Substituted Pyrazoles and Their Heteroannulated Analogs-Recent Syntheses and Biological Activities

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Aug 27

PMID 34443583

Citations 7

Authors

Mohamed Ramadan

Ashraf A Aly

Lamiaa E Abd El-Haleem

Mohammed B Alshammari

Stefan Brase

Affiliations

Soon will be listed here.

Abstract

Pyrazoles are considered privileged scaffolds in medicinal chemistry. Previous reviews have discussed the importance of pyrazoles and their biological activities; however, few have dealt with the chemistry and the biology of heteroannulated derivatives. Therefore, we focused our attention on recent topics, up until 2020, for the synthesis of pyrazoles, their heteroannulated derivatives, and their applications as biologically active moieties. Moreover, we focused on traditional procedures used in the synthesis of pyrazoles.

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References

Lv X, Li Q, Ren Z, Chu M, Sun J, Zhang X . (E)-1,3-diphenyl-1H-pyrazole derivatives containing O-benzyl oxime moiety as potential immunosuppressive agents: Design, synthesis, molecular docking and biological evaluation. Eur J Med Chem. 2016; 108:586-593. DOI: 10.1016/j.ejmech.2015.12.020. View

El-Sayed M, Abdel-Aziz N, Abdel-Aziz A, El-Azab A, Asiri Y, Eltahir K . Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors: Molecular docking study. Bioorg Med Chem. 2011; 19(11):3416-24. DOI: 10.1016/j.bmc.2011.04.027. View

Jiang B, Ye Q, Fan W, Wang S, Tu S, Li G . Four-component strategy for selective synthesis of azepino[5,4,3-cd]indoles and pyrazolo[3,4-b]pyridines. Chem Commun (Camb). 2014; 50(46):6108-11. PMC: 4060249. DOI: 10.1039/c4cc00740a. View

Malamas M, Erdei J, Gunawan I, Barnes K, Hui Y, Johnson M . New pyrazolyl and thienyl aminohydantoins as potent BACE1 inhibitors: exploring the S2' region. Bioorg Med Chem Lett. 2011; 21(18):5164-70. DOI: 10.1016/j.bmcl.2011.07.057. View

Kamal A, Shaik A, Jain N, Kishor C, Nagabhushana A, Supriya B . Design and synthesis of pyrazole-oxindole conjugates targeting tubulin polymerization as new anticancer agents. Eur J Med Chem. 2015; 92:501-13. DOI: 10.1016/j.ejmech.2013.10.077. View

Abdellatif K, Fadaly W, Kamel G, Elshaier Y, El-Magd M . Design, synthesis, modeling studies and biological evaluation of thiazolidine derivatives containing pyrazole core as potential anti-diabetic PPAR-γ agonists and anti-inflammatory COX-2 selective inhibitors. Bioorg Chem. 2018; 82:86-99. DOI: 10.1016/j.bioorg.2018.09.034. View

Beyzaei H, Motraghi Z, Aryan R, Zahedi M, Samzadeh-Kermani A . Green One-pot Synthesis of Novel Polysubstituted Pyrazole Derivatives as Potential Antimicrobial Agents. Acta Chim Slov. 2018; 64(4):911-918. DOI: 10.17344/acsi.2017.3609. View

Schenone S, Bruno O, Bondavalli F, Ranise A, Mosti L, Menozzi G . Antiproliferative activity of new 1-aryl-4-amino-1H-pyrazolo[3,4-d]pyrimidine derivatives toward the human epidermoid carcinoma A431 cell line. Eur J Med Chem. 2004; 39(11):939-46. DOI: 10.1016/j.ejmech.2004.07.010. View

Mowbray C, Burt C, Corbau R, Gayton S, Hawes M, Perros M . Pyrazole NNRTIs 4: selection of UK-453,061 (lersivirine) as a development candidate. Bioorg Med Chem Lett. 2009; 19(20):5857-60. DOI: 10.1016/j.bmcl.2009.08.080. View

10.

Babinski D, Aguilar H, Still R, Frantz D . Synthesis of substituted pyrazoles via tandem cross-coupling/electrocyclization of enol triflates and diazoacetates. J Org Chem. 2011; 76(15):5915-23. PMC: 3155889. DOI: 10.1021/jo201042c. View

11.

Ozdemir A, Altintop M, Kaplancikli Z, Can O, Ozkay U, Turan-Zitouni G . Synthesis and evaluation of new 1,5-diaryl-3-[4-(methyl-sulfonyl)phenyl]-4,5-dihydro-1H-pyrazole derivatives as potential antidepressant agents. Molecules. 2015; 20(2):2668-84. PMC: 6272793. DOI: 10.3390/molecules20022668. View

12.

Chou P, Chi Y . Phosphorescent dyes for organic light-emitting diodes. Chemistry. 2006; 13(2):380-95. DOI: 10.1002/chem.200601272. View

13.

Ji G, Wang X, Zhang S, Xu Y, Ye Y, Li M . Synthesis of 3-trifluoromethylpyrazoles via trifluoromethylation/cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent. Chem Commun (Camb). 2014; 50(33):4361-3. DOI: 10.1039/c4cc01280a. View

14.

Alnufaie R, Alsup N, Kc H, Newman M, Whitt J, Chambers S . Design and synthesis of 4-[4-formyl-3-(2-naphthyl)pyrazol-1-yl]benzoic acid derivatives as potent growth inhibitors of drug-resistant Staphylococcus aureus. J Antibiot (Tokyo). 2020; 73(12):818-827. PMC: 7655718. DOI: 10.1038/s41429-020-0341-2. View

15.

Farag A, Mayhoub A, Barakat S, Bayomi A . Synthesis of new N-phenylpyrazole derivatives with potent antimicrobial activity. Bioorg Med Chem. 2008; 16(8):4569-78. DOI: 10.1016/j.bmc.2008.02.043. View

16.

Bondock S, Fadaly W, Metwally M . Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur J Med Chem. 2010; 45(9):3692-701. DOI: 10.1016/j.ejmech.2010.05.018. View

17.

Charris-Molina A, Castillo J, Macias M, Portilla J . One-Step Synthesis of Fully Functionalized Pyrazolo[3,4-b]pyridines via Isobenzofuranone Ring Opening. J Org Chem. 2017; 82(23):12674-12681. DOI: 10.1021/acs.joc.7b02471. View

18.

Sivaramakarthikeyan R, Iniyaval S, Saravanan V, Lim W, Mai C, Ramalingan C . Molecular Hybrids Integrated with Benzimidazole and Pyrazole Structural Motifs: Design, Synthesis, Biological Evaluation, and Molecular Docking Studies. ACS Omega. 2020; 5(17):10089-10098. PMC: 7203960. DOI: 10.1021/acsomega.0c00630. View

19.

Chevallet P, Kilic F, Erol K . Synthesis of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activity. Eur J Med Chem. 2000; 35(6):635-41. DOI: 10.1016/s0223-5234(00)00152-5. View

20.

McElroy W, Tan Z, Ho G, Paliwal S, Li G, Seganish W . Potent and Selective Amidopyrazole Inhibitors of IRAK4 That Are Efficacious in a Rodent Model of Inflammation. ACS Med Chem Lett. 2015; 6(6):677-82. PMC: 4468401. DOI: 10.1021/acsmedchemlett.5b00106. View