Title compds. [I; R1 = H, alkyl, halo, N3, alkylthio, PhS, PhCH2S, alkoxyalkyloxy, amino; R2-R4 = H, alkyl, (substituted) aryl; R5, R6 = H,, OH, amino, alkoxy, (substituted) aryloxy, PhCH2O, amino, halo, CF3, OCF3, NO2, alkyl, carboxy, carbalkoxy, carbamoyl, alkylcarbamoyl; R5R6 = methylenedioxy, carbonyldioxy, carbonyldiamino; X = OH, (substituted) alkoxy, amino, heterocyclyl], were prepd. Thus, (E,E)-5-(5,6-dichloro-1H-indol-2-yl)-2-methyl-2,4-pentadienoic acid (prepn. given) and 3-diethylamino-1-propylamine, HOBT, and DCC were refluxed in MeCN/THF to give 36.4% (E,E)-5-(5,6-dichloro-1H-indol-2-yl)-N-[3-(diethylamino)propyl]-2-methyl-2,4-pentadienamide. The latter inhibited chicken osteoclast bafilomycin-sensitive ATPase with IC50 = 1.2 μM.
Preparation of 5-(indol-2-yl)-2,4-pentadienoates as inhibitors of bone resorption / C. Farina, S. Gagliardi, E. Consolandi, G. Nadler, P. Seneci.
Titolo: | Preparation of 5-(indol-2-yl)-2,4-pentadienoates as inhibitors of bone resorption. |
Autori: | SENECI, PIERFAUSTO (Ultimo) |
Enti collegati: | Smithkline Beecham S.P.A., Italy |
Codice di pubblicazione: | C07D209-18 |
Data di pubblicazione: | 1998 |
Parole Chiave: | OSTEOPOROSIS ; indolylheterocycles ; medicinal chemistry |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica Settore CHIM/08 - Chimica Farmaceutica Settore BIO/14 - Farmacologia |
Citazione: | Preparation of 5-(indol-2-yl)-2,4-pentadienoates as inhibitors of bone resorption / C. Farina, S. Gagliardi, E. Consolandi, G. Nadler, P. Seneci. |
Numero di deposito: | WO 9801423 |
Appare nelle tipologie: | 09 - Brevetto, privativa o norma |