Sulfur Derivatives of 1,2,4-Triazole: Recently Developed Compounds, Structure Activity Relationship, and Biological Activity: Review article

Authors

  • Azhar Mahdi Jasim Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Baghdad, Iraq
  • Tagreed N-A Omar Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Baghdad, Iraq
  • Shayma L. Abdulhadi Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad

DOI:

https://doi.org/10.31351/vol33iss4pp1-21

Keywords:

1,2,4-triazole-3-thiones, 1,2,4-triazole-3-thiols, Heterocyclic Compound, Derivatives, Biological Activity

Abstract

The term of heterocyclic chemistry focuses only on heterocyclic compounds, which consider as a percentage of organic chemistry, they equal to greater than sixty-five. These compounds are widely founded in nature and most of them are important to life. In the past few years, scientist fused on 1,2,4-triazoles and their condensed heterocyclic ring due to their medicinal significance, 1,2,4-triazole containing Sulphur atom is one of the important heterocyclic moieties due to its broad range of biological activities also their derivatives can accommodate one of the alternatives as electronic effect as exchanges of the electronic density (electron donating or withdrawing) groups ; for all what mentioned above they are consider as a core molecule in development of large number of medicinal compounds. 1,2,4-Triazole have wide range of pharmacological motivating drug possibility such as analgesic, anti-microbial, anti-inflammatory, anti-convulsant, antioxidant, anti-septic, anti-cancer, diuretics, anti-diabetic, anti-urease, and anti-migraine agents. This review focus on 1,2,4-triazole Sulfur based compounds about their different biological activities and the relationship with their chemistry.

 

How to Cite

1.
Jasim AM, Omar TN-A, Abdulhadi SL. Sulfur Derivatives of 1,2,4-Triazole: Recently Developed Compounds, Structure Activity Relationship, and Biological Activity: Review article. Iraqi Journal of Pharmaceutical Sciences [Internet]. 2024 Dec. 20 [cited 2024 Dec. 21];33(4):1-21. Available from: https://bijps.uobaghdad.edu.iq/index.php/bijps/article/view/2857

Publication Dates

Received

2023-08-06

Revised

2023-08-15

Accepted

2023-10-24

Published Online First

2024-12-20

References

Gonnet L, Baron M, Baltas M. Synthesis of biologically relevant 1,2,3-and 1,3,4-triazoles: From classical pathway to green chemistry. Molecules. 2021 Sep 1;26(18).

Prashanthi Evangelin M, Pavani Y, Kumar P, Monica K, Venni D, Uma Sukeerthika S, et al. An updated review on 1, 2, 4 triazoles. Journal of Pharmacognosy and Phytochemistry. 2019;8(4):292–9.

Kabir E, Uzzaman M. A review on biological and medicinal impact of heterocyclic compounds. Results Chem. 2022 Jan 1;4.

Al-Mulla A. A Review: Biological importance of heterocyclic compounds. Der Pharma chemica [Internet]. 2017;9(13):141–7. Available from: www.derpharmachemica.com

Jampilek J. Heterocycles in medicinal chemistry. Molecules. 2019 Oct 25;24(21).

Depa N, Erothu H. Synthesis, and biological activity compounds of nitrogen-containing heterocyclic compounds: A review. Rasayan Journal of Chemistry. 2022 Jul 1;15(3):1709–17.

Malani AH, Mor / J, Makwana AH, Makwana H. A brief review article: Various synthesis and therapeutic importance of 1, 2, 4-triazole and its derivatives. Mor J Chem [Internet]. 2017; 5:41–58. Available from: http://revues.imist.ma/?journal=morjchem&page=login

Martins P, Jesus J, Santos S, Raposo LR, Roma-Rodrigues C, Baptista PV, et al. Heterocyclic anticancer compounds: Recent advances and the paradigm shift towards the use of nanomedicine’s toolbox. Molecules. 2015 Sep 1;20(9):16852–91.

Omar AM, Saleh NM, Abdel-Rahman AAH, El-Adl K. Review article; anticancer activity of some fused heterocyclic moieties containing nitrogen and/ or sulfur heteroatoms. J Pharm Sci. 2020,62.

Mustafa YF. Synthesis, characterization and antibacterial activity of novel heterocycle, coumacine, and two of its derivatives. Saudi Pharmaceutical Journal. 2018 Sep 1;26(6):870–5.

Karpun Y. Synthesis, structure and properties of novel S-substituted BIS-1,2,4-triazoles. Hacettepe University Journal of The Faculty of Pharmacy. 2021;4(3):152–63.

Gadhave PP, Dighe NS, Pattan SR, Deotarse P, Musmade DS, Shete R V. Current biological and synthetic profile of triazoles: A review. Annals of Biological Research [Internet]. 2010;1(1):82–9. Available from: www.scholarsresearchlibrary.com

Dai J, Tian S, Yang X, Liu Z. Synthesis methods of 1,2,3-/1,2,4-triazoles: A review. Front Chem. 2022 Sep 26;10.

Khan IA, Ahmad M, Aslam S, Saif MJ, Zahoor F, Naqvi SAR, et al. Recent advances in the synthesis of triazole derivatives. AFINIDAD LXXII. 2015; 569:64–77.

Dina Saleem M. Ameen, Mohammed Dheyaa Hamdi, Ayad Kareem Khan. Synthesis and biological activities of some 1,2,4-triazole derivatives: A review. Al Mustansiriyah Journal of Pharmaceutical Sciences. 2022 Oct 24;22(3):65–81.

Shneine JK, Alaraji YH. Chemistry of 1,2,4-trazole: A review article. International Journal of Science and Research [Internet]. 2013;5. Available from: www.ijsr.net

Aouad MR, Mayaba MM, Naqvi A, Bardaweel SK, Al-blewi FF, Messali M, et al. Design, synthesis, in silico and in vitro antimicrobial screenings of novel 1,2,4-triazoles carrying 1,2,3-triazole scaffold with lipophilic side chain tether. Chem Cent J. 2017 Nov 21;11(1).

Abo-Bakr AM. Synthesis and antibacterial activity of some new functionalized derivatives of 4-amino-5-benzyl-4H- [1,2,4]-triazole-3-thiol. International Journal of Science and Research [Internet]. 2014;3(11):15–23. Available from: www.ijsr.net

Belkadi M, Othman AA. Regioselective Glycosylation: Synthesis, characterization and biological activity of new acyclo C-nucleosides bearing 5-(substituted)-1,3,4-oxazole-2-thione, 5-(substituted)-4-amino-1,2,4-triazole-3-thiol and 5-(substituted)-1,2,4-triazole-3-thiones moieties. Trends Appl Sci Res. 2011;6(1):19–33.

Pharma D, Agrawal R, Pancholi SS. Synthesis, characterization and evaluation of antimicrobial activity of a series of 1,2,4-triazoles. Der Pharma Chemica [Internet]. 2011;3(6):32–40. Available from: www.derpharmachemica.com

Ghattas AEBAG, Moustafa HM, Hassanein EAA, Hussein BRM. Synthesis and antibacterial activity of some new 4-anilino-5-phenyl-4H-1,2,4-triazole-3-thiol derivatives. Arabian Journal of Chemistry. 2016 Nov 1;9: S1654–9.

El-Essawy FA, El-Sayed WA, El-Kafrawy SA, Morshedy AS, Abdel-Rahman AH. Anti-hepatitis B virus activity of new 1,2,4-triazol-2-yl-and 1,3,4-oxadiazol-2-yl-2-pyridinone derivatives. Z Naturforsch [Internet]. 2008; 63:667–74. Available from: http://www.znaturforsch.com

Wujec M, Swatko-Ossor M, Mazur L, Rzaczynska Z, Siwek A. Synthesis, structure and investigations of tuberculosis inhibition activities of new 4-methyl-1-substituted-1H-1,2,4-triazole-5(4H)-thione 1893. J Heterocyclic Chem. 2008; 45:1893.

Jalihal PC, Rajoriya V, Kashaw V, Kashaw SK. Isoniazid Based 1,2,4- Triazoles: Design, Synthesis, And Biological Evaluation. IJPBS | [Internet]. 2018; 8:43–53. Available from: www.ijpbs.comorwww.ijpbsonline.com

Mahdi MF, Khan AK, Abdulla MT. Molecular Docking, ADME Study, Synthesis and characterization of new 4-amino-5-aryl-4H-1,2,4-triazole-3-thiol derivatives. J Pharm Negat Results. 2022; 13:5491–8.

Amir M, Kumar S. Synthesis and evaluation of anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation properties of ibuprofen derivatives. Acta Pharmaceutica. 2007 Mar;57(1):31–45.

Kumar H, Javed SA, Khan SA, Amir M. 1,3,4-Oxadiazole/thiadiazole and 1,2,4-triazole derivatives of biphenyl-4-yloxy acetic acid: Synthesis and preliminary evaluation of biological properties. Eur J Med Chem. 2008 Dec;43(12):2688–98.

Shiradkar MR, Ghodake M, Bothara KG, Bhandari S V, Nikalje A, Chakravarthy Akula K, et al. Synthesis and anticonvulsant activity of clubbed thiazolidinone-barbituric acid and thiazolidinone-triazole derivatives. ARKIVOC. 2007; xiv:58–74.

Kane JM, Dudley MW, Sorensen SM, Miller FP. 2,4-Dihydro-3H-1,2,4-triazole-3-thiones as potential antidepressant agents. j med chem. 1988; 31:1253–8.

Othman AA, Kihel M, Amara S. 1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antibacterial agents. Arabian Journal of Chemistry. 2019 Nov 1;12(7):1660–75.

Lin G, Chen Z, Duan W, Wang X, Lei F. Synthesis and biological activity of novel myrtenal-derived 2-acyl-1,2,4-triazole-3-thione compounds. Chinese Journal of Organic Chemistry. 2018 Aug 1;38(8):2085–92.

Maddila S, Momin M, Gorle S, Palakondu L, Jonnalagadda SB. Synthesis and antioxidant evaluation of noval phenothiazine linked substituted benzylidene amino-1,2,4-triazole derivatives. J Chil Chem Soc. 2015;60(2).

Barbuceanu SF, Ilies DC, Saramet G, Uivarosi V, Draghici C, Radulescu V. Synthesis and antioxidant activity evaluation of new compounds from hydrazinecarbothioamide and 1,2,4-triazole class containing diarylsulfone and 2,4-difluorophenyl moieties. Int J Mol Sci. 2014 Jun 17;15(6):10908–25.

Al Sheikh Ali A, Khan D, Naqvi A, Al-Blewi FF, Rezki N, Aouad MR, et al. Design, synthesis, molecular modeling, anticancer studies, and density functional theory calculations of 4-(1,2,4-Triazol-3-ylsulfanylmethyl)-1,2,3-triazole derivatives. ACS Omega. 2021 Jan 12;6(1):301–16.

Zein N, Shaban SM, Shafek SH, Baghi H, Aiad I, Omran M. Synthesis and characterization of new 1,2,4-triazole anticancer scaffold derivatives: In vitro study. Egypt J Chem. 2021 Aug 1;64(8):4005–15.

Ahmad A, Varshney H, Rauf A, Sherwani A, Owais M. Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives. Arabian Journal of Chemistry. 2017 May 1;10: S3347–57.

Yin L, Wang L, Liu XJ, Cheng FC, Shi DH, Cao ZL, et al. Synthesis and bioactivity of novel C2-glycosyl triazole derivatives as acetylcholinesterase inhibitors. Heterocycl Comm. 2017 Jun 1;23(3):231–6.

Mansoory JH, Rajput SS. Synthesis, reactivity and biological evaluation of triazole: Recent review article developments. Int J Pharm Pharm Sci. 2015;7(5):20–32.

Rollas S, Tatar E, Abacı G. Development of a new and efficient synthesis method of 1,2,4-triazole-5-thione derivatives. MARMARA PHARMACEUTCAL JOURNAL. 2013 Sep 4;3(17):181–181.

Shaker RM. The chemistry of mercapto-and thione-substituted 1,2,4-triazoles and their utility in heterocyclic synthesis. ARKIVOC. 2006; ix:59–112.

Mroczek T, Plech T, Wujec M. Novel concept of discrimination of 1,2,4-triazole-3-thione and 3-thiol tautomers. J Chromatogr Sci. 2017 Feb 1;55(2):117–29.

Büyükkidan B, Büyükkidan N, Atar A. New schiff bases derived from 3,4-diamino-1H-1,2,4-triazole-5(4H)-thione: synthesis and characterization. Journal of Scientific Reports-A. 2022; 48:25–41.

Coyanis EM, Della CO, Âdova V, Haas A, Winter M. Preparation, characterization and thiol±thione tautomeric studies of 2-thiono-4-methyl-5-(2,2,2-trifuoro-1-trifuoromethylethyl)-1,3-thiazoline. J Fluor Chem. 2002; 117:185–92.

Plech T, Luszczki JJ, Wujec M, Flieger J, Pizoń M. Synthesis, characterization and preliminary anticonvulsant evaluation of some 4-alkyl-1,2,4-triazoles. Eur J Med Chem. 2013 Feb; 60:208–15.

Varynskyi BA, Scherback MA, Kaplaushenko AG, Yurchenko IA. The study of thione-thiol tautomerism of 4-amino-5-(4-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione by HPLC-MS method. J Chem Pharm Res [Internet]. 2014;6(5):1342–50. Available from: www.jocpr.com

Özdemir N, Türkpençe D. Theoretical investigation of thione-thiol tautomerism, intermolecular double proton transfer reaction and hydrogen bonding interactions in 4-ethyl-5-(2-hydroxyphenyl)-2H-1,2,4-triazole-3(4H)-thione. Comput Theor Chem. 2013 Dec 1; 1025:35–45.

Delaere D, Raspoet G, Nguyen MT. Thiol-thione tautomerism in thioformic acid: Importance of specific solvent interactions. Journal of Physical Chemistry A. 1999 Jan 7;103(1):171–7.

Jayaram PN, Roy G, Mugesh G. Effect of thione-thiol tautomerism on the inhibition of lactoperoxidase by anti-thyroid drugs and their analogues. J Chem Sci. 2008;120(1):143–54.

Gao F, Wang T, Xiao J, Huang G. Antibacterial activity study of 1,2,4-triazole derivatives. Eur J Med Chem. 2019 Jul 1; 173:274–81.

Cui X, Lü Y, Yue C. Development and research progress of anti-drug-resistant bacteria drugs. Infect Drug Resist. 2021; 14:5575–93.

Nordmann P. Carbapenemase-producing Enterobacteriaceae: Overview of a major public health challenge. Med Mal Infect. 2014 Feb;44(2):51–6.

Bonomo RA. β-Lactamases: A focus on current challenges. Cold Spring Harb Perspect Med. 2017 Jan 1;7(1).

Tooke CL, Hinchliffe P, Bragginton EC, Colenso CK, Hirvonen VHA, Takebayashi Y, et al. β-Lactamases and β-lactamase inhibitors in the 21st century. J Mol Biol. 2019 Aug 23;431(18):3472–500.

Legru A, Verdirosa F, Hernandez JF, Tassone G, Sannio F, Benvenuti M, et al. 1,2,4-Triazole-3-thione compounds with a 4-ethyl alkyl/aryl sulfide substituent are broad-spectrum metallo-b-lactamase inhibitors with re-sensitization activity. Eur J Med Chem [Internet]. 2021;226. Available from: https://hal.science/hal-03719307

Gavara L, Legru A, Verdirosa F, Sevaille L, Nauton L, Corsica G, et al. 4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-b-lactamase inhibitors. Bioorg Chem [Internet]. 2021;113. Available from: https:// hal.science/ hal-03358457

Sevaille L, Gavara L, Bebrone C, De Luca F, Nauton L, Achard M, et al. 1,2,4-Triazole-3-thione Compounds as Inhibitors of Dizinc Metallo-lactamases. ChemMedChem. 2017 Jun 21;12(12):972–85.

González-Bello C, Rodríguez D, Pernas M, Rodríguez Á, Colchón E. β-Lactamase inhibitors to restore the efficacy of antibiotics against superbugs. J Med Chem. 2020 Mar 12;63(5):1859–81.

Bush K, Bradford PA. β-lactams and β-lactamase inhibitors: An overview. Cold Spring Harb Perspect Med. 2016 Aug 1;6(8).

Eiamphungporn W, Schaduangrat N, Malik AA, Nantasenamat C. Tackling the antibiotic resistance caused by class a β-lactamases through the use of β-lactamase inhibitory protein. Int J Mol Sci. 2018 Aug 1;19(8).

Ono K, Kitamura Y, Zhang T, Tsutsuki H, Rahman A, Ihara T, et al. Cysteine hydropersulfide inactivates β-Lactam antibiotics with formation of ring-opened carbothioic S-acids in bacteria. ACS Chem Biol. 2021 Apr 16;16(4):731–9.

Linciano P, Gianquinto E, Montanari M, Maso L, Bellio P, Cebrián-Sastre E, et al. 4-amino-1,2,4-triazole-3-thione as a promising scaffold for the inhibition of serine and metallo-β-lactamases. Pharmaceuticals. 2020 Mar 1;13(3).

Strzelecka M, Świątek P. 1,2,4-triazoles as important antibacterial agents. Pharmaceuticals. 2021 Mar 1;14(3).

Popiołek Ł, Kosikowska U, Mazur L, Dobosz M, Malm A. Synthesis and antimicrobial evaluation of some novel 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Medicinal Chemistry Research. 2013 Jul;22(7):3134–47.

Holmes AH, Moore LSP, Sundsfjord A, Steinbakk M, Regmi S, Karkey A, et al. Understanding the mechanisms and drivers of antimicrobial resistance. The Lancet. 2016 Jan 9;387(10014):176–87.

Al-Aabdullah ES, Asiri HH, Lahsasni S, Habib EE, Ibrahim TM, El-Emam AA. Synthesis, antimicrobial, and anti-inflammatory activity, of novel s-substituted and n-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols. Drug Des Devel Ther. 2014 May 12; 8:505–17.

Alyahyaoy HA, Alrubaie LA, Mohammed-Ali MA, Hraishawi RMO, Alyahyaoy HA. Synthesis, characterization and antibacterial evaluation of new 1,2,4-triazole-3-thiol derivatives GRAPHICAL ABSTRACT. International Journal of Green Pharmacy. 2019;13(3):281–8.

Karpun Y, Parchenko V, Fotina T, Demianenko D, Fotin A, Nahornyi V, et al. The investigation of antimicrobial activity of some substituted bis-1,2l4-triazole-3-thiones. Pharmacia. 2021; 68(4): 797–804.

Smith I. Mycobacterium tuberculosis pathogenesis and molecular determinants of virulence. Clin Microbiol Rev. 2003 Jul 1;16(3):463–96.

Vögeli B, Rosenthal RG, Stoffel GMM, Wagner T, Kiefer P, Cortina NS, et al. InhA, the enoyl-thioester reductase from Mycobacterium tuberculosis forms a covalent adduct during catalysis. Journal of Biological Chemistry. 2018 Nov 2;293(44):17200–7.

Vora D, Upadhyay N, Tilekar K, Jain V, Ramaa CS. Development of 1,2,4-triazole-5-thione derivatives as potential inhibitors of enoyl acyl carrier protein reductase (Inha) in tuberculosis. Iranian Journal of Pharmaceutical Research. 2019 Sep 1;18(4):1742–58.

Berida T, Mckee SR, Chatterjee S, Li W, Pandey P, Tripathi SK, et al. Discovery, synthesis, and optimization of 1,2,4-triazolyl pyridines targeting mycobacterium tuberculosis. bioRxiv [Internet]. 2022; Available from: https://doi.org/10.1101/2022.11.14.516356

Wang Y, Xu K, Bai G, Huang L, Wu Q, Pan W, et al. Synthesis and antifungal activity of novel triazole compounds containing piperazine moiety. Molecules. 2014;19(8):11333–40.

A Ezelarab HA, Hassan HA, Abbas SH, Abd El-Baky RM, El-Din Abuo-Rahma GA. Design, synthesis and antifungal activity of 1,2,4-triazole and 1,3,4-oxadiazole-ciprofloxacin hybrids. J Adv Biomed & Pharm Sci J Adv Biomed & Pharm Sci [Internet]. 2018; 1:78–84. Available from: http://jabps.journals.ekb.eg

Hassan MZ, Alsayari A, Asiri YI, Bin Muhsinah A. 1,2,4-Triazole-3-thiones: Greener, one-pot, ionic liquid mediated synthesis and antifungal activity. polycycl aromat compd. 2023;43(1):167–75.

Wu S, Zhang W, Qi L, Ren Y, Ma H. Investigation on 4-amino-5-substituent-1,2,4-triazole-3-thione Schiff bases an antifungal drug by characterization (spectroscopic, XRD), biological activities, molecular docking studies and electrostatic potential (ESP). J Mol Struct. 2019 Dec 5; 1197:171–82.

Radwan AA, Alanazi FK, Al-Agamy MH. 1,3,4-Thiadiazole and 1,2,4-triazole-3(4H)-thione bearing salicylate moiety: Synthesis and evaluation as anti-Candida albicans. Brazilian Journal of Pharmaceutical Sciences. 2017;53(1).

Al AA, Hassa AA, Makhlou MM, Bräse S. Chemistry and biological activities of 1,2,4- Triazolethiones-antiviral and anti-infective drugs. Molecules. 2020 Jul 1;25(13).

Zaher NH, Mostafa MI, Altaher AY. Design, synthesis and molecular docking of novel triazole derivatives as potential CoV helicase inhibitors. Acta Pharmaceutica. 2020 Jun 1;70(2):145–59.

Frączek T, Paneth A, Kamiński R, Krakowiak A, Paneth P. Searching for novel scaffold of triazole non-nucleoside inhibitors of HIV-1 reverse transcriptase. J Enzyme Inhib Med Chem. 2016 May 3;31(3):481–9.

Zuo W, Kwok HF. Development of marine-derived compounds for cancer therapy. Mar Drugs. 2021 Jun 1;19(6).

Šermukšnytė A, Kantminienė K, Jonuškienė I, Tumosienė I, Petrikaitė V. The effect of 1,2,4-triazole-3-thiol derivatives bearing hydrazone moiety on cancer cell migration and growth of melanoma, breast, and pancreatic cancer spheroids. Pharmaceuticals. 2022 Aug 1;15(8).

Abdelrehim ESM. Synthesis and screening of new [1,3,4] oxadiazole, [1,2,4] triazole, and [1,2,4] triazolo [4,3- b] [1,2,4] triazole derivatives as potential antitumor agents on the colon carcinoma cell line (HCT-116). ACS Omega. 2021 Jan 19;6(2):1687–96.

Haggam RA, Assy MG, Sherif MH, Galahom MM. A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity. European Journal of Chemistry. 2018 Jun 30;9(2):99–106.

Maddali NK, Ivaturi VKV, Murthy Yellajyosula LN, Malkhed V, Brahman PK, Pindiprolu SKSS, et al. New 1,2,4-triazole scaffolds as anticancer agents: synthesis, biological evaluation and docking studies. ChemistrySelect. 2021 Jul 13;6(26):6788–96.

Cozza G, Pinna LA. Casein kinases as potential therapeutic targets. Expert Opin Ther Targets. 2016 Mar 3;20(3):319–40.

Pitucha M, Janeczko M, Klimek K, Fornal E, Wos M, Pachuta-Stec A, et al. 1,2,4-Triazolin-5-thione derivatives with anticancer activity as CK1γ kinase inhibitors. Bioorg Chem. 2020 Jun 1;99.

Han Mİ, Tunç CÜ, Atalay P, Erdoğan Ö, Ünal G, Bozkurt M, et al. Design, synthesis, and in vitro and in vivo anticancer activity studies of new (S)-Naproxen thiosemicarbazide/1,2,4-triazole derivatives. New Journal of Chemistry. 2022;13.

Czylkowska A, Lanka S, Szczesio M, Czarnecka K, Szymański P, Pitucha M, et al. new derivatives of 5-((1-methyl-pyrrol-2-yl) methyl)-4-(naphthalen-1-yl)-1,2,4-triazoline-3-thione and Its coordination compounds with anticancer activity. Int J Mol Sci. 2022 Aug 1;23(16).

Chen L, Deng H, Cui H, Fang J, Zuo Z, Deng J, et al. Oncotarget 7204 www.impactjournals.com/oncotarget Inflammatory responses and inflammation-associated diseases in organs. Oncotarget [Internet]. 2018;9(6):7204–18. Available from: www.impactjournals.com/oncotarget/

Angajala KK, Vianala S, Macha R, Raghavender M, Thupurani MK, Pathi PJ. Synthesis, anti-inflammatory, bactericidal activities and docking studies of novel 1,2,3-triazoles derived from ibuprofen using click chemistry. Springerplus. 2016 Dec 1;5(1).

Liu C, Bian M, Yu L, Wei C. Synthesis and anti-inflammatory activity evaluation of 5-(1-benzyl-1H- [1,2,3] triazol-4-yl)-4-phenyl-4H- [1,2,4] triazole-3-thiol derivatives. Indian Journal of Pharmaceutical Education and Research. 2018 Jul 1;52(3):505–13.

Yasin M, Shahid W, Ashraf M, Saleem M, Muzaffar S, Aziz-Ur-Rehman, et al. 4-Chlorophenyl- N-furfuryl-1,2,4-triazole methylacetamides as significant 15-lipoxygenase inhibitors: An efficient approach for finding lead anti-inflammatory compounds. ACS Omega. 2022 Jun 14;7(23):19721–34.

Azim T, Wasim M, Akhtar MS, Akram I. An in vivo evaluation of anti-inflammatory, analgesic and anti-pyretic activities of newly synthesized 1, 2, 4 Triazole derivatives. BMC Complement Med Ther. 2021 Dec 1;21(1).

Zaheer M, Zia-Ur-Rehman M, Munir R, Jamil N, Ishtiaq S, Zaib Saleem RS, et al. (Benzylideneamino) triazole-thione derivatives of flurbiprofen: An efficient microwave-assisted synthesis and in vivo analgesic potential. ACS Omega. 2021 Nov 23;6(46):31348–57.

Abdellatif KRA, Abdelall EKA, Elshemy HAH, Philoppes JN, Hassanein EHM, Kahk NM. Optimization of pyrazole-based compounds with 1,2,4-triazole-3-thiol moiety as selective COX-2 inhibitors cardioprotective drug candidates: Design, synthesis, cyclooxygenase inhibition, anti-inflammatory, ulcerogenicity, cardiovascular evaluation, and molecular modeling studies. Bioorg Chem. 2021 Sep 1;114.

Kumar H, Bhardwaj K, Nepovimova E, Kuča K, Dhanjal DS, Bhardwaj S, et al. Antioxidant functionalized nanoparticles: A combat against oxidative stress. Nanomaterials. 2020 Jul 1;10(7):1–31.

Kaur P, Chawla A. 1,2,4-Triazole: A review of pharmacology. International Research Journal of Pharmacy. 2017 Aug 3;8(7):10–29.

Hassan F, Hameed AA. Synthesis, characterization and antioxidant activity of some 4-amino-5-phenyl-4h-1,2,4-trazole-3-thiol derivatives. Int J Appl Sci Technol [Internet]. 2014;4(2):202–11. Available from: https://www.researchgate.net/publication/323401757

Ihnatova T, Kaplaushenko A, Frolova Y, Pryhlo E. Synthesis and antioxidant properties of some new 5-phenethyl-3-thio-1,2,4-triazoles. Pharmacia. 2021;68(1):129–33.

Shcherbyna RO. The synthesis and prediction of biological activity in silico for new alkyl derivatives of 4-r-3-(morfolinometylen)-4H-1,2,4-triazole-5-thioles. Ukraïns’kij bìofarmacevtičnij žurnal. 2016 Jun 13;0(3(44)):34–8.

Shcherbyna R, Pruhlo Y, Duchenko M, Kulagina M, Kudria V, Valentyna V. Evaluation of Antioxidant activity of 1, 2, 4-triazole derivatives with morpholine moiety. Hacettepe University Journal of the Faculty of Pharmacy. 2022;42(2):73–82.

Kumari M, Tahlan S, Narasimhan B, Ramasamy K, Lim SM, Shah SAA, et al. Synthesis and biological evaluation of heterocyclic 1,2,4-triazole scaffolds as promising pharmacological agents. BMC Chem. 2021 Dec 1;15(1).

Channa Basappa V, Hamse Kameshwar V, Kumara K, Achutha DK, Neratur Krishnappagowda L, Kariyappa AK. Design and synthesis of coumarin-triazole hybrids: Biocompatible anti-diabetic agents, in silico molecular docking and ADME screening. Heliyon. 2020 Oct 1;6(10).

Song MX, Deng XQ. Recent developments on triazole nucleus in anticonvulsant compounds: A review. Vol. 33, Journal of Enzyme Inhibition and Medicinal Chemistry. Taylor and Francis Ltd; 2018. p. 453–78.

Kaproń B, Łuszczki JJ, Siwek A, Karcz T, Nowak G, Zagaja M, et al. Preclinical evaluation of 1,2,4-triazole-based compounds targeting voltage-gated sodium channels (VGSCs) as promising anticonvulsant drug candidates. Bioorg Chem. 2020 Jan 1;94.

Verma KK, Singh UK, Jain J. Design, Synthesis and biological activity of Some 4, 5-disubstituted-2, 4- dihydro-3H-1, 2, 4- triazole-3-thione derivatives. Cent Nerv Syst Agents Med Chem. 2019 Jul 24;19(3):197–205.

Downloads

Published

2024-12-20