Potential cerebral perfusion agents. Synthesis and evaluation of berberine analogues | Zendy

Srivastava Prem C. | Zendy; Tedjamulia Marvin L. | Zendy; Knapp Furn F. | Zendy

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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.

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