Synthesis, antimalarial evaluation and structure-activity relationship in a series of dibenzlmethylamine (Dibemethin) derivatives of 4-amino-7-chloroquinoline

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.

Grantor dc:publisher.institution

Department of Chemistry

Year dc:date.issued

2008

Author dc:creator

• Zishiri, Vincent Kudakwashe

Advisors dc:contributor.advisor

• Egan, Timothy J
• Hunter, Roger

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/11427/6280

OAI identifier oai:identifier

oai:open.uct.ac.za:11427/6280