Novel Selenoureas Based on Alkaloid Skeleton: Synthesis and Catalytic Investigations

Overview

Journal Materials (Basel)

Publisher MDPI

Date 2021 Feb 2

PMID 33525376

Citations 2

Authors

Mariola Zielinska-Blajet

Joanna Najdek

Affiliations

Soon will be listed here.

Abstract

An efficient approach to the synthesis of chiral selenoureas consisting of alkaloid scaffolds was described. The new selenoureas were assessed as bifunctional organocatalysts in the asymmetric Michael addition reactions under mild conditions. The best results were obtained for selenoureas bearing the 4-fluorophenyl group. These catalysts promoted the reactions with enantioselectivities of up to 96% ee. Additionally, the catalytic performance of the thiourea and selenourea counterpart was compared.

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References

Parvin T, Yadav R, Choudhury L . Recent applications of thiourea-based organocatalysts in asymmetric multicomponent reactions (AMCRs). Org Biomol Chem. 2020; 18(29):5513-5532. DOI: 10.1039/d0ob00595a. View

Vakulya B, Varga S, Csampai A, Soos T . Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts. Org Lett. 2005; 7(10):1967-9. DOI: 10.1021/ol050431s. View

Li X, Deng H, Zhang B, Li J, Zhang L, Luo S . Physical organic study of structure-activity-enantioselectivity relationships in asymmetric bifunctional thiourea catalysis: hints for the design of new organocatalysts. Chemistry. 2009; 16(2):450-5. DOI: 10.1002/chem.200902430. View

Sharma S, Maurya R, Min K, Jeong G, Kim D . Odorless isocyanide chemistry: an integrated microfluidic system for a multistep reaction sequence. Angew Chem Int Ed Engl. 2013; 52(29):7564-8. DOI: 10.1002/anie.201303213. View

Serdyuk O, Heckel C, Tsogoeva S . Bifunctional primary amine-thioureas in asymmetric organocatalysis. Org Biomol Chem. 2013; 11(41):7051-71. DOI: 10.1039/c3ob41403e. View

Ruberte A, Ramos-Inza S, Aydillo C, Talavera I, Encio I, Plano D . Novel ,'-Disubstituted Acylselenoureas as Potential Antioxidant and Cytotoxic Agents. Antioxidants (Basel). 2020; 9(1). PMC: 7023466. DOI: 10.3390/antiox9010055. View

Sivapriya K, Suguna P, Banerjee A, Saravanan V, Rao D, Chandrasekaran S . Facile one-pot synthesis of thio and selenourea derivatives: a new class of potent urease inhibitors. Bioorg Med Chem Lett. 2007; 17(22):6387-91. DOI: 10.1016/j.bmcl.2007.07.085. View

Jorres M, Schiffers I, Atodiresei I, Bolm C . Asymmetric Michael additions of α-nitrocyclohexanone to aryl nitroalkenes catalyzed by natural amino acid-derived bifunctional thioureas. Org Lett. 2012; 14(17):4518-21. DOI: 10.1021/ol302005f. View

Picci G, Mocci R, Ciancaleoni G, Lippolis V, Zielinska-Blajet M, Caltagirone C . Bis-Selenoureas for Anion Binding: A 1H NMR and Theoretical Study. Chempluschem. 2020; 85(7):1389-1395. DOI: 10.1002/cplu.202000260. View

10.

Zhang Z, Bao Z, Xing H . N,N'-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea: a privileged motif for catalyst development. Org Biomol Chem. 2014; 12(20):3151-62. DOI: 10.1039/c4ob00306c. View

11.

Ishihara H, Koketsu M, Fukuta Y, Nada F . Reaction of lithium aluminum hydride with elemental selenium: its application as a selenating reagent into organic molecules. J Am Chem Soc. 2001; 123(34):8408-9. DOI: 10.1021/ja005800o. View

12.

Alcolea V, Plano D, Karelia D, Antonio Palop J, Amin S, Sanmartin C . Novel seleno- and thio-urea derivatives with potent in vitro activities against several cancer cell lines. Eur J Med Chem. 2016; 113:134-44. DOI: 10.1016/j.ejmech.2016.02.042. View

13.

Diaz M, de Lucio H, Moreno E, Espuelas S, Aydillo C, Jimenez-Ruiz A . Synthesis and Leishmanicidal Activity of Novel Urea, Thiourea, and Selenourea Derivatives of Diselenides. Antimicrob Agents Chemother. 2019; 63(5). PMC: 6496061. DOI: 10.1128/AAC.02200-18. View

14.

Manzano R, Andres J, Alvarez R, Muruzabal M, de Lera A, Pedrosa R . Enantioselective conjugate addition of nitro compounds to α,β-unsaturated ketones: an experimental and computational study. Chemistry. 2011; 17(21):5931-8. DOI: 10.1002/chem.201100241. View

15.

Steppeler F, Iwan D, Wojaczynska E, Wojaczynski J . Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry. Molecules. 2020; 25(2). PMC: 7024223. DOI: 10.3390/molecules25020401. View

16.

Merino-Montiel P, Maza S, Martos S, Lopez O, Maya I, Fernandez-Bolanos J . Synthesis and antioxidant activity of O-alkyl selenocarbamates, selenoureas and selenohydantoins. Eur J Pharm Sci. 2013; 48(3):582-92. DOI: 10.1016/j.ejps.2012.12.016. View

17.

Jakab G, Tancon C, Zhang Z, Lippert K, R Schreiner P . (Thio)urea organocatalyst equilibrium acidities in DMSO. Org Lett. 2012; 14(7):1724-7. DOI: 10.1021/ol300307c. View

18.

Hussain R, Badshah A, Tahir M, Tamoor-ul-Hassan , Bano A . Synthesis, chemical characterization, DNA binding, antioxidant, antibacterial, and antifungal activities of ferrocence incorporated selenoureas. J Biochem Mol Toxicol. 2013; 28(2):60-8. DOI: 10.1002/jbt.21536. View

19.

Corey E, Zhang F . Enantioselective Michael addition of nitromethane to alpha, beta-enones catalyzed by chiral quaternary ammonium salts. A simple synthesis of (R)-baclofen. Org Lett. 2001; 2(26):4257-9. DOI: 10.1021/ol0068344. View

20.

Connon S . Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts. Chem Commun (Camb). 2008; (22):2499-510. DOI: 10.1039/b719249e. View