Online citations, reference lists, and bibliographies.

Recent Progress On Pyrazole Scaffold-based Antimycobacterial Agents.

Rangappa S Keri, Karam Chand, Thippeswamy Ramakrishnappa, Bhari Mallanna Nagaraja
Published 2015 · Chemistry, Medicine
Cite This
Download PDF
Analyze on Scholarcy
Share
New and reemerging infectious diseases will continue to pose serious global health threats well into the 21st century and according to the World Health Organization report, these are still the leading cause of death among humans worldwide. Among infectious diseases, tuberculosis claims approximately 2 million deaths per year worldwide. Also, agents that reduce the duration and complexity of the current therapy would have a major impact on the overall cure rate. Due to the development of resistance to conventional antibiotics there is a need for new therapeutic strategies to combat Mycobacterium tuberculosis. Subsequently, there is an urgent need for the development of new drug candidates with newer targets and alternative mechanism of action. In this perspective, pyrazole, one of the most important classes of heterocycles, has been the topic of research for thousands of researchers all over the world because of its wide spectrum of biological activities. To pave the way for future research, there is a need to collect the latest information in this promising area. In the present review, we have collated published reports on the pyrazole core to provide an insight so that its full therapeutic potential can be utilized for the treatment of tuberculosis. In this article, the possible structure-activity relationship of pyrazole analogs for designing better antituberculosis (anti-TB) agents has been discussed and is also helpful for new thoughts in the quest for rational designs of more active and less toxic pyrazole-based anti-TB drugs.
This paper references
10.1016/j.ejmech.2004.09.005
Some pyrrole substituted aryl pyridazinone and phthalazinone derivatives and their antihypertensive activities.
Şeref Demirayak (2004)
10.1016/j.ejmech.2011.07.029
A facile four-component sequential protocol in the expedient synthesis of novel 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones in water and their antitubercular evaluation.
Pethaiah Gunasekaran (2011)
10.1136/gut.51.5.756
Rifampicin and treatment of cholestatic pruritus
Alan Frederick Hofmann (2002)
10.1016/j.bmc.2006.02.046
Synthesis of pyrazole-based hybrid molecules: search for potent multidrug resistance modulators.
Palwinder Singh (2006)
Tuberculosis -A comprehensive Clinical reference
H. Simon Schaaf (2009)
10.1021/jm000170m
Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-alpha-selective agonists.
Shaun R. Stauffer (2000)
10.1016/j.bmcl.2012.05.063
Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives.
Ravindra B Pathak (2012)
10.1080/15257779908043068
The synthesis and antiviral activity of 4-fluoro-1-beta-D-ribofuranosyl-1H-pyrazole-3-carboxamide.
Richard Storer (1999)
10.1016/j.bmc.2008.08.016
Synthesis, biological evaluation and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis.
Daniele Castagnolo (2008)
10.1021/jm950377t
Tetrahydronaphthalenes: influence of heterocyclic substituents on inhibition of steroid enzymes P450 arom and P450 17.
Gerald A. Wächter (1996)
10.1016/j.ejmech.2011.08.014
Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity.
Alessandro Balbi (2011)
10.1590/S0042-96862005001100016
Treatment of tuberculosis: present status and future prospects.
Philip C Onyebujoh (2005)
10.1136/bmj.1.4854.130
Bactericidal Activity of Streptomycin and Isoniazid Against Tubercle Bacilli
B. Singh (1954)
10.1016/j.bmcl.2011.10.059
Synthesis, antitubercular evaluation and 3D-QSAR study of N-phenyl-3-(4-fluorophenyl)-4-substituted pyrazole derivatives.
Rupesh C. Khunt (2012)
10.1021/jm0407714
4,5-dihydro-1H-pyrazole derivatives with inhibitory nNOS activity in rat brain: synthesis and structure-activity relationships.
María Encarnación Camacho (2004)
10.1007/s00044-012-0351-0
Synthesis and antitubercular activity of novel pyrazole–quinazolinone hybrid analogs
Unnat Pandit (2012)
10.1586/14787210.3.6.981
Diagnosis of latent Mycobacterium tuberculosis infection: is the demise of the Mantoux test imminent?
James S. Rothel (2005)
10.1378/chest.94.4.845
The role of pyrazinamide in tuberculosis chemotherapy.
Mark A. Steele (1988)
10.1007/s00044-012-0222-8
Coumarinyl pyrazole derivatives of INH: promising antimycobacterial agents
Prashant Aragade (2012)
10.1021/jf802489e
Synthesis and antiviral activities of pyrazole derivatives containing an oxime moiety.
Guiping Ouyang (2008)
10.1021/jm970453n
Medicinal and Pharmaceutical Chemistry. By Harkishan Singh and V. K. Kapoor. Vallabh Prakashan Publishers, Delhi. 1996. viii + 671 pp. 19 × 25 cm. ISBN 81-85731-00-4. $70 (Rs 560).
John L. Neumeyer (1997)
10.1021/JM0611915
Synthesis, crystal structure, and activity of pyrazole-based inhibitors of p38 kinase.
Matthew J. Graneto (2007)
10.1146/annurev.micro.55.1.139
Nonreplicating persistence of mycobacterium tuberculosis.
Lawrence G. Wayne (2001)
10.2174/2211362611208020117
Molecular Properties Prediction and Synthesis of Novel Pyrazoline Carboxamide Analogs as Antitubercular Agents
Mohamed Jawed Ahsan (2012)
10.1016/J.EJMECH.2007.03.030
Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents.
Adnan A Bekhit (2008)
10.1086/355699
Robert Koch A Life In Medicine And Bacteriology
Melanie Keller (2016)
Fipronil: A new soil and foliar broad spectrum insecticide
F. Colliot (1992)
10.1007/s00044-013-0487-6
Green approach towards synthesis of substituted pyrazole-1,4-dihydro,9-oxa,1,2,6,8-tetrazacyclopentano[b]naphthalene-5-one derivatives as antimycobacterial agents
Santosh S. Chobe (2013)
10.1016/j.ejmech.2011.09.035
Synthesis and antimycobacterial evaluation of 3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide analogues.
Mohamed Jawed Ahsan (2011)
10.1016/j.ejmech.2014.07.008
Design, synthesis and characterization of fluoro substituted novel pyrazolylpyrazolines scaffold and their pharmacological screening.
Sharad C. Karad (2014)
10.1592/phco.21.13.1037.34625
Population pharmacokinetics of intravenous and intramuscular streptomycin in patients with tuberculosis.
Ming-Jun Zhu (2001)
10.1039/c3ob27290g
Synthesis and biological evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives.
Paul Horrocks (2013)
Heterocyclic Chemistry, 4th edition, New Age
R. K. Bansal (2013)
10.1016/j.bmc.2009.05.058
Synthesis, biological evaluation, and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis: part 2. Synthesis of rigid pyrazolones.
Daniele Castagnolo (2009)
10.1038/nrd4001
Advances in the development of new tuberculosis drugs and treatment regimens
Alimuddin Zumla (2013)
10.1111/j.1747-0285.2011.01233.x
Synthesis and biological evaluation of some novel 1,4-dihydropyridines as potential antitubercular agents.
Amit R. Trivedi (2011)
10.1021/jf991065s
Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (Alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (Thiadiazoles).
Hao Chen (2000)
10.1086/338342
Molecular evidence of endogenous reactivation of Mycobacterium tuberculosis after 33 years of latent infection.
Troels Lillebaek (2002)
10.1056/NEJM199309093291108
Treatment of multidrug-resistant tuberculosis.
Michael D. Iseman (1993)
10.1016/j.bmcl.2012.02.101
Synthesis and in vitro anticancer and antitubercular activity of diarylpyrazole ligated dihydropyrimidines possessing lipophilic carbamoyl group.
Rama Krishna Yadlapalli (2012)
10.1016/j.bmcl.2011.07.035
Discovery of novel antitubercular 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues.
Mohamed Jawed Ahsan (2011)
10.1016/j.ejmech.2011.05.056
Application of Ullmann and Ullmann-Finkelstein reactions for the synthesis of N-aryl-N-(1H-pyrazol-3-yl) acetamide or N-(1-aryl-1H-pyrazol-3-yl) acetamide derivatives and pharmacological evaluation.
Rebecca Deprez-Poulain (2011)
10.1021/jm00075a014
Nonpeptide angiotensin II antagonists derived from 1H-pyrazole-5-carboxylates and 4-aryl-1H-imidazole-5-carboxylates.
Wallace T. Ashton (1993)
10.1016/j.bmcl.2011.07.068
Synthesis and biological evaluation of some novel N-aryl-1,4-dihydropyridines as potential antitubercular agents.
Amit R. Trivedi (2011)
10.1021/jm070566z
Synthesis, cannabinoid receptor affinity, and molecular modeling studies of substituted 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides.
Romano Silvestri (2008)
Extrapulmonary tuberculosis: an overview.
Marjorie P Golden (2005)
WO2012049161 A1
P. J. Castro (2011)
10.1016/j.bmc.2007.06.004
A new therapeutic approach in Alzheimer disease: some novel pyrazole derivatives as dual MAO-B inhibitors and antiinflammatory analgesics.
Nesrin Gökhan-Kelekçi (2007)
10.1007/s00044-013-0815-x
Discovery of new antitubercular agents by combining pyrazoline and benzoxazole pharmacophores: design, synthesis and insights into the binding interactions
Dharmarajsinh N. Rana (2013)
10.1016/j.ijid.2010.06.017
Tuberculosis: a comprehensive clinical reference. Editors: Schaaf HS, Zumla A. 1014 pages, Elsevier, Inc.; 2009, ISBN 978-1-4160-3988-4.
Douglas Wilson (2010)
10.1007/s00044-013-0803-1
Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents
Vikramdeep Monga (2013)
10.1016/S1074-5521(99)80037-4
Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens.
B E Fink (1999)
Robert Koch - A Life in Medicine and Bacteriology
Thomas D. Brock (1988)
10.2174/13895575113139990078
Pyrazole derivatives as antitumor, anti-inflammatory and antibacterial agents.
J Y Liu (2013)
10.1002/ardp.200800027
Facile one-pot synthesis and antimycobacterial evaluation of pyrazolo[3,4-d]pyrimidines.
Amit Trivedi (2008)
Pyrazoles as Potent Antimicrobial Agents, Lambert
A. Harish (2012)
10.1002/jhet.5570350507
3(2H)‐pyridazinones: Some recent aspects of synthetic and medicinal chemistry
Péater Máatyus (1998)
Medicinal and pharmaceutical chemistry
John Bedford Stenlake (1979)
10.1016/j.bmcl.2011.06.018
Design, synthesis and antimycobacterial evaluation of novel 3-substituted-N-aryl-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide analogues.
Mohamed Jawed Ahsan (2011)
10.1021/JF072077D
Synthetic pyrazole derivatives as growth inhibitors of some phytopathogenic fungi.
Chiara Beatrice Vicentini (2007)
10.1515/9783111576855-009
D
Saskia Bonjour (1824)
10.1016/j.ejmech.2009.01.032
Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities.
Mohamed Abdel-Aziz (2009)
10.1126/science.116.3006.129
The chemical approach to the control of tuberculosis.
H. Herbert. Fox (1952)
10.1016/S0014-827X(01)01098-9
Synthesis and antimycobacterial activity of 5-aryl-1-isonicotinoyl-3-(pyridin-2-yl)-4, 5-dihydro-1H-pyrazole derivatives.
Maria Grazia Mamolo (2001)
10.1016/j.lfs.2013.12.005
Antinociceptive, anti-inflammatory and antipyretic effects of 1.5-diphenyl-1H-Pyrazole-3-carbohydrazide, a new heterocyclic pyrazole derivative.
David do Carmo Malvar (2014)
10.1016/j.ejmech.2013.10.004
Pyrazole scaffold: a remarkable tool in the development of anticancer agents.
Harish Kumar (2013)
10.1016/j.ejmech.2010.05.049
N'-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene] 2/4-substituted hydrazides: synthesis and anticonvulsant activity.
Darpan Kaushik (2010)
10.1021/jm00158a041
Pyrazole derivatives. 5. Synthesis and antineoplastic activity of 3-(2-chloroethyl)-3,4-dihydro-4-oxopyrazolo[5,1-d]-1,2,3, 5-tetrazine-8-carboxamide and related compounds.
C. C. Cheng (1986)
10.1016/j.ejmech.2011.07.007
One-pot synthesis of pyrazoline derivatised carbazoles as antitubercular, anticancer agents, their DNA cleavage and antioxidant activities.
Tasneem Taj (2011)
10.1016/S0968-0896(00)00226-1
Triarylpyrazoles with basic side chains: development of pyrazole-based estrogen receptor antagonists.
Shaun R. Stauffer (2001)
10.1016/j.ejmech.2010.10.005
Synthesis and biological evaluation of N-substituted-3,5-diphenyl-2-pyrazoline derivatives as cyclooxygenase (COX-2) inhibitors.
Rossella Fioravanti (2010)
10.1021/cr2000459
From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles.
Santos Fustero (2011)
10.1177/089686080002000109
Effect of Pyrazinamide and Probenecid on Peritoneal Urate Transport Kinetics during Continuous Ambulatory Peritoneal Dialysis
Sophia Spaia (2000)
10.1016/S0040-4020(01)93171-0
The synthesis of l-α-amino-β-(pyrazolyl-N)-propionic acid in Citrullus vulgaris
Naoyoshi Sugimoto (1960)
10.1016/j.ijantimicag.2008.03.019
Synthesis and in vitro antimycobacterial activity of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-4,5-dihydro-1H-1-(isonicotinoyl) pyrazoles.
Pedro Eduardo Almeida da Silva (2008)
10.1007/BF00771896
Synthesis of isoniazid from 4-cyanopyridine
T. P. Sycheva (2004)
10.1016/B978-1-4160-3988-4.00006-8
Chapter 6 – The genus Mycobacterium and the Mycobacterium tuberculosis complex
John M. Grange (2009)
10.2298/jsc0607713c
Synthesis and selective antitubercular and antimicrobial inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazole derivatives
Praful T. Chovatia (2006)
10.1016/j.bmcl.2008.01.065
Design, synthesis, and evaluation of novel ethambutol analogues.
Raghunandan Yendapally (2008)
10.1093/clinids/5.Supplement_3.S402
History of the development of rifampin.
Piero Sensi (1983)
10.2174/157488410791110797
Clinical pharmacology and lesion penetrating properties of second- and third-line antituberculous agents used in the management of multidrug-resistant (MDR) and extensively-drug resistant (XDR) tuberculosis.
Véronique Dartois (2010)
10.1016/j.microc.2003.12.003
Voltammetric assay of rifampicin and isoniazid drugs, separately and combined in bulk, pharmaceutical formulations and human serum at a carbon paste electrode
E. Hammam (2004)
10.1016/j.bmcl.2010.09.137
Pyrazole derivatives from azines of substituted phenacyl aryl/cyclohexyl sulfides and their antimycobacterial activity.
Ramaiyan Manikannan (2010)
10.1021/ja01134a045
Experimental Chemotherapy of Tuberculosis. II. The Synthesis of Pyrazinamides and Related Compounds1
S. S. Kushner (1952)
10.1021/ml4002248
Identification of 1-[4-Benzyloxyphenyl)-but-3-enyl]-1H-azoles as New Class of Antitubercular and Antimicrobial Agents.
Namrata Anand (2013)



This paper is referenced by
10.1002/psc.3018
Pyrazole amino acids: hydrogen bonding directed conformations of 3-amino-1H-pyrazole-5-carboxylic acid residue.
Anna Kusakiewicz-Dawid (2017)
10.3390/molecules22091447
Solution NMR Studies of Mycobacterium tuberculosis Proteins for Antibiotic Target Discovery
Do-Hee Kim (2017)
10.1039/C7RE00125H
Telescoped continuous flow generation of a library of highly substituted 3-thio-1,2,4-triazoles
Mariana Celestina Frojuello Costa Bernstorff Damião (2017)
10.1007/s11164-016-2851-x
New benzothiazole/benzoxazole-pyrazole hybrids with potential as COX inhibitors: design, synthesis and anticancer activity evaluation
Amany Belal (2017)
10.1007/s00044-016-1678-8
Synthesis and antimicrobial studies of azomethine and N-arylamine derivatives of 4-(4-formyl-3-phenyl-1H-pyrazol-1-yl)benzoic acid as potent anti-methicillin-resistant Staphylococcus aureus agents
J. Brider (2016)
10.1016/j.ejmech.2019.06.070
Evolution in medicinal chemistry of sorafenib derivatives for hepatocellular carcinoma.
Fangmin Chen (2019)
10.1002/slct.201902126
Ultrasonic Cavitation Facilitates Rapid Synthesis of Trisubstituted Pyrazole Scaffolds through Michael Addition/Domino Cyclization
Damodharan Kannan (2019)
10.1039/c5ob02390d
Synthesis of tetra-substituted 5-trifluoromethylpyrazoles via sequential halogenation/palladium-catalyzed C-C and C-N cross-coupling.
Carson W. Wiethan (2016)
10.1016/j.bmcl.2016.12.068
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.
Devin Allison (2017)
10.1016/BS.AIHCH.2017.02.001
The Literature of Heterocyclic Chemistry, Part XV, 2015
Leonid I. Belen’kii (2018)
10.1002/slct.201902262
Synthetic Utilization of α,β‐Chalcone Dibromide In Heterocyclic Chemistry and Stereoselective Debromination
Raj Kamal (2019)
10.1016/J.CDC.2018.06.003
Microwave assisted synthesis, computational study and biological evaluation of novel quinolin-2(1H)-one based pyrazoline hybrids
Shivarudrappa H. Pattanashetty (2018)
10.1155/2020/8021920
Synthesis of New Oxindoles and Determination of Their Antibacterial Properties
Pablo E. Romo (2020)
10.3390/molecules23030592
Synthesis of Dihydrooxepino[3,2-c]Pyrazoles via Claisen Rearrangement and Ring-Closing Metathesis from 4-Allyloxy-1H-pyrazoles
Yoshihide Usami (2018)
10.21608/ejchem.2017.1824.1151
Microwave-Assisted Synthesis and Cytotoxicity Evaluation of Some Novel Pyrazole Containing Imidiazole, Pyrazole, Oxazole, Thiadiazole and Benzochromene derivatives
Hend N. Hafez (2017)
10.1002/EJOC.201800208
Mild and Regioselective Synthesis of 3‐CF3‐Pyrazoles by the AgOTf‐Catalysed Reaction of CF3‐Ynones with Hydrazines
Maxim A Topchiy (2018)
10.1016/J.MOLSTRUC.2017.11.031
Molecular structure, spectroscopic and docking analysis of 1,3-diphenylpyrazole-4-propionic acid: A good prostaglandin reductase inhibitor
Thirumurugan Kavitha (2018)
10.22159/IJPPS.2017V9I11.20469
DEVELOPMENT OF NEW PYRAZOLE HYBRIDS AS ANTITUBERCULAR AGENTS: SYNTHESIS, BIOLOGICAL EVALUATION AND MOLECULAR DOCKING STUDY
Sameer I. Shaikh (2017)
10.1021/acs.jmedchem.7b00793
Substituted N-Phenyl-5-(2-(phenylamino)thiazol-4-yl)isoxazole-3-carboxamides Are Valuable Antitubercular Candidates that Evade Innate Efflux Machinery.
Elisa Azzali (2017)
10.1007/s10593-018-2241-y
Synthetic profiles to pyrazolylquinoxalines
Mohammed Baashen (2018)
10.1007/s11172-018-2104-9
Hydroxy- and alkoxymethylation of polyfluoroalkyl pyrazoles
А. Е. Ivanova (2018)
10.1016/j.bioorg.2019.02.044
Structure-based design, synthesis and biological evaluation of a newer series of pyrazolo[1,5-a]pyrimidine analogues as potential anti-tubercular agents.
Palmi Modi (2019)
10.1016/J.TETLET.2019.01.021
First synthesis and further derivatization of furo[3,2-c]pyrazol-6-ones
Clément Jacob (2019)
10.1016/J.JFLUCHEM.2017.12.011
Regiocontrolled N-, O- and C-methylation of 1-phenyl-3-polyfluoroalkyl-1H-pyrazol-5-ols
Natalia A. Nemytova (2018)
ANTI-TUBERCULAR AND ANTIMICROBIAL ACTIVITIES OF NOVEL HETEROCYCLIC SUBSTITUTED BENZIMIDAZOLE DERIVATIVES
Krishna Veni Chikkula (2018)
10.1039/C6RA20929G
Correction: The first computational study for the oxidative aromatization of pyrazolines and 1,4-dihydropyridines using 1,2,4-triazolinediones: an anomeric-based oxidation
Mahya Kiafar (2016)
10.1016/j.bmcl.2019.04.026
Ultrasonication-ionic liquid synergy for the synthesis of new potent anti-tuberculosis 1,2,4-triazol-1-yl-pyrazole based spirooxindolopyrrolizidines.
Vinay Pogaku (2019)
10.1002/CHIN.201527304
Recent Progress on Pyrazole Scaffold-Based Antimycobacterial Agents
Rangappa S Keri (2015)
10.1007/s11164-016-2848-5
Novel and convenient one-pot strategy for regioselective synthesis of new 5-aryl-3-methyl-1-phenyl-1,2-dihydro-7aH-pyrazolo[3,4-c]pyridazin-7a-ol derivatives
Mehdi Rimaz (2017)
10.1039/C5RA12968K
Theoretical and experimental investigation of the polyeletrophilic β-enamino diketone: straightforward and highly regioselective synthesis of 1,4,5-trisubstituted pyrazoles and pyrazolo[3,4-d]pyridazinones
Michael J. V. da Silva (2016)
10.1007/s11164-018-3260-0
Sodium ascorbate as an expedient catalyst for green synthesis of polysubstituted 5-aminopyrazole-4-carbonitriles and 6-amino-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles
Hamzeh Kiyani (2018)
10.1515/znb-2017-0209
2-Naphthol-pyrazole conjugates as substrates in the Mannich reaction
Gheorghe Roman (2018)
See more
Semantic Scholar Logo Some data provided by SemanticScholar