Premium
Potential cerebral perfusion agents. Synthesis and evaluation of berberine analogues
Author(s) -
Srivastava Prem C.,
Tedjamulia Marvin L.,
Knapp Furn F.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230440
Subject(s) - chemistry , berberine , sodium borohydride , hydrochloride , bromine , bromide , iodine , sodium bromide , berberine hydrochloride , sodium , derivative (finance) , nuclear chemistry , organic chemistry , catalysis , financial economics , economics
The synthesis and tissue distribution studies in rats of tetra[ 3 H]‐hydroberberine ([ 3 H] 2 ) and 8‐( p ‐[ 125 I]iodobenzyl)tetrahydroberberine ([ 125 I] 6 ) are described. Compound 2 was synthesized by sodium borohydride reduction of berberine hydrochloride ( 1 ). Treatment of berberine hydrochloride with p ‐bromo‐benzylmagnesium bromide gave 8‐( p ‐bromobenzyl)dihydroberberine ( 4 ) which after sodium borohydride reduction and iodine‐125 bromine exchange gave [ 125 I] 6 . The unsubstituted tetrahydro compound [ 3 H] 2 showed significantly higher brain uptake (2.2% dose/gm after 5 minutes) as compared to the corresponding 8‐substituted derivative [ 125 I] 6 . Both radiolabeled compounds washed out from the brain relatively quickly.