Synthesis, antimalarial evaluation and structure-activity relationship in a series of dibenzlmethylamine (Dibemethin) derivatives of 4-amino-7-chloroquinoline
Doctoral Thesis
2008
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University of Cape Town
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Abstract
A series of twelve 4-amino-7-chloroquinolines containing (N, N-dibenzylmethylamine) dibemethin side chains attached to the amino group of the quinoline were synthesized by reaction of aminomethyl dibemethins with 4,7-dichloroquinoline to give “dibemethinoquines”. The attachment between the quinoline ring and the side chain was varied from ortho, to meta to para. The aminomethyl dibemethin side chains were synthesized using the Staudinger reduction of azides or the reductive amination via oxime of an aldehyde. Derivatives in which the para substituent on the terminal phenyl ring were altered from the parent compound (X = H) by replacement with Cl, OCH₃ orNMe₂ group were also synthesized. The choice of substituents was based on the Topliss scheme.
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Includes abstract.
Includes bibliographical references (leaves 138-154).
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Zishiri, V. 2008. Synthesis, antimalarial evaluation and structure-activity relationship in a series of dibenzlmethylamine (Dibemethin) derivatives of 4-amino-7-chloroquinoline. University of Cape Town.