Synthesis of raloxifene-like quinoxaline derivatives by intramolecular electrophilic cyclization with disulfides.

Humans Cyclization Quinoxalines / pharmacology Raloxifene Hydrochloride / pharmacology Disulfides
Disulfide HL-60 Intramolecular electrophilic cyclization SK-BR-3 Thieno[2,3–b]quinoxaline

Journal

Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377

Informations de publication

Date de publication:
01 09 2023
Historique:
received: 09 06 2023
revised: 14 07 2023
accepted: 24 07 2023
medline: 21 8 2023
pubmed: 3 8 2023
entrez: 2 8 2023
Statut: ppublish

Résumé

The intramolecular electrophilic cyclization of alkynes with disulfides to form thieno[2,3-b]quinoxaline structures and to introduce thioether substituents afforded quinoxaline derivatives (7a-7d, 8a-8d). Among obtained eight derivatives, the raloxifene analogues (7c, 8b) showed specifically high cytotoxicity against breast cancer cells (SK-BR-3), and raloxifene analogues (8a) showed the highest cytotoxicity against human leukemia cells (HL-60). None of the raloxifene analogues (7a-7d, 8a-8d) showed cytotoxicity against human lung fibroblasts (WI-38), which are normal cells.

Identifiants

DOI: 10.1016/j.bmcl.2023.129415 PMID: 37532107
pubmed: 37532107
pii: S0960-894X(23)00293-7
doi: 10.1016/j.bmcl.2023.129415
pii:
doi:

Substances chimiques

Quinoxalines 0
Raloxifene Hydrochloride 4F86W47BR6
Disulfides 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

129415

Informations de copyright

Copyright © 2023 Elsevier Ltd. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Auteurs

Yuhi Umezu (Y)

Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.

Eito Horiyama (E)

Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.

Yuto Nakai (Y)

Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.

Masayuki Ninomiya (M)

Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan; Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.

Atsuyoshi Nishina (A)

Department of Applied Chemistry, College of Science and Technology, Nihon University, 1-5-1 Kandasurugadai, Chiyoda, Tokyo 101-0062, Japan; School of Health and Nutrition, Tokai Gakuen University, 2-901 Nakahira, Tenpaku-ku, Nagoya, Aichi 468-8514, Japan.

Mamoru Koketsu (M)

Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. Electronic address: koketsu.mamoru.e0@f.gifu-u.ac.jp.

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Classifications MeSH

questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Synthesis of raloxifene-like quinoxaline...
questionsmedicales.fr › Métabolisme › Cyclisation › Synthesis of raloxifene-like quinoxaline...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Quinoxalines › Synthesis of raloxifene-like quinoxaline...
questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Hydrocarbures cycliques › Hydrocarbures aromatiques › Dérivés du benzène › Composés benzylidéniques › Stilbènes › Tamoxifène › Chlorhydrate de raloxifène › Synthesis of raloxifene-like quinoxaline...
questionsmedicales.fr › Composés chimiques organiques › Composés du soufre › Sulfures › Disulfures › Synthesis of raloxifene-like quinoxaline...