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Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-ones.

Abstract：

:In this work, we further investigated a previously introduced class of cholinesterase inhibitors. The removal of the carbamic function from the lead compound xanthostigmine led to a reversible cholinesterase inhibitors 3. Some new 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-one analogs were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The length of the alkoxy chain of compound 3 was increased and different substituents were introduced. From the IC(50) values, it clearly appears that the carbamic residue is crucial to obtain highly potent AChE inhibitors. On the other hand, peculiarity of these compounds is the high selectivity toward BuChE with respect to AChE, being compound 12 the most selective one (6000-fold). The development of selective BuChE inhibitors may be of great interest to clarify the physiological role of this enzyme and to provide novel therapeutics for various diseases.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Piazzi L,Belluti F,Bisi A,Gobbi S,Rizzo S,Bartolini M,Andrisano V,Recanatini M,Rampa A

doi

10.1016/j.bmc.2006.09.026

subject

Has Abstract

pub_date

2007-01-01 00:00:00

pages

575-85

issue

1

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(06)00757-7

journal_volume

15

pub_type

杂志文章

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