Pd-Catalyzed Coupling of Bromo-N- (β-glucopyranosyl)quinolin-2-ones with Amides: Synthesis of N-glucosyl-6BrCaQ Conjugates with Potent Anticancer Activity

Wafa Redjdal; Sara Benmahdjoub; Thi Thanh Hyen Luong; Belkacem Benmerad; Franck Le Bideau; Juliette Vergnaud; Samir Messaoudi

doi:10.1002/cmdc.202400195

Pd-Catalyzed Coupling of Bromo-N- (β-glucopyranosyl)quinolin-2-ones with Amides: Synthesis of N-glucosyl-6BrCaQ Conjugates with Potent Anticancer Activity

Wafa Redjdal, Sara Benmahdjoub, Thi Thanh Hyen Luong, Belkacem Benmerad, Franck Le Bideau, Juliette Vergnaud, Samir Messaoudi

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

Abstract

A series of N-glycosyl- 6BrCaQ conjugates was synthesized through a Pd-catalyzed cross-coupling reaction between brominated N-glycosyl quinolin-2-one derivatives and various nitrogen nucleophiles. Antiproliferative assays revealed that this new series of analogues represents a promising class of antitumor compounds as illustrated by the high biological activity observed for several derivatives towards different cancer cell lines compared to the non-glycosylated congeners.

Original language	English
Article number	e202400195
Journal	ChemMedChem
Volume	19
Issue number	15
DOIs	https://doi.org/10.1002/cmdc.202400195
Publication status	Published - 1 Aug 2024

Keywords

Antiproleferative activity
Buchwald-Hartwig Cross-Coupling
HPS90
N-glycosides
TRAP1

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Pd-Catalyzed Coupling of Bromo-N- (β-glucopyranosyl)quinolin-2-ones with Amides: Synthesis of N-glucosyl-6BrCaQ Conjugates with Potent Anticancer Activity",

abstract = "A series of N-glycosyl- 6BrCaQ conjugates was synthesized through a Pd-catalyzed cross-coupling reaction between brominated N-glycosyl quinolin-2-one derivatives and various nitrogen nucleophiles. Antiproliferative assays revealed that this new series of analogues represents a promising class of antitumor compounds as illustrated by the high biological activity observed for several derivatives towards different cancer cell lines compared to the non-glycosylated congeners.",

keywords = "Antiproleferative activity, Buchwald-Hartwig Cross-Coupling, HPS90, N-glycosides, TRAP1",

author = "Wafa Redjdal and Sara Benmahdjoub and Luong, \{Thi Thanh Hyen\} and Belkacem Benmerad and \{Le Bideau\}, Franck and Juliette Vergnaud and Samir Messaoudi",

note = "Publisher Copyright: {\textcopyright} 2024 The Authors. ChemMedChem published by Wiley-VCH GmbH.",

year = "2024",

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doi = "10.1002/cmdc.202400195",

language = "English",

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T2 - Synthesis of N-glucosyl-6BrCaQ Conjugates with Potent Anticancer Activity

AU - Redjdal, Wafa

AU - Benmahdjoub, Sara

AU - Luong, Thi Thanh Hyen

AU - Benmerad, Belkacem

AU - Le Bideau, Franck

AU - Vergnaud, Juliette

AU - Messaoudi, Samir

PY - 2024/8/1

Y1 - 2024/8/1

N2 - A series of N-glycosyl- 6BrCaQ conjugates was synthesized through a Pd-catalyzed cross-coupling reaction between brominated N-glycosyl quinolin-2-one derivatives and various nitrogen nucleophiles. Antiproliferative assays revealed that this new series of analogues represents a promising class of antitumor compounds as illustrated by the high biological activity observed for several derivatives towards different cancer cell lines compared to the non-glycosylated congeners.

AB - A series of N-glycosyl- 6BrCaQ conjugates was synthesized through a Pd-catalyzed cross-coupling reaction between brominated N-glycosyl quinolin-2-one derivatives and various nitrogen nucleophiles. Antiproliferative assays revealed that this new series of analogues represents a promising class of antitumor compounds as illustrated by the high biological activity observed for several derivatives towards different cancer cell lines compared to the non-glycosylated congeners.

KW - Antiproleferative activity

KW - Buchwald-Hartwig Cross-Coupling

KW - HPS90

KW - N-glycosides

KW - TRAP1

U2 - 10.1002/cmdc.202400195

DO - 10.1002/cmdc.202400195

M3 - Article

C2 - 38687188

AN - SCOPUS:85195852768

SN - 1860-7179

VL - 19

JO - ChemMedChem

JF - ChemMedChem

IS - 15

M1 - e202400195

ER -

Pd-Catalyzed Coupling of Bromo-N- (β-glucopyranosyl)quinolin-2-ones with Amides: Synthesis of N-glucosyl-6BrCaQ Conjugates with Potent Anticancer Activity

Abstract

Keywords

UN SDGs

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