SYNTHESES OF SOME NOVEL (E)-1-(4′-BROMOPHENYL)-3-(4-
(DIPHENYLAMINO)PHENYL)PROP-2-EN-1-ONE CHALCONES AND THEIR BIOLOGICAL
STUDIES
ABDULRAZAQ TUKUR * , JAMES DAMA HABILA, RACHAEL GBEKELE-OLUWA AYO AND
OGUNKEMI RISIKAT AGBEKE IYUN
Department of Chemistry, Ahmadu Bello University, Zaria, Nigeria.
Afr. J Pharm Res Dev; Volume 13(1): 144-159 (2021)
ABSTRACT
The increase in the resistance of microorganisms to available chemotherapeutic agents are imperative issues in
drug design and development, prompting researchers to look for novel compounds that can combat multidrug
resistant organisms. Recently, chalcones have been proved to be attractive moieties in drug discovery. The target
triphenylamine chalcones were prepared using the Claisen-Schmidt condensation process of various substituted
acetophenone/propiophenones and 4-(Diphenylamino) benzaldehyde, in the presence of NaOH (10 %) in ethanol
at room temperature, and recrystallized using ethanol. The nucleophilic enolate attack on the electrophilic carbonyl
carbon of 4-(Diphenylamino) benzaldehyde resulted in the formation of a new carbon-carbon bond. Eight novel
triphenylamine chalcones with different substitution patterns were successfully synthesized, the percentage yield
of the compounds were between 30 – 92 %. The triphenylamine chalcones were characterized by means of FT-IR
and NMR analyses. The outcome for evaluation of the biological studies revealed that all the synthesized
compounds possess remarkable activities against the tested microbes, by showing a significant zone of inhibitions
relative to that of the standard drugs used. The investigation indicated that 1b had the highest ZOI (30 mm), lowest
MIC (12.5 µg/ml) and MBC/MFC (50 µg/ml) on Aspergillus niger.
Email of correspondence: abdulrazaqtukur@gmail.com
KEYWORDS: Antibiotics; Condensation; Recrystallization; Acetophenone; Propiophenone.