Three-component condensation of iminoazolidines with aldehydes and 5-aminopyrazole

Komogortsev, Andrey N.; Lichitsky, Boris V.; Dudinov, A. A.; Krylov, K. S.; Bogacheva, Anna M.; Кобелева, О. И.; Barachevskii, V. A.; Krayushkin, M. M.

doi:10.1016/j.mencom.2013.07.015

Cited by 10 publications

(6 citation statements)

References 8 publications

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“…The 5-arylidene-4-thiazolidinones in the Michael reaction with 5-aminopyrazole in acetic acid afforded fused heterocyclic systems 252 containing anazolone moiety. The reaction involved the intramolecular cyclization of the appropriate intermediates and oxidative aromatization [497] (Scheme 124).…”

mentioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

147

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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mentioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

147

133

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“…state IR spectroscopy results presented by Valls and coworkers, 17 the compound was assigned as 4-imino-1,3-thiazol-2(5H)-one (tautomeric form B, Scheme 3). It should be noted that the physicochemical and spectroscopic data (IR and 1 H and 13 C NMR) are the same as for 4-amino-1,3-thiazol-2(5H)-one discussed here.…”

Section: Letter Syn Lettmentioning

confidence: 83%

“…The above-mentioned compounds, especially N-3-unsubstituted derivatives have been previously reported as 4-amino-8 or often 4-imino-2thiazolidinones. 7,12,13 Currently, the existence of only amino forms and the absence of possible amino-imino tautomerism have been shown for such compounds (based on an aromatic amines, R=Ar, Scheme 2). 4,11 Hence, the aim of present research was the synthesis of new 5-ene-4-aminothiazol-2(5H)-ones as potential biologically active compounds.…”

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confidence: 99%

One-Pot Synthesis of 5-Ene-4-aminothiazol-2(5H)-ones and Chromeno[2,3-d]thiazol-2-ones

Kaminskyy

Subtel’na

Pyrih

et al. 2017

Synlett

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“…). [35] Cyclization Strategies: Intramolecular cyclization reactions play a pivotal role in the synthesis of imidazolidine derivatives. Cyclization via condensation reactions involving appropriate precursors has proven effective in constructing imidazolidine ring systems.…”

Section: Other Synthesis Approaches Used For Accessing Imidazolidinon...mentioning

confidence: 99%

Imidazolidinones Derivatives As Pioneering Anticancer Agents: Unraveling Insights Through synthesis And Structure‐Activity Exploration

Dewangan,

Rawat,

Singh Thakur

2024

ChemistrySelect

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Imidazolidinone derivatives have emerged as promising anticancer agents, captivating the attention of researchers in medicinal chemistry. Imidazolidinones, characterized by their unique chemical structure, have demonstrated versatility in synthetic methodologies. Researchers have developed a variety of derivatives, each with distinct modifications, allowing for fine‐tuning of pharmacological properties. This review explores the journey of imidazolidinone compounds, from synthesis to structure‐activity exploration, and investigates their anticancer mechanistic pathways. The synthesis methodologies, including diverse approaches and reaction conditions, were examined. Structural modifications are discussed, showing the versatility sof imidazolidinone scaffolds. Mechanistic insights into their anticancer mechanisms, in vitro, ex‐vivo and in vivo activities, with their challenges in development are critically analyzed. This paper concludes by emphasizing the potential of imidazolidinone derivatives and suggesting future research directions in the pursuit of novel and effective anticancer therapeutics.

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Three-component condensation of iminoazolidines with aldehydes and 5-aminopyrazole

Cited by 10 publications

References 8 publications

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

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

One-Pot Synthesis of 5-Ene-4-aminothiazol-2(5H)-ones and Chromeno[2,3-d]thiazol-2-ones

Imidazolidinones Derivatives As Pioneering Anticancer Agents: Unraveling Insights Through synthesis And Structure‐Activity Exploration

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