Structural and theoretical studies of [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid as HIV-1 integrase inhibitor

Pierre Vandurm; Christine Cauvin; Allan Guiguen; Benoît Georges; Kiet Le Van; Valérie Martinelli; Christelle Cardona; Gladys Mbemba; Jean François Mouscadet; László Hevesi; Carine Van Lint; Johan Wouters

doi:10.1016/j.bmcl.2009.06.044

Structural and theoretical studies of [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid as HIV-1 integrase inhibitor

Pierre Vandurm, Christine Cauvin, Allan Guiguen, Benoît Georges, Kiet Le Van, Valérie Martinelli, Christelle Cardona, Gladys Mbemba, Jean François Mouscadet, László Hevesi, Carine Van Lint, Johan Wouters

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

Résumé

Ethyl [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl]-4-hydroxy-2-oxo-3-butenoate 1 and [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid 2 were synthesized as potential HIV-1 integrase inhibitors and evaluated for their enzymatic and antiviral activity, acidic compound 2 being more potent than ester compound 1. X-ray diffraction analyses and theoretical calculations show that the diketoacid chain of compound 2 is preferentially coplanar with the quinolinone ring (dihedral angle of 0-30°). Docking studies suggest binding modes in agreement with structure-activity relationships.

langue originale	Anglais
Pages (de - à)	4806-4809
Nombre de pages	4
journal	Bioorganic & Medicinal Chemistry Letters
Volume	19
Numéro de publication	16
Les DOIs	https://doi.org/10.1016/j.bmcl.2009.06.044
Etat de la publication	Publié - 15 août 2009

SDG des Nations Unies

Ce résultat contribue à ou aux Objectifs de développement durable suivants

Accès au document

10.1016/j.bmcl.2009.06.044

Autres fichiers et liens

Link to publication in Scopus

CCDC 730039: Experimental Crystal Structure Determination
Vandurm, P. (Contributeur), Cauvin, C. (Contributeur), Guiguen, A. (Contributeur), Georges, B. (Contributeur), Le Van, K. (Contributeur), Martinelli, V. (Contributeur), Cardona, C. (Contributeur), Mbemba, G. (Contributeur), Mouscadet, J.-F. (Contributeur), Hevesi, L. (Contributeur), Le Van, K. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2010
DOI: 10.5517/ccshnnk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccshnnk&sid=DataCite
Ensemble de données

Contient cette citation

Vandurm, P., Cauvin, C., Guiguen, A., Georges, B., Van, K. L., Martinelli, V., Cardona, C., Mbemba, G., Mouscadet, J. F., Hevesi, L., Lint, C. V., & Wouters, J. (2009). Structural and theoretical studies of [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid as HIV-1 integrase inhibitor. Bioorganic & Medicinal Chemistry Letters, 19(16), 4806-4809. https://doi.org/10.1016/j.bmcl.2009.06.044

@article{ff5790f799e849b58e8db77cddd5f55d,

title = "Structural and theoretical studies of [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-buteno{\"i}c acid as HIV-1 integrase inhibitor",

abstract = "Ethyl [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl]-4-hydroxy-2-oxo-3-butenoate 1 and [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-buteno{\"i}c acid 2 were synthesized as potential HIV-1 integrase inhibitors and evaluated for their enzymatic and antiviral activity, acidic compound 2 being more potent than ester compound 1. X-ray diffraction analyses and theoretical calculations show that the diketoacid chain of compound 2 is preferentially coplanar with the quinolinone ring (dihedral angle of 0-30°). Docking studies suggest binding modes in agreement with structure-activity relationships.",

keywords = "β-Diketo, HIV-1, Integrase inhibitors, Quinolinone",

author = "Pierre Vandurm and Christine Cauvin and Allan Guiguen and Beno{\^i}t Georges and Van, {Kiet Le} and Val{\'e}rie Martinelli and Christelle Cardona and Gladys Mbemba and Mouscadet, {Jean Fran{\c c}ois} and L{\'a}szl{\'o} Hevesi and Lint, {Carine Van} and Johan Wouters",

year = "2009",

month = aug,

day = "15",

doi = "10.1016/j.bmcl.2009.06.044",

language = "English",

volume = "19",

pages = "4806--4809",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier",

number = "16",

}

Vandurm, P, Cauvin, C, Guiguen, A, Georges, B, Van, KL, Martinelli, V, Cardona, C, Mbemba, G, Mouscadet, JF, Hevesi, L, Lint, CV & Wouters, J 2009, 'Structural and theoretical studies of [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid as HIV-1 integrase inhibitor', Bioorganic & Medicinal Chemistry Letters, VOL. 19, Numéro 16, p. 4806-4809. https://doi.org/10.1016/j.bmcl.2009.06.044

Structural and theoretical studies of [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid as HIV-1 integrase inhibitor. / Vandurm, Pierre; Cauvin, Christine; Guiguen, Allan et al.
Dans: Bioorganic & Medicinal Chemistry Letters, Vol 19, Numéro 16, 15.08.2009, p. 4806-4809.

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

TY - JOUR

T1 - Structural and theoretical studies of [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid as HIV-1 integrase inhibitor

AU - Vandurm, Pierre

AU - Cauvin, Christine

AU - Guiguen, Allan

AU - Georges, Benoît

AU - Van, Kiet Le

AU - Martinelli, Valérie

AU - Cardona, Christelle

AU - Mbemba, Gladys

AU - Mouscadet, Jean François

AU - Hevesi, László

AU - Lint, Carine Van

AU - Wouters, Johan

PY - 2009/8/15

Y1 - 2009/8/15

N2 - Ethyl [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl]-4-hydroxy-2-oxo-3-butenoate 1 and [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid 2 were synthesized as potential HIV-1 integrase inhibitors and evaluated for their enzymatic and antiviral activity, acidic compound 2 being more potent than ester compound 1. X-ray diffraction analyses and theoretical calculations show that the diketoacid chain of compound 2 is preferentially coplanar with the quinolinone ring (dihedral angle of 0-30°). Docking studies suggest binding modes in agreement with structure-activity relationships.

AB - Ethyl [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl]-4-hydroxy-2-oxo-3-butenoate 1 and [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid 2 were synthesized as potential HIV-1 integrase inhibitors and evaluated for their enzymatic and antiviral activity, acidic compound 2 being more potent than ester compound 1. X-ray diffraction analyses and theoretical calculations show that the diketoacid chain of compound 2 is preferentially coplanar with the quinolinone ring (dihedral angle of 0-30°). Docking studies suggest binding modes in agreement with structure-activity relationships.

KW - β-Diketo

KW - HIV-1

KW - Integrase inhibitors

KW - Quinolinone

UR - http://www.scopus.com/inward/record.url?scp=67651091690&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2009.06.044

DO - 10.1016/j.bmcl.2009.06.044

M3 - Article

C2 - 19556126

AN - SCOPUS:67651091690

SN - 0960-894X

VL - 19

SP - 4806

EP - 4809

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 16

ER -

Structural and theoretical studies of [6-bromo-1-(4-fluorophenylmethyl)-4(1H)-quinolinon-3-yl)]-4-hydroxy-2-oxo-3-butenoïc acid as HIV-1 integrase inhibitor

Résumé

SDG des Nations Unies

Accès au document

Autres fichiers et liens

Empreinte digitale

Ensembles de données

CCDC 730039: Experimental Crystal Structure Determination

Contient cette citation