740
Views
78
CrossRef citations to date
0
Altmetric
Original Research

One-Pot Synthesis of Novel Thiazoles as Potential Anti-Cancer Agents

, , ORCID Icon, , , ORCID Icon & ORCID Icon show all
Pages 1363-1375 | Published online: 03 Apr 2020

References

  • TorreLA, BrayF, SiegelRL, FerlayJ. Lortet‑TieulentJ, JemalA. Global cancer statistics, 2012. CA Cancer J Clin. 2015;65:87–108.25651787
  • CoghlinC, MurrayGI. Biomarkers of colorectal cancer: recent advances and future challenges. Proteomics Clin Appl. 2015;9:64‑71. doi:10.1002/prca.201400082
  • MeierP, FinchA, EvanG. Apoptosis in development. Nature. 2000;407:796–801. doi:10.1038/3503773411048731
  • WillisSN, AdamsJM. Life in the balance: how BH3-only proteins induce apoptosis. Curr Opin Cell Biol. 2005;17:617–625. doi:10.1016/j.ceb.2005.10.00116243507
  • YouleRJ, StrasserA. The BCL-2 protein family: opposing activities that mediate cell death. Nat Rev Mol Cell Biol. 2008;9(1):47–59. doi:10.1038/nrm230818097445
  • DixMM, SimonGM, CravattBF. Global mapping of the topography and magnitude of proteolytic events in apoptosis. Cell. 2008;134(4):679–691. doi:10.1016/j.cell.2008.06.03818724940
  • KotschyA, SzlavikZ, MurrayJ, et al. The MCL1 inhibitor S63845 is tolerable and effective in diverse cancer models. Nature. 2016;538(7626):477–482. doi:10.1038/nature1983027760111
  • da SilvaEB, SilvaDAO, OliveiraAR, et al. Desing and synthesis of potent anti-Trypanosoma cruzi agents new thiazoles derivatives which induce apoptotic parasite death. Eur J Med Chem. 2017;130:39–50. doi:10.1016/j.ejmech.2017.02.02628242550
  • EspíndolaJWP, de Oliveira CardosoMV, de Oliveira FilhoGB, et al. Synthesis and structure–activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma Cruzi Cruzain. Eur J Med Chem. 2015;101:818–835. doi:10.1016/j.ejmech.2015.06.04826231082
  • NetalkarPP, NetalkarSP, RevankarVK. Transition metal complexes of thiosemicarbazone: synthesis, structures and in vitro antimicrobial studies. Polyhedron. 2015;100:215–222. doi:10.1016/j.poly.2015.07.075
  • HuWX, ZhouW, XiaCN, WenX. Synthesis and anticancer activity of thiosemicarbazones. Bioorg Med Chem Lett. 2006;16:2213–2218. doi:10.1016/j.bmcl.2006.01.04816458509
  • WangY, WangZ, KuangH, et al. Synthesis and antitumor activity of 2‐isocamphanyl thiosemicarbazone derivatives via ROS‐enhanced mitochondria damage. Chem Biol Drug Des. 2019. doi:10.1111/cbdd.13492
  • SujathaK, VedulaRR. Novel one-pot expeditious synthesis of 2, 4-disubstituted thiazoles through a three-component reaction under solvent free conditions. Synth Commun. 2018;48:302–308. doi:10.1080/00397911.2017.1399422
  • AbdallaMA, GomhaSM, AbdelazizM, SeragN. Synthesis and antiviral evaluation of some novel thiazoles and 1,3-thiazines substituted with pyrazole moiety against rabies virus. Turk J Chem. 2016;40:441–453. doi:10.3906/kim-1506-13
  • S MG, K DK. A convenient ultrasound-promoted synthesis and cytotoxic activity of some new thiazole derivatives bearing a coumarin nucleus. Molecules. 2012;17:9335–9347. doi:10.3390/molecules1708933522864241
  • NayakS, GaonkarSL. A Review on recent synthetic strategies and pharmacological importance of 1, 3-thiazole derivatives. Mini Rev Med Chem. 2019;19:215–238. doi:10.2174/138955751866618081611215130112994
  • KumarS, AggarwalR. Thiazole: a privileged motif in marine natural products. Mini Rev Org Chem. 2019;16:26–34. doi:10.2174/1570193X15666180412152743
  • GomhaS, EdreesM, AltalbawyF. Synthesis and characterization of some new bis-pyrazolyl-thiazoles incorporating the thiophene moiety as potent anti-tumor agents. Int J Mol Sci. 2016;17:1499. doi:10.3390/ijms17091499
  • GomhaSM, SalahTA, AbdelhamidAO. Synthesis, characterization, and pharmacological evaluation of some novel thiadiazoles and thiazoles incorporating pyrazole moiety as anticancer agents. Monatsh Chem. 2015;146:149–158. doi:10.1007/s00706-014-1303-9
  • Dos Santos SilvaTD, BomfimLM, da Cruz RodriguesACB, et al. Anti-liver cancer activity in vitro and in vivo induced by 2-pyridyl 2, 3-thiazole derivatives. Toxicol Appl Pharmacol. 2017;329:212–223. doi:10.1016/j.taap.2017.06.00328610992
  • MorigiR, LocatelliA, LeoniA, RambaldiM. Recent patents on thiazole derivatives endowed with antitumor activity. Recent Pat Anticancer Drug Discov. 2015;10:280–297. doi:10.2174/157489281066615070811043226152151
  • BremnerWS, OrganMG. Multicomponent reactions to form heterocycles by microwave-assisted continuous flow organic synthesis. J Comb Chem. 2007;9:14–16. doi:10.1021/cc060130p17206827
  • MurataT, MuraiM, IkedaY, MikiK, OheK. Pd-and Cu-catalyzed one-pot multicomponent synthesis of hetero α, α′-dimers of heterocycles. Org Lett. 2012;14:2296–2299. doi:10.1021/ol300718x22533860
  • AbdelrazekFM, GomhaSM, ShaabanME, et al. One-pot three-component synthesis and molecular docking of some novel 2-thiazolyl pyridines as potent antimicrobial agents. Mini Rev Med Chem. 2019;19:527–538. doi:10.2174/138955751866618101912410430360710
  • GomhaSM, MuhammadZA, Abdel‐azizMR, Abdel‐azizHM, GaberHM, ElaasserMM. One‐pot synthesis of new thiadiazolyl‐pyridines as anticancer and antioxidant agents. J Heterocycl Chem. 2018;55:530–536. doi:10.1002/jhet.3088
  • GomhaSM, EdreesMM, FatyRA, MuhammadZA, MabkhotYN. Microwave-assisted one pot three-component synthesis of some novel pyrazole scaffolds as potent anticancer agents. Chem Cent J. 2017;11:37. doi:10.1186/s13065-017-0266-429086808
  • GomhaS, KhederN, AbdelhamidA, MabkhotY. One pot single step synthesis and biological evaluation of some novel bis(1,3,4-thiadiazole) derivatives as potential cytotoxic agents. Molecules. 2016;21:1532. doi:10.3390/molecules21111532
  • GomhaSM. A facile one-pot synthesis of 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4- triazolo[4,5-a]pyrimidin-5-ones. Monatsh Chem. 2009;140:213–220. doi:10.1007/s00706-008-0060-z
  • GomhaSM, AbdelrazekFM. A Facile three component-one-pot synthesis of some novel tri-cyclic hetero-ring systems. J Heterocycl Chem. 2016;53:1892–1896. doi:10.1002/jhet.2503
  • GomhaSM, RiyadhSM. Synthesis of triazolo[4,3-b][1,2,4,5]tetrazines and triazolo[3,4-b][1,3,4]thiadiazines using chitosan as ecofriendly catalyst under microwave irradiation. Arkivoc. 2009;xi:58–68.
  • GomhaSM, AbdallaMA, AbdelazizM, SeragN. Eco-friendly one-pot synthesis and antiviral evaluation of pyrazolyl chalcones and pyrazolines of medicinal interest. Turk J Chem. 2016;40:484–498. doi:10.3906/kim-1510-25
  • AbbasIM, RiyadhSM, AbdallahMA, GomhaSM. A novel route to tetracyclic fused tetrazines and thiadiazines. J Heterocycl Chem. 2006;43:935–942. doi:10.1002/jhet.5570430419
  • AbbasIM, GomhaSM, ElaasserMM, BauomiMA. Synthesis and biological evaluation of new pyridines containing imidazole moiety as antimicrobial and anticancer agents. Turk J Chem. 2015;39:334–346. doi:10.3906/kim-1410-25
  • GomhaSM, RiyadhSM, MahmmoudEA, ElaasserMM. Synthesis and anticancer activity of arylazothiazoles and 1,3,4-thiadiazoles using chitosan-grafted-poly(4-vinylpyridine) as a novel copolymer basic catalyst. Chem Heterocycl Compd. 2015;51:1030–1038. doi:10.1007/s10593-016-1815-9
  • EldehnaWM, Abo-AshourMF, NocentiniA, et al. Novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene) thiazolidin-2-ylidene) amino) benzene sulfonamides: synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular modelling studies. Eur J Med Chem. 2017;139:250–262. doi:10.1016/j.ejmech.2017.07.07328802125
  • MaccioniE, CardiaMC, DistintoS, BonsignoreL, De LoguA. An investigation of the biological effect of structural modifications of isothiosemicarbazones and their cyclic analogues. Il Farmaco. 2003;58:951–959. doi:10.1016/S0014-827X(03)00154-X13679191
  • ShawaliAS, GomhaSM. A new entry for short and regioselective synthesis of [1, 2, 4] triazolo [4, 3-b][1, 2, 4]-triazin-7(1H)-ones. J Prakt Chemie Chem. 2000;342:599–604. doi:10.1002/1521-3897(200006)342:6<599::AID-PRAC599>3.0.CO;2-7
  • TsujimotoY. Cell death regulation by the Bcl-2 protein family in the mitochondria. J Cell Physiol. 2003;195:158–167. doi:10.1002/jcp.1025412652643
  • WuZ-R, LiuJ, LiJ-Y, et al. Synthesis and biological evaluation of hydroxycinnamic acid hydrazide derivatives as inducer of caspase-3. Eur J Med Chem. 2014;85:78–783. doi:10.1016/j.ejmech.2014.08.040