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Synthesis and evaluation of aplysinopsin analogs as inhibitors of human monoamine oxidase A and B.

Abstract：

:Aplysinopsins are tryptophan-derived natural products that have been isolated from a variety of marine organisms. Previous studies have shown aplysinopsin analogs to possess a variety of biological activities, including modulation of neurotransmissions. A series of fifty aplysinopsin analogs was synthesized and assayed for monoamine oxidase A and B inhibitory activity. Three compounds displayed significant MAO inhibitory activity and selectivity. The compound (E)-5-[(6-bromo-1H-indol-3-yl)methylene]-2-imino-1,3-dimethylimidazolidin-4-one (3x) possessed an IC(50) of 5.6 nM at MAO-A and had a selectivity index of 80.24. An SAR study revealed that multiple N-methylations, one of which should be at position N-2', and bromination at C-5 or C-6 are important factors for MAO-A potency and selectivity.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Lewellyn K,Bialonska D,Chaurasiya ND,Tekwani BL,Zjawiony JK

doi

10.1016/j.bmcl.2012.06.058

subject

Has Abstract

pub_date

2012-08-01 00:00:00

pages

4926-9

issue

15

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(12)00809-8

journal_volume

22

pub_type

杂志文章

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