Abstract:
: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.
journal_name
Arch Pharm (Weinheim)journal_title
Archiv der Pharmazieauthors
Eger K,Frey Mdoi
10.1002/ardp.19923250904keywords:
subject
Has Abstractpub_date
1992-09-01 00:00:00pages
551-6issue
9eissn
0365-6233issn
1521-4184journal_volume
325pub_type
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