Antioxidant and cytotoxic properties of novel spirocyclic benzothiazolines

Year 2017, Volume: 21 Issue: 4, 978 - 986, 01.12.2017

Gökçe Cihan-üstündağ , Nurten Özsoy Ezgi Öztaş Nilgün Karalı Gültaze Çapan

Abstract

In this work, we report the synthesis, structural characterization

and evaluation of in vitro antioxidant and cytotoxic properties

of novel spirobenzothiazolines (1a-e, 2a-e). 5-nonsubstituted

spirobenzothiazolines (1a-e) demonstrated notable inhibitory

capacity on lipid peroxidation (LPO), reducing power and

scavinging effects on diphenylpicryl hydrazine (DPPH˙)

and 2,2’-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid

(ABTS˙+) radicals, that were similar to that of α-tocopherol.

The most potent antioxidant was compound 1a (incorporating

an ethyl group on the cyclohexane ring) with an anti-LPO

activity 2-fold higher than that of α-tocopherol. Compound

1a exhibited anti-LPO and DPPH˙ scavenging activities at

concentrations lower than those cytotoxic for mouse normal

fibroblast (NIH/3T3) cells and was also found to be slightly

more selective for cancer cells (human prostat adenocarcinoma

cell/PC-3) than normal mammalian cells.

Keywords

Benzothiazole; spiroheterocycle; antioxidant activity; cytotoxic activity

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