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Article

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

1
Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawińskiego 5a, 02-106 Warsaw, Poland
2
Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland
*
Authors to whom correspondence should be addressed.
Academic Editor: Andrea Penoni
Molecules 2020, 25(4), 906; https://doi.org/10.3390/molecules25040906
Received: 3 February 2020 / Revised: 14 February 2020 / Accepted: 15 February 2020 / Published: 18 February 2020
(This article belongs to the Special Issue Synthesis of Heterocyclic Compounds)
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. View Full-Text
Keywords: unsymmetrical dibenzo[b,f][1,5]diazocines; isatoic anhydrides; crystallographic analysis; cytotoxicity; heterocycles unsymmetrical dibenzo[b,f][1,5]diazocines; isatoic anhydrides; crystallographic analysis; cytotoxicity; heterocycles
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MDPI and ACS Style

Bieszczad, B.; Garbicz, D.; Trzybiński, D.; Mielecki, D.; Woźniak, K.; Grzesiuk, E.; Mieczkowski, A. Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design. Molecules 2020, 25, 906. https://doi.org/10.3390/molecules25040906

AMA Style

Bieszczad B, Garbicz D, Trzybiński D, Mielecki D, Woźniak K, Grzesiuk E, Mieczkowski A. Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design. Molecules. 2020; 25(4):906. https://doi.org/10.3390/molecules25040906

Chicago/Turabian Style

Bieszczad, Bartosz, Damian Garbicz, Damian Trzybiński, Damian Mielecki, Krzysztof Woźniak, Elżbieta Grzesiuk, and Adam Mieczkowski. 2020. "Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design" Molecules 25, no. 4: 906. https://doi.org/10.3390/molecules25040906

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