Synthesis and Biological Activities of Some 1,2,4-Triazole Derivatives: A Review

Authors

  • Dina Saleem M. Ameen Pharmaceutical Chemistry Department, College of Pharmacy, Mustansiriyah University, Baghdad-Iraq
  • Mohammed Dheyaa Hamdi Pharmaceutical Chemistry Department, College of Pharmacy, Mustansiriyah University, Baghdad-Iraq
  • Ayad Kareem Khan Pharmaceutical Chemistry Department, College of Pharmacy, Mustansiriyah University, Baghdad-Iraq

DOI:

https://doi.org/10.32947/ajps.v22i3.890

Keywords:

Heterocyclic, Triazole, Biological Activities

Abstract

This review is about 1,2,4-triazoles include their synthesis; their physio-chemical properties, SAR, reactions, derivatives. Finally, their biological activities with a demonstrated showing

 

different requirements to achieve different activity

References

- Strzelecka, M. and P. Świątek, 1, 2, 4-Triazoles as Important Antibacterial Agents. Pharmaceuticals, 2021. 14(3): p. 224. DOI: https://doi.org/10.3390/ph14030224

- Maddila, S., R. Pagadala, and S. B Jonnalagadda, 1, 2, 4-Triazoles: A review of synthetic approaches and the biological activity. Letters in Organic Chemistry, 2013. 10(10): p. 693-714. DOI: https://doi.org/10.2174/157017861010131126115448

- Bihdan, O.A., et al., 1, 2, 4-Triazole derivatives with halogen substituted fragments, their synthesis, modification and biological properties. Research Journal of Pharmaceutical Biological and Chemical Sciences, 2018. 9(1): p. 22-29.

- Shahzadi, I., et al., Synthesis, Hemolytic Studies, and In Silico Modeling of Novel Acefylline–1, 2, 4-Triazole Hybrids as Potential Anti-cancer Agents against MCF-7 and A549. ACS omega, 2021. 6(18): p. 11943-11953. DOI: https://doi.org/10.1021/acsomega.1c00424

- Jiang, B., et al., Corrosion inhibition performance of triazole derivatives on Copper-Nickel alloy in 3.5 wt.% NaCl solution. Journal of Materials Engineering and Performance, 2015. 24(12): p. 4797-4808. DOI: https://doi.org/10.1007/s11665-015-1759-8

- Miller, S.A., J.P. Ferreira, and J.T. LeJeune, Antimicrobial Use and Resistance in Plant Agriculture: A One Health Perspective. Agriculture, 2022. 12(2): p. 289. DOI: https://doi.org/10.3390/agriculture12020289

- Pereira, D., et al., Recent Advances in Bioactive Flavonoid Hybrids Linked by 1, 2, 3-Triazole Ring Obtained by Click Chemistry. Molecules, 2021. 27(1): p. 230. DOI: https://doi.org/10.3390/molecules27010230

- Aflak, N., et al., Sustainable construction of heterocyclic 1, 2, 3-triazoles by strict click [3+ 2] cycloaddition reactions between azides and alkynes on copper/carbon in water. Frontiers in chemistry, 2019. 7: p. 81. DOI: https://doi.org/10.3389/fchem.2019.00081

- Gupta, R.R., M. Kumar, and V. Gupta, Heterocyclic Chemistry: Volume II: Five-Membered Heterocycles. 2013: Springer Science & Business Media.

- Ranasinghe, N., et al., Flow and Microwave Induced Pellizzari Reactions: Synthesis of Heterocyclic Analogues of the Benzoxazepine Antipsychotic Agents Loxapine and JL-13. Advances in Chemistry, 2017. 2017. DOI: https://doi.org/10.1155/2017/8147421

- Atkinson, M. and J. Polya, 657. Triazoles. Part I. Unsymmetrical Einhorn–Brunner and related Pellizzari reactions. Journal of the Chemical Society (Resumed), 1952: p. 3418-3422. DOI: https://doi.org/10.1039/JR9520003418

- Kaur, P. and A. Chawla, 1, 2, 4-Triazole: a review of pharmacological activities. Int. Res. J. Pharm, 2017. 8(7): p. 10-29. DOI: https://doi.org/10.7897/2230-8407.087112

- Wang, L.-Y., et al., One-flask synthesis of 1, 3, 5-trisubstituted 1, 2, 4-triazoles from nitriles and hydrazonoyl chlorides via 1, 3-dipolar cycloaddition. RSC Advances, 2014. 4(27): p. 14215-14220. DOI: https://doi.org/10.1039/C4RA00113C

- Saavedra, J.Z., et al., Reaction of InCl3 with various reducing agents: InCl3–NaBH4-mediated reduction of aromatic and aliphatic nitriles to primary amines. The Journal of Organic Chemistry, 2012. 77(1): p. 221-228. DOI: https://doi.org/10.1021/jo201809a

- Miura, T., et al., Regioselective 1, 3-Dipolar Cycloaddition of Nitriles with Nitrile Imines Generated from Tetrazoles. Chemistry Letters, 2021. 50(1): p. 131-135. DOI: https://doi.org/10.1246/cl.200634

- Yang, D., et al., Copper‐Catalyzed Synthesis of 1, 2, 4‐Benzothiadiazine 1, 1‐Dioxide Derivatives by Coupling of 2‐Halobenzenesulfonamides with Amidines. Advanced Synthesis & Catalysis, 2009. 351(11‐12): p. 1999-2004. DOI: https://doi.org/10.1002/adsc.200900101

- Xu, H., et al., Copper-catalyzed one-pot synthesis of 1, 2, 4-triazoles from nitriles and hydroxylamine. The Journal of Organic Chemistry, 2015. 80(3): p. 1789-1794. DOI: https://doi.org/10.1021/jo502709t

- Hassan, S. and T.J. Mueller, Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition. Advanced Synthesis & Catalysis, 2015. 357(4): p. 617-666. DOI: https://doi.org/10.1002/adsc.201400904

- Lee, J., et al., Synthesis of 1, 3, 5-trisubstituted-1, 2, 4-triazoles by microwave-assisted N-acylation of amide derivatives and the consecutive reaction with hydrazine hydrochlorides. Tetrahedron, 2012. 68(8): p. 2045-2051. DOI: https://doi.org/10.1016/j.tet.2012.01.003

- Van Otterlo, W.A. and I.R. Green, A review on recent syntheses of Amaryllidaceae alkaloids and isocarbostyrils (time period mid-2016 to 2017). Natural Product Communications, 2018. 13(3): p. 1934578X1801300305. DOI: https://doi.org/10.1177/1934578X1801300305

- de la Hoz, A., A. Díaz-Ortiz, and P. Prieto, Microwave-assisted green organic synthesis. 2016. DOI: https://doi.org/10.1039/9781782623632-00001

- Guihéneuf, K.W.C., et al., Microwaves in Heterocyclic Chemistry. Synthesis, 2012. 16: p. 1.

- Suramwar, N.V., S.R. Thakare, and N.T. Khaty, Room Temperature N-Arylation of 1, 2, 4-Triazoles under Ligand-Free Condition. Organic Chemistry International, 2012. 2012. DOI: https://doi.org/10.1155/2012/515092

- Domini, C.E., et al., Merging metallic catalysts and sonication: A periodic table overview. Catalysts, 2017. 7(4): p. 121. DOI: https://doi.org/10.3390/catal7040121

- Cristau, H.J., et al., Highly efficient and mild copper‐catalyzed N‐and C‐arylations with aryl bromides and iodides. Chemistry–A European Journal, 2004. 10(22): p. 5607-5622. DOI: https://doi.org/10.1002/chem.200400582

- MALANI, A.H., A.H. Makwana, and H.R. Makwana, A brief review article: Various synthesis and therapeutic importance of 1, 2, 4-triazole and its derivatives. Moroccan Journal of Chemistry, 2017. 5(1): p. 5-1 (2017) 41-58.

- Zheng, Y.-Y., et al., Study of benzofuroquinolinium derivatives as a new class of potent antibacterial agent and the mode of inhibition targeting FtsZ. Frontiers in Microbiology, 2018: p. 1937. DOI: https://doi.org/10.3389/fmicb.2018.01937

- Smith, I., Mycobacterium tuberculosis pathogenesis and molecular determinants of virulence. Clinical Microbiology Reviews, 2003. 16(3): p. 463-496. DOI: https://doi.org/10.1128/CMR.16.3.463-496.2003

- Seung, K.J., S. Keshavjee, and M.L. Rich, Multidrug-resistant tuberculosis and extensively drug-resistant tuberculosis. Cold Spring Harbor Perspectives in Medicine, 2015. 5(9): p. a017863. DOI: https://doi.org/10.1101/cshperspect.a017863

- Küçükgüzel, I., et al., Synthesis of some 3-(arylalkylthio)-4-alkyl/aryl-5-(4-aminophenyl)-4H-1, 2, 4-triazole derivatives and their anticonvulsant activity. Il Farmaco, 2004. 59(11): p. 893-901. DOI: https://doi.org/10.1016/j.farmac.2004.07.005

- Nguyen, T.-T., et al., In vitro antimycobacterial studies of flavonols from Bauhinia vahlii Wight and Arn. Biotech, 2021. 11(3): p. 1-5. DOI: https://doi.org/10.1007/s13205-021-02672-4

- Tan, Z., et al., Triazole-containing hybrids with anti-Mycobacterium tuberculosis potential–Part I: 1, 2, 3-Triazole. Future Medicinal Chemistry, 2021. 13(07): p. 643-662. DOI: https://doi.org/10.4155/fmc-2020-0301

- Hargrove, T.Y., et al., Structural analyses of Candida albicans sterol 14α-demethylase complexed with azole drugs address the molecular basis of azole-mediated inhibition of fungal sterol biosynthesis. Journal of Biological Chemistry, 2017. 292(16): p. 6728-6743. DOI: https://doi.org/10.1074/jbc.M117.778308

- Zuccolo, M., et al., Dual-active antifungal agents containing strobilurin and SDHI-based pharmacophores. Scientific Reports, 2019. 9(1): p. 1-12. DOI: https://doi.org/10.1038/s41598-019-47752-x

- Gavara, L., et al., 4-Amino-1, 2, 4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors. European Journal of Medicinal Chemistry, 2020. 208: p. 112720. DOI: https://doi.org/10.1016/j.ejmech.2020.112720

- Strasfeld, L. and S. Chou, Antiviral drug resistance: mechanisms and clinical implications. Infectious Disease Clinics, 2010. 24(3): p. 809-833. DOI: https://doi.org/10.1016/j.idc.2010.07.001

- Coelmont, L., et al., Ribavirin antagonizes the in vitro anti-hepatitis C virus activity of 2′-C-methylcytidine, the active component of valopicitabine. Antimicrobial agents and chemotherapy, 2006. 50(10): p. 3444-3446. DOI: https://doi.org/10.1128/AAC.00372-06

- Martins, P., et al., Heterocyclic anticancer compounds: recent advances and the paradigm shift towards the use of nanomedicine’s tool box. Molecules, 2015. 20(9): p. 16852-16891. DOI: https://doi.org/10.3390/molecules200916852

- Rashdan, H.R. and I.A. Shehadi, Triazoles Synthesis & Applications as Nonsteroidal Aromatase Inhibitors for Hormone-Dependent Breast Cancer Treatment. Heteroatom Chemistry, 2022. 2022. DOI: https://doi.org/10.1155/2022/5349279

- Prachayasittikul, V., et al., Investigation of aromatase inhibitory activity of metal complexes of 8-hydroxyquinoline and uracil derivatives. Drug Design, Development and Therapy, 2014. 8: p. 1089. DOI: https://doi.org/10.2147/DDDT.S67300

- Kharb, R., P.C. Sharma, and M.S. Yar, Pharmacological significance of triazole scaffold. Journal of enzyme inhibition and medicinal chemistry, 2011. 26(1): p. 1-21. DOI: https://doi.org/10.3109/14756360903524304

- Guo, H.-Y., et al., Application of triazoles in the structural modification of natural products. Journal of Enzyme Inhibition and Medicinal Chemistry, 2021. 36(1): p. 1115-1144. DOI: https://doi.org/10.1080/14756366.2021.1890066

- Parker, J.E., et al., Resistance to antifungals that target CYP51. Journal of Chemical Biology, 2014. 7(4): p. 143-161. DOI: https://doi.org/10.1007/s12154-014-0121-1

- Sheehan, D.J., C.A. Hitchcock, and C.M. Sibley, Current and emerging azole antifungal agents. Clinical microbiology reviews, 1999. 12(1): p. 40-79. DOI: https://doi.org/10.1128/CMR.12.1.40

- Pianalto, K.M. and J.A. Alspaugh, New horizons in antifungal therapy. Journal of Fungi, 2016. 2(4): p. 26. DOI: https://doi.org/10.3390/jof2040026

- Maza, S., et al., Synthesis, structural investigation and NLO properties of three 1, 2, 4-triazole Schiff bases. Journal of Molecular Structure, 2020. 1219: p. 128492. DOI: https://doi.org/10.1016/j.molstruc.2020.128492

- Mast, N., et al., Antifungal azoles: structural insights into undesired tight binding to cholesterol-metabolizing CYP46A1. Molecular Pharmacology, 2013. 84(1): p. 86-94. DOI: https://doi.org/10.1124/mol.113.085902

- Warrilow, A.G., et al., Azole affinity of sterol 14α-demethylase (CYP51) enzymes from Candida albicans and Homo sapiens. Antimicrobial agents and chemotherapy, 2013. 57(3): p. 1352-1360. DOI: https://doi.org/10.1128/AAC.02067-12

- Monk, B.C., et al., Fungal Lanosterol 14α-demethylase: A target for next-generation antifungal design. Biochimica et Biophysica Acta (BBA)-Proteins and Proteomics, 2020. 1868(3): p. 140206. DOI: https://doi.org/10.1016/j.bbapap.2019.02.008

- Sagatova, A.A., et al., Structural insights into binding of the antifungal drug fluconazole to Saccharomyces cerevisiae lanosterol 14α-demethylase. Antimicrobial agents and chemotherapy, 2015. 59(8): p. 4982-4989. DOI: https://doi.org/10.1128/AAC.00925-15

- Sagatova, A.A., et al., Triazole resistance mediated by mutations of a conserved active site tyrosine in fungal lanosterol 14α-demethylase. Scientific reports, 2016. 6(1): p. 1-11. DOI: https://doi.org/10.1038/srep26213

- Gupta, V.K., R.L. Mach, and S. Sreenivasaprasad, Fungal Biomolecules: sources, applications and recent developments. John Wiley & Sons, 2015. DOI: https://doi.org/10.1002/9781118958308

- Senerovic, L., et al., Quinolines and quinolones as antibacterial, antifungal, anti-virulence, antiviral and anti-parasitic agents. Advances in Microbiology, Infectious Diseases and Public Health, 2019: p. 37-69. DOI: https://doi.org/10.1007/5584_2019_428

- Nguyen, L.A., H. He, and C. Pham-Huy, Chiral drugs: an overview. International journal of biomedical science: IJBS, 2006. 2(2): p. 85.

- Kumari, S., et al., Amide bond bioisosteres: Strategies, synthesis, and successes. Journal of Medicinal Chemistry, 2020. 63(21): p. 12290-12358. DOI: https://doi.org/10.1021/acs.jmedchem.0c00530

- Kazeminejad, Z., et al., Novel 1, 2, 4-Triazoles as Antifungal Agents. BioMed Research International, 2022. 2022. DOI: https://doi.org/10.1155/2022/4584846

- Ley, S.V., Quaternary stereocenters: challenges and solutions for organic synthesis. John Wiley & Sons, 2006

- Heeres, J., L. Meerpoel, and P. Lewi, Conazoles. Molecules, 2010. 15(6): p. 4129-4188. DOI: https://doi.org/10.3390/molecules15064129

- Chen, A.Y., et al., Targeting metalloenzymes for therapeutic intervention. Chemical reviews, 2018. 119(2): p. 1323-1455. DOI: https://doi.org/10.1021/acs.chemrev.8b00201

- Xie, L., et al., Harzianic acid from Trichoderma afroharzianum is a natural product inhibitor of acetohydroxyacid synthase. Journal of the American Chemical Society, 2021. 143(25): p. 9575-9584. DOI: https://doi.org/10.1021/jacs.1c03988

- Deming, T.J., Synthesis of side-chain modified polypeptides. Chemical reviews, 2016. 116(3): p. 786-808. DOI: https://doi.org/10.1021/acs.chemrev.5b00292

- Liu, X., et al., Antifungal compounds against Candida infections from traditional Chinese medicine. BioMed Research International, 2017. 2017. DOI: https://doi.org/10.1155/2017/4614183

- Zhou, H.-X. and X. Pang, Electrostatic interactions in protein structure, folding, binding, and condensation. Chemical reviews, 2018. 118(4): p. 1691-1741. DOI: https://doi.org/10.1021/acs.chemrev.7b00305

- Lepak, A.J. and D.R. Andes, Antifungal pharmacokinetics and pharmacodynamics. Cold Spring Harbor Perspectives in Medicine, 2015. 5(5): p. a019653. DOI: https://doi.org/10.1101/cshperspect.a019653

- Singh, S., Chemistry, design, and structure− activity relationship of cocaine antagonists. Chemical reviews, 2000. 100(3): p. 925-1024. DOI: https://doi.org/10.1021/cr9700538

- Lommerse, J.P., S.L. Price, and R. Taylor, Hydrogen bonding of carbonyl, ether, and ester oxygen atoms with alkanol hydroxyl groups. Journal of computational chemistry, 1997. 18(6): p. 757-774. DOI: https://doi.org/10.1002/(SICI)1096-987X(19970430)18:6<757::AID-JCC3>3.0.CO;2-R

- Dalvit, C., C. Invernizzi, and A. Vulpetti, Fluorine as a hydrogen‐bond acceptor: Experimental evidence and computational calculations. Chemistry–A European Journal, 2014. 20(35): p. 11058-11068. DOI: https://doi.org/10.1002/chem.201402858

- Matin, M.M., et al., Triazoles and their derivatives: Chemistry, synthesis, and therapeutic applications. Frontiers in molecular biosciences, 2022: p. 303. DOI: https://doi.org/10.3389/fmolb.2022.864286

- Viegas, D.J., et al., Antiviral activity of 1, 4-disubstituted-1, 2, 3-triazoles against HSV-1 in vitro. Antiviral Therapy, 2020. 25(8): p. 399-410. DOI: https://doi.org/10.3851/IMP3387

- Kokoris, M.S. and M.E. Black, Characterization of herpes simplex virus type 1 thymidine kinase mutants engineered for improved ganciclovir or acyclovir activity. Protein science, 2002. 11(9): p. 2267-2272. DOI: https://doi.org/10.1110/ps.2460102

- Lauria, A., et al., 1, 2, 3‐Triazole in heterocyclic compounds, endowed with biological activity, through 1, 3‐dipolar cycloadditions. European Journal of Organic Chemistry, 2014. 2014(16): p. 3289-3306. DOI: https://doi.org/10.1002/ejoc.201301695

- Vértessy, B.G. and J. Tóth, Keeping uracil out of DNA: physiological role, structure and catalytic mechanism of dUTPases. Accounts of chemical research, 2009. 42(1): p. 97-106. DOI: https://doi.org/10.1021/ar800114w

- Montana, M., et al., Quinoxaline derivatives as antiviral agents: a systematic review. Molecules, 2020. 25(12): p. 2784. DOI: https://doi.org/10.3390/molecules25122784

- Sebastian, L., et al., Pentoxifylline inhibits replication of Japanese encephalitis virus: a comparative study with ribavirin. International journal of antimicrobial agents, 2009. 33(2): p. 168-173. DOI: https://doi.org/10.1016/j.ijantimicag.2008.07.013

- Musharrafieh, R., et al., Development of broad-spectrum enterovirus antivirals based on quinoline scaffold. Bioorganic chemistry, 2020. 101: p. 103981. DOI: https://doi.org/10.1016/j.bioorg.2020.103981

- Ji, X. and Z. Li, Medicinal chemistry strategies toward host targeting antiviral agents. Medicinal Research Reviews, 2020. 40(5): p. 1519-1557. DOI: https://doi.org/10.1002/med.21664

- Seck, I. and F. Nguemo, Triazole, imidazole, and thiazole-based compounds as potential agents against coronavirus. Results in chemistry, 2021. 3: p. 100132. DOI: https://doi.org/10.1016/j.rechem.2021.100132

- Xiao, Y., et al., Synthesis of 10, 10′-bis (trifluoromethyl) marinopyrrole A derivatives and evaluation of their antiviral activities in vitro. European Journal of Medicinal Chemistry, 2022. 238: p. 114436. DOI: https://doi.org/10.1016/j.ejmech.2022.114436

- Hernández-López, H., et al., Synthesis of 1, 4-biphenyl-triazole derivatives as possible 17β-HSD1 inhibitors: An in Silico Study. ACS omega, 2020. 5(23): p. 14061-14068. DOI: https://doi.org/10.1021/acsomega.0c01519

- Zhang, Y., et al., Effects of the fusion design and immunization route on the immunogenicity of Ag85A-Mtb32 in adenoviral vectored tuberculosis vaccine. Human Vaccines & Immunotherapeutics, 2015. 11(7): p. 1803-1813. DOI: https://doi.org/10.1080/21645515.2015.1042193

- Alsayed, S.S., et al., Design, synthesis and antimycobacterial evaluation of novel adamantane and adamantanol analogues effective against drug-resistant tuberculosis. Bioorganic chemistry, 2021. 106: p. 104486. DOI: https://doi.org/10.1016/j.bioorg.2020.104486

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Published

2022-10-24

How to Cite

Dina Saleem M. Ameen, Mohammed Dheyaa Hamdi, & Ayad Kareem Khan. (2022). Synthesis and Biological Activities of Some 1,2,4-Triazole Derivatives: A Review. Al Mustansiriyah Journal of Pharmaceutical Sciences, 22(3), 65–81. https://doi.org/10.32947/ajps.v22i3.890