Regio- and stereo-chemical ring-opening reactions of the 2,3-epoxy alcohol derivative with nucleophiles: Explanation of the structures and C-2 selectivity supported by theoretical computations

Gündoğdu, Özlem; Atalay, Abdurrahman; Çelebioğlu, Neslihan; Anil, Barış; Şahin, Ertan; Şanlı‐Mohamed, Gülşah; Bozkaya, Uğur; Kara, Yunus

doi:10.1016/j.molstruc.2022.133163

Cited by 4 publications

(4 citation statements)

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“…For the synthesis of target isoindole‐1,3‐dione derivatives, we initiated with the synthesis of 2‐alkyl/aryl‐5‐hydroxy‐3a,4,5,7a‐tetrahydro‐1 H ‐isoindole‐1,3(2 H )‐dione ( 8 ) from 3‐sulfolene by using a known method as described in the literatüre (Gündoğdu et al, 2022; Tan et al, 2011). The reaction of 3‐sulfolene ( 5 ) with maleic anhydride ( 6 ) gave cyclic anhydride 7 .…”

Section: Resultsmentioning

confidence: 99%

“…Allyl alcohols 10a‐c were synthesized from reduction of hydroperoxides obtained by the reaction of singlet oxygen with bicyclic imides 8a–c (Scheme 3) (Gündoğdu et al, 2022; Tan et al, 2011).…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, the structures of the opening products were determined comparatively. The 1 H and 13 C NMR spectra of the ring‐opening product synthesized in previous studies and whose structure was determined by x‐ray were compared with the NMR spectra of the synthesized products and the structure of each product was determined (Gündoğdu et al, 2022). For instance, when the proton signals belonging to groups such as ‐Bn, −Et, −Me which are attached to the nitrogen (N) atom are excluded, almost the same signal groups are seen for each ring‐opening product and resonate in the same region.…”

Section: Resultsmentioning

confidence: 99%

“…Allyl alcohols 10a-c were synthesized as described in literature (Gündoğdu et al, 2022;Tan et al, 2011Tan et al, , 2014.…”

Section: Chemical Partmentioning

confidence: 99%

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Synthesis, cytotoxicity, and antibacterial studies of 2,4,5,6‐substituted hexahydro‐1H‐isoindole‐1,3(2H)‐dione

Yetişkin,

Gündoğdu,

Mete

et al. 2023

Chem Biol Drug Des

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In this study, synthesis of novel isoindole‐1,3‐dione analogues bearig halo, hydroxy, and acetoxy groups at the position 4,5,6 of the bicyclic imide ring was performed to examine their potential anticancer effects against some cell lines. A multistep chemical pathway was used to synthesize the derivatives. The cytotoxic effect of trisubstituted isoindole derivatives were evaluated by determining cellular viability using the MTT assay against A549, PC‐3, HeLa, Caco‐2, and MCF‐7 cell lines. The C‐2 selective ring‐opening products were obtained from the ring‐opening reaction of 5‐alkyl/aryl‐2‐hydroxyhexahydro‐4H‐oxireno[2,3‐e]isoindole‐4,6(5H)‐diones with nucleophiles such as chloride (Cl−) and bromide (Br−) ions. In addition, the ring‐opening products halodiols were converted to their related acetates. The anticancer activity of synthesized isoindole‐1,3‐dione derivatives was investigated against HeLa, A549, MCF‐7, PC3, and Caco‐2 cells in vitro and resulted in varies cytotoxic effect depend on the group attached to the isoindole molecule. Furthermore, the evaluation of the antimicrobial action of trisubstituted isoindole derivatives against Gram‐positive (Staphylococcus aureus) and Gram‐negative (Escherichia coli) bacteria was assessed and found out selective inhibition of the both bacterial growth via different trisubstituted isoindole derivatives. The results of this work encourage further research on the potential utilization of trisubstituted isoindole derivatives as cytotoxic and antimicrobial agents.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Allyl alcohols 10a-c were synthesized as described in literature (Gündoğdu et al, 2022;Tan et al, 2011Tan et al, , 2014.…”

Section: Chemical Partmentioning

confidence: 99%

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