Synthesis, Anticancer and Antibacterial Activity of Mannose-based bis-1,2,3-Triazole Derivatives
Main Article Content
Abstract
In the current work, aromatic amines and alkyl halides have been converted to the corresponding azides 2a‒d and 4a-d by the reaction with sodium nitrite and sodium azide respectively for amines and sodium azide for halides. Then, dipropargyl ether derivative of D-mannose 8 has been synthesized from diacetone mannose that has been obtained by the treatment of D-mannose (5) with dry acetone in the presence of sulfuric acid. Then, aldol condensation has been used to prepare diol 7 from the mannose diacetonide 6. The reaction of compound 7 with propargyl bromide in alkaline media has been afforded dipropargyl derivative 8. In a parallel step, both dialkyne with aromatic and aliphatic azide have been coupled to produce 1,2,3-triazole derivatives 9a‒d in the presence of Cu(I) salts. All synthesized compounds have been characterized by 1D and 2D NMR spectra alongside with HRMS data. The antibacterial activity against both gram-positive and gram-negative has been tested. Moreover, the anticancer activity has also been evaluated against AMJ13 cell line.
Received 9/5/2022, Accepted 19/7/2022, Published Online First 20/1/2023
Article Details
This work is licensed under a Creative Commons Attribution 4.0 International License.
How to Cite
References
Rebecca L. Siegel MPH, Kimberly D. Miller MPH, Hannah E. Fuchs BS, Ahmedin Jemal DVM. Cancer Statistics, 2021. CA Cancer J Clin. 2021; 71:7–33. Available from: https://doi.org/10.3322/caac.21654.
Mandalapu D, Saini KS, Gupta S, Sharma V, Malik MY, Chaturvedi S, Bala V, Thakur S, Maikhuri JP, Wahajuddin M, Konwar R. Synthesis and biological evaluation of some novel triazole hybrids of curcumin mimics and their selective anticancer activity against breast and prostate cancer cell lines. Bioorg Med Chem Lett. 2016 ;26(17):4223-4232. Available from: https://www.sciencedirect.com/science/article/pii/S0960894X16307818
Panda S, Pradhan N, Chatterjee S, Morla S, Saha A, Roy A, Kumar S, Bhattacharyya A, Manna D. 4, 5-Disubstituted 1, 2, 3-triazoles: effective inhibition of indoleamine 2, 3-dioxygenase 1 enzyme regulates T cell activity and mitigates tumor growth. Sci Rep. 2019; 9(1): 1-6. Available from: https://doi.org/10.1038/s41598-019-54963-9
Le TT, Le PT, Dam HT, Vo DD, Le TT. Anticancer Activity of New 1,2,3-Triazole-Amino Acid Conjugates. Molbank. 2021; 2021(2): M1204. Available from: https://doi.org/10.3390/M1204.
Carreiro EP, Sena AM, Puerta A, Padrón JM, Burke AJ. Synthesis of Novel 1,2,3-Triazole-Dihydropyrimidinone Hybrids Using Multicomponent 1,3-Dipolar Cycloaddition (Click)–Biginelli Reactions: Anticancer Activity. Synlett. 2020; 31(06): 615-621. Available from: https://doi.org/10.1055/s-0039-1690781.
Gomes AT, Fernandes R, Ribeiro CF, Tomé JP, Neves MG, Silva FD, Ferreira VF, Cavaleiro JA. Synthesis, characterization and photodynamic activity against bladder cancer cells of novel triazole-porphyrin derivatives. Molecules. 2020; 25(7): 1607. Available from: https://pubmed.ncbi.nlm.nih.gov/32244514.
Nerella S, Kankala S, Gavaji B. Synthesis of podophyllotoxin-glycosyl triazoles via click protocol mediated by silver (I)-N-heterocyclic carbenes and their anticancer evaluation as topoisomerase-II inhibitors. Nat Prod Res. 2021; 35(1): 9–16. Available from: https://doi.org/10.1080/14786419.2019.1610958.
Oubella A, Bimoussa A, N’ait Oussidi A, Fawzi M, Auhmani A, Morjani H, Riahi A, Esseffar MH, Parish C, Ait Itto MY. New 1, 2, 3-Triazoles from (R)-Carvone: Synthesis, DFT Mechanistic Study and In Vitro Cytotoxic Evaluation. Molecules. 2022; 27(3): 769. Available from: https://www.mdpi.com/1420-3049/27/3/769.
Zhou M, Kan M-Y. The varying impacts of COVID-19 and its related measures in the UK: A year in review. PLoS ONE. 2021; 16(9): e0257286. https://doi.org/10.1371/journal.pone.0257286.
Ali ZZ, Abdulla AM. Synthesis and Antimicrobial Schreening of New 4, 5, 6, 7-Tatra Hydro Benzo Thiophene Derivatives. Baghdad Sci J. 2019; 16(1): 68‒77. Available from: http://dx.doi.org/10.21123/bsj.2019.16.1.0068.
AL-Joubory AK, Abdullah LW, Mohammed AJ. Synthesis, Characterization and Biological Activity Evaluation of Some Pyrazoles, Thiazoles and Oxazoles Derived from 2-Mercaptoaniline. Baghdad Sci J. 2021; 18(1 (Suppl.)):764‒774. Available from: http://doi.org/10.21123/bsj.2021.18.1(Suppl.).0764.
Said MA, Khan DJ, Al-Blewi FF, Al-Kaff NS, Ali AA, Rezki N, et al. New 1, 2, 3-Triazole Scaffold Schiff Bases as Potential Anti-COVID-19: Design, Synthesis, DFT-Molecular Docking, and Cytotoxicity Aspects. Vaccines. 2021; 9(9): 1012. Available from: https://www.mdpi.com/2076-393X/9/9/1012.
Holanda VN, Lima EM, Silva WV, Maia RT, Medeiros RD, Ghosh A, Lima VL, Figueiredo RC. Identification of 1, 2, 3-triazole-phthalimide derivatives as potential drugs against COVID-19: a virtual screening, docking and molecular dynamic study. J Biomol Struct. 2021: 1-9. Available from: https://doi.org/10.1080/07391102.2020.1871073.
Higashitani F, Hyodo A, Ishida N, Inoue M, Mitsuhashi S. Inhibition of beta-lactamases by tazobactam and in-vitro antibacterial activity of tazobactam combined with piperacillin. J Antimicrob Chemother. 1990; 25(4): 567–574. Available from: https://doi.org/10.1093/jac/25.4.567.
Neu HC, Fu KP. Cefatrizine activity compared with that of other cephalosporins. Antimicrob Agents Chemother. 1979; 15(2): 209–212. Available from: https://doi.org/10.1128/AAC.15.2.209.
Soltis MJ, Yeh HJ, Cole KA, Whittaker N, Wersto RP, Kohn EC. Identification and characterization of human metabolites of CAI [5-amino-1-1(4’-chlorobenzoyl-3,5-dichlorobenzyl)-1,2,3-triazole- 4-carboxamide). Drug Metab Dispos. 1996; 24(7): 799–806. Available from: https://pubmed.ncbi.nlm.nih.gov/8818579/
Sheng C, Zhang W. New lead structures in antifungal drug discovery. Curr Med Chem. 2011; 18(5): 733–766. Available from: https://doi.org/10.2174/092986711794480113.
Perabo FG, Wirger A, Kamp S, Lindner H, Schmidt DH, Müller SC, Kohn EC. Carboxyamido-triazole (CAI), a signal transduction inhibitor induces growth inhibition and apoptosis in bladder cancer cells by modulation of Bcl-2. Anticancer Res. 2004; 24(5A): Available from: 2869-2878. https://pubmed.ncbi.nlm.nih.gov/15517890/
Yadav M, Lal K, Kumar A, Kumar A, Kumar D. Indole-chalcone linked 1,2,3-triazole hybrids: Facile synthesis, antimicrobial evaluation and docking studies as potential antimicrobial agents. J Mol Struct. 2022; 132867. Available from: https://www.sciencedirect.com/science/article/pii/S0022286022005397.
Marzi M, Farjam M, Kazeminejad Z, Shiroudi A, Kouhpayeh A, Zarenezhad E. A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR). Tiwari VK, editor. J Chem. 2022; 2022: 7884316. Available from: https://doi.org/10.1155/2022/7884316.
Kandula MK, Gundluru M, Nemallapudi BR, Gundala S, Kotha P, Zyryanov GV, Chadive S, Cirandur SR. Synthesis, antioxidant activity, and α‐glucosidase enzyme inhibition of α‐aminophosphonate derivatives bearing piperazine‐1,2,3‐triazole moiety. J Heterocycl Chem. 2021; 58(1): 172-181. Available from: https://doi.org/10.1002/jhet.4157.
Kuczynska K, Bończak B, Rárová L, Kvasnicová M, Strnad M, Pakulski Z, et al. Synthesis and cytotoxic activity of 1,2,3-triazoles derived from 2,3-seco-dihydrobetulin via a click chemistry approach. J Mol Struct. 2022;1250:131751. Available from: https://www.sciencedirect.com/science/article/pii/S0022286021018767
Mohammed AI, Dawood AH, Ali KF, Al-mosawi M. Microwave assisted synthesis of new heterocyclic compounds: 1, 2, 3-Triazoles and Tetrazoles and study of their biological activity. Asian J Chem. 2012;24(12):5592‒5596. Available from: https://asianjournalofchemistry.co.in/user/journal/viewarticle.aspx?ArticleID=24_12_47.
Mohammed AI, Jwad RS, Al-Radha NA. Copper (I) catalyzed synthesis and biological evaluation of tetrakis-1,2,3-triazoles based on D-iditol. Int J Chem Sc. 2013; 11(1): 1–11. Available from: https://www.tsijournals.com/articles/copper-i-catalyzed-synthesis-and-biologicalevaluation-of-tetrakis123triazoles-basedon-diditol.pdf.
Mohammed AI, Mansour NH, Mahdi LS. Synthesis and antibacterial activity of 1-N-(β-d-glucopyranosyl)-4-((1-substituted-1H-1,2,3-triazol-4-yl)ethoxymethyl)-1,2,3-triazoles. Arab J Chem . 2017; 10: S3508–S3514. Available from: https://www.sciencedirect.com/science/article/pii/S1878535214000513.
Grob NM, Schibli R, Béhé M, Valverde IE, Mindt TL. 1,5-Disubstituted 1,2,3-Triazoles as Amide Bond Isosteres Yield Novel Tumor-Targeting Minigastrin Analogs. ACS Med Chem Lett. 2021; 12(4): 585–592. Available from: https://doi.org/10.1021/acsmedchemlett.0c00636.
Mohamed HA, Abdel-Wahab BF, Fahmy HM. Thiazole Azodyes Containing Sulfonamide Moiety for UV Protection and Antimicrobial of Cotton Fabrics. Polycycl Aromat Compd. 2022; 42(1): 195–203. Available from: https://doi.org/10.1080/10406638.2020.1723655.
Raviprabha K, Bhat RS. Corrosion Inhibition Effect of Ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate on Aluminium Alloy in Hydrochloric Acid. Prot Met Phys Chem Surf. 2021; 57(1): 181–189. Available from: https://doi.org/10.1134/S2070205120060209.
Narea P, Hernández B, Cisterna J, Cárdenas A, Llanos J, Amo-Ochoa P, Zamora F, Priego JL, Cortijo M, Delgado GE, Brito I. Heterobimetallic three-dimensional 4d-4f coordination polymers based on 5-methyl-1-(pyridyn-4-ylmethyl)-1H-1,2,3-triazole-3, 4-dicarboxylate. J Solid State Chem. 2022; 310: 123027. Available from: https://www.sciencedirect.com/science/article/pii/S0022459622001517.
Jourdain A, Obadia M, Duchet-Rumeau J, Bernard J, Serghei A, Tournilhac F, et al. Comparison of poly(ethylene glycol)-based networks obtained by cationic ring opening polymerization of neutral and 1,2,3-triazolium diepoxy monomers. Polym Chem. 2020;11(11):1894-905.Available from: http://dx.doi.org/10.1039/C9PY01923E.
Xing Q, Zhou C, Jiang S, Chen S, Deng GJ. Acid-catalyzed three-component addition of carbonyl compounds with 1,2,3-triazoles and indoles. Org Biomol Chem. 2021; 19(36): 7838–7842. Available from: http://dx.doi.org/10.1039/D1OB01451J.
Xia M, Chen Y, Chen Z, Yu W, Cheng H, Feng C, et al. 1,2,3-Triazole lamellar liquid crystal and its non-covalent palladium complex dimer: structure, mesomorphism and self-assembly properties. Liq Cryst. 2022; 49(1): 72-84.Available from: https://doi.org/10.1080/02678292.2021.1944358.
Mohammed AI, Abboud ZH, Alghanimi AHO. Synthesis of D-mannitol substituted ether-linked bis-1,2,3-triazoles as models of gemini surfactants. Tetrahedron Lett. 2012; 53(38): 5081–5083. Available from: https://www.sciencedirect.com/science/article/pii/S004040391201180X.
Rani A, Saini P, Singh G, Singh H, Kaur G, Singh J. ‘Quick CuAAC’Chemistry for Hg (II) and Mn (II) ion sensing via 9H-carbazole derivatives. Inorg Chim Acta. 2021; 527: 120560.Available from: https://www.sciencedirect.com/science/article/pii/S0020169321003169.
Rostovtsev V V, Green LG, Fokin V V, Sharpless KB. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes. Angew Chemie Int Ed. 2002; 41(14): 2596–2599. Available from: https://doi.org/10.1002/1521-3773(20020715)41:14%3C2596::AID-ANIE2596%3E3.0.CO.
Tornøe CW, Christensen C, Meldal M. Peptidotriazoles on solid phase:[1,2,3]-triazoles by regiospecific copper (I)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem. 2002; 67(9): 3057‒3064. Available from: https://doi.org/10.1021/jo011148j,
Jwad RS. Synthesis and variable temperature NMR study of glucose based 1,2,3-triazole. AIP Conf Proc. 2020;2290(1):30012. Available from: https://aip.scitation.org/doi/abs/10.1063/5.0027407
Mahdi LS, Mohammed AI, Mohammed MJ. Convenient synthesis of dipropargyl ether derivative of D-mannose. AIP Conf Proc. 2020; 2290(1): 30024. Available from: https://aip.scitation.org/doi/abs/10.1063/5.0027403.
Copeland C, Mcadam DP, Stick R V. The reaction of N-dichloromethylene-N,N-dialkylammonium chlorides with free sugars: an efficient synthesis of glycosyl chlorides. Aust J Chem. 1983; 36(6): 1239–1247. Available from: https://doi.org/10.1071/CH9831239.
Tan DX, You J, Xu MR, Wu Y. Greatly Accelerated Condensation of D-Mannose Diacetonide with Aqueous Formaldehyde (Formalin). J Org Chem. 2016; 81(15): 6792-67924. Available from: https://doi.org/10.1021/acs.joc.6b01000.
Jwad RS. Synthesis of 1-Nonyl-4-[(6-Deoxy-1,2:3,4-Di-O-Isopropylidene-α-D-Galactos-6-yl) oxymethyl] 1H-1,2,3-Triazole Via Click Chemistry. ANJS. 2011; 14(1): 1‒10. Available from: https://doi.org/10.22401/JNUS.14.1.08.
Kutonova KV, Trusova ME, Postnikov PS, Filimonov VD, Parello J. A simple and effective synthesis of aryl azides via arenediazonium tosylates. Synthesis. 2013; 45(19): 2706‒2710. Available from: https://doi.org/10.1055/s-0033-1339648.
Reddy LV, Reddy PV, Mishra NN, Shukla PK, Yadav G, Srivastava R, et al. Synthesis and biological evaluation of glycal-derived novel tetrahydrofuran 1,2,3-triazoles by ‘click ‘chemistry. Carbohydr Res. 2010;345(11):1515-1521. Available from: https://doi.org/10.1016/j.carres.2010.03.031.
Al-Ziaydi AG, Al-Shammari AM, Hamzah MI, Jabir MS. Hexokinase inhibition using D-Mannoheptulose enhances oncolytic newcastle disease virus-mediated killing of breast cancer cells. Cancer Cell Int. 2020; 20(1): 1-10. Available from: https://doi.org/10.1186/s12935-020-01514-2.
Al-Salman HNK, Ali ET, Jabir M, Sulaiman GM, Al-Jadaan SAS. 2-Benzhydrylsulfinyl-N-hydroxyacetamide-Na extracted from fig as a novel cytotoxic and apoptosis inducer in SKOV-3 and AMJ-13 cell lines via P53 and caspase-8 pathway. Eur Food Res Technol. 2020; 246(8): 1591–1608. Available from: Available from: https://doi.org/10.1007/s00217-020-03515-x.
Kareem SH, Naji AM, Taqi ZJ, Jabir MS. Polyvinylpyrrolidone loaded-MnZnFe2O4 magnetic nanocomposites induce apoptosis in cancer cells through mitochondrial damage and P53 pathway. J Inorg Organomet Polym Mater. 2020; 30(12): 5009–5023. Available from: https://doi.org/10.1007/s10904-020-01651-1.
Jabir MS, Hussien AA, Sulaiman GM, Yaseen NY, Dewir YH, Alwahibi MS, Soliman DA, Rizwana H. Green synthesis of silver nanoparticles from Eriobotrya japonica extract: a promising approach against cancer cells proliferation, inflammation, allergic disorders and phagocytosis induction. Artif Cells Nanomed Biotechnol. 2021; 49(1): 48‒60. Available from: https://doi.org/10.1080/21691401.2020.1867152.
Khashan KS, Abdulameer FA, Jabir MS, Hadi AA, Sulaiman GM. Anticancer activity and toxicity of carbon nanoparticles produced by pulsed laser ablation of graphite in water. Adv Nat Sci Nanosci Nanotechnol. 2020; 11(3): 35010. Available from: https://doi.org/10.1088/2043-6254/aba1de.
Sameen AM, Jabir MS, Al-Ani MQ. Therapeutic combination of gold nanoparticles and LPS as cytotoxic and apoptosis inducer in breast cancer cells. AIP Conf Proc. 2020: 020215-1-6. Available from: https://doi.org/10.1063/5.0000161.
Bahjat HH, Ismail RA, Sulaiman GM, Jabir MS. Magnetic field-assisted laser ablation of titanium dioxide nanoparticles in water for anti-bacterial applications. J Inorg Organomet Polym Mater. 2021; 31(9): 3649–3656. Available from: https://doi.org/10.1007/s10904-021-01973-8.
Jihad MA, Noori F, Jabir MS, Albukhaty S, AlMalki FA, Alyamani AA. Polyethylene Glycol Functionalized Graphene Oxide Nanoparticles Loaded with Nigella sativa Extract: A Smart Antibacterial Therapeutic Drug Delivery System. Molecules. 2021; 26(11): 3067. Available from: https://doi.org/10.3390/molecules26113067.
Egorov NS. Antibiotics: A Scientific Approach. Moscow. Mir Publishers.1985; Print.
Ho P-T. Branched-chain sugars. Reaction of furanoses with formaldehyde: A simple synthesis of D-and L-apiose. Can J Chem. 1979; 57(4): 381–383. Available from: https://doi.org/10.1139/v79-063.
Reddy LV, Reddy PV, Mishra NN, Shukla PK, Yadav G, Srivastava R, Shaw AK. Synthesis and biological evaluation of glycal-derived novel tetrahydrofuran 1,2,3-triazoles by ‘click’chemistry. Carbohydr Res. 2010; 345(11): 1515‒1521. Available from: https://doi.org/10.1016/j.carres.2010.03.031.
Doiron JE, Le CA, Ody BK, Brace JB, Post SJ, Thacker NL, Hill HM, Breton GW, Mulder MJ, Chang S, Bridges TM. Evaluation of 1,2,3‐Triazoles as Amide Bioisosteres In Cystic Fibrosis Transmembrane Conductance Regulator Modulators VX‐770 and VX‐809. Eur J Chem. 2019; 25(14): 3662‒3674. Available from: https://doi.org/10.1002/chem.201805919.