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Structure‐Activity Relationship Studies of Novel Pyrazolo[1,5‐ c ][1,3]benzoxazines: Synthesis and Benzodiazepine Receptor Affinity
Author(s) -
Varano Flavia,
Catarzi Daniela,
Colotta Vittoria,
Cecchi Lucia,
Filacchioni Guido,
Galli Alessandro,
Costagli Chiara
Publication year - 1996
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19963291204
Subject(s) - chemistry , substituent , heteroatom , stereochemistry , acceptor , tricyclic , benzodiazepine , chemical synthesis , biological activity , structure–activity relationship , receptor , combinatorial chemistry , ring (chemistry) , in vitro , organic chemistry , biochemistry , physics , condensed matter physics
Abstract Some 2‐arylpyrazolo[1,5‐ c ][1,3]benzoxazin‐5‐ones 1 and 5‐oxopyrazolo[1,5‐ c ][1,3]benzoxazin‐2‐carboxylates 2 were prepared and biologically evaluated for their binding at benzodiazepine receptor (BZR) in rat cortical membranes. Structure‐activity relationship studies suggest that, although proton donor d and proton acceptor a 1 are both optional pharmacophoric descriptors, at least one of them must be present for good BZR affinity. When the proton donor d is not present, the heteroatom acceptor a 1 is necessary either in the tricyclic core or in the appended substituent at the C‐2 to obtain sub‐micromolar BZR affinity.