New spiroindolinones bearing 5-chlorobenzothiazole moiety

Abstract

In this study, 5-chloro-3H-spiro-[1,3-benzothiazole-2,3 0 -indole]-2 0 (1 0 H)-one derivatives 3a-l were synthesized by the reaction of 1H-indole-2,3-diones 1a-l with 2-amino-4-chlorothiophenol 2 in ethanol. 3a-l were tested for their abilities to inhibit lipid peroxidation (LP), scavenge DPPH and ABTS þ radicals, and to reduce Fe 3þ to Fe 2þ . Most of the tested compounds exhibited potent scavenging activities against ABTS þ radical, reducing powers and strong inhibitory capacity on LP. 3 a, 3 d, 3e, 3h, 3j and 3 k chosen as prototypes were evaluated in the National Cancer Institute's in vitro primary anticancer assay. The greatest growth inhibitions were observed against a non-small cell lung cancer cell line HOP-92 for R 1 -fluoro substituted 3 d and a renal cancer cell line RXF-393 for R-chloro substituted 3 e in the primary screen.

Spirocyclic derivatives as antioxidants: a review

“…62 DPPH, ABTS, and anti-liposomal peroxidation tests were assessed for spiroxindoles C22-C26. 63,64 The results obtained showed that these compounds have EC 50 values of 0.98, 1.30, 13.00, 8.33 and 4.19 mM, respectively, in the DPPH assay, EC 50 of 0.98, 1.02, 0.99, 1.16 and 1.55 mM in the ABTS test and EC 50 of 0.04, 0.03, 0.11, 0.12 and 0.12 mM in the anti-LPO test. Additionally, compounds C22-C26 were compared with vitamin C and tocopherol as positive controls that respectively presented EC 50 values of 0.36 and 0.35 mM in the DPPH test and 1.20 and 1.20 mM in the ABTS test.…”

“…Syntheses of compounds C22-C26 are shown in Scheme 8. 63,64 Likewise, the AO activities of oxindoles C27-C30 were determined by the DPPH radical scavenging test. For compounds C27 and C28, IC50 values were determined, which were respectively 32.50 mM and 0.44 mg mL À1 .…”

Antioxidant and cytotoxic properties of novel spirocyclic benzothiazolines

“…In two early reports, spiroindolinones incorporating a benzothiazole or 5-chlorobenzothiazole moiety (III) (Figure 1) have been described as promising antioxidants with potent scavenging activities against DPPH˙ and (ABTS˙+) radicals and reducing powers and significant inhibitory capacity on lipid peroxidation. Compounds have also been found to be cytotoxic against some cancer cell lines in anticancer screening [16,17]. Likewise, the antioxidant properties of several small spiroheterocyclic molecules have been reported in different papers [18][19][20][21].…”