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Synthesis 2024; 56(09): 1429-1437
DOI: 10.1055/a-2231-4922
DOI: 10.1055/a-2231-4922
paper
Solvent-Free Efficient Synthesis of New 4-Thiazolidinones with a Fructose Scaffold through a Microwave-Assisted Cascade Multicomponent Reaction
This work was supported by grants from Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET, Buenos Aires, Argentina, PIP11220210100251CO01-CONICET) and UNS (Universidad Nacional del Sur, Bahía Blanca, Argentina, PGI24Q/102). A fellowship from CONICET to F.L. is acknowledged.
Abstract
Using a chemoselective, sustainable and highly efficient method, new 4-thiazolidinones and 1,4-thiazepan-3-ones substituted with a glycosidic residue derived from d-fructose were synthesized. Microwave-assisted cascade multicomponent reaction under solvent-free conditions gave very good yields in short reaction times, which was followed by a nontoxic purification method of one of the diastereomers by precipitation–centrifugation. The new purified compounds isolated as diastereomers were evaluated as factor Xa (FXa) inhibitors.
Key words
4-thiazolidinones - 1,4-thiazepan-3-ones - carbohydrates - chemoselectivity - multicomponent reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2231-4922.
- Supporting Information
Publication History
Received: 17 November 2023
Accepted after revision: 18 December 2023
Accepted Manuscript online:
18 December 2023
Article published online:
12 February 2024
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References
- 1 Kappe CO, Stadler A, Dallinger D. Microwaves in Organic and Medicinal Chemistry, 2nd ed. Wiley-VCH; Weinheim: 2012
- 2 Microwaves in Organic Synthesis, 3rd ed. de la Hoz A, Loupy A. Wiley-VCH; Weinheim: 2012
- 3 Advances in Microwave Chemistry, 1st ed. Banik BK, Bandyopadhyay D. CRC Press/Taylor & Francis Group; Boca Raton (FL, USA): 2019
- 4a Zhi S, Ma X, Zhang W. Org. Biomol. Chem. 2019; 17: 7632
- 4b Multicomponent Reactions towards Heterocycles: Concepts and Applications. Van der Eycken EV, Sharma UK. Wiley-VCH; Weinheim: 2022
- 4c Kumar A, Khan A, Malhotra S, Mosurkal R, Dhawan A, Pandey MK, Parmar VS. Chem. Soc. Rev. 2016; 45: 6855
- 5 Omri M, Pourceau G, Becuwe M, Wadouachi A. ACS Sustainable Chem. Eng. 2016; 4: 2432
- 6 Barradas JS, Errea MI, D’Accorso NB. Carbohydr. Res. 2012; 355: 79
- 7 Barradas JS, Errea MI, Sepúlveda CS, Damonte EB, D’Accorso NB. J. Heterocycl. Chem. 2014; 51: 96
- 8 Saini N, Sharma A, Thakur VK, Makatsoris C, Dandia A, Bhagat M, Sharma PC. Curr. Res. Green Sustainable Chem. 2020; 3: 100021
- 9 Lesyk R. J. Med. Sci. 2020; 89: e407
- 10 Chahal V, Kakkar R. Struct. Chem. 2020; 31: 1599
- 11 Nirwan S, Chahal V, Kakkar R. J. Heterocycl. Chem. 2019; 56: 1239
- 12 Bhat MA, Al-Omar MA, Naglah AM, Khan AA. Molecules 2020; 25: 3570
- 13 Desai NC, Jadeja KA, Jadeja DJ, Khedkar VM, Jha PC. Synth. Commun. 2021; 51: 952
- 14 Mishchenko M, Shtrygol S, Kaminskyy D, Lesyk R. Sci. Pharm. 2020; 88: 16
- 15 Kolarević A, Ilić BS, Kocić G, Džambaski Z, Šmelcerović A, Bondžić BP. J. Cell. Biochem. 2019; 120: 264
- 16a Zhang Y, Tangadanchu VK. R, Cheng Y, Yang RG, Lin JM, Zhou CH. ACS Med. Chem. Lett. 2018; 9: 244
- 16b Zhang Y, Tangadanchu VK. R, Bheemanaboina RR. Y, Cheng Y, Zhou CH. Eur. J. Med. Chem. 2018; 155: 579
- 17 Iqbal S, Khan MA, Javaid K, Sadiq R, Fazal-ur-Rehman S, Choudhary MI, Basha FZ. Bioorg. Chem. 2017; 74: 72
- 18 Ghani U, Albarrag A, Yurttaş L, Demirci F, Kaplancikli ZA. ChemistrySelect 2018; 3: 7921
- 19 Chen K, Yao X, Tang T, Chen LM, Xiao C, Wang JY, Zheng X. Med. Chem. Res. 2021; 30: 519
- 20 Pinto DJ. P, Qiao JX, Knabb RM. Expert Opin. Ther. Pat. 2012; 22: 645
- 21 Rodríguez DF, Durán-Osorio F, Duarte Y, Olivares P, Moglie Y, Dua K, Zacconi FC. Pharmaceutics 2022; 14: 33
- 22 Kumar A, Kuang Y, Liang Z, Sun X. Mater. Today Nano 2020; 11: 100076
- 23 Nain S, Singh R, Ravichandran S. Adv. J. Chem., Sect. A 2019; 2: 94
- 24 Lim FP. L, Dolzhenko AV. In Green Sustainable Process for Chemical and Environmental Engineering and Science: Sustainable Organic Synthesis, Chap. 1. Inamuddin, Boddula R, Asiri AM. Elsevier; Amsterdam: 2020
- 25a Farrán A, Cai C, Sandoval M, Xu Y, Liu J, Hernáiz MJ, Linhardt RJ. Chem. Rev. 2015; 115: 6811
- 25b Basu A, Kunduru KR, Abtew E, Domb AJ. Bioconjugate Chem. 2015; 26: 1396
- 26a Ayyash AN, Hammady AO. J. Phys.: Conf. Ser. 2020; 1660: 012025
- 26b Rezaei M, Mohammadi HT, Mahdavi A, Shourian M, Ghafouri H. Int. J. Biol. Macromol. 2018; 108: 205
- 26c Ardiansah B. Int. J. ChemTech Res. 2018; 11: 22
- 26d Zhang P, Min Z, Gao Y, Bian J, Lin X, He J, Ye D, Li Y, Peng C, Cheng Y, Chu Y. J. Med. Chem. 2021; 64: 7341
- 27 Shi F, Zeng X.-N, Cao X.-D, Zhang S, Jiang B, Zheng W.-F, Tu S.-J. Bioorg. Med. Chem. Lett. 2012; 22: 743
- 28 Martins Alho MA, Baggio R, D’Accorso NB. ARKIVOC 2013; (iii): 129
- 29 Cubero II, Plaza Lopez-Espinosa MT. Carbohydr. Res. 1990; 205: 293
- 30 CCDC 1523727 (4a), CCDC 2306569 (5b) and CCDC 2306571 (6d) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
- 31 Tu S.-J, Cao X.-D, Hao W.-J, Zhang X.-H, Yan S, Wu S.-S, Han Z.-G, Shi F. Org. Biomol. Chem. 2009; 7: 557
- 32 Secrieru A, O’Neill PM, Cristiano ML. S. Molecules 2020; 25: 42
- 33 Bolognese A, Correale G, Manfra M, Lavecchia A, Novellino E, Barone V. Org. Biomol. Chem. 2004; 2: 2809