Method for preparing anthracene - 9,10-bis - carbonilhidrazonas and derived from the same

摘要

The invention provides novel anthracene -9,10-bis-carbonyl- hydrazones and derivatives thereof useful as antibacterial agents, for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers. The novel compounds are represented by the formula: IMAGE wherein A, B and C form an anthracene or a 9,10-dihydro anthracene nucleus, Z is a trivalent moiety of the formulae: IMAGE wherein n is 0, 1, 2 or 3 and R is hydrogen, alkyl having up to 4 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, phenyl or benzyl; R1 is hydrogen or alkyl having up to 4 carbon atoms; R2 is hydrogen, alkyl having up to 4 carbon atoms, phenyl or monovalent moieties of the formula: IMAGE wherein m is 2, 3, 4 or 5, R7 is amino anilino, hydrazino, monohydroxyalkylamino having from 2 to 4 carbon atoms and wherein the carbon atom alpha to the nitrogen atom may not bear a hydroxy group, alkylamino having up to 4 carbon atoms, dialkylamino where each alkyl group has up to 4 carbon atoms, cycloalkylamino having from 3 to 6 carbon atoms, benzylamino, alpha - phenethylamino, beta -phenethylamino 2-furfurylamino, 3-furfurylamino, alpha - thenylamino, beta -thenylamino, alpha - pyridylmethylamino, beta - pyridylmethylamino, gamma - pyridylmethylamino, indanylamino, pyrrolidino, piperidino, morpholino, thiomorpholino, N-methyl-piperazino, alkoxy having up to 4 carbon atoms or alkylthio having up to 4 carbon atoms, X is oxo, thioxo, imino or alkylimino having up to 4 carbon atoms, and Y is oxy, thio or a divalent group of the formula: IMAGE wherein R8 is hydrogen, alkyl having up to 4 carbon atoms or monohydroxyalkyl having from 2 to 4 carbon atoms and wherein the carbon atom alpha to the nitrogen atom may not bear a hydroxy group; R3, R4, R5 and R6 are each individually selected from the group consisting of hydrogen, halogen, hydroxy, nitro, amino, sulfonamido, alkyl having up to 4 carbon atoms and alkoxy having up to 4 carbon atoms; and R3 and R4 which they are attached form a phenyl group provided that in that case R1 is hydrogen and R2 is IMAGE wherein m and R8 are as defined above and the pharmacologically acceptable acid-addition and quaternary ammonium salts thereof.