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KMID : 0370219820260020091
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Yakhak Hoeji
1982 Volume.26 No. 2 p.91 ~ p.96
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Studies on the Synthesis of Bis-dithiocarbamates as Prodrugs of Isothiocyanates
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심영섭/Shim YS
정오영/김완주/이문희/Chung OY/Kim WJ/Lee MH
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Abstract
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In an attempt to design prodrugs for the derivatives of the Isothiocyanates R-N=C=S were synthesized eleven novel bis-dithiocarbamates. The best way of preparing the dithiocarbamates was the formation of the dithiocarbonates followed by the reaction of the dithiocarbonates with amines. Thus, the treatment of the diols with carbon disulfide in the presense of potassium hydroxide afforded the potassium salts of the dithiocarbonic acids. The potassium salts were then reacted with alkyl halides to give the dithiocarbonates, which upon treatment with amines Produced the dithiocarbamates. In case of vicinal diol (n=o in the above formula), only one of the hydroxy groups was reacted to give the mono-dithiocarbonate. The dithiocarbonates failed to react with amides and aromatic amines. Dithiocarbonates of the different types were obtained when the active double bonds, such as CH2=CH-Z, (Z are electron withdrawing groups), were allowed to react with the free dithiocarbonic acids produced in situ by carefully neutralizing the potassium salts of the corresponding acids. These compounds are considered to be of some value as prodrugs for the active double bonds.
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