Novel indolene-spiro-hydroxytetronimides as potential antineoplastic and antiviral agents

In a continuing search for new antineoplastic and antiviral agents, the preparation of some substituted indol-2(3H)-one-3-spiro-2'-3',4'-dihydroxy-5'-imino-2',5'-dihydrofurans was designed. The synthesis was achieved by reacting isatin, 1-alkyl- or 1-aralkylisatin derivative with glyoxal sodium bisulfite and potassium cyanide. However, when 1-substituted aminomethyl derivatives of isatin or of 5-bromoisatin were used in this reaction, the indolone-spiro-hydroxytetronimide unsubstituted at position 1 was, unexpectedly, the only product isolated. Two compounds were tested against P-388 lymphocytic leukemia in mice and were inactive.