Synthesis, Antioxidant, and Cytotoxic Activities of <i>N</i>‐<scp>A</scp>zole Substituted Thiomorpholine Derivatives

Reddy, P. Ramachandra; Reddy, Guda Mallikarjuna; Padmaja, A.; Padmavathi, V.; Kondaiah, Paturu; Krishna, Narra Siva

doi:10.1002/ardp.201300299

Cited by 10 publications

(5 citation statements)

References 52 publications

(38 reference statements)

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“…Towards this direction, the relatively increased lipophilicity of the compounds may also assist (Table 2), making the access to the lipid phase more facile. The results of the ferulic acid compounds 1 and 2 are in accordance with previous findings from our laboratory [27]. Nevertheless, the activity of compound 2 is much higher, and a potential explanation may be the existence of two molecular parts with extended conjugation on the structure.…”

Section: Effect On Lipid Peroxidationsupporting

confidence: 91%

Ferulic, Sinapic, 3,4-Dimethoxycinnamic Acid and Indomethacin Derivatives with Antioxidant, Anti-Inflammatory and Hypolipidemic Functionality

2023

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A series of thiomorpholine and cinnamyl alcohol derivatives, conjugated with cinnamic acid-containing moieties, such as ferulic acid, sinapic acid and 3,4-dimethoxycinnamic acid, were synthesized and tested for their antioxidant, anti-inflammatory and hypolipidemic properties. An indomethacin ester with 2,6-di-tert-butyl-4-(hydroxymethyl)phenol was also prepared for reasons of comparison. The majority of the compounds demonstrated considerable antioxidant capacity and radical scavenging activity, reaching up to levels similar to the well-known antioxidant trolox. Some of them had an increased anti-inflammatory effect on the reduction of carrageenan-induced rat paw edema (range 17–72% at 150 μmol/kg), having comparable activity to the NSAIDs (non-steroidal anti-inflammatory drugs) used as reference. They had moderate activity in soybean lipoxygenase inhibition. All the tested compounds exhibited a significant decrease in lipidemic indices in Triton-induced hyperlipidemia in rats, whilst the most active triglycerides and total cholesterol decreased by 72.5% and 76%, respectively, at 150 μmol/kg (i.p.), slightly better than that of simvastatin, a well-known hypocholesterolemic drug, but with negligible triglyceride-lowering effect. Since our designed compounds seem to exhibit multiple pharmacological activities, they may be of use in occasions involving inflammation, oxidative stress, lipidemic deregulation and degenerative conditions.

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Section: Effect On Lipid Peroxidationsupporting

confidence: 91%

Ferulic, Sinapic, 3,4-Dimethoxycinnamic Acid and Indomethacin Derivatives with Antioxidant, Anti-Inflammatory and Hypolipidemic Functionality

2023

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“…Another direction in the chemistry of N-arylmaleimides, which is well represented in the literature, is the building of thiomorpholine rings when they interact with 1,4-N,Sbinucleophiles [38,44] (Scheme 14). This framework is a common pharmacophoric element and it exhibits selective enzyme inhibition for many receptors and other types of molecular targets [45][46][47][48][49][50][51].…”

Section: Reactions With S-and O-containing Dinucleophilesmentioning

confidence: 99%

Recyclization of Maleimides by Binucleophiles as a General Approach for Building Hydrogenated Heterocyclic Systems

Vandyshev

Shikhaliev

2022

Molecules

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The building of heterocyclic systems containing hydrogenated fragments is an important step towards the creation of biologically-active compounds with a wide spectrum of pharmacological activity. Among the numerous methods for creating such systems, a special place is occupied by processes using N-substituted maleimides as the initial substrate. This molecule easily reacts in Diels-Alder/retro-Diels-Alder reactions, Michael additions with various nucleophiles, and co-polymerization processes, as have been described in numerous detailed reviews. However, information on the use of maleimides in cascade heterocyclization reactions is currently limited. This study is devoted to a review and analysis of existing literature data on the processes of recyclization of N-substituted maleimides with various C,N-/N,N-/S,N-di- and polynucleophilic agents, such as amidines, guanidines, diamines, aliphatic ketazines, aminouracils, amino- and mercaptoazoles, aminothiourea, and thiocarbomoyl pyrazolines, among others. The significant structural diversity of the recyclization products described in this study illustrates the powerful potential of maleimides as a building block in the organic synthesis of biologically-active compounds with hydrogenated heterocyclic fragments.

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“…Previously, we have reported on the synthesis and anti‐ microbial activities of thiomorpholine derivatives and there are several reports in the literature describing the biological importance thiomorpholine derivatives. These hybrids are frequently associated with medicinal applications such as antihelicobacter pylori, antibacterial, cytotoxic, antimycobacterial and antioxidant activities . In addition, these derivatives found to serve as DPP‐IV, type 5 17‐β‐hydroxysteroid dehydrogenase (AKR1C 3 ), selective cathepsin S, and p38 inhibitors .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Thiomorpholine 1,1-Dioxide Derived 1,2,3-Triazole Hybrids as Potential Anticancer Agents

et al. 2017

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In this report, we describe the synthesis and biological evaluation of a new series of (4‐((1‐(aryl)‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)(1,1‐dioxidothiomorpholino)methanone derivatives (6 a‐6 n). All the new derivatives were well analyzed by 1H NMR, 13C NMR, FTIR, mass spectral and elemental data. The synthesized compounds were screened for in vitro anticancer activity against three cancer cell lines (MCF‐7, HeLa, and HEK293) and compared with standard drug cisplatin. Three (6 b, 6 g and 6 i) out of fourteen derivatives exhibited potent anticancer activity against MCF‐7, HeLa, and HEK293. Two (6 b and 6 g) potent hybrids were screened for in vivo studies against EAC bearing mice and found to possess potential anticancer activity.

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Synthesis, Antioxidant, and Cytotoxic Activities of N‐Azole Substituted Thiomorpholine Derivatives

Cited by 10 publications

References 52 publications

Ferulic, Sinapic, 3,4-Dimethoxycinnamic Acid and Indomethacin Derivatives with Antioxidant, Anti-Inflammatory and Hypolipidemic Functionality

Ferulic, Sinapic, 3,4-Dimethoxycinnamic Acid and Indomethacin Derivatives with Antioxidant, Anti-Inflammatory and Hypolipidemic Functionality

Recyclization of Maleimides by Binucleophiles as a General Approach for Building Hydrogenated Heterocyclic Systems

Synthesis and Biological Evaluation of Novel Thiomorpholine 1,1-Dioxide Derived 1,2,3-Triazole Hybrids as Potential Anticancer Agents

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