Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors

Julien R.C. Prevost; Arina Kozlova; Bouazza Es Saadi; Esra Yildiz; Sara Modaffari; Didier M. Lambert; Lionel Pochet; Johan Wouters; Eduard Dolušić; Raphaël Frédérick

doi:10.1016/j.tetlet.2018.10.055

Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors

Julien R.C. Prevost, Arina Kozlova, Bouazza Es Saadi, Esra Yildiz, Sara Modaffari, Didier M. Lambert, Lionel Pochet, Johan Wouters, Eduard Dolušić, Raphaël Frédérick

Research output: Contribution to journal › Article › peer-review

Abstract

Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents could be easily prepared by a rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or inconvenient reagents such as elemental halogens. These useful products can serve as starting materials for other reactions or as pharmacologically interesting compounds. In our work we have shown that the resulting 5-bromothiazole compounds could lead to monoacylglycerol lipase (MAGL) inhibition in the μM range.

Original language	English
Pages (from-to)	4315-4319
Number of pages	5
Journal	Tetrahedron Letters
Volume	59
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2018.10.055
Publication status	Published - 5 Dec 2018

Keywords

Electrophilic aromatic substitution
Halogenation
Monoacylglycerol lipase
Oxidation
Thiazoles

Access to Document

10.1016/j.tetlet.2018.10.055

Cite this

Prevost, J. R. C., Kozlova, A., Es Saadi, B., Yildiz, E., Modaffari, S., Lambert, D. M., Pochet, L., Wouters, J., Dolušić, E., & Frédérick, R. (2018). Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors. Tetrahedron Letters, 59(49), 4315-4319. https://doi.org/10.1016/j.tetlet.2018.10.055

@article{7e1925178f9b4dd3908ad2612b867d05,

title = "Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors",

abstract = "Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents could be easily prepared by a rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or inconvenient reagents such as elemental halogens. These useful products can serve as starting materials for other reactions or as pharmacologically interesting compounds. In our work we have shown that the resulting 5-bromothiazole compounds could lead to monoacylglycerol lipase (MAGL) inhibition in the μM range.",

keywords = "Electrophilic aromatic substitution, Halogenation, Monoacylglycerol lipase, Oxidation, Thiazoles",

author = "Prevost, {Julien R.C.} and Arina Kozlova and {Es Saadi}, Bouazza and Esra Yildiz and Sara Modaffari and Lambert, {Didier M.} and Lionel Pochet and Johan Wouters and Eduard Dolu{\v s}i{\'c} and Rapha{\"e}l Fr{\'e}d{\'e}rick",

note = "Funding Information: We are grateful to Arnaud Mars for his contribution to this project, Dr. Marie-France Herent and Prof. Giulio Muccioli (UCLouvain, LDRI, BPBL, Belgium) for helpful discussions and assistance with HRMS and Nikolay Tumanov (PC 2 platform, UNamur, Belgium) for assistance with X-ray diffraction experiments. This work was supported by the Universit{\'e} catholique de Louvain ( UCLouvain, Belgium ), the National Fund for Scientific Research (F.R.S.- FNRS, Belgium ) from which RF is an honorary research associate, the T{\'e}l{\'e}vie (Belgium), the Fonds Maisin (Belgium), the Fonds Sp{\'e}ciaux de Recherche (FSR, Belgium), the Actions de Recherche Concert{\'e}es (ARC, Belgium) and the Fondatioun Kriibskrank Kanner (Luxembourg). RF and ED shares the last authorship position. Funding Information: We are grateful to Arnaud Mars for his contribution to this project, Dr. Marie-France Herent and Prof. Giulio Muccioli (UCLouvain, LDRI, BPBL, Belgium) for helpful discussions and assistance with HRMS and Nikolay Tumanov (PC2 platform, UNamur, Belgium) for assistance with X-ray diffraction experiments. This work was supported by the Universit{\'e} catholique de Louvain (UCLouvain, Belgium), the National Fund for Scientific Research (F.R.S.-FNRS, Belgium) from which RF is an honorary research associate, the T{\'e}l{\'e}vie (Belgium), the Fonds Maisin (Belgium), the Fonds Sp{\'e}ciaux de Recherche (FSR, Belgium), the Actions de Recherche Concert{\'e}es (ARC, Belgium) and the Fondatioun Kriibskrank Kanner (Luxembourg). RF and ED shares the last authorship position. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = dec,

day = "5",

doi = "10.1016/j.tetlet.2018.10.055",

language = "English",

volume = "59",

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T1 - Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors

AU - Prevost, Julien R.C.

AU - Kozlova, Arina

AU - Es Saadi, Bouazza

AU - Yildiz, Esra

AU - Modaffari, Sara

AU - Lambert, Didier M.

AU - Pochet, Lionel

AU - Wouters, Johan

AU - Dolušić, Eduard

AU - Frédérick, Raphaël

N1 - Funding Information: We are grateful to Arnaud Mars for his contribution to this project, Dr. Marie-France Herent and Prof. Giulio Muccioli (UCLouvain, LDRI, BPBL, Belgium) for helpful discussions and assistance with HRMS and Nikolay Tumanov (PC 2 platform, UNamur, Belgium) for assistance with X-ray diffraction experiments. This work was supported by the Université catholique de Louvain ( UCLouvain, Belgium ), the National Fund for Scientific Research (F.R.S.- FNRS, Belgium ) from which RF is an honorary research associate, the Télévie (Belgium), the Fonds Maisin (Belgium), the Fonds Spéciaux de Recherche (FSR, Belgium), the Actions de Recherche Concertées (ARC, Belgium) and the Fondatioun Kriibskrank Kanner (Luxembourg). RF and ED shares the last authorship position. Funding Information: We are grateful to Arnaud Mars for his contribution to this project, Dr. Marie-France Herent and Prof. Giulio Muccioli (UCLouvain, LDRI, BPBL, Belgium) for helpful discussions and assistance with HRMS and Nikolay Tumanov (PC2 platform, UNamur, Belgium) for assistance with X-ray diffraction experiments. This work was supported by the Université catholique de Louvain (UCLouvain, Belgium), the National Fund for Scientific Research (F.R.S.-FNRS, Belgium) from which RF is an honorary research associate, the Télévie (Belgium), the Fonds Maisin (Belgium), the Fonds Spéciaux de Recherche (FSR, Belgium), the Actions de Recherche Concertées (ARC, Belgium) and the Fondatioun Kriibskrank Kanner (Luxembourg). RF and ED shares the last authorship position. Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/12/5

Y1 - 2018/12/5

N2 - Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents could be easily prepared by a rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or inconvenient reagents such as elemental halogens. These useful products can serve as starting materials for other reactions or as pharmacologically interesting compounds. In our work we have shown that the resulting 5-bromothiazole compounds could lead to monoacylglycerol lipase (MAGL) inhibition in the μM range.

AB - Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents could be easily prepared by a rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or inconvenient reagents such as elemental halogens. These useful products can serve as starting materials for other reactions or as pharmacologically interesting compounds. In our work we have shown that the resulting 5-bromothiazole compounds could lead to monoacylglycerol lipase (MAGL) inhibition in the μM range.

KW - Electrophilic aromatic substitution

KW - Halogenation

KW - Monoacylglycerol lipase

KW - Oxidation

KW - Thiazoles

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DO - 10.1016/j.tetlet.2018.10.055

M3 - Article

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SN - 0040-4039

VL - 59

SP - 4315

EP - 4319

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors

Abstract

Keywords

Access to Document

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High Performance Computing Technology Platform

Physical Chemistry and characterization(PC2)

CCDC 1851262: Experimental Crystal Structure Determination

CCDC 1851263: Experimental Crystal Structure Determination

Cite this

Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Equipment

High Performance Computing Technology Platform

Physical Chemistry and characterization(PC2)

Datasets

CCDC 1851262: Experimental Crystal Structure Determination

CCDC 1851263: Experimental Crystal Structure Determination

Cite this