[2-Amino-3-cyano-dihydroindol-5-ones. 3. The chemical reactivity of a new class of compounds].
The chemical reactivity of cytotoxic 5-indolone derivatives is examined in order to get ideas about their behaviour in biological systems. Dienone-phenol-rearrangement preserving the indole ring system could not be achieved, aromatization of 1b gives the phenol derivative 3 alpha. In diluted NaOH ester hydrolysis occurs (1a,b----4a,b). Hydrolysis in conc. H2SO4 yields the amides 5a,b,d. In ethanolic HCl the ammonium salts 6a,b,d are formed. Acylation of 1a to 8 reveals the endocyclic N-atom as the nucleophilic center. Benzaldehyde being a strong electrophile adds to 1b in position 4. Weaker electrophiles such as dimethyl acetylenedicarboxylate (ADC) only react with the amides 5b,d to give 11 and 12. Nucleophiles (water, ethanol, n-propylamine) add to the delta 6-double bond yielding 14-16.
Eger
K
K
Pharmazeutisches Institut der Universität, Tübingen.
Frey
M
M
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D007211:Indoles
2-Amino-3-cyano-dihydroindol-5-one, 3. Mitt.: Beiträge zur chemischen Reaktivität einer neuen Verbindungsklasse.