyrazole. Chem Data Collect 2017;9:80-8.
Rangaswamy J, Kumar HV, Harini ST, Naik N. Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4, 5-dihydro-1H-pyrazole scaffolds: A new class of antimicrobials and antioxidants. Arabian J Chem 2017;10:S2685-696.
Published
How to Cite
Issue
Section
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.
