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Synthesis of phenserine analogues and evaluation of their cholinesterase inhibitory activities.

Abstract：

:Phenserine is a potentially attractive drug for Alzheimer's disease. In order to further expand SAR study for inhibitions of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), the methyl group at the 3a-position of phenserine was replaced with an alkyl or alkenyl group, and its phenylcarbamoyl moiety was substituted at the o- or p-position. The synthetic methodology for these phenserine analogues includes the efficient cascade reactions for introduction of the 3a-substituent and assembly of the quaternary carbon center followed by reductive cyclization to the key pyrroloindoline structure. The bulkiness of the substituent at 3a-position of phenserine derivatives tends to reduce the inhibitory effect on AChE activity in the following order: methyl > ethyl > vinyl > propyl ≈ allyl > reverse-prenyl groups. Among the series synthesized, the 3a-ethyl derivative demonstrated the highest AChE selectivity. In construct, the 3a-reverse-prenyl derivative indicated modest BuChE selectivity.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Shinada M,Narumi F,Osada Y,Matsumoto K,Yoshida T,Higuchi K,Kawasaki T,Tanaka H,Satoh M

doi

10.1016/j.bmc.2012.06.048

subject

Has Abstract

pub_date

2012-08-15 00:00:00

pages

4901-14

issue

16

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(12)00535-4

journal_volume

20

pub_type

杂志文章

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