Synthesis of new spiroindolinones incorporating a benzothiazole moiety as antioxidant agents

Karalı, Nilgün; Güzel, Özlen; Özsoy, Nurten; Özbey, Süheyla; Salman, Aydın

doi:10.1016/j.ejmech.2009.12.001

Cited by 125 publications

(55 citation statements)

References 36 publications

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“…Additionally, 2'-hydroxycinnamaldehyde and the analogue 2'-benzoyloxycinnamaldehyde induce apoptosis in cancer cells via the induction of cellular reactive oxygen species (ROS) [18]. Recently antitumor activities of various cinnamic acid derivatives were explored by many research groups [19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

et al. 2014

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Cinnamic acids have been identified as interesting compounds with antioxidant, anti-inflammatory and cytotoxic properties. In the present study, simple cinnamic acids were synthesized by Knoevenagel condensation reactions and evaluated for the above biological activities. Compound 4ii proved to be the most potent LOX inhibitor. Phenylsubstituted acids showed better inhibitory activity against soybean LOX, and it must be noted that compounds 4i and 3i with higher lipophilicity values resulted less active than compounds 2i and 1i. The compounds have shown very good activity in different antioxidant assays. The antitumor properties of these derivatives have been assessed by their 1/IC 50 inhibitory values in the proliferation of HT-29, A-549, OAW-42, MDA-MB-231, HeLa and MRC-5 normal cell lines. The compounds presented low antitumor activity considering the IC 50 values attained for the cell lines, with the exception of compound 4ii. Molecular docking studies were carried out on cinnamic acid derivative 4ii and were found to be in accordance with our experimental biological results.

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Section: Introductionmentioning

confidence: 99%

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

et al. 2014

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“…In the case of 1-methyl-1H-indole-2,3-dione, only XIII was obtained under the same conditions (Figure 2) [35][36][37] . The reaction of 1H-indole-2,3-dione with 2-aminothiophenol was reported to result in the formation of XIII in ethanol [38][39][40] .…”

Section: Chemistrymentioning

confidence: 99%

“…5-Chloro-3H-spiro[1,3-benzothiazole-2,3 0 -indol]-2 0 (1 0 H)-ones 3 a-l were synthesized by the reaction of 2-amino-4-chlorothiophenol 2 with 1H-indole-2,3-diones 1 a-l in ethanol (Figure 3) 39,40 . The structures of spiroindolinones were confirmed by analytical and spectral (IR, 1 H-NMR, 13 C-NMR (APT), HSQC-2D, HMBC-2D, ESMS and LCMS-APCI) data.…”

Section: Chemistrymentioning

confidence: 99%

New spiroindolinones bearing 5-chlorobenzothiazole moiety

Ermut¹,

Karalı²,

Özsoy

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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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.

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“…(Fig 43). [61] The reaction sequence startsbygeneratingcarbanionontreating5-substituted1H-indole-2,3-diones with NaH in DMF, followed by addition of iodomethane to get access to 5-substituted and other diseases has led to new medical insight and. Minimizing an oxidative damage is primary prevention or treatment of these diseases, since antioxidants may stop the free-radical formation, or interrupt an oxidizing chain reaction.…”

Section: Fig 39mentioning

confidence: 99%

Synthesis, Biological Activity and Recent Advancement of Benzothiazoles: A Classical Review

Anand¹

2017

WJPPS

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Synthesis of new spiroindolinones incorporating a benzothiazole moiety as antioxidant agents

Cited by 125 publications

References 36 publications

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

New spiroindolinones bearing 5-chlorobenzothiazole moiety

Synthesis, Biological Activity and Recent Advancement of Benzothiazoles: A Classical Review

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