2005
DOI: 10.1007/s11172-006-0203-5
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4-(N,N-Dialkylthiocarbamoylthio)-5-nitropyrimidines as new potential nitric oxide donors

Abstract: On heating at pH 6.86, 4 (N,N dialkylthiocarbamoylthio) 5 nitropyrimidines are trans formed into dithiolopyrimidines, which are either oxidized to bis(4 dialkylthiocarbamoyl pyrimidin 5 yl) disulfides or converted into 4,6 diamino 5 nitropyrimidine derivatives with carbon disulfide elimination. The direction of the reaction is determined by the nature of a substituent in position 2 of pyrimidine and the bulk of the thiocarbamate substituent. Mecha nistic schemes for these processes were proposed.

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Cited by 5 publications
(2 citation statements)
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“…The nitric oxide (NO) donor, 6-methoxy-5-nitropyrimidin-4-yl pyrrolidine-1-carbodithioate (20), at a final concentration of 100 μM was used to assess the effect of nitrosative stress on M. tuberculosis viability. For starvation of M. tuberculosis , cultures were washed in phosphate buffered saline (PBS) twice before being resuspended in PBS.…”
Section: Methodsmentioning
confidence: 99%
“…The nitric oxide (NO) donor, 6-methoxy-5-nitropyrimidin-4-yl pyrrolidine-1-carbodithioate (20), at a final concentration of 100 μM was used to assess the effect of nitrosative stress on M. tuberculosis viability. For starvation of M. tuberculosis , cultures were washed in phosphate buffered saline (PBS) twice before being resuspended in PBS.…”
Section: Methodsmentioning
confidence: 99%
“…Scheme 49 shows the pathway of subse quent transformations of this alkaloid through thebaine (75) and codeine (55) into morphine (54). The formation of salutaridine (in liver and plant microsomes) assumes the involvement of reticuline (76).…”
Section: Scheme 48mentioning
confidence: 99%