N-[4- (R',R"-phenylazo) aryl]aminolupinanes with antitubercular activity
Vazzana, I.; Sparatore, F.; Fadda, G.; Manca, C.
Farmaco 48(6): 737-747
1993
ISSN/ISBN: 0014-827X PMID: 8373501 Document Number: 412330
A set of twelve N-[4-(R-phenylazo)aryl]aminolupinanes (10a-c; 11a-i) was prepared by coupling the suitably substituted phenyldiazonium salts with N-(2,3-xylyl)-aminolupinane and with N-(5,6,7,8-tetrahydronaphth-1-yl)- aminolupinane. These compounds, as well as the N-(4-amino-2,3-xylyl)aminolupinane and the N-(4-amino-5,6,7,8-tetrahydronaphth-1-yl)-aminolupinane, that could be obtained from the former through an in vivo reductive cleavage of the azo group, exhibited a high activity against Mycobacterium tuberculosis H37RV with M.I.C. in the range 0.1-1 microgram/ml.