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  • Synthetic Strategy And Pharmacological Approaches Of Benzopyrazole: A Review

  • 1PG Scholar, Department of Pharmaceutical chemistry, BLDEA’s SSM College of Pharmacy and Research centre Vijayapur-586103
    2Associate Professor, Department of Pharmaceutical Chemistry, BLDEA’s SSM College of Pharmacy and Research centre Vijayapur-586103

Abstract

Indazole-containing derivatives represent one of the most important heterocycles in drug molecules. The presence of two nitrogen sites located in adjacent positions in the molecular structure allows indazole, at low concentrations in mildly acid or basic media, to form 1H and 2H tautomers via acid-base interactions as well as symmetrical dimers by hydrogen bonding. Indazole is also known as 1H-Benzopyrazole, 2-Azaindole. Synonyms of indazoles are 1H-Indazole, 2H-indazole, Isoindazole1,2-Diazaindene and Benzopyrazole. The first compound known to contain the indazole ring system was indazole and its preparation, by heating o-hydrazinobenzoic acid was reported in 1880 by Fischer. Indazole itself was first prepared a few years later by Fischer and Kuzel. Since then, several approaches for the preparation of indazole and its derivatives have been developed. Indazole shows many biological activities like anti-cancer, anti-microbial, anti-tubercular, antioxidant, anti-platelet and neuroprotective activity. This review aims to summaries the recent method of synthesis of Indazole derivatives and advanced biological activity study of the Indazole derivatives.

Keywords

Heterocyclic compounds, Indazole, Biological activity, Pharmacological uses

Reference

  1. https://www.britannica.com/science/heterocyclic-compound.
  2. Digambar D. Gaikwad, Archana D. Chapolikara, Chandrashekhar G. Synthesis of indazole motifs and their medicinal importance: An overview, European Journal of Medicinal Chemistry 90 (2015) 707-731
  3. https://www.alfa.com/en/indazoles/
  4. Dunga AK, Allaka TR, Kethavarapu Y, Nechipadappu SK, Pothana P, Ravada K, Kashanna J, Kishore PV. Design, synthesis and biological evaluation of novel substituted indazole-1, 2, 3-triazolyl-1, 3, 4-oxadiazoles: Antimicrobial activity evaluation and docking study. Results in Chemistry. 2022 Jan 1; 4:100605. 
  5. AzadehNakhai, Synthetic Studies of Nitrogen-Containing Heterocycles, Particularly Pyrazole and Benzotriazine Derivatives Published by KarolinskaInstitutet and printed by Universitetsservice US-AB. 2009. P.4, ISBN 978-91-7409-687-3.
  6. Digambar D Gaikwad, Archana D Chapolikar ,Chandrashekhar G Devkate , Abraham J Domb ,ChemInform, Synthesis of Indazole Motifs and Their Medicinal Importance: An Overview, European Journal of Medicinal Chemistry, Article, Dec 2015.
  7. https://pubchem.ncbi.nlm.nih.gov/compound/Indazole
  8. Varughese DJ, Manhas MS, Bose AK. Microwave enhanced greener synthesis of indazoles via nitrenes. Tetrahedron letters. 2006 Sep 18; 47(38):6795-7.
  9. Lukin K, Hsu MC, Fernando D, Leanna MR. New practical synthesis of indazoles via condensation of O-fluorobenzaldehydes and their O-methyloximes with hydrazine. The Journal of organic chemistry. 2006 Oct 13; 71(21):8166-72.
  10. Li X, Ye X, Wei C, Shan C, Wojtas L, Wang Q, Shi X. Diazo activation with diazonium salts: synthesis of indazole and 1, 2, 4-triazole. Organic Letters. 2020 May 28; 22 (11):4151-5.
  11. Nandish Talpada1, Suryajit Rathod1, Nimesh Chauhan1, Hitendra Mali1, Prashant Arya2, Tushar Patel: Synthesis and Characterization of Indazole Derivative via Suzuki Coupling Reaction. International Journal of creative research thoughts. 2020 Dec 12; Vol.8,ISSN: 2320-2882
  12. Koduri GB, Bollikolla HB. Novel Substituted IndazolesTowards Potential Antimicrobial Agents.
  13. Dunga AK, Allaka TR, Kethavarapu Y, Nechipadappu SK, Pothana P, Ravada K, Kashanna J, Kishore PV. Design, synthesis and biological evaluation of novel substituted indazole-1, 2, 3-triazolyl-1, 3, 4-oxadiazoles: Antimicrobial activity evaluation and docking study. Results in Chemistry. 2022 Jan 1; 4:100605.
  14. Saketi JM, Boddapati SM, Adil SF, Shaik MR, Alduhaish O, Siddiqui MR, Bollikolla HB. Pd (PPh3) 4 catalyzed synthesis of indazole derivatives as potent anticancer drug. Applied Sciences. 2020 May 29; 10(11):3792.
  15. Pérez-Villanueva J, Yépez-Mulia L, González-Sánchez I, Palacios-Espinosa JF, Soria-Arteche O, Sainz-Espuñes TD, Cerbón MA, Rodríguez-Villar K, Rodríguez-Vicente AK, Cortés-Gines M, Custodio-Galván Z. Synthesis and biological evaluation of 2 H-indazole derivatives: Towards antimicrobial and anti-inflammatory dual agents. Molecules. 2017 Oct 31; 22(11):1864.
  16. Shamim, S., Khan, K.M., Ullah, N., Mahdavi, M., Faramarzi, M.A., Larijani, B., Salar, U., Rafique, R., Taha, M. and Perveen, S., 2021. Synthesis, in vitro, and in silico evaluation of Indazole Schiff bases as potential ?-glucosidase inhibitors. Journal of Molecular Structure, 1242, p.130826.
  17. Rafique R, Khan KM, Chigurupati S, Wadood A, Rehman AU, Salar U, Venugopal V, Shamim S, Taha M, Perveen S. Synthesis, in vitro ?-amylase inhibitory, and radicals (DPPH & ABTS) scavenging potentials of new N-sulfonohydrazide substituted indazoles. Bioorganic chemistry. 2020 Jan 1;94:103410.
  18. Polo E, Trilleras J, Ramos J, Galdámez A, Quiroga J, Gutierrez M. Efficient MW-assisted synthesis, spectroscopic characterization, X-ray and antioxidant properties of indazole derivatives. Molecules. 2016 Jul 9; 21(7):903.
  19. Naaz F, Srivastava R, Singh A, Singh N, Verma R, Singh VK, Singh RK. Molecular modeling, synthesis, antibacterial and cytotoxicity evaluation of sulfonamide derivatives of benzimidazole, indazole, benzothiazole and thiazole. Bioorganic & medicinal chemistry. 2018 Jul 23; 26 (12):3414-28.
  20. Mohamed Abdelahi MM, El Bakri Y, Lai CH, Subramani K, Anouar EH, Ahmad S, Benchidmi M, Mague JT, Popovi?-Djordjevi? J, Goumri-Said S. Novel 3-chloro-6-nitro-1 H-indazole derivatives as promising antileishmanial candidates: synthesis, biological activity, and molecular modelling studies. Journal of Enzyme Inhibition and Medicinal Chemistry. 2022 Dec 31; 37(1):151-67.
  21. Vyas DH, Tala SD, Akbari JD, Dhaduk MF, Joshi HS. Synthesis, antimicrobial and antitubercular activity of some cyclohexenone and indazole derivatives.
  22. Jismy, B., El Qami, A., Pišlar, A., Kos, J., Gobec, S., Knez, D. and Abarbri, M., 2021. Pyrimido [1, 2-b] indazole derivatives: Selective inhibitors of human monoamine oxidase B with neuroprotective activity. European Journal of Medicinal Chemistry, 209, p.112911.

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Kousalya Patil
Corresponding author

PG Scholar, Department of Pharmaceutical chemistry, BLDEA’s SSM College of Pharmacy and Research centre Vijayapur-586103

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Dr. Somashekhar M Metri
Co-author

Associate Professor, Department of Pharmaceutical Chemistry, BLDEA’s SSM College of Pharmacy and Research centre Vijayapur-586103

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Divya Shirke
Co-author

PG Scholar, Department of Pharmaceutical chemistry, BLDEA’s SSM College of Pharmacy and Research centre Vijayapur-586103

Kousalya Patil*, Dr. Somashekhar M Metri, Divya Shirke, Synthetic Strategy And Pharmacological Approaches Of Benzopyrazole: A Review, Int. J. in Pharm. Sci., 2023, Vol 1, Issue 7, 261-268. https://doi.org/10.5281/zenodo.8161568

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