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3-Aza-6,8-dioxabicyclo[3.2.1]octanes as new enantiopure heteroatom-rich tropane-like ligands of human dopamine transporter.

Abstract：

:CNS diseases such as Parkinson, schizophrenia, and attention deficit hyperactivity disorder (ADHD) are characterized by a significant alteration of dopamine transporter (DAT) density. Thus, the development of compounds that are able to selectively interact with DAT is of great interest. Herein we describe the design and synthesis of a new set of 3-aza-6,8-dioxabicyclo[3.2.1]octanes having a tropane-like structure with additional heteroatoms at positions 3 and 6. The compounds were evaluated for their in vitro receptor binding properties toward human dopamine (hDAT) and serotonin (hSERT) transporters using [3H]WIN35,428 and [3H]citalopram as specific radioligands, respectively. Biological assays revealed that some compounds having the N-3 atom substituted with aryl groups possess significant affinity and selectivity for monoamine transporters, and in particular, compound 5d displayed an IC50 of 21 nM toward DAT, and a good selectivity toward SERT (IC50=1042 nM). These results suggest that 3-aryl-3-aza-6,8-dioxabicyclo[3.2.1]octanes may represent a new class of DAT ligands.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Cini N,Danieli E,Menchi G,Trabocchi A,Bottoncetti A,Raspanti S,Pupi A,Guarna A

doi

10.1016/j.bmc.2006.04.019

subject

Has Abstract

pub_date

2006-08-01 00:00:00

pages

5110-20

issue

15

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(06)00286-0

journal_volume

14

pub_type

杂志文章

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