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

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	4315-4319
Nombre de pages	5
journal	Tetrahedron Letters
Volume	59
Numéro de publication	49
Les DOIs	https://doi.org/10.1016/j.tetlet.2018.10.055
Etat de la publication	Publié - 5 déc. 2018

Accès au document

10.1016/j.tetlet.2018.10.055

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Physico-chimie et caractérisation (PC2)
Wouters, J. (!!Manager), Aprile, C. (!!Manager) & Fusaro, L. (!!Manager)
Plateforme technologique Caracterisation physico-chimiques
Equipement/installations: Plateforme technolgique
Plateforme Technologique Calcul Intensif
Champagne, B. (!!Manager)
Plateforme technologique Calcul intensif
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CCDC 1851262: Experimental Crystal Structure Determination
Prevost, J. R. C. (Créateur), Kozlova, A. (Créateur), Saadi, B. E. (Contributeur), Yildiz, E. (Créateur), Modaffari, S. (Contributeur), Lambert, D. M. (Créateur), Pochet, L. (Contributeur), Wouters, J. (Contributeur), Dolušić, E. (Contributeur) & Frédérick, R. (Contributeur), University of Namur, 5 déc. 2018
DOI: 10.5517/ccdc.csd.cc204d4q, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc204d4q&sid=DataCite
Ensemble de données
CCDC 1851263: Experimental Crystal Structure Determination
Prevost, J. R. C. (Créateur), Kozlova, A. (Créateur), Saadi, B. E. (Contributeur), Yildiz, E. (Créateur), Modaffari, S. (Contributeur), Lambert, D. M. (Créateur), Pochet, L. (Contributeur), Wouters, J. (Contributeur), Dolušić, E. (Contributeur) & Frédérick, R. (Contributeur), University of Namur, 5 déc. 2018
DOI: 10.5517/ccdc.csd.cc204d5r, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc204d5r&sid=DataCite
Ensemble de données

Contient cette citation

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",

pages = "4315--4319",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "49",

}

Prevost, JRC, Kozlova, A, Es Saadi, B, Yildiz, E, Modaffari, S, Lambert, DM, 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, VOL. 59, Numéro 49, p. 4315-4319. https://doi.org/10.1016/j.tetlet.2018.10.055

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=85055619488&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.10.055

DO - 10.1016/j.tetlet.2018.10.055

M3 - Article

AN - SCOPUS:85055619488

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

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Équipement

Physico-chimie et caractérisation (PC2)

Plateforme Technologique Calcul Intensif

Ensembles de données

CCDC 1851262: Experimental Crystal Structure Determination

CCDC 1851263: Experimental Crystal Structure Determination

Contient cette citation