Synthesis and Antioxidant Activity Evaluation of Novel 5,7-dimethyl-3<i>H</i>-Thiazolo[4,5-B]Pyridines

Чабан, Т. І.; Ogurtsov, V. V.; Chaban, I. G.; Klenina, Olena; Komarytsia, Josef D.

doi:10.1080/10426507.2013.777723

Cited by 23 publications

(23 citation statements)

References 18 publications

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“…Moreover, the methylene group in 4-thiazolidinone can be coupled with the aryl-diazonium salt in EtOH/NaOH to form the corresponding arylhydrazone (10) [3,74] (Scheme 6). Similar to 5arylidene-4-thiazolidinones, in all cases only Z-isomers were formed (confirmed by X-ray data) [75].…”

Section: Modification Of the C5 Position Of The Thiazolidinone Corementioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

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: Modification Of the C5 Position Of The Thiazolidinone Corementioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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“…In addition, the 13 C-NMR spectrum showed four signals at δ 23.4, 23.7, 23.9, and 24.5 ppm equivalent to the four CH 2 groups, two signals at δ 38.7 and 59.5 ppm for the CH and C-4 pyran, a signal at δ 116. 8 The MCR of compound 1 with either of malononitrile or ethyl cyanoacetate and salicylaldehyde in 1,4-dioxane containing ammonium acetate gave the pyridine derivatives 6a,b, respectively. Structures of compounds 6a and 6b were proved by their respective analytical and spectral data.…”

Section: Chemistrymentioning

confidence: 99%

“…For thiazolo[4,5‐ b ]pyridines derivatives were also shown to possess strong inhibitory actions for Ab42 fibrillization at the micromolar level for Alzheimer disease treatment . The significant antiexudative, antimicrobial, and antioxidant effects of some thiazolo[4,5‐ b ]pyridine derivatives had been also reported . Some of their analogues were known as H3 receptor antagonists or act as antagonists of metabotropic glutamate receptors 5 (mGluR5) while others were showed as potent inhibitors with respect to the receptors of the epidermal growth factor .…”

Section: Introductionmentioning

confidence: 99%

“…[4] The significant antiexudative, antimicrobial, and antioxidant effects of some thiazolo [4,5-b]pyridine derivatives had been also reported. [5][6][7][8][9][10][11] Some of their analogues were known as H3 receptor antagonists [12,13] or act as antagonists of metabotropic glutamate receptors 5 (mGluR5) [14] while others were showed as potent inhibitors with respect to the receptors of the epidermal growth factor. [15] Some of them are able to activate the GK enzyme in vitro and significantly reduce glucose level.…”

Section: Introductionmentioning

confidence: 99%

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Novel Pyrano[2,3‐d]thiazole and Thiazolo[4,5‐b]pyridine Derivatives: One‐pot Three‐component Synthesis and Biological Evaluation as Anticancer Agents, c‐Met, and Pim‐1 Kinase Inhibitors

Abdallah

Mohareb

Abdelazeem

2019

Journal of Heterocyclic Chem

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Preparation of pyrano[2,3‐d]thiazole and thiazolo[4,5‐b]pyridine derivatives through multicomponent reactions (MCRs) was achieved by the reaction of 2‐(2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophen‐3‐yl)thiazol‐4(5H)‐one with various active methylene reagents such as ethyl cyanoacetate or malononitrile in basic conditions containing diverse aromatic aldehyde. Furthermore, this study aims to evaluate the in vitro cytotoxic activity of the synthetic compounds against six cancer cell lines, and all the prepared compounds revealed valuable activity compared with the CHS‐828, which is the 2‐[6‐(4‐chlorophenoxy)hexyl]‐1‐cyano‐3‐pyridin‐4‐ylguanidine as the standard drug. Some of the pyrano[2,3‐d]thiazole and thiazolo[4,5‐b]pyridine derivatives showed the highest antitumor activity towards the six cancer cell lines. Moreover, (c‐Met) enzymatic activity of the most potent compounds showed that compounds 3b 2‐(2‐amino‐4,5,6,7 tetrahydrobenzo[b]thiophen‐3‐yl)‐5‐hydroxy‐7‐(2‐hydroxy‐phenyl)‐7H‐pyrano[2,3‐d]thiazole‐6 carbonitrile and 5e 2‐(2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophen‐3‐yl)‐5‐hydroxy‐7‐phenyl‐4,7‐dihydrothiazolo[4,5‐b]pyridine‐6‐carbonitrile were with higher activities than foretinib. Three compounds were selected to examine their Pim‐1 kinase where compounds 3b and 7b showed the highest inhibitions.

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“…The interaction of the substance mentioned above with some β-carbonyl compounds leads to formation of the hard-to-get 3H-thiazolo [4,5-b]pyridines with the yield of 79-100% [7][8][9][10] (Scheme 3).…”

Section: Issn 2308-8303mentioning

confidence: 99%