Recent developments in synthetic chemistry and biological activities of pyrazole derivatives

Muhammad Faisal1, Aamer Saeed1, Sarwat Hussain2, Parsa Dar2, Fayaz Ali Larik1
1Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan
2Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan

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Eftekhari-Sis B, Zirak M and Akbari A 2013 Arylglyoxals in Synthesis of Heterocyclic Compounds Chem. Rev. 113 2958

Ansari A, Ali A and Asif M 2017 Biologically active pyrazole derivatives New New J. Chem. 41 16

Ju Y and Varma R S 2006 Aqueous N-Heterocyclization of Primary Amines and Hydrazines with Dihalides: Microwave-Assisted Syntheses of N-Azacycloalkanes, Isoindole, Pyrazole, Pyrazolidine, and Phthalazine Derivatives J. Org. Chem. 71 135

Zárate-Zárate D, Aguilar R, Hernández-Benitez R I, Labarrios E M, Delgado F and Tamariz J 2015 Synthesis of $${\upalpha }$$-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products Tetrahedron 71 6961

Gordon E M, Barrett R W, Dower W J, Fodor S P A and Gordon M A 1994 Gallop Applications of Combinatorial Technologies to Drug Discovery. 1. Background and Peptide Combinatorial Libraries J. Med. Chem. 37 1385

Ardiansah B 2017 Recent reports on pyrazole-based bioactive compounds as candidate for anticancer agents Asian J. Pharm. Clin. Res. 12 45

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

Pai G and Chattopadhyay A P 2016 N-arylation of nitrogen containing heterocycles with aryl halides using copper nanoparticle catalytic system Tetrahedron Lett. 57 3140

Bekhit A A, Hassan A M, Abd El Razik H A, El-Miligy M M, El-Agroudy E J and Bekhit Ael-D 2015 New heterocyclic hybrids of pyrazole and its bioisosteres: Design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents Eur. J. Med. Chem. 94 30

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

Surendra Kumar R, Arif I A, Ahamed A and Idhayadhulla A 2016 Antiinflammatory and antimicrobial activities of novel pyrazole analogues Saudi J. Biol. Sci. 23 614

Alam R, Wahi D, Singh R, Sinha D, Tandon V, Grover A and Rahisuddin 2016 Design, synthesis, cytotoxicity, Hu Topoll$${\upalpha }$$ inhibitory activity and molecular docking studies of pyrazole derivatives as anticancer agents Bioorg. Chem. 69 77

Shamsuzzaman S, Siddiqui T, Alam M G and Dar A M 2015 Synthesis, characterization and anticancer studies of new steroidal oxadiazole, pyrrole and pyrazole derivatives J. Saudi Chem. Soc. 19 387

Faisal M, Hussain S, Haider A, Saeed A and Larik F A 2018 Assessing the effectiveness of oxidative approaches for the synthesis of aldehydes and ketones from oxidation of iodomethyl group Chem. Pap. 73 1053

Kees K L, Fitzgerald J J, Steiner K E, Mattes, Mihan B, Tosi T, Mondoro D and McCaleb M L 1996 New potent antihyperglycemic agents in db/db mice: synthesis and structure-activity relationship studies of (4-substituted benzyl) (trifluoromethyl)pyrazoles and -pyrazolones J. Med. Chem. 39 3920

Bailey D M, Hansen P E, Hlavac A G, Baizman E R, Pearl J, Defelice A F and Feigenson M E 1985 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants J. Med. Chem. 28 256

Michon V, Penhoat C H D, Tombret F, Gillardin J M, Lepage F and Berthon L 1995 Preparation, structural analysis and anticonvulsant activity of 3- and 5-aminopyrazole $$N$$-benzoyl derivatives Eur. J. Med. Chem. 30 147

Wiley R H and Wiley P 1964 Pyrazolones, Pyrazolidones and Derivatives (New York: Wiley) p. 102

Jamwal A, Javed A and Bhardwaj V 2013 A review on pyrazole derivatives of pharmacological potential J. Pharm. BioSci. 3 114

Haufel J, Breitmaier E 1974 Synthesis of Pyrazolo Heteroaromatic Compounds by Means of 5-Amino-3-methyl-1-phenylpyrazole-4-carbaldehyde Angew. Chem. 13 604

Heller S T and Natarajan S R 2006 1,3-Diketones from Acid Chlorides and Ketones: A Rapid and General One-Pot Synthesis of Pyrazoles Org. Lett. 8 2675

Faisal M, Saeed A, Larik F A, Ghumro S A, Rasheed S and Channar P A 2018 WOWS Sol–Gel Based Synthesis and Structural, Morphological, Electrical and Magnetic Characterization of Co-Sm Doped M-Type Barium Hexaferrite Materials J. Electron. Mater. 47 7011

Wyde P R, Gilbert B E and Ambrose M W 1989 Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo Antiviral Res. 11 15

Bakr F A W and Kamal M D 2012 Synthesis and applications of bipyrazole systems ARKIVOC 1 491

Xia M, Zhang T, Wang Y and Xing G 2006 “Tetrahydroindole derivatives and tetrahydroindazole derivatives, and use thereof” WO 2006133634

Rosati O, Curini M, Marcotullio M C, Macchiarulo A, Perfumi M, Mattioli L, Rismondo F and Cravotto G 2007 Synthesis, docking studies and anti-inflammatory activity of 4,5,6,7-tetrahydro-2H-indazole derivatives Bioorg. Med. Chem. 15 3463

Nakhai A 2009 In Synthetic studies of Nitrogen containing heterocycles, particularly pyrazole and benzotriazine derivatives (Biovetenskaper och näringslära/Biosciences and Nutrition) (Stockholm: Karolinska Institutet) p. 111

Ansari A, Ali A and Asif M 2017 biologically active pyrazole derivatives New J. Chem. 41 16

Md J A, Ozair A, Perwaiz A and Mohammad J N 2015 A Review on Pyrazole chemical entity and Biological Activity International J. Pharm. Sci. Res. 6 1433

Dewangan D, Kumar T, Alexander A, Nagori K and Tripathi D K 2003 Pyrazole: Their Chemistry and Pharmacological Potentials: A Review Curr. Pharmac. Res. Sat. 4 369

Arunachalam S, Gowrishankar N L, Krishnan A, Prakash M, Muhsin T, Naseena U and Poornima G 2018 A brief review on pyrazole derivatives possesing variouspharmacological and biological evaluation World J. Pharm. Pharma. Sci. 5 1496

Raj K B 2007 Heterocyclic Chemistry $$4^{{\rm th}}$$ edn. (New International Publishers)

Krygowski T M, Anulewicz R, Cyrafiski M K, Puchala A, Rasata D 1998 Separation of the energetic and geometric contribution to the aromaticity. Part IX. Aromaticity of pyrazoles in dependence on the kind of substitution Tetrahedron 54 12295

Behr L C, Fusco R and Jarboe C H 1967 The Chemistry of Heterocyclic Chemistry: Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings (Wiley & Sons: London) p. 113

Ragab E A, Metwally N H and Mohamed M S 2017 Synthesis of some novel pyrazolo [1, 5-a] quinazolines and their fused derivatives Synth. Commun. 2 148

Arunachalam S, Gowrishankar N L, Krishnan A, Prakash M, Muhsin T, Naseena U and Poornima G 2018 A brief review on pyrazole derivatives possessing various pharmacological and biological evaluation World J. Pharm. Pharma. Sci. 5 1496

Ciccolini C, Mari M, Lucarini S, Mantellini F, Piersanti G and Favi G 2018 Polycyclic Indolines by an Acid-Mediated Intramolecular Dearomative Strategy: Reversing Indole Reactivity in the Pictet-Spengler-Type Reaction Adv. Synth. Cat. 360 4060

Desalegn N 2005 Kinetic Studies of The Thermolysis of 3-Halogenated-4, 5-Dihydro-3h-Pyrazoles (Georgia State University: Atlanta, Georgia) p. 84

Corradi A, Leonelli C, Rizzuti A, Rosa R, Veronesi P, Grandi R, Baldassari S and Villa C 2007 New “green” approaches to the synthesis of pyrazole derivatives Molecules 7 1482

Beyzaei H, Motraghi Z, Aryan R, Zahedi M M and Samzadeh-Kermani A 2017 Green One-pot Synthesis of Novel Polysubstituted Pyrazole Derivatives as Potential Antimicrobial Agents Acta Chim. Slov. 64 4 911

Motamedi A, Sattari E, Mirzaei P, Armaghan M and Bazgir A 2014 An efficient and green synthesis of phthalide-fused pyrazole and pyrimidine derivatives Tetrahedron Lett. 55 2366

Kangani M, Hazeri N, Mghsoodlou M T, Habibi-khorasani S M and Salahi S 2015 Green synthesis of 1, 4-dihydropyrano [2, 3-c] pyrazole derivatives using maltose as biodegradable catalyst Res. Chem. Inter. 4 2513

Soltanzadeh Z, Imanzadeh G, Noroozi-Pesyan N and Şahin E 2017 Green synthesis of pyrazole systems under solvent-free conditions Green Chem. Lett. Rev. 3 148

Khurana J M and Chaudhary A 2012 Efficient and Green Synthesis of 4 H-pyrans and 4 H-pyrano [2, 3-c] Pyrazoles Catalyzed by Task-specific Ionic Liquid [bmim] OH under Solvent-free Conditions Green Chem. Lett. Rev. 4 633

Zolfigol M A, Afsharnadery F, Baghery S, Salehzadeh S and Maleki F 2015 Catalytic applications of [HMIM] C (NO 2) 3: as a nano ionic liquid for the synthesis of pyrazole derivatives under green conditions and a mechanistic investigation with a new approach RSC Adv. 92 75555

Safaei S, Mohammadpoor-Baltork I, Khosropour A R, Moghadam M, Tangestaninejad S and Mirkhani V 2013 Copper (II) ionic liquid catalyzed cyclization–aromatization of hydrazones with dimethyl acetylenedicarboxylate: a green synthesis of fully substituted pyrazoles New J. Chem. 7 2037

Shelke S N, Mhaske G R, Bonifácio V D and Gawande M B 2012 Green synthesis and anti-infective activities of fluorinated pyrazoline derivatives Bioorg. Med. Chem. Lett. 22 5727

Maddila S, Rana S, Pagadala R, Kankala S, Maddila S and Jonnalagadda S B 2015 Synthesis of pyrazole-4-carbonitrile derivatives in aqueous media with $$\text{ CuO/ZrO }_{2}$$ as recyclable catalyst Cat. Comm. 61 26

Heravi M M and Daraie M 2016 A novel and efficient five-component synthesis of pyrazole based pyrido [2, 3-d] pyrimidine-diones in water: a triply green synthesis Molecules 4 441

Siddiqui Z N and Farooq F 2012 Silica supported sodium hydrogen sulfate ($$\text{ NaHSO }_{4}$$–$$\text{ SiO }_{2}$$): A novel, green catalyst for synthesis of pyrazole and pyranyl pyridine derivatives under solvent-free condition via heterocyclic $${\upbeta }$$-enaminones J. Mol. Cat. A: Chem. 363 451

Zonouz A M., Eskandari I and Khavasi H R 2012 A green and convenient approach for the synthesis of methyl 6-amino-5-cyano-4-aryl-2, 4-dihydropyrano [2, 3-c] pyrazole-3-carboxylates via a one-pot, multi-component reaction in water Tetrahedron Lett. 41 5519

Al-Matar, H M, Khalil K D, Adam A Y and Elnagdi M H 2010 Green one pot solvent-free synthesis of pyrano [2, 3-c]-pyrazoles and pyrazolo [1, 5-a] pyrimidines Molecules 9 6619

Polshettiwar V and Varma R S 2010 Nano-organocatalyst: magnetically retrievable ferrite-anchored glutathione for microwave-assisted Paal–Knorr reaction, aza-Michael addition, and pyrazole synthesis Tetrahedron 5 1091

Kumari K, Raghuvanshi D S, Jouikov V and Singh K N 2012 Sc $$\text{(OTf) }_{3}$$-catalyzed, solvent-free domino synthesis of functionalized pyrazoles under controlled microwave irradiation Tetrahedron Lett. 9 1130

Hasaninejad A and Firoozi S 2013 Catalyst-free, one-pot, three-component synthesis of 5-amino-1, 3-aryl-1$$ H $$-pyrazole-4-carbonitriles in green media Mol. Div. 3 459

Saha A, Payra S and Banerjee S 2015 One-pot multicomponent synthesis of highly functionalized bio-active pyrano [2, 3-c] pyrazole and benzylpyrazolyl coumarin derivatives using ZrO 2 nanoparticles as a reusable catalyst Green Chem. 5 2859

Khurana J M, Nand B and Kumar S 2011 Rapid synthesis of polyfunctionalized pyrano [2, 3-c] pyrazoles via multicomponent condensation in room-temperature ionic liquids Synth. Comm. 3 405

Srivastava M, Rai P, Singh J and Singh J 2013 An environmentally friendlier approach—ionic liquid catalysed, water promoted and grinding induced synthesis of highly functionalised pyrazole derivatives RSC Adv. 38 16994

Frizzo C P, Marzari M R, Buriol L, Moreira D N, Rosa F A, Vargas P S, Zanatta N, Bonacorso H G and Martins M A 2009 Ionic liquid effects on the reaction of $${\upbeta }$$-enaminones and tert-butylhydrazine and applications for the synthesis of pyrazoles Cat. Comm. 15 1967

Hany F A and Mohamed H E 2009 Recent developments in aminopyrazole chemistry ARKIVOC 1 198

Von R 1849 Pyrrole reaction R. Chem. Ber. 27 685

Taylor E C and Hartke K S J 1959 The Reaction of Malononitrile with Substituted Hydrazines: New Routes to 4-Aminopyrazolo[3,4-d]pyrimidines Am. Chem. Soc. 81 2456

Eberts F S 1961 1, 1, 3-Tricyano-2-amino-1-propene (U-9189), a Biologically active component of aqueous solutions of malononitrile Arch. Biochem. Biophys. 95 305

Shruti K, Krunal P, Nilesh D, Palak S, Parita S and Shruti Kushwah 2012 Synthesis of pyrazole azo dyes Ijprbs 2 287

Barry H M, Mark H, Bury and Roy M 2001 “Pyyrole synthesis” U.S. Patent 6200371 B1

Hamid M H, Nada M A and Huwaida M H 2010 Synthesis of pyrazole Nat. Sci. 2 1349

Sabir H, Deepika K and Mukta S 2010 Synthesis and Biological Evaluation of Some New 1-substituted-3,5-dimethyl-4-[(Substituted Phenyl) Diazenyl] Pyrazole Derivatives Am.-Eur. J. Sci. Res. 4 257

Ibrahim M K A, Ramiz M M M and El-Ghandour A H H 1989 Synthesis of n-(azolyl)-alpha-ketohydrazidoyl chlorides, azolotriazole and azolotriazine derivatives J. Chem. Soc. Pak. 11 291

Swelam S A, El-Said N S, Aly A S and Abdel-Fatth A M 2009 Production of pyrans, pyridazines, pyrimidines, pyrazines and triazine compounds using benzoylacetonitriles as a precursor Inter. J. Pharm. Tech. Res. 1 445

Ahmed E, Fadda A A, Khalil A M, Ameen T A E and Farid A B 2009 Synthesis, antitumor evaluation, molecular modeling and quantitative structure-activity relationship (QSAR) of some novel arylazopyrazolodiazine and triazine analogs Bioorg. Med. Chem. 17 5096

Niţu S V, Bercean V N, Badea V and Csunderlik C 2008 Azoic Compounds Obtained from 1H-4-ethoxycarbonyl-3-methyl-5-aminopyrazole and 1, 3-disubstituted 1H-pyrazol-5-ones Chem. Bull. 53 1

Metwally M A, Gouda M A, Ammar N H and Khalil A M 2012 Inter. J. Mod. Org. Chem. 1 96

Fati K and Fikret K 2008 Synthesis of some novel pyrazolo [5, 1-c][1, 2, 4] triazine derivatives and investigation of their absorption spectra Dye Pig. 76 97

Fati K and Fikret K 2008 Synthesis and absorption spectra of some novel heterocyclic disazo dyes derived from pyridone and pyrazolone derivatives Dye Pig. 76 147

Ahmed A F, Samir B, Ramy R and Hassan A 2008 Cyanoacetamide Derivatives as Synthons in Heterocyclic Synthesis Turk. J. Chem. 32 259

Abu-Shanab F A, Mousa S A, Eshak E A, Sayed A Z and Al-Harrasi A 2011 Dimethylformamide dimethyl acetal (DMFDMA) in heterocyclic synthesis: Synthesis of polysubstituted pyridines, pyrimidines, pyridazine and their fused derivatives Int. J. Org. Chem. 1 207

Abdel-Zaher A E, H H D, Nouria A A and Elnagdia M H 2007 Chemistry of carbofunctionally substituted hydrazones ARKIVOC 2 272

Abunada N M, Hassaneen, Kandile N G and Miqdad O A 2008 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 13 1011

Chawla R, Sahoo U, Arora A, Sharma P C and Radhakrishnan V 2010 Microwave assisted synthesis of some novel 2-pyrazoline derivatives as possible antimicrobial agents Acta Pol. Pharm. 67 1 55

Jadhav S B, Shastri R A, Gaikwad K V and Gaikwad S V 2009 Synthesis and antimicrobial studies of some novel pyrazoline and isoxazoline derivatives Eur. J. Chem. 6 83

Kaur H, Kumar S, Singh I and Kumar A 2010 Synthesis, characterization and antibacterial activity of various substituted oxadiazolylpyrazolinyl/isoxa-zolinylcoumarin derivatives Int. J. Pharm. Sci. Res. 1 58

Faidallah H M, Rostom S A and Al-Saadi M S 2010 Synthesis and biological evaluation of some new substituted fused pyrazole ring systems as possible anticancer and antimicrobial agents JKAU Sci 22 177

Dean A. Heathcote, Hetal P, Sebastian H B K, Pascale H, Manikandan P, Mary A, Seshu K K, Ashutosh S J,Bodo S, Marion B, Andreas B, Jan B and Alekasandra S 2010 A novel pyrazolo [1, 5-a] pyrimidine is a potent inhibitor of cyclin-dependent protein kinases 1, 2, and 9, which demonstrates antitumor effects in human tumor xenografts following oral administration J. Med. Chem. 53 8508

Zask A, Verheijen J C, Curran K, Kaplan J, Richard D J, Nowak P, Malwitz D J, Brooijmans N, Bard J, Svenson K and Lucas J 2009 ATP-competitive inhibitors of the mammalian target of rapamycin: design and synthesis of highly potent and selective pyrazolopyrimidines J. Med. Chem. 52 5013

Guertin D A and Sabatini D M 2007 Defining the Role of mTOR in Cancer Cancer Cell 12 9

Chiang G G and Abraham R T 2007 Targeting the mTOR signaling network in cancer Trends Mol. Med. 13 433

Bhaskar V H and Mohitea P B 2011 Synthesis analgesic, anti-inflammatory and antimicrobial activities of some 1-[5-(substituted phenyl)-4,5-dihydro-1hpyrazol-3-yl]-5-phenyl-1h-tetrazole J. Optoelectron. Biomed. Mat. 3 7

Venkataraman S, Jain S, Shah K and Upmanyu N 2010 Synthesis and biological activity of some novel pyrazolines Acta Pol. Pharm. 67 361

Sridevi C, Balaji K and Naidu A 2011 Synthesis and pharmacological evaluation of some phenylpyrazolo indoquinoxaline derivatives E-J. Chem. 8 924

Menozzi G, Merello L, Fossa P, Silvia S, Angelo R, Luisa M, Francesco B, Roberta L, Chiara M, Valeria M, Paolo L, C and Elena T 2009 Synthesis and evaluation of electron-rich curcumin analogues Bioorg. Med. Chem. Lett. 1 360

Ayoob B, Maryam M K and Ali A S 2008 One-pot synthesis and antibacterial activities of pyrazolo[4’,3’:5,6]pyrido[2,3-d]pyrimidine-dione derivatives Bioorg. Med. Chem. Lett. 21 5800

Kumar R, Malik S and Chandra R 2009 Synthesis and antimicrobial activity of 4-[5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl]-dihydropyridines and 4-[5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl]-3, 4-dihydropyrimidin-2-ones Indian J. Chem. B 49 718

Sahu S K, Banerjee M, Samantray A, Behera C and Azam M A 2008 Synthesis and antiviral evaluation of some new pyrazole and pyrazolopyrimidine derivatives Trop J. Pharm. Res. 7 961

Sivakumar K K, Rajasekaran A, Ponnilavarasan I, Somasundaram A and Kamalaveni S 2010 Synthesis and evaluation of anti-microbial analgesic activity of some (4Z) -3-methyl-1-[(2-oxo-2H-chromen-4-yl) carbonyl] -1H-pyrazole-4, 5-dione-4- [(substitutedphenyl) hydrazone] Der Pharm. Lett. 2 211

Dias L R and Salvador R R S 2012 Pyrazole Carbohydrazide Derivatives of Pharmaceutical Interest Pharmaceuticals 5 317

Prathap K J, Himaja M, Mali S V, Karigar A A and Sikarwar M S 2011 Synthesis of New 3-Aryl-1-(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)-1H-pyrazole-4-carbaldehydes as Antitubercular Agents Drug Inv. 3 10

El-Sabbagh O I, Baraka M M, Ibrahim S M, Pannecouque P, Andrei G, Snoeck R, Balzarini J and Rashad A 2009 Synthesis and antiviral activity of new pyrazole and thiazole derivatives Eur. J. Med. Chem. 44 3746

Rashad A E, Hegab M I, Abdel-Megeid R E,Micky J A and Abdel-Megeid F M E 2008 Synthesis and antiviral evaluation of some new pyrazole and fused pyrazolopyrimidine derivatives Bioorg. Med. Chem. 16 7102

El-Badawi S M A and Bakhiet A O 2012 Chemotherapeutic and economic potentials of some lactiferous plants J. Med. Plant Res. 6 3278

Priyadarsini P, Ujwala, B, Venkata R C and Madhava R V 2012 Synthesis and antimicrobial activity of some novel pyrazoles Der Pharm. Lett. 4 1123

Hassan S Y 2013 Synthesis, Antibacterial and antifungal activity of some new pyrazoline and pyrazole derivatives Molecules 18 2683

Turan Z G, Chevallet P, Kilic T S and Erolic K 2000 Synthesis of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activityEur. J. Med. Chem. 35 635

Silver K S and Soderlund D M 2005 Action of pyrazoline type insecticides at neuronal target side Pestic. Biochem. Physiol. 81 136

Godey M C M, Fighera M R, Souza F R, Rubin M A, Oliveira M R, Zennata N and Mello C F 2004 $${\upalpha }2$$-Adrenoceptors and 5-HT receptors mediate the antinociceptive effect of new pyrazolines, but not of dipyrone Eur. J. Pharma. 496 93

Chimenti P, Granese A, Rivanera D, Lilli D, Scaltrito M M and Brenciaglia M I 2005 Synthesis and in vitro selective anti-Helicobacter pylori activity of pyrazoline derivatives Bioorg. Med. Chem. Lett. 15 603

Salgin-Goksen U, Yabanoglu-Ciftci S, Ercan A, Yelekci K, Ucar G and Gokhan-Kelekci N 2013 Evaluation of selective human MAO inhibitory activities of some novel pyrazoline derivatives J. Neural. Transm. 120 863

Bonesi M, Loizzo M R, Statti G A, Michel S, Tillequin F and Menichini 2010 The synthesis and angiotensin converting enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives Bioorg. Med. Chem. Lett. 20 1990

Gao M, Wang M, Miller K D and Zheng Q H 2001 Synthesis and preliminary in vitro biological evaluation of new carbon-11-labeled celecoxib derivatives as candidate PET tracers for imaging of COX-2 expression in cancer Eur. J. Med. Chem. 46 4760

Mumolo M, Zumieri D, Fulgani V, Vio L and Bunfi E 2001 Synthesis and antimycobacterial activity of 5-aryl-1-isonicotinyl-3-(pyridyl-2-yl)-4,5-dihydro-1Hpyrazole derivatives Frmaco 56 593

Ozdamir A and Zitouni G T 2008 Novel analogues of 2- pyrazoline: Synthesis, characterization and antimycobacterial evaluation Turk. J. Chem. 32 529

Zampieri D, Mamolo M G, Lourini E, Sciolino G, Bunfi E and Vio L 2008 Antifungal and antimycobacterial activity of 1-(3, 5-diaryl-4, 5-dihydro-1H-pyrazol-4-yl)-1H-imidazole derivatives Bioorg. Med. Chem. 16 4516

Sreenivasa G M, Jaychandran E, Shivkumar B, Kumar K J and Vijay K V 2009 Synthesis of bioactive molecule fluoro benzothiazole comprising potent heterocyclic moieties for anthelmintic activity Arch. Pharm. Sci. Res. 1 150

Faisal M, Larik F A and Saeed A 2018 A highly promising approach for the one-pot synthesis of biscoumarins using HY zeolite as recyclable and green catalyst J. Porous Mater. 26 455

Charles E M, Catherine B, Romuald C, Simon G, Michael H, Manos P, Isabelle T, David A P, Faye J Q, Matthew D S, Paul A S and Rob W 2009 Pyrazole NNRTIs 4: selection of UK-453,061 (lersivirine) as a development candidate Bioorg. Med. Chem. Lett. 19 5857

Kasralikar H M, Jadhavar S C, Goswami S V, Kaminwar N S and Bhusare S R 2019 Design, Synthesis and Molecular Docking of Pyrazolo [3, 4d] thiazole hybrids as Potential Anti-HIV-1 NNRT Inhibitors Bioorg. Chem. 86 437

Vekariya M K, Vekariya R H, Patel K D, Raval N P, Shah P U, Rajani D P and Shah N K 2018 Pyrimidine-Pyrazole Hybrids as Morpholinopyrimidine-Based Pyrazole Carboxamides: Synthesis, Characterisation, Docking, ADMET Study and Biological Evaluation Chem. Select. 3 6998

Nassar E 2010 Synthesis, (in vitro) Antitumor and Antimicrobial Activity of some Pyrazoline, Pyridine, and Pyrimidine Derivatives Linked to Indole Moiety J. Am. Sci. 6 8

Feng J, Qi H, Sun X, Feng S, Liu Z, Song Y and Qiao X 2018 Synthesis of novel pyrazole derivatives as promising DNA-binding agents and evaluation of antitumor and antitopoisomerase I/II activities Chem. Pharm. Bull. c18 546

Pasin J S M, Ferreria A P O, Saraiva A L L, Ratzlaff V, Andrighetto R, Machado P, Marchesam S, Zanette R A and Martins M A P 2010 Antipyretic and antioxidant activities of 5- trifluoromethyl-4,5-dihydro-1H-pyrazoles in rats Braz. J. Med. Biol. Res. 43 1193

Chimenti F, Bolasco A, Manna F, Secci D, Chimenti P, Befani O, Turini P, Giovannini V, Mondovì B, Cirilli R and Torre F L 2004 Synthesis and selective inhibitory activity of 1-acetyl-3, 5-diphenyl-4, 5-dihydro-(1 H)-pyrazole derivatives against monoamine oxidase J. Med. Chem. 47 2071

Abdel-Aziz M, Abuo-Rahman G E A and Hassan A A 2009 Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities Eur. J. Med. Chem. 44 3480

Wu Y, Huang Y P, Zhou S C, Tan Y Q, Xu B G, Liang Z and Deng X Q 2018 Synthesis of 1, 3-Diaryl Pyrazole Derivatives and Evaluation of Anticonvulsant and Antimicrobial Activities Lat. Am. J. Pharm. 37 1017

Dileep Kumar A, Bharath S, Dharmappa R N, Naveen S, Lokanath N K and Ajay Kumar K 2018 Design, synthesis and spectroscopic and crystallographic characterisation of novel functionalized pyrazole derivatives: biological evaluation for their cytotoxic, angiogenic and antioxidant activities Res. Chem. Intermediat. 44 5635

Cheng L, Shen Z H, Xu T M, Tan C X, Weng J Q, Han L, Peng W L and Liu X H 2018 Synthesis and Nematocidal Activity of N-Substituted 3-Methyl-1H-pyrazole-4-carboxamide Derivatives Against Meloidogyne incognita J. Heterocycl. Chem. 55 946

Fei C, Chen Y, Jiang Z and Jiang D 2018 Thioether-bridged arylalkyl-linked N-phenylpyrazole derivatives: Design, synthesis, insecticidal activities, structure-activity relationship and molecular-modeling studies Bioorg. Med. Chem. Lett. 28 1792

Dai H, Huang M, Qian J, Liu J, Meng C, Li Y, Ming G, Zhang T, Wang S, Shi Y and Yao Y 2019 Excellent antitumor and antimetastatic activities based on novel coumarin/pyrazole oxime hybrids Eur. J. Med. Chem. 166 470