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Research Articles

Novel hybrid molecules based on disulfides and 1,2,4-triazole as antiproliferative agents

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Pages 114-121 | Received 20 Jun 2022, Accepted 20 Aug 2022, Published online: 27 Aug 2022

References

  • Miller, K. D.; Fidler-Benaoudia, M.; Keegan, T. H.; Hipp, H. S.; Jemal, A.; Siegel, R. L. Cancer Statistics for Adolescents and Young Adults, 2020. CA Cancer J. Clin. 2020, 70, 443–459. DOI: 10.3322/caac.21637.
  • Bera, H.; Lee, M. H.; Sun, L. Y.; Dolzhenko, A. V.; Chui, W. K. Synthesis, anti-Thymidine Phosphorylase Activity and Molecular Docking of 5-Thioxo-[1,2,4]Triazolo[1,5-a][1,3,5] Triazin-7-Ones. Bioorg. Chem. 2013, 50, 34–40. DOI: 10.1016/j.bioorg.2013.07.004.
  • Mustafa, M.; Anwar, S.; Elgamal, F.; Ahmed, E. R.; Aly, O. M. Potent Combretastatin A-4 Analogs Containing 1,2,4-Triazole: Synthesis, Antiproliferative, anti-Tubulin Activity, and Docking Study. Eur. J. Med. Chem. 2019, 183, 111697.DOI: 10.1016/j.ejmech.2019.111697.
  • Kahveci, B.; MenteşE, E.; Akkaya, E.; Yılmaz, F.; Doğan, İS.; Özel, A. Synthesis of Some Novel 1,2,4-Triazol-3-One Derivatives Bearing the Salicyl Moiety and Their Anticonvulsant Activities. Arch. Pharm. (Weinheim) 2014, 347, 449–455. DOI: 10.1002/ardp.201300427.
  • Łuszczki, J. J.; Lepiech, J.; Zagaja, M.; Wróblewska-Łuczka, P.; Florek-Łuszczki, M.; Bojar, H.; Walczak, A.; Plech, T. Anticonvulsant and Neurotoxic Effects of a Novel 1,2,4-Triazole-3-Thione Derivative (TPF-34) and Its Isobolographic Interaction Profile with Classical Antiepileptic Drugs in Mice. Pharmacol. Rep. 2020, 72, 87–95. DOI: 10.1007/s43440-019-00044-7.
  • Assarzadeh, M. J.; Almasirad, A.; Shafiee, A.; Koopaei, M. N.; Abdollahi, M. Synthesis of New Thiazolo[3,2-b][1,2,4]Triazole-6(5H)-one Derivatives as Potent Analgesic and Anti Inflammatory Agents. Med. Chem. Res. 2014, 23, 948–957. DOI: 10.1007/s00044-013-069.
  • Ahirwar, J.; Ahirwar, D.; Lanjhiyana, S.; Jha, A. K.; Dewangan, D.; Badwaik, H. Analgesic and anti-Inflammatory Potential of Merged Pharmacophore Containing 1,2,4-Triazoles and Substituted Benzyl Groups via Thio Linkage. J. Heterocyclic Chem. 2018, 55, 2130–2141. DOI: 10.1002/jhet.3258.
  • Chelamalla, R.; Akena, V.; Manda, S. Synthesis of N′-Arylidene-2-(5-Aryl-1H-1,2,4-Triazol-3-Ylthio)Acetohydrazides as Antidepressants. Med Chem. Res. 2017, 26, 1359–1366. DOI: 10.1007/s00044-017-1854-5.
  • Jubie, S.; Sikdar, P.; Antony, S.; Kalirajan, R.; Gowramma, B.; Gomathy, S.; Elango, K. Synthesis and Biological Evaluation of Some Schiff Bases of [4-(Amino)-5-Phenyl-4H-1,2,4-Triazole-3-Thiol]. Pak. J. Pharm. Sci. 2011, 24, 109–112. DOI: 10.1021/np2000649.
  • Madhu Sekhar, M.; Yamini, G.; Divya, K. R. G.; Padmavathi, V.; Padmaja, A. Synthesis and Bioassay of a New Class of Disubstituted 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles and 1,2,4-Triazoles. Med. Chem. Res. 2019, 28, 1049–1062. DOI: 10.1007/s00044-019-02360-2.
  • Beyzaei, H.; Khosravi, Z.; Aryan, R.; Ghasemi, B. A Green One-Pot Synthesis of 3(5)-Substituted 1,2,4-Triazol-5(3)-Amines as Potential Antimicrobial Agents. J. Iran. Chem. Soc. 2019, 16, 2565–2573. DOI: 10.1007/s13738-019-01714-2.
  • Abed, N. A.; Hammouda, M. M.; Ismail, M. A.; Abdel-Latif, E. Synthesis of New Heterocycles Festooned with Thiophene and Evaluating Their Antioxidant Activity. J. Heterocyclic Chem. 2020, 57, 4153–4163. DOI: 10.1002/jhet.4122.
  • Manap, S. Synthesis and in Vitro Antioxidant and Antimicrobial Activities of Novel 3-Alkyl(Aryl)-4-[3-Methoxy-4-(2-Furylcarbonyloxy)-Benzylidenamino]-4,5-Dihydro-1H-1,2,4-Triazol-5-Ones, and Their N-Acetyl, N-Mannich Base Derivatives. J. Iran. Chem. Soc. 2022, 19, 1347–1368. DOI: 10.1007/s13738-021-02386-7.
  • Wu, W.-N.; Jiang, Y.-M.; Fei, Qiang.; Du, H.-T. Synthesis and Fungicidal Activity of Novel 1,2,4-Triazole Derivatives Containing a Pyrimidine Moiety. Phosphorus Sulfur Silicon Relat. Elem. 2019, 194, 1171–1175. DOI: 10.1080/10426507.2019.1633321.
  • Nuha, D.; Evren, A. E.; Cankılıc, M. Y.; Yurttaş, L. Design and Synthesis of Novel 2,4,5-Thiazole Derivatives as 6-APA Mimics and Antimicrobial Activity Evaluation. Phosphorus Sulfur Silicon Relat. Elem. 2021, 196, 954–960. DOI: 10.1080/10426507.2021.1946537.
  • Patel, N. B.; Khan, I. H. Synthesis of 1,2,4-Triazole Derivatives Containing Benzothiazoles as Pharmacologically Active Molecule. J. Enzym. Inhib. Med. Chem. 2011, 26, 527–534. DOI: 10.3109/14756366.2010.535794.
  • Zhu, J. J.; He, L. H.; Luo, J.; Xiong, J.; Wang, T. Design, Synthesis, and Herbicidal Activity of Novel Pyrimidine Derivatives Containing 1,2,4-Triazole. Phosphorus Sulfur Silicon Relat. Elem. 2021, 196, 948–953. DOI: 10.1080/10426507.2021.1946063.
  • Ozdemir, Y.; Bekircan, O.; Baltaş, N.; Menteşe, E. Synthesis and Pancreatic Lipase Inhibitory Activities of Some 1,2,4-Triazol-5(3)-One Derivatives. J. Heterocyclic Chem. 2020, 57, 4239–4253. DOI: 10.1002/jhet.4130.
  • Nassar, I. F.; Att-Allah, S. R.; Hemdan, M. M. Utility of Thiophene-2-Carbonyl Isothiocyanate as a Precursor for the Synthesis of 1,2,4-Triazole, 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Derivatives with Evaluation of Their Antitumor and Antimicrobial Activities. Phosphorus Sulfur Silicon Relat. Elem. 2018, 193, 630–636. DOI: 10.1080/10426507.2018.1487435.
  • Huo, J. L.; Wang, S.; Yuan, X. H.; Yu, B.; Zhao, W.; Liu, H. M. Discovery of [1,2,4]Triazolo[1,5-a]Pyrimidines Derivatives as Potential Anticancer Agents. Eur. J. Med. Chem. 2021, 211, 113108. DOI: 10.1016/j.ejmech.2020.113108.
  • Mohassab, A. M.; Hassan, H. A.; Abdelhamid, D.; Gouda, A. M.; Youssif, B. G. M.; Tateishi, H.; Otsuka, M.; Abdel-Aziz, M. Design and Synthesis of Novel Quinoline/Chalcone/1,2,4-Triazole Hybrids as Potent Antiproliferative Agent Targeting EGFR and BRAFV600E Kinases. Bioorg. Chem. 2021, 201, 104510. DOI: 10.1016/j.bioorg.2020.104510.
  • Tian, N. N.; Wu, H. X.; Zhang, H. W.; Yang, D. N.; Lv, X.; Yang, Z. C.; Zhang, T. T.; Quan, D. L.; Zhou, L.; Xie, Y.; et al. Discovery of [1,2,4]Triazolo[4,3-a]Pyridines as Potent Smoothened Inhibitors Targeting the Hedgehog Pathway with Improved Antitumor Activity in Vivo. Bioorg. Med. Chem. 2020, 28, 115584. DOI: 10.1016/j.bmc.2020.115584.
  • Guillon, C.; Vetrano, A. M.; Saxena, J.; Hunter, A.; Verderone, G.; Finetti, T. M.; Wisnoski, J.; Dematteo, P. W.; Rapp, R. D.; Heindel, N. D.; et al. Derivatives of 1,2,4-Triazole Imines Acting as Dual iNOS and Tumor Cell Growth Inhibitors. Bioorg. Chem. 2020, 103, 104128. DOI: 10.1016/j.bioorg.2020.104128.
  • Sheppard, J. G.; Frazier, K. R.; Saralkar, P.; Hossain, M. F.; Geldenhuys, W. J.; Long, T. E. Disulfiram-Based Disulfides as Narrow-Spectrum Antibacterial Agents. Bioorg. Med. Chem. Lett. 2018, 28, 1298–1302. DOI: 10.1016/j.bmcl.2018.03.023.
  • Turos, E.; Revell, K. D.; Ramaraju, P.; Gergeres, D. A.; Greenhalgh, K.; Young, A.; Sathyanarayan, N.; Dickey, S.; Lim, D.; Alhamadsheh, M. M.; Reynolds, K. Unsymmetric Aryl-Alkyl Disulfide Growth Inhibitors of Methicillin-Resistant Staphylococcus Aureus and Bacillus Anthracis. Bioorg. Med. Chem. 2008, 16, 6501–6508. DOI: 10.1016/j.bmc.2008.05.032.
  • Capperucci, A.; Coronnello, M.; Salvini, F.; Tanini, D.; Dei, S.; Teodori, E.; Giovannelli, L. Synthesis of Functionalised Organochalcogenides and in Vitro Evaluation of Their Antioxidant Activity. Bioorg. Med. 2021, 110, 104812. DOI: 10.1016/j.bioorg.2021.104812.
  • Osipova, V.; Polovinkina, M.; Gracheva, Y.; Shpakovsky, D.; Osipova, A.; Berberova, N. Antioxidant Activity of Some Organosulfur Compounds in Vitro. Arab. J. Chem. 2021, 14, 103068. DOI: 10.1016/j.arabjc.2021.103068.
  • Lee, T. H.; Khan, Z.; Subedi, L.; Kim, S. Y.; Lee, K. R. New Bis-Thioglycosyl-1,1′-Disulfides from Nasturtium Officinale R. Br. and Their anti-Neuroinflammatory Effect. Bioorg. Chem. 2019, 86, 501–506. DOI: 10.1016/j.bioorg.2019.01.062.
  • Jadhav, K. B.; Stein, C.; Makarewicz, O.; Pradel, G.; Lichtenecker, R. J.; Sack, H.; Heinemann, S. H.; Arndt, H. D. Bioactivity of Topologically Confined Gramicidin a Dimmers. Bioorg. Med. Chem. 2017, 25, 261–268. DOI: 10.1016/j.bmc.2016.10.033.
  • Branowska, D.; Ławecka, J.; Sobiczewski, M.; Karczmarzyk, Z.; Wysocki, W.; Wolińska, E.; Olender, E.; Mirosław, B.; Perzyna, A.; Bielawska, A.; Bielawski, K. Synthesis of Unsymmetrical Disulfanes Bearing 1,2,4-Triazine Scaffold and Their in Vitro Screening towards anti-Breast Cancer Activity. Monatsh. Chem. 2018, 149, 1409–1420. DOI: 10.1007/s00706-018-2206-y.
  • You, B. R.; Shin, H. R.; Park, W. H. PX-12 Inhibits the Growth of A549 Lung Cancer Cells via G2/M Phase Arrest and ROS-Dependent Apoptosis. Int. J. Oncol. 2014, 44, 301–308. DOI: 10.3892/ijo.2013.2152.
  • Diraimondo, T. R.; Plugis, N. M.; Jin, X.; Khosla, C. Selective Inhibition of Extracellular Thioredoxin by Asymmetric Disulfides. J. Med. Chem. 2013, 56, 1301–1310. DOI: 10.1021/jm301775s.
  • Zhu, S. J.; Ying, H. Z.; Wu, Y.; Qiu, N.; Liu, T.; Yang, B.; Dong, X. W.; Hu, Y. Z. Design, Synthesis and Biological Evaluation of Novel Podophyllotoxin Derivatives Bearing 4β-Disulfide/Trisulfide Bond as Cytotoxic Agents. RSC Adv. 2015, 5, 103172–103183. DOI: 10.1039/C5RA12837D.
  • Shiri, P. Novel Hybrid Molecules Based on Triazole-β-Lactam as Potential Biological Agents. Mini Rev. Med. Chem. 2021, 21, 536–553. DOI: 10.2174/1389557520666201027160436.
  • Takate, S. J.; Shinde, A. D.; Karale, B. K.; Akolkar, H.; Nawale, L.; Sarkar, D. E.; Mhaske, P. C. Thiazolyl-Pyrazole Derivatives as Potential Antimycobacterial Agents. Bioorg. Med. Chem. Lett. 2019, 29, 1199–1202. DOI: 10.1016/j.bmcl.2019.03.020.
  • Bommagani, S.; Penthala, N. R.; Balasubramaniam, M.; Kuravi, S.; Caldas-Lopes, E.; Guzman, M. L.; Balusu, R.; Crooks, P. A. A Novel Tetrazole Analogue of Resveratrol is a Potent Anticancer Agent. Bioorg. Med. Chem. Lett. 2019, 29, 172–178. DOI: 10.1016/j.bmcl.2018.12.006.
  • Sekhar, M. M.; Nagarjuna, U.; Padmavathi, V.; Padmaja, A.; Reddy, N. V.; Vijaya, T. Synthesis and Antimicrobial Activity of Pyrimidinyl 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles and 1,2,4-Triazoles. Eur. J. Med. Chem. 2018, 145, 1–10. DOI: 10.1016/j.ejmech.2017.12.067.
  • Sirakawa, K.; Aki, O.; Tsujikawa, T.; Tsuda, T. S-Alkylthioisothioureas. I. Chem. Pharm. Bull. 1970, 18, 235–242. DOI: 10.1248/cpb.18.235.
  • Murty, M. S. R.; Ram, K. R.; Rao, B. R.; Rao, R. V.; Katiki, M. R.; Rao, J. V.; Pamanji, R.; Velatooru, L. R. Synthesis, Characterization, and Anticancer Studies of S and N Alkyl Piperazine-Substituted Positional Isomers of 1,2,4-Triazole Derivatives. Med. Chem. Res. 2014, 23, 1661–1671. DOI: 10.1007/s00044-013-0757-3.

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