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Antiradiation agents. 3-[(Alkylthio)alkyl]thiazolidines and substituted 2-{[(3-thiazolidinyl)alkyl]thio}pyridines and -quinolines

Authors :
Roger D. Westland
Richard A. Cooley
Marie M. Grenan
M. L. Zwiesler
M. H. Lin
Source :
Journal of Medicinal Chemistry. 16:328-331
Publication Year :
1973
Publisher :
American Chemical Society (ACS), 1973.

Abstract

5-Halo- and 3,5-dihalo-2-{((3-thiazolidinyl)alkyl! thio)pyridine hydrochlorides (alkyl = ( CH/sub 2/)/sub 3-8.10/! and substituted and unsubstituted 2-{1(3-thiazolidinyl)alkyl! thio}quinoline hydrochlorides STAalkyl = (CH/sub 2/)/sub 5.6! were prepared by alkylation of 2(1H)-pyridinethiones and 2(1H)-quinolinethiones with 3-(chloroalkyl)thiazolidines. The series was extended to 3-STA(alkylthio)alkyl!thiazolidine hydrochlorides (CH/sub 3/(CH/sub 2)/sub n/sub 1/ -S-(CH/sub 2/)/sub n/sub 2/, in volving 27 combinations of n/sub 1/ = 0-9 and n/sub 2/ = 2-7! by alkylation of alkanethiols. Several compounds exhibited promising antiradiation activity, either by ip or po administration. Generally the compounds were more active in the po test. 5-Chloro-2-{STA7-(3- thiazolidinyl)heptyl!thio}pyridine hydrochloride given po at 75 mg/kg (ca 0.13 LD/ sub 50/) afforded 60% survival in the 30-day test. 3-STA5- (Pentylthio)pentyl!thiazolidine hydrochloride resulted in 92% survival (30-day) of the mice when given po at 125 mg/kg (0.2 LD/sub 50/). (auth)

Details

ISSN :
15204804 and 00222623
Volume :
16
Database :
OpenAIRE
Journal :
Journal of Medicinal Chemistry
Accession number :
edsair.doi.dedup.....20ca7113a3518124ff39c3b607f8e2d7
Full Text :
https://doi.org/10.1021/jm00262a004