Synthesis and elastase-inhibiting activity of 2-pyridinyl-isothiazol-3(2H)-one 1,1-dioxides.

Abstract:

:The synthesis of a series of new isothiazol-3(2H)-one 1,1-dioxides with halogenated (mostly fluorinated) pyridinyl and pentafluorophenyl substituents at 2-position is reported. These compounds (18-24) became easily accessible from 2-thiocyanato-1-carboxaldehydes and aminopyridines, pentafluoroaniline, respectively, by an isothiazolium cyclization-oxidation route. Compound 21 exhibited an IC(50) value of 3.1 microM toward human leukocyte elastase. The proteases cathepsin G, trypsin, cathepsin L, and angiotensin-converting enzyme, and the serine esterases acetylcholinesterase and cholesterol esterase were not inhibited by 21.

journal_name

Bioorg Med Chem

authors

Eilfeld A,González Tanarro CM,Frizler M,Sieler J,Schulze B,Gütschow M

doi

10.1016/j.bmc.2008.07.049

subject

Has Abstract

pub_date

2008-09-01 00:00:00

pages

8127-35

issue

17

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00662-7

journal_volume

16

pub_type

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