Diastereoselective Sonochemical Synthesis of Spirocyclopropaneoxindoles and Evaluation of Their Antioxidant and Cytotoxic Activities

Abstract

An efficient diastereoselective synthesis of spirocyclopropaneoxindoles is reported using three‐component reactions of various phenacylidenetriphenylphosphorane, isatins and phenacyl bromide under ultrasonic irradiation. The structures of synthesized spirocyclopropaneoxindoles were characterized by their spectral data. The antioxidant activities of the synthesized compounds were evaluated by 1,1‐diphenyl‐2‐picrylhydrazyl radical scavenging assay. Among the products, those with NH group in their structure exhibited higher antioxidant activities than other derivatives. Also, in vitro cytotoxicity of compounds 4b, 4e, 4j, 4k were examined against heLa cancer cell lines using MTT assay. The results revealed that compound 4j with chlorine substituent on phenyl group displayed higher cytotoxicity activity (IC50=4.50±0.30 μg/mL) after 48 h.

Spirocyclic derivatives as antioxidants: a review

“…16 The synthesis and AO activity, using the DPPH test, of a new spirocyclopropanoxyindole [2.4.0] compound (A4) has been reported. 17 This compound showed moderately good activity, with an inhibition percentage at 1 mg mL À1 of 63.90%, compared to vitamin C as standard, with 82.30% inhibition at the same concentration. Scheme 2 shows the general procedure for the synthesis of compound A4.…”

“…80 The spiro compound [4.5.0] D1, called Ribesin H, was isolated from R. nigrum leaves; its AO activity was assessed using SOA and DPPH tests. During the SOA test, compound D1 presented better results for concentration (EC 50 3.26 mM) as compared to the butylated hydroxyanisole (BHA) used as a positive control (EC 50 17.02 mM). Additionally, in the DPPH test, compound D1 showed an EC 50 value of 50 mM, in contrast to the BHA, which presented an EC 50 value of 26.71 mM (see Fig.…”

Spirooxindole: A Versatile Biologically Active Heterocyclic Scaffold

“…Ultrasonic irradiation of isatins, phenacyl bromides, and phenacylidenetriphenylphosphorane 98 in water containing Et 3 N at 20–30 °C (60 W) afforded the corresponding spirocyclopropaneoxindoles 99 in high yields ( Scheme 32 ). Some of the synthesized compounds revealed promising antiproliferation properties against HeLa (cervical) cancer cell line in the MTT assay (IC 50 = 9.30, 4.50; 6.33, 1.86 for the most effective agent synthesized with R = H, R′ = Cl, R″ = [1-(4-bromobenzyl)-1 H -1,2,3-triazol-4-yl] and Doxorubicin at 24 h and 48 h, respectively) [ 52 ].…”

One‐pot synthesis of new hydantoin (thiohydantoin) derivatives and evaluation of their antibacterial and antioxidant activities

“…As demonstrated in Figure 2, all of the synthesized compounds showed high DPPH inhibition potency (77.4%-83.9%) that could be due to existence of heteroatoms possessing lone pair electrons and exchangeable protons on their NH 2 and OH groups. [37] 2.2 | Antibacterial activity…”