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Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design

Bieszczad, Bartosz and Garbicz, Damian and Trzybiński, Damian and Mielecki, Damian and Woźniak, Krzysztof and Grzesiuk, Elzbieta and Mieczkowski, Adam (2020) Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design. Molecules, 25 (4). p. 906. ISSN 1420-3049

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Official URL: https://www.mdpi.com/1420-3049/25/4/906

Abstract

A novel approach for the synthesis of unsymmetrically substituted dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones has been developed. This facile three-step method uses variously substituted 1H-benzo[d][1,3]oxazine-2,4-diones (isatoic anhydrides) and 2-aminobenzoic acids as a starting materials. The obtained products were further transformed into N-alkyl-, N-acetyl- and dithio analogues. Developed procedures allowed the synthesis of unsymmetrical dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones and three novel heterocyclic scaffolds: benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione and pyrazino[3,2-c][1,5]benzodiazocine-6,12(5H,11H)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two cancer (HeLa, U87) and two normal lines (HEK293, EUFA30) as well as antibacterial activity were determined. The obtained dibenzo[b,f][1,5]diazocine(5H,11H)6,12-dione framework could serve as a privileged structure for the drug design and development.

Item Type:Article
Subjects:Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
Divisions:Department of Biophysics
Department of Molecular Biology
ID Code:1849
Deposited By: Dr Adam Mieczkowski
Deposited On:19 Feb 2020 13:11
Last Modified:19 Feb 2020 13:11

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