Hydrazine → HCID 86746053, compound

Participants

Reaction Steps

In yet another preferred embodiment, a novel thiosemicarbazide bifunctional compound was formed (FIG. 4). In this embodiment, potassium phthalimide was reacted with 1,4-dibromo-2-butene to form 1-bromo-4-(N-phtalimido)-2butene. This compound was reacted with potassium thioacetate to form 1-(acetylthio)-4-(N-phthalimido)-2-butene which was then reacted with hydrazine and was treated with methoxycarbonylsulfenyl chloride followed by 2-mercaptopyridine to form 1-amino-4-[(2-pyridinyl)dithio]-2-butene hydrochloride. This compound was combined with TEA followed by di-2-pyridyl thionocarbonate, then t-butyl carbazate was added to form the t-boc derivative of N-[4-[(2-pyridinyl)dithio]-2-butenyl]-hydrazinecarbothioamide, compound 12. This compound was dissolved in TFA to form a compound in the form of a gum, which was then reacted with adriamycin hydrochloride and TFA to form the thiosemicarbazone derivative of ADM having a thiosemicarbazone bond at the C-13 position of the ADM (compound 3, FIG. 1) and having a reactive pyridinyldithio moiety.

Provenance & Evidence