Title compds. [I; Y = SO2, NR; R = H, alkyl; X = H, alkyl, CO, SO, SO2, COR2, SOR2, SO2R2; R2 = H, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxycarbonyl, (substituted) Ph, benzyl, naphthyl, biphenyl, heterocyclyl; n = 0-6; R4 = H, OH, CO2H, CN, alkyl, alkoxy, alkenyl, alkynyl, alkoxycarbonyl, CO, SO, SO2, COR5, SOR5, SO2R2, OCOR5, OSOR5, OSO2R5, CO2R5, SO2R5, SO2OR5, NHR5, NHCOR5, NHSO2R5, SR5, SCOR5; R5 = H, alkyl, alkoxy, alkenyl, alkynyl, alkoxycarbonyl, (substituted) Ph, benzyl, naphthyl, biphenyl, heterocyclyl; R6, R7 = H, OH, halo, CN, NH2, NO2, CO2R3, alkyl, alkoxy, alkenyl, alkynyl, alkoxycarbonyl; R3 = H, alkyl, alkenyl, alkynyl], were prepd. Thus, 1-(2-aminophenylsulfonyl)pyrrole (prepn. given) reacted with Et 2,2-dimethoxyacetate in refluxing EtOH in the presence of 4-toluenesulfonic acid overnight to give 41% Et 10.11-dihydropyrrolo[1,2-b][1,2,5]benzothiadiazepine-11-carboxylate 5,5-dioxide (RS-678). RS-678 at 10 μM in mixed lymphocytic cultures from marrow or peripheral blood of patients suffering from chronic myelogenous leukemia gave DNA fragmentation and strong activation of caspase 9.
Preparation of pyrrolobenzothiadiazepines and related compounds as anticancer drugs / Silvestri, Romano; Marfe', G.; Abruzzese, E.; Catalano, G.; DI STEFANO, C.; Novellino, E.; SINIBALDI SALIMEI, P.; LA REGINA, Giuseppe; Lavecchia, A.. - (2007).
Preparation of pyrrolobenzothiadiazepines and related compounds as anticancer drugs.
SILVESTRI, Romano;LA REGINA, GIUSEPPE;
2007
Abstract
Title compds. [I; Y = SO2, NR; R = H, alkyl; X = H, alkyl, CO, SO, SO2, COR2, SOR2, SO2R2; R2 = H, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxycarbonyl, (substituted) Ph, benzyl, naphthyl, biphenyl, heterocyclyl; n = 0-6; R4 = H, OH, CO2H, CN, alkyl, alkoxy, alkenyl, alkynyl, alkoxycarbonyl, CO, SO, SO2, COR5, SOR5, SO2R2, OCOR5, OSOR5, OSO2R5, CO2R5, SO2R5, SO2OR5, NHR5, NHCOR5, NHSO2R5, SR5, SCOR5; R5 = H, alkyl, alkoxy, alkenyl, alkynyl, alkoxycarbonyl, (substituted) Ph, benzyl, naphthyl, biphenyl, heterocyclyl; R6, R7 = H, OH, halo, CN, NH2, NO2, CO2R3, alkyl, alkoxy, alkenyl, alkynyl, alkoxycarbonyl; R3 = H, alkyl, alkenyl, alkynyl], were prepd. Thus, 1-(2-aminophenylsulfonyl)pyrrole (prepn. given) reacted with Et 2,2-dimethoxyacetate in refluxing EtOH in the presence of 4-toluenesulfonic acid overnight to give 41% Et 10.11-dihydropyrrolo[1,2-b][1,2,5]benzothiadiazepine-11-carboxylate 5,5-dioxide (RS-678). RS-678 at 10 μM in mixed lymphocytic cultures from marrow or peripheral blood of patients suffering from chronic myelogenous leukemia gave DNA fragmentation and strong activation of caspase 9.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
