The design and synthesis of several hybrid intercalator-linked porphyrins and their corresponding metalloporphyrin derivatives designed as cellular DNA targetted anticancer agents is described. 9-Chloro-7-methylimidazo[4,5-f]quinoline was condensed with ethylenediamine, 1,4-phenylenediamine and 2,5-toluenediamine to give compounds Ia–c. Naphtho[2,1-b]thiophene-4-carboxylic acid was condensed with 1,6-hexanediamine, 1,10-decanediamine, and 1,12-dodecanediamine to give compounds IIa–c and IIIa–c. Compounds Ia–c and IIa-c were condensed with deuterioporphyrin monomethyl ester and deuterioporphyrin to yield compounds IVa–j. Compounds IVa–h were refluxed with MnCl2 or CoCl2 in DMF to give metalloporphyrins Va–j. Compounds Ia–c, IIa–c, IIIa–c, IVa–j, and Va–j were characterized by IR, NMR, and MS (FAB) spectral data. Kassoc value for intercalative binding of these porphyrin derivatives to calf thymus DNA is in the range 1.9−3.0 × 106 L M−1.
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