NDLI: Practical synthesis of potential endothelin receptor antagonists of 1,4-benzodiazepine-2,5-dione derivatives bearing substituents at the C3-, N1- and N4-positions

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Practical synthesis of potential endothelin receptor antagonists of 1,4-benzodiazepine-2,5-dione derivatives bearing substituents at the C₃-, N₁- and N₄-positions

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Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

Practical synthesis of potential endothelin receptor antagonists of 1,4-benzodiazepine-2,5-dione derivatives bearing substituents at the C₃-, N₁- and N₄-positions

Content Provider	Royal Society of Chemistry (RSC)
Author	Tsai, Yeun-Min Chang, Yu Ko, Bor-Wen Fang, Jim-Min Chen, Ming-Yi Yu, Hui-Ming Cheng, Ming-Fu Ho, Tong-Ing
Copyright Year	2006
Abstract	The expedient synthesis of various 1,4-benzodiazepine-2,5-dione compounds, particularly those having substituents at the C3-, N1- and N4-positions is achieved. The important features in these synthetic strategies include: (i) using the coupling reaction of isatoic anhydride with α-amino ester for direct construction of the core structure of 1,4-benzodiazepine-2,5-dione; (ii) using potassium carbonate as the base of choice for selective alkylation at the N1-site, while using lithiated 2-ethylacetanilide as the required base to furnish the N4-alkylation; and (iii) using 2-nitrobenzoyl chloride as a synthetic equivalent of anthranilic acid to facilitate the polyethylene resin-bound liquid-phase combinatorial synthesis. The prepared 1,4-benzodiazepine-2,5-dione compounds are evaluated for endothelin receptor antagonism by a functional assay that measures the inhibitory activity against the change of intramolecular calcium ion concentration induced by endothelin-1. The preliminary results indicate that 1,4-benzodiazepine-2,5-diones bearing two flanked aryl substituents at the N1- and N4-sites show better inhibitory activity than the corresponding unalkylated and N-monoalkylated compounds. A promising candidate, 1-benzyl-7-chloro-3-isopropyl-4-(3-methoxybenzyl)-1,4-benzodiazepine-2,5-dione (17b), exhibits an IC50 value in low nM range.
Starting Page	510
Ending Page	518
Page Count	9
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	4
Issue Number	3
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b514937a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Estrogen receptor Polyethylene Endothelin Calcium Benzodiazepine Isatoic anhydride Ion Ester Chloride Carboxylic acid IC50 Group N Propyl group Aryl Combinatorics Benzyl group Coupling reaction Potassium carbonate
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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Eco-friendly synthesis of 1,4-benzodiazepine-2,5-diones in the ionic liquid [bmim]Br

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2-Bromo-N1, N1, N4, N4-tetramethyl-benzene-1,4-diamine

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Intrinsic sensing fluorescent probe for the solid phase synthesis of 1,4-benzodiazepine-2,5-dione

Practical synthesis of potential endothelin receptor antagonists of 1,4-benzodiazepine-2,5-dione derivatives bearing substituents at the C₃-, N₁- and N₄-positions

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