TRIFLUORO-ACETYLATION OF NATURALLY OCCURRING PHENOLS AND STUDY OF ANTI-PROLIFERATIVE ACTIVITY OF RESPECTIVE PRODUCTS
Ajoy K. Bauri*, Ines Castro Dionicio, Eric Salinas Arellano, Sabine Foro and Esperanza J. Carcache de Blanco*
ABSTRACT
A methodology has been developed to introduce trifluoro acetyl moiety into acyl part of naturally occurring
phenols, malabaricones (A-D) and acyl phenol (AP) isolated from methanol extract the rind of Myristica
malabarica. This reaction is similar to Friedel Crafts acetylation reaction; a regio-selective trifluoro-acylation
reaction has been achieved using of trifluoro acetic acid as reagent under specific reaction condition. These
naturally occurring phenols undergo deacylation followed by trifluoro-acetylation to yield dihydroxy trifluoroacetyl
benzenes and respective fatty acids. The introduction of trifluoro acetyl moiety took place at ortho position
to one of the hydroxy groups of their acyl moieties to yield compound (1) as major product [2, 4-dihydroxy
trifluoro-acetyl benzene] along with ipso product (2) as very minor amount [2, 6-dihydroxy trifluoro-acetyl
benzene]. When acyl phenol (AP) was used as substrate for trifluoro-acetylation reaction under similar reaction
condition only product (1) was obtained as sole product without forming ipso product (2) [2, 4-dihydroxy
trifluoro-acetyl benzene]. This trifluoro-acetylation reaction has also been conducted in presence of different
transition metals and their salts, but no products were observed. In general, this methodology can be applied for
synthesis of small molecules like dihydroxy trifluoro acetyl benzene; it can be used as [18F] labeled
radiopharmaceutical diagnosing agent for PET imaging using 2, 6-dihydroxy acetophenone or its related
compounds as substrates. In contrast other dihydroxy acetophenone did not proceed trifluoro-acetylation reaction
under this reaction conditions. The cell cytoxicity of these reaction products was screened against various human
cancer cell lines in comparison with paclitaxel as control. It was found that compound 1 [2, 4-dihydroxy trifluoro
acetyl benzene] exhibited anti-proliferative activity against different human cancer cell lines.
Keywords: Natural phenols; M. malabarica; TFA reaction products; anti-proliferative activity; SRB assay.
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