Synthesis of Antimicrobial Benzimidazole-Pyrazole Compounds and Their Biological Activities

Overview

Journal Antibiotics (Basel)

Specialty Pharmacology

Date 2021 Aug 27

PMID 34439052

Citations 22

Authors

Maria Marinescu

Affiliations

Soon will be listed here.

Abstract

The synthesis of new compounds with antimicrobial and antiviral properties is a central objective today in the context of the COVID-19 pandemic. Benzimidazole and pyrazole compounds have remarkable biological properties, such as antimicrobial, antiviral, antitumor, analgesic, anti-inflammatory, anti-Alzheimer's, antiulcer, antidiabetic. Moreover, recent literature mentions the syntheses and antimicrobial properties of some benzimidazole-pyrazole hybrids, as well as other biological properties thereof. In this review, we aim to review the methods of synthesis of these hybrids, the antimicrobial activities of the compounds, their correlation with various groups present on the molecule, as well as their pharmaceutical properties.

Citing Articles

Molecular modeling studies, in vitro antioxidant and antimicrobial assay and BSA affinity of novel benzyl-amine derived scaffolds as CYP51B inhibitors.

Marjanovic J, Matic J, Milanovic Z, Divac V, Kosanic M, Petkovic M Mol Divers. 2024; .

PMID: 39656377 DOI: 10.1007/s11030-024-11074-6.

Synthesis, antimicrobial, antioxidant, tyrosinase inhibitory activities, and computational studies of novel chromen[2,3-c]pyrazole derivatives.

Loganathan V, Mani A, Akbar I, Ahamed A, Alodaini H, Gerbu D Mol Divers. 2024; .

PMID: 39623135 DOI: 10.1007/s11030-024-11051-z.

New 3-Hydroxypyridine-4-one Analogues: Their Synthesis, Antimicrobial Evaluation, Molecular Docking, and ADME Prediction.

Sadeghian S, Zare F, Saghaie L, Fassihi A, Zare P, Sabet R Med Chem. 2024; 20(9):900-911.

PMID: 38840401 DOI: 10.2174/0115734064307744240523112710.

A new polyazomethine-based pyrazole moiety and its reinforced nanocomposites @ ZnO for antimicrobial applications.

Hakami A, Alorfi H, Farghaly T, Hussein M Des Monomers Polym. 2024; 27(1):1-20.

PMID: 38756722 PMC: 11097710. DOI: 10.1080/15685551.2024.2352897.

Investigation of Structural and Antibacterial Properties of WS-Doped ZnO Nanoparticles.

Beytur S, Essiz S, Ozugur Uysal B ACS Omega. 2024; 9(3):4037-4049.

PMID: 38284036 PMC: 10809239. DOI: 10.1021/acsomega.3c09041.

References

Ai X, Pu X, Yi Y, Liu Y, Xu S, Liang J . Synthesis and Pharmacological Evaluation of Novel Pleuromutilin Derivatives with Substituted Benzimidazole Moieties. Molecules. 2016; 21(11). PMC: 6273978. DOI: 10.3390/molecules21111488. View

Bistrovic A, Krstulovic L, Harej A, Grbcic P, Sedic M, Kostrun S . Design, synthesis and biological evaluation of novel benzimidazole amidines as potent multi-target inhibitors for the treatment of non-small cell lung cancer. Eur J Med Chem. 2017; 143:1616-1634. DOI: 10.1016/j.ejmech.2017.10.061. View

Breijyeh Z, Jubeh B, Karaman R . Resistance of Gram-Negative Bacteria to Current Antibacterial Agents and Approaches to Resolve It. Molecules. 2020; 25(6). PMC: 7144564. DOI: 10.3390/molecules25061340. View

Kim T, Yang H, Park B, Jung S, Park J, Park K . Discovery of benzimidazole derivatives as modulators of mitochondrial function: A potential treatment for Alzheimer's disease. Eur J Med Chem. 2016; 125:1172-1192. DOI: 10.1016/j.ejmech.2016.11.017. View

Zhu W, Bao X, Ren H, Da Y, Wu D, Li F . N-Phenyl indole derivatives as AT1 antagonists with anti-hypertension activities: Design, synthesis and biological evaluation. Eur J Med Chem. 2016; 115:161-78. DOI: 10.1016/j.ejmech.2016.03.021. View

Santos N, Carreira A, Silva V, Braga S . Natural and Biomimetic Antitumor Pyrazoles, A Perspective. Molecules. 2020; 25(6). PMC: 7144110. DOI: 10.3390/molecules25061364. View

Al-Azmi A, Mahmoud H . Facile Synthesis and Antimicrobial Activities of Novel 1,4-Bis(3,5-dialkyl-4-1,2,4-triazol-4-yl)benzene and 5-Aryltriaz-1-en-1-yl-1-phenyl-1-pyrazole-4-carbonitrile Derivatives. ACS Omega. 2020; 5(17):10160-10166. PMC: 7203961. DOI: 10.1021/acsomega.0c01001. View

Charifson P, Grillot A, Grossman T, Parsons J, Badia M, Bellon S . Novel dual-targeting benzimidazole urea inhibitors of DNA gyrase and topoisomerase IV possessing potent antibacterial activity: intelligent design and evolution through the judicious use of structure-guided design and structure-activity relationships. J Med Chem. 2008; 51(17):5243-63. DOI: 10.1021/jm800318d. View

Mandour A, El-Sawy E, Ebaid M, Hassan S . Synthesis and potential biological activity of some novel 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles. Acta Pharm. 2012; 62(1):15-30. DOI: 10.2478/v10007-012-0007-0. View

10.

Karaburun A, Kaya Cavusoglu B, Acar Cevik U, Osmaniye D, Saglik B, Levent S . Synthesis and Antifungal Potential of Some Novel Benzimidazole-1,3,4-Oxadiazole Compounds. Molecules. 2019; 24(1). PMC: 6337182. DOI: 10.3390/molecules24010191. View

11.

Onnis V, Demurtas M, Deplano A, Balboni G, Baldisserotto A, Manfredini S . Design, Synthesis and Evaluation of Antiproliferative Activity of New Benzimidazolehydrazones. Molecules. 2016; 21(5). PMC: 6273944. DOI: 10.3390/molecules21050579. View

12.

Liu H, Gao W, Tangadanchu V, Zhou C, Geng R . Novel aminopyrimidinyl benzimidazoles as potentially antimicrobial agents: Design, synthesis and biological evaluation. Eur J Med Chem. 2017; 143:66-84. DOI: 10.1016/j.ejmech.2017.11.027. View

13.

Domiati S, El-Mallah A, Ghoneim A, Bekhit A, El Razik H . Evaluation of anti-inflammatory, analgesic activities, and side effects of some pyrazole derivatives. Inflammopharmacology. 2016; 24(4):163-72. DOI: 10.1007/s10787-016-0270-7. View

14.

Bondock S, Khalifa W, Fadda A . Synthesis and antimicrobial activity of some new 4-hetarylpyrazole and furo[2,3-c]pyrazole derivatives. Eur J Med Chem. 2011; 46(6):2555-61. DOI: 10.1016/j.ejmech.2011.03.045. View

15.

Whitt J, Duke C, Ali M, Chambers S, Khan M, Gilmore D . Synthesis and Antimicrobial Studies of 4-[3-(3-Fluorophenyl)-4-formyl-1-pyrazol-1-yl]benzoic Acid and 4-[3-(4-Fluorophenyl)-4-formyl-1-pyrazol-1-yl]benzoic Acid as Potent Growth Inhibitors of Drug-Resistant Bacteria. ACS Omega. 2019; 4(10):14284-14293. PMC: 6733178. DOI: 10.1021/acsomega.9b01967. View

16.

Corona A, Onnis V, Deplano A, Bianco G, Demurtas M, Distinto S . Design, synthesis and antiviral evaluation of novel heteroarylcarbothioamide derivatives as dual inhibitors of HIV-1 reverse transcriptase-associated RNase H and RDDP functions. Pathog Dis. 2017; 75(6). PMC: 6433301. DOI: 10.1093/femspd/ftx078. View

17.

Wang Y, Shi T, Zhu H, Liu C . Synthesis, biological evaluation and molecular docking of benzimidazole grafted benzsulfamide-containing pyrazole ring derivatives as novel tubulin polymerization inhibitors. Bioorg Med Chem. 2019; 27(3):502-515. DOI: 10.1016/j.bmc.2018.12.031. View

18.

Gaba M, Singh S, Mohan C . Benzimidazole: an emerging scaffold for analgesic and anti-inflammatory agents. Eur J Med Chem. 2014; 76:494-505. DOI: 10.1016/j.ejmech.2014.01.030. View

19.

Marquez-Navarro A, Nogueda-Torres B, Hernandez-Campos A, Soria-Arteche O, Castillo R, Rodriguez-Morales S . Anthelmintic activity of benzimidazole derivatives against Toxocara canis second-stage larvae and Hymenolepis nana adults. Acta Trop. 2008; 109(3):232-5. DOI: 10.1016/j.actatropica.2008.11.014. View

20.

Wang Y, Shi T, Fu J, Zhu H . Discovery of novel bacterial FabH inhibitors (Pyrazol-Benzimidazole amide derivatives): Design, synthesis, bioassay, molecular docking and crystal structure determination. Eur J Med Chem. 2019; 171:209-220. DOI: 10.1016/j.ejmech.2019.03.026. View