[12-acyl-6,1 2-dihydro-6-phenyl-[1 ]benzofuro[2,3-c]- and -[1,5]benzothieno[2,3-c]-[1 ,5]-benzothiazepines--tetracyclic diltiazem derivatives].
The reaction of the tetracycles 1 with chloroacetylchloride yields the amides 2. The structure of 2a was proven by X-ray analysis. The amides 2 exist as diastereomers in solution because of planar chirality. From the N-chloroacetyl compounds only 2a, b could be substituted with diethylamine to give 3a, b. Reduction experiments of 3a, b with DIBAH do not afford diltiazem analogues; instead, the starting compounds la, b are formed by hydrolysis.
Görlitzer
K
K
Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Germany. k.goerlitzer@tu-bs.de
Preu
L
L
Wichers
M
M
Jones
P G
PG
D001572:Benzofurans / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D004110:Diltiazem / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006868:Hydrolysis; D007202:Indicators and Reagents; D008958:Models, Molecular; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013841:Thiazepines / Q000138:chemical synthesis*
D001572:Benzofurans; D007202:Indicators and Reagents; D013841:Thiazepines; D004110:Diltiazem