Journal of Heterocyclic Chemistry p. 1351 - 1355 (1993)
Update date:2022-08-11
Topics:
Hasan
Knapp Jr.
Kilbourn
Buchsbaum
The design, synthesis and biological activities of several acyclonucleoside analogues related to misonidazole are described. The hydroxy-5, bromo-6, iodo-7, and fluoro-8 derivatives of ethoxymethylazomycin and iodopropenyloxymethylazomycin (12) have been prepared. Alkylation of silylated azomycin with haloethoxy-methylene chloride gave the corresponding acyclonucleosides. Similarly, propargyloxymethylene chloride gave propargyloxymethylazomycin (10), which after hydrostannylation and subsequent iododestannylation yielded iodopropenyloxymethylazomycin (12). The radiolabeled [125I] or [18F] compounds were prepared from the corresponding substrates. Biodistribution results of the radiolabeled analogues in mice showed that compound 7 had good tumor uptake (2.0% injected dose/g at 1 hour). The high radioactive levels in blood and stomach, however, were perhaps due to in vivo deiodination or metabolism. Compound [125I]- 12 showed the highest tumor uptake (4.8 and 3.6% injected dose/g at 1 and 4 hours respectively) of all of the compounds tested. Relatively low thyroid uptake of radioactivity in mice dosed with compound [125I]-12 indicates significantly reduced in vivo deiodination in comparison to compound [125I]-7.
View Morewebsite:http://www.chemdow.com
Contact:0086-10-82435335
Address:Room 401,Unit 3,4th Floor,Shangdijiayuan,Shangdi East Road, Haidian District,Beijing
Guangxi Nanning Guangtai Agriculture Chemical Co.,Ltd
Contact:+86-771-2311266
Address:Room703,Building12, Software Park Phase II,NO.68,Keyuan Road,Nanning City,Guangxi,China
Huludao Tianqi Shengye Chemical Co.,Ltd.
Contact:0086 429 2075777
Address:Area B,Shipbuilding Industry Park,Beigang District,Huludao City,Liaoning prov.,China
Fujian Wanke Pharmaceutical Co., LTD.
Contact:+86-598-5026002
Address:Economic development zone,jiangle county
Contact:86-532-68629711 13780605697
Address:NO 220 YANAN 3 ROAD,(POST ADMINISTRATION BUILDING),QINGDAO,CHINA
Doi:10.1021/jacs.7b09645
(2017)Doi:10.1021/ja01189a040
(1948)Doi:10.1016/0020-1650(68)80066-2
(1968)Doi:10.1021/om5008852
(2014)Doi:10.1021/ja01505a053
(1960)Doi:10.1039/b315732f
(2004)