Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family

Bataille, Carole J. R.; Brennan, Méabh B.; Byrne, Sandie; Davies, Stephen G.; Durbin, Matthew J.; Fedorov, O.; Huber, Kilian; Jones, Alan M.; Knapp, S.; Gu, Lin; Nadali, Anna; Quevedo, Camilo; Russell, Angela J.; Walker, Robert; Westwood, R.; Wynne, Graham M.

doi:10.1016/j.bmc.2017.02.056

Cited by 43 publications

(17 citation statements)

References 64 publications

(55 reference statements)

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“…Another interesting class of heterocyclic compounds is 5-(1H-Indol-3-ylmethylene) -2thioxothiazolidin-4-ones with wide spectrum of biological activities as well. Among them are antitumor [26,27] and antimicrobial [28,29], inhibitors of proteases anthrax lethal factor, inhibitors against neurotoxin type A [28], aldose reductase [30], PIM kinase [31], PI3Kα [32], IKKβ [33], and GSK-3 [34] enzymes.…”

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confidence: 99%

5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)alkancarboxylic Acids as Antimicrobial Agents: Synthesis, Biological Evaluation, and Molecular Docking Studies

Horishny

Карцев²,

Geronikaki

et al. 2020

Molecules

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Background: Infectious diseases symbolize a global consequential strain on public health security and impact on the socio-economic stability all over the world. The increasing resistance to the current antimicrobial treatment has resulted in crucial need for the discovery and development of novel entity for the infectious treatment with different modes of action that could target both sensitive and resistant strains. Methods: Compounds were synthesized using classical methods of organic synthesis. Results: All 20 synthesized compounds showed antibacterial activity against eight Gram-positive and Gram-negative bacterial species. It should be mentioned that all compounds exhibited better antibacterial potency than ampicillin against all bacteria tested. Furthermore, 18 compounds appeared to be more potent than streptomycin against Staphylococcus aureus, Enterobacter cloacae, Pseudomonas aeruginosa, Listeria monocytogenes, and Escherichia coli. Three the most active compounds 4h, 5b, and 5g appeared to be more potent against MRSA than ampicillin, while streptomycin did not show any bactericidal activity. All three compounds displayed better activity also against resistant strains P. aeruginosa and E. coli than ampicillin. Furthermore, all compounds were able to inhibit biofilm formation 2-to 4-times more than both reference drugs. Compounds were evaluated also for their antifungal activity against eight species. The evaluation revealed that all compounds exhibited antifungal activity better than the reference drugs bifonazole and ketoconazole. Molecular docking studies on antibacterial and antifungal targets were performed in order to elucidate the mechanism of antibacterial activity of synthesized compounds. Conclusion: All tested compounds showed good antibacterial and antifungal activity better than that of reference drugs and three the most active compounds could consider as lead compounds for the development of new more potent agents.

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confidence: 99%

5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)alkancarboxylic Acids as Antimicrobial Agents: Synthesis, Biological Evaluation, and Molecular Docking Studies

Horishny

Карцев²,

Geronikaki

et al. 2020

Molecules

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“…Compound 94 was identified as the most active substance (38.92% inhibition vs. HT-29 and 35.96% inhibition vs. SJSA1) and has a high survival rate of 92.01% from NIH3T3 cell lines (Table 5). Bataille and coworkers [127] synthesized novel 4-thiazolidinone derivatives and evaluated their anticancer activity for cancer in blood and lymph tissue via inhibition of the PIM kinase family by differential scanning fluorimetry (DSF). The in vitro antiproliferative activity was evaluated in two cancer cell lines (MV4-11 and K562) against selected inhibitors.…”

Section: Scheme 71 Synthesis Of Thiazolidine Derivatives 88a-dmentioning

confidence: 99%

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

Sahiba¹,

Sethiya²,

Soni³

et al. 2020

Top Curr Chem (Z)

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In past decades, interdisciplinary research has been of great interest for scholars. Thiazolidine motifs behave as a bridge between organic synthesis and medicinal chemistry and compel researchers to explore new drug candidates. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. The presence of sulfur enhances their pharmacological properties, and, therefore, they are used as vehicles in the synthesis of valuable organic combinations. They show varied biological properties viz. anticancer, anticonvulsant, antimicrobial, anti-inflammatory, neuroprotective, antioxidant activity and so on. This diversity in the biological response makes it a highly prized moiety. Based on literature studies, various synthetic approaches like multicomponent reaction, click reaction, nano-catalysis and green chemistry have been employed to improve their selectivity, purity, product yield and pharmacokinetic activity. In this review article, we have summarized systematic approaches for the synthesis of thiazolidine and its derivatives, along with their pharmacological activity, including advantages of green synthesis, atom economy, cleaner reaction profile and catalyst recovery which will help scientists to probe and stimulate the study of these scaffolds.

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“…The group of natural heterocyclic sulfur compounds includes not only the six-membered ring cyclic ketimines such as CK, LK, and TK but also the class of five-membered ring heterocycles like terrestrial and marine thiazolidine and thiazoline derivatives such as thioproline, ovothiols, and thiazoline carboxylic acids (e.g., 2-amino-2-thiazoline-4-carboxylic acid (ATCA)) [ 41 , 215 – 218 ] ( Figure 23 ).…”

Section: Biochemical Aspects Of Endogenous Sulfurous Metabolitesmentioning

confidence: 99%

Chemistry and Biochemistry of Sulfur Natural Compounds: Key Intermediates of Metabolism and Redox Biology

Francioso

Conrado

Mosca

et al. 2020

Oxidative Medicine and Cellular Longevity

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Sulfur contributes significantly to nature chemical diversity and thanks to its particular features allows fundamental biological reactions that no other element allows. Sulfur natural compounds are utilized by all living beings and depending on the function are distributed in the different kingdoms. It is no coincidence that marine organisms are one of the most important sources of sulfur natural products since most of the inorganic sulfur is metabolized in ocean environments where this element is abundant. Terrestrial organisms such as plants and microorganisms are also able to incorporate sulfur in organic molecules to produce primary metabolites (e.g., methionine, cysteine) and more complex unique chemical structures with diverse biological roles. Animals are not able to fix inorganic sulfur into biomolecules and are completely dependent on preformed organic sulfurous compounds to satisfy their sulfur needs. However, some higher species such as humans are able to build new sulfur-containing chemical entities starting especially from plants’ organosulfur precursors. Sulfur metabolism in humans is very complicated and plays a central role in redox biochemistry. The chemical properties, the large number of oxidation states, and the versatile reactivity of the oxygen family chalcogens make sulfur ideal for redox biological reactions and electron transfer processes. This review will explore sulfur metabolism related to redox biochemistry and will describe the various classes of sulfur-containing compounds spread all over the natural kingdoms. We will describe the chemistry and the biochemistry of well-known metabolites and also of the unknown and poorly studied sulfur natural products which are still in search for a biological role.

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Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family

Cited by 43 publications

References 64 publications

5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)alkancarboxylic Acids as Antimicrobial Agents: Synthesis, Biological Evaluation, and Molecular Docking Studies

5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)alkancarboxylic Acids as Antimicrobial Agents: Synthesis, Biological Evaluation, and Molecular Docking Studies

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

Chemistry and Biochemistry of Sulfur Natural Compounds: Key Intermediates of Metabolism and Redox Biology

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