Hindered phenolic aminothiazoles – Synthesis, α-glucosidase, α-amylase inhibitory and antioxidant activities

Sandhya Vyjayanthy Satheesh, Akhila Vijayan Radha, Krishnapriya Krishnan Nair Girija, Kallikat Narayanan Rajasekharan, Priya Rani Maheswari

Abstract


Base catalysed heterocyclization of either 1-aryl-3-(N-nitro­amidino)thioureas or 1-aryl-3-cyanothioureas by reaction with 2-bromo-3',5'-di-t-butyl-4'-hydroxyacetophenone afforded 4-amino-2-arylamino-5-(3,5-di-t-butyl-4-hydroxybenzoyl)thiazoles, designed as molecular hybrids of hindered phenolic and 2-aminothiazole moieties. These compounds were screened for their carbohydrate hydrolyzing enzymes inhibition activity. Thus, 4-amino-5-(3,5-di-t-butyl-4-hydroxybenzoyl)-2-(phenylamino)thiazole exhi­bit­ed α-gluco­sidase inhibition activity with an  IC50 value of 117.02 µM while the standard compound acarbose showed an  IC50 value of 48.26 µM and 4-amino-5-(3,5-di-t-butyl-4-hydroxybenzoyl)-2-(4-methylphenylamino)thiazo­le showed good α-amylase inhibition activity with an IC50 value of 283.19 µM compared to acarbose (IC50  531.91 µM). The antioxidant activities of hindered phenolic thiazoles were also investigated and the 2-(4-methoxyphenylamino) derivative showed an antioxidant activity better than that of butylated hydroxy anisole under 2,2-diphenyl-1-picryl hydrazyl radical scavenging assay, better than that of  either vitamin C or curcumin under ferric ion reducing antioxidant potential assay and comparable with that of butylated hydroxy anisole under β-carotene bleaching assay.


Keywords


2,4-diaminothiazolyl; 3,5-di-t-butyl-4-hydroxyphenyl; hindered phenol; enzyme inhibition.

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DOI: http://dx.doi.org/10.2298/JSC161005084S

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