Phosphate Mimics: Cyclic Compounds

Nottbohm, Amanda C.; Hergenrother, Paul J.

doi:10.1002/9780470048672.wecb641

Cited by 7 publications

(6 citation statements)

References 75 publications

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“…For instance, 65 is an efficient inhibitor of MurC (UDP-N-acetylmuramate/L-alanine ligase) [139] and 66 e of MurG [189]. It should be emphasized that the 4-thiazolidinone and rhodanine cores are treated as novel phosphate mimics [190] (Scheme 34).…”

Section: Antimicrobial Agentsmentioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

144

133

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The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

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Section: Antimicrobial Agentsmentioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

144

133

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“…For example, the use of derivatives of the phosphate ester, such as phosphonates and thiophosphonates, has been a widespread tactic to bring untested functionalities into molecules. 2 d ,3…”

Section: Introductionmentioning

confidence: 99%

The phosphate ester group in secondary metabolites

2022

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“…7B ). Previous studies have shown that phosphate groups can be mimicked by neutral scaffolds ( 41 ). For instance, a neutral diphosphate mimic has been demonstrated to inhibit the activity of human O-GlcNAc transferase (OGT), an enzyme that recognizes UDP-GlcNAc harboring a diphosphate group ( 42 ).…”

Section: Resultsmentioning

confidence: 99%