(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione—Synthesis and Crystallographic Studies

(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione—Synthesis and Crystallographic Studies

(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione was obtained in a three-step, one-pot synthesis, starting from optically pure (S)-2-piperazine carboxylic acid dihydrochloride. Selective acylation of the β-nitrogen atom followed by condensation wit...

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Veröffentlicht in:MolBank 2017-12, Vol.2017 (4), p.M964
Hauptverfasser: Mieczkowski, Adam, Trzybiński, Damian, Wilczek, Marcin, Psurski, Mateusz, Bagiński, Maciej, Bieszczad, Bartosz, Mroczkowska, Magdalena, Woźniak, Krzysztof
Format: Artikel
Sprache:eng
Schlagworte:
(S)-2-piperazinecarboxylic acid
Acylation
Amino acids
Anhydrides
Cancer
Chromatography
Crystallography
Cytotoxicity
Hydrogen bonds
Investigations
isatoic anhydride
Peptides
Synthesis
tricyclic benzodiazepines
Writing
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Zusammenfassung:(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione was obtained in a three-step, one-pot synthesis, starting from optically pure (S)-2-piperazine carboxylic acid dihydrochloride. Selective acylation of the β-nitrogen atom followed by condensation with isatoic anhydride and cyclization with HATU/DIPEA to a seven-member benzodiazepine ring, led to the tricyclic benzodiazepine derivative. Crystallographic studies and initial biological screening were performed for the title compound.
ISSN:1422-8599
1422-8599
DOI:10.3390/M964