[Studies on substances with antiblastic activity. IX. Anthramycin and analogs. IX. Synthesis of 7-methoxy-8-hydroxy-10,11-dihydro-5H-pyrrolo[2,1-c] [1,4] benzodiazepine and other compounds related to oxotomaymycin].
The synthesis of some pyrrolobenzodiazepine derivatives related to oxotomaymycin, an antibiotic recovered together with tomaymycin from fermentation broths of Streptomyces achromogenes var. tomaymycetics, is described. Reaction between 2-nitro-4-benzyloxy-5-methoxybenzylbromide and pyrrole-2-carboxyaldehyde afforded 1-(2-nitro-4-benzyloxy-5-methoxybenzyl)pyrrole-2-carboxyaldehyde. Catalytic reduction of this compound with hydrogen in the presence of Pd/C gave 10,11-dihydro-8-hydroxy-7-methoxy-5H-pyrrolo[2.1-c] [1,4]benzodiazepine. Amides obtained from condensation between 2-nitro-4-benzyloxy-5-methoxybenzoic acid chloride and proline or hydroxyproline were reduced catalytically to 2,3-dihydro-8-hydroxy-7-methoxy-1H-pyrrolo [2,1-c] [1,4]benzodiazepine-5,11 (10H, 11aH)-dione and its 2-hydroxyderivative respectively. The synthesis of 10,11-dihydro-8-hydroxy-9-methoxy-5-pyrrolo [2,1-c] [1,4]benzodiazepine is also reported.
D000876:Anthramycin / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D001569:Benzodiazepines / Q000138:chemical synthesis*; D001570:Benzodiazepinones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared
D001570:Benzodiazepinones; D000876:Anthramycin; D001569:Benzodiazepines
Richerche su sotanze ad attivtià antiblastica. Nota LX - Antramicina e composti analoghi. Parte IX: Sintesi della 7-metossi-8-idrossi-10,11-diidro-5H-pirrolo[2,4-c] [1,4]benzodiazepina e di altri composti correlati con la oxotomaimicina.