electrostatic binding to a DNA phosphate group. Loss of correlation found with the parameters associated with the diamino side chain in series III when series I and III were combined suggests that perhaps different substitu-ents at position 7 dictate different drug-DNA orientations which therein alter the manner in which the 4-diamino side chain is able to interact with the DNA backbone.Antimalarials. 7-Chloro-4-(substituted amino)quinolines
from EtOH and dioxane to give 1.8 g (64%) of 16 as reddish gray needles, mp 210°dec.The 3-Me analog 17 and the 5-(5-nltro-2-furylacrylidene-1 hiazolidene-2,4-diones 21-25 were prepd similarly.5-(2-Furylidene)-2-methylrhodanine ( 27).soln of 3.0 g (0.02 mole) of 3-methylrhodanine, 2.0 g (0.02 mole) of furfural, and 0.5 ml of piperidine was heated under reflux in 30 ml of 95% EtOH for 30 min. The cryst which formed on cooling were collected, dried, and recrystd from 95% EtOH to give 4.25 g (95% ) of 27 as long golden yellow needles, mp 142-143°.5-(2-Furylidene)rhodanine ( 26) and the thiazolidine-2,4-diones 28 and 29 were prepd similarly.5-(2-Furylacryliderte)thiazolidene-2,4-dione (31). A mixt of 1.2 g (0.01 mole) of thiazolidine-2,4-dione, 1.2 g (0.01 mole) of Singh, ct a/.2-furylacrolein, and 0.5 ml of piperidine in 30 ml of 95% EtOH was refluxed for 1 hr. The mixt was allowed to cool overnight causing the pptn of a yellow solid which was collected, dried, and recrystd from EtOH and dioxane to give 1.5 g (71 % ) 30 as reddish brown needles, mp 217-218°. MD-2869 and is Contribution No. 887 from the Army Research Program on Malaria.
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