Discovery of benzothiazole-based thiazolidinones as potential anti-inflammatory agents: anti-inflammatory activity, soybean lipoxygenase inhibition effect and molecular docking studies

Haroun, Michelyne; Petrou, Anthi; Tratrat, Christophe; Kositsi, Katerina; Gavalas, Antonis; Geronikaki, Athina; Venugopala, Katharigatta N.; Harsha, N. Sree

doi:10.1080/1062936x.2022.2084772

Cited by 11 publications

(9 citation statements)

References 59 publications

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“…These results are similar to previous study [45] The presence of the electron withdrawing NO 2 substituent on the ring may be detrimental with the fungal target in the case of C. albicans and similar to previous studies, in our work same was observed in the case of R. oryzae [46] Among the synthesized derivatives, a compound S14 (R 2 =R 3 =OCH 3 ) and S16 (R 1 =R 5 =Cl) displayed the highest anti‐inflammatory potential along with compound S9 (R 2 =OCH 2 CH 3 , R 4 =OH) which were similar to the results of Haroun et al [47] …”

Section: Resultssupporting

confidence: 92%

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Synthesis, Biological Evaluation andin SilicoStudies of 3‐Hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide Derivatives

Kamboj

Thakral

Kumar

et al. 2023

Chemistry & Biodiversity

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In the present study, a series of 3‐hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide derivatives were synthesized, characterized and evaluated for theirin vitroactivity, i. e., antimicrobial, antioxidant and anti‐inflammatory. The target compounds were synthesized by condensation reaction of 3‐hydroxy‐2‐naphthoic acid hydrazide with substituted benzaldehydes which were subjected to cyclization reaction with thioglycolic acid and ZnCl2 to get target compounds. The synthesized 3‐hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide derivatives were examined for their antimicrobial activity and 3‐hydroxy‐N‐(4‐oxo‐2‐(3,4,5‐trimethoxyphenyl)thiazolidin‐3‐yl)‐2‐naphthamide (S20) exhibited the highest antimicrobial potential. The N′‐(2,3‐dichlorobenzylidene)‐3‐hydroxy‐2‐naphthohydrazide (S5) displayed good antifungal potential against Rhizopus oryzae, whereas N′‐(2,3‐dichlorobenzylidene)‐3‐hydroxy‐2‐naphthohydrazide (S20) showed the highest antioxidant potential and N‐(2‐(2,6‐dichlorophenyl)‐4‐oxothiazolidin‐3‐yl)‐3‐hydroxy‐2‐naphthamide (S16) displayed the highest anti‐inflammatory activity. The results of molecular docking studies revealed that existence of hydrogen bonding and hydrophobic interactions with their respective proteins. In silico ADMET studies were carried out by Molinspiration, Pre‐ADMET and OSIRIS property explorer to predict the pharmacokinetic behaviour of synthesized 3‐hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide derivatives.

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Section: Resultssupporting

confidence: 92%

“…The presence of the electron withdrawing NO 2 substituent on the ring may be detrimental with the fungal target in the case of C. albicans and similar to previous studies, in our work same was observed in the case of R. oryzae [46] …”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation andin SilicoStudies of 3‐Hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide Derivatives

Kamboj

Thakral

Kumar

et al. 2023

Chemistry & Biodiversity

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“…Biological activity prediction for fifty-four chemical structures was carried out using PASS [ 61 ]. This program was successfully used in the search for COX/LOX inhibitors earlier [ 62 ]. Each predicted biological activity for a particular compound is characterized by the Pa value, which reflects the probability of belonging to the class of “actives”.…”

Section: Resultsmentioning

confidence: 99%

Discovery of 5-Methylthiazole-Thiazolidinone Conjugates as Potential Anti-Inflammatory Agents: Molecular Target Identification and In Silico Studies

et al. 2022

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A series of previously synthesized 5-benzyliden-2-(5-methylthiazole-2-ylimino)thiazoli- din-4-one were evaluated for their anti-inflammatory activity on the basis of PASS predictive outcomes. The predictive compounds were found to demonstrate moderate to good anti-inflammatory activity, and some of them displayed better activity than indomethacin used as the reference drug. Structure–activity relationships revealed that the activity of compounds depends not only on the nature of the substituent but also on its position in the benzene ring. The most active compounds were selected to investigate their possible mechanism of action. COX and LOX activity were determined and found that the title compounds were active only to COX-1 enzymes with an inhibitory effect superior to the reference drug naproxen. As for LOX inhibitory activity, the derivatives failed to show remarkable LOX inhibition. Therefore, COX-1 has been identified as the main molecular target for the anti-inflammatory activity of our compounds. The docking study against COX-1 active site revealed that the residue Arg 120 was found to be responsible for activity. In summary, the 5-thiazol-based thiazolidinone derivatives have been identified as a novel class of selective COX-1 inhibitors.

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“…These tests examined the enzymecatalysed reaction rate, structure-activity relationship, and various factors affecting the reaction rate. [19][20][21][22] Efforts to establish sensitive and simple methods for separating and purifying enzyme inhibitors from natural products are ongoing. For certain mixtures with complex compositions, especially for the separation of triterpenoids, commonly used techniques include column chromatography, semi-preparative high-performance liquid chromatography (semi-preparative HPLC), and high-speed countercurrent chromatography (HSCCC), among others.…”

Section: Introductionmentioning

confidence: 99%

Efficient and fast screening and separation based on computer‐aided screening and complex chromatography methods for lipoxygenase inhibitors from Ganoderma lucidum

Nong,

Zhou,

et al. 2024

Phytochemical Analysis

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IntroductionAccurate screening and targeted preparative isolation of active substances from natural medicines have long been technical challenges in natural medicine research.ObjectivesThis study outlines a new approach for improving the efficiency of natural product preparation, focusing on the rapid and accurate screening of potential active ingredients in Ganoderma lucidum and efficient preparation of lipoxidase inhibitors, with the aim of providing new ideas for the treatment of Alzheimer's disease with G. lucidum.MethodsThe medicinal plant G. lucidum was selected through ultrafiltration coupled with liquid chromatography and mass spectrometry (UF–LC–MS) and computer‐assisted screening for lipoxygenase (LOX) inhibitors. In addition, the inhibitory effect of the active compounds on LOX was studied using enzymatic reaction kinetics, and the underlying mechanism is discussed. Finally, based on the earlier activity screening guidelines, the identified ligands were isolated and purified through complex chromatography (high‐speed countercurrent chromatography and semi‐preparative high‐performance liquid chromatography).ResultsFive active ingredients, ganoderic acids A, B, C2, D2, and F, were identified and isolated from G. lucidum. We improved the efficiency and purity of active compound preparation using virtual computer screening and enzyme inhibition assays combined with complex chromatography.ConclusionThe innovative methods of UF–LC–MS, computer‐aided screening, and complex chromatography provide powerful tools for screening and separating LOX inhibitors from complex matrices and provide a favourable platform for the large‐scale production of bioactive substances and nutrients.

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Discovery of benzothiazole-based thiazolidinones as potential anti-inflammatory agents: anti-inflammatory activity, soybean lipoxygenase inhibition effect and molecular docking studies

Cited by 11 publications

References 59 publications

Synthesis, Biological Evaluation andin SilicoStudies of 3‐Hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide Derivatives

Synthesis, Biological Evaluation andin SilicoStudies of 3‐Hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide Derivatives

Discovery of 5-Methylthiazole-Thiazolidinone Conjugates as Potential Anti-Inflammatory Agents: Molecular Target Identification and In Silico Studies

Efficient and fast screening and separation based on computer‐aided screening and complex chromatography methods for lipoxygenase inhibitors from Ganoderma lucidum

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