Recent Advances in the Synthesis of Oxazole-Based Molecules Via Van Leusen Oxazole Synthesis

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2020 Apr 5

PMID 32244317

Citations 14

Authors

Xunan Zheng

Wei Liu

Dawei Zhang

Affiliations

Soon will be listed here.

Abstract

Oxazole compounds, including one nitrogen atom and one oxygen atom in a five-membered heterocyclic ring, are present in various biological activities. Due to binding with a widespread spectrum of receptors and enzymes easily in biological systems through various non-covalent interactions, oxazole-based molecules are becoming a kind of significant heterocyclic nucleus, which have received attention from researchers globally, leading them to synthesize diverse oxazole derivatives. The van Leusen reaction, based on tosylmethylisocyanides (TosMICs), is one of the most appropriate strategies to prepare oxazole-based medicinal compounds. In this review, we summarize the recent advances of the synthesis of oxazole-containing molecules utilizing the van Leusen oxazole synthesis from 1972, aiming to look for potential oxazole-based medicinal compounds, which are valuable information for drug discovery and synthesis.

Citing Articles

Pharmacological investigations of newly synthesized oxazolones and imidazolones as COX-2 inhibitors.

Saleem Naz Babari I, Islam M, Saeed H, Nadeem H, Rathore H Saudi Pharm J. 2024; 32(11):102191.

PMID: 39507051 PMC: 11539464. DOI: 10.1016/j.jsps.2024.102191.

Multimodal 4-arylchromene derivatives with microtubule-destabilizing, anti-angiogenic, and MYB-inhibitory activities.

Kohler L, Reich S, Yusenko M, Klempnauer K, Begemann G, Schobert R Cancer Drug Resist. 2023; 6(1):59-77.

PMID: 37065868 PMC: 10099595. DOI: 10.20517/cdr.2022.90.

Multicomponent Reaction-Assisted Drug Discovery: A Time- and Cost-Effective Green Approach Speeding Up Identification and Optimization of Anticancer Drugs.

Graziano G, Stefanachi A, Contino M, Prieto-Diaz R, Ligresti A, Kumar P Int J Mol Sci. 2023; 24(7).

PMID: 37047554 PMC: 10095429. DOI: 10.3390/ijms24076581.

A New Naphthopyran Derivative Combines -Myb Inhibition, Microtubule-Targeting Effects, and Antiangiogenic Properties.

Kohler L, Reich S, Yusenko M, Klempnauer K, Shaikh A, Ahmed K ACS Med Chem Lett. 2022; 13(11):1783-1790.

PMID: 36385941 PMC: 9661705. DOI: 10.1021/acsmedchemlett.2c00403.

Chemo- and Stereoselective Synthesis of Substituted Thiazoles from -Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts.

Yaragorla S, Sneha Latha D ACS Omega. 2022; 7(38):34693-34706.

PMID: 36188313 PMC: 9520744. DOI: 10.1021/acsomega.2c05085.

References

Kotha S, Todeti S, Gopal M, Datta A . Synthesis and Photophysical Properties of -Symmetric Star-Shaped Molecules Containing Heterocycles Such as Furan, Thiophene, and Oxazole. ACS Omega. 2019; 2(10):6291-6297. PMC: 6645079. DOI: 10.1021/acsomega.7b00941. View

Li D, Gao N, Zhu N, Lin Y, Li Y, Chen M . Discovery of the disubstituted oxazole analogues as a novel class anti-tuberculotic agents against MDR- and XDR-MTB. Bioorg Med Chem Lett. 2015; 25(22):5178-81. DOI: 10.1016/j.bmcl.2015.09.072. View

Nagashima S, Matsushima Y, Hamaguchi H, Nagata H, Kontani T, Moritomo A . Novel quinuclidinyl heteroarylcarbamate derivatives as muscarinic receptor antagonists. Bioorg Med Chem. 2014; 22(13):3478-87. DOI: 10.1016/j.bmc.2014.04.031. View

Sisko J, Kassick A, Mellinger M, Filan J, Allen A, Olsen M . An investigation of imidazole and oxazole syntheses using aryl-substituted TosMIC reagents. J Org Chem. 2000; 65(5):1516-24. DOI: 10.1021/jo991782l. View

Yasaei Z, Mohammadpour Z, Shiri M, Tanbakouchian Z, Fazelzadeh S . Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole. Front Chem. 2019; 7:433. PMC: 6587330. DOI: 10.3389/fchem.2019.00433. View

Taha M, Ismail N, Imran S, Anouar E, Selvaraj M, Jamil W . Synthesis and molecular modelling studies of phenyl linked oxadiazole-phenylhydrazone hybrids as potent antileishmanial agents. Eur J Med Chem. 2016; 126:1021-1033. DOI: 10.1016/j.ejmech.2016.12.019. View

Rizeq N, Georgiades S . Investigation of 'Head-to-Tail'-Connected Oligoaryl N,O-Ligands as Recognition Motifs for Cancer-Relevant G-Quadruplexes. Molecules. 2017; 22(12). PMC: 6149995. DOI: 10.3390/molecules22122160. View

Zhang H, Zhao Z, Zhou C . Recent advance in oxazole-based medicinal chemistry. Eur J Med Chem. 2017; 144:444-492. DOI: 10.1016/j.ejmech.2017.12.044. View

Zhang M, Jia C, Gu Y, Mulholland N, Turner S, Beattie D . Synthesis and antifungal activity of novel indole-replaced streptochlorin analogues. Eur J Med Chem. 2016; 126:669-674. DOI: 10.1016/j.ejmech.2016.12.001. View

10.

Zhong Z, Zhang D, Peng Z, Li Y, Shan G, Zuo L . Synthesis and antiviral activity of a novel class of (5-oxazolyl)phenyl amines. Eur J Med Chem. 2013; 69:32-43. DOI: 10.1016/j.ejmech.2013.07.053. View

11.

Ma Z, Ma Z, Zhang D . Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds. Molecules. 2018; 23(10). PMC: 6222313. DOI: 10.3390/molecules23102666. View

12.

da Rosa R, Moraes M, Zimmermann L, Schenkel E, Steindel M, Campos Bernardes L . Design and synthesis of a new series of 3,5-disubstituted isoxazoles active against Trypanosoma cruzi and Leishmania amazonensis. Eur J Med Chem. 2017; 128:25-35. DOI: 10.1016/j.ejmech.2017.01.029. View

13.

Pedras M, Abdoli A . Metabolism of the phytoalexins camalexins, their bioisosteres and analogues in the plant pathogenic fungus Alternaria brassicicola. Bioorg Med Chem. 2013; 21(15):4541-9. DOI: 10.1016/j.bmc.2013.05.026. View

14.

Sagud I, Bozic S, Marinic Z, Sindler-Kulyk M . Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles. Beilstein J Org Chem. 2014; 10:2222-9. PMC: 4168845. DOI: 10.3762/bjoc.10.230. View

15.

Zhang M, Chen Q, Mulholland N, Beattie D, Irwin D, Gu Y . Synthesis and fungicidal activity of novel pimprinine analogues. Eur J Med Chem. 2012; 53:283-91. DOI: 10.1016/j.ejmech.2012.04.012. View

16.

Abhale Y, Sasane A, Chavan A, Shekh S, Deshmukh K, Bhansali S . Synthesis and antimycobacterial screening of new thiazolyl-oxazole derivatives. Eur J Med Chem. 2017; 132:333-340. DOI: 10.1016/j.ejmech.2017.03.065. View

17.

Lechel T, Kumar R, Bera M, Zimmer R, Reissig H . The LANCA three-component reaction to highly substituted β-ketoenamides - versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives. Beilstein J Org Chem. 2019; 15:655-678. PMC: 6423578. DOI: 10.3762/bjoc.15.61. View

18.

Yoon D, Wu S, Seethala R, Golla R, Nayeem A, Everlof J . Discovery of pyridyl sulfonamide 11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors for the treatment of metabolic disorders. Bioorg Med Chem Lett. 2014; 24(21):5045-9. DOI: 10.1016/j.bmcl.2014.09.012. View

19.

Yamamuro D, Uchida R, Ohtawa M, Arima S, Futamura Y, Katane M . Synthesis and biological activity of 5-(4-methoxyphenyl)-oxazole derivatives. Bioorg Med Chem Lett. 2014; 25(2):313-6. DOI: 10.1016/j.bmcl.2014.11.042. View

20.

Mathiyazhagan A, Anilkumar G . Recent advances and applications of p-toluenesulfonylmethyl isocyanide (TosMIC). Org Biomol Chem. 2019; 17(28):6735-6747. DOI: 10.1039/c9ob00847k. View