Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent

Lashmanova, E. A.; Kirdyashkina, Anastasiya I.; Слепухин, П. А.; Shiryaev, A. K.

doi:10.1016/j.tetlet.2018.02.014

Cited by 12 publications

(6 citation statements)

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“…Other possible applications include their use as antimalarials and inhibitors of HIV reverse transcriptase [9,26], as well as antagonists of the 5-HT2 serotonin receptor, with potential interest for the treatment of depression [27,28]. Other non-therapeutic uses for thiazolo[3,2- a ]pyrimidines include inhibition of mild steel corrosion [29], and dimeric thiazolo[3,2- a ]pyrimidinones have been proposed for the development of pigments, sensitizers in solar cells, and molecular switches [30]. As part of a program aiming to obtain new potent AD modifying agents, we report herein a new small series of AChE inhibitors based on a fused thiazolopyrimidine core.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, and Biological Evaluation of Fused Thiazolo[3,2-a]Pyrimidines as New Acetylcholinesterase Inhibitors

et al. 2019

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A new series of thiazolo[3,2-a]pyrimidine bromide salt derivatives 7a–d were synthesized from 3,4-dihydropyrimidinethione precursors. The target compounds were fully characterized by 1D- and 2D-NMR, high resolution ESI-MS/MS and single crystal X-ray diffraction analysis, which confirmed a regioselective 5H cyclization of the dihydropyrimidinethiones. All target compounds were evaluated in vitro as human acetylcholinesterase (hAChE) inhibitors via an Ellman-based colorimetric assay and showed good inhibition activities (better than 70% at 10 µM and IC50 values in the 1 µM range). Molecular docking simulations for all target products into hAChE were performed and confirmed strong binding to the enzyme. These results provide a promising and new starting point to improve acetylcholinesterase inhibitors and explore novel treatment options against Alzheimer’s disease.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, and Biological Evaluation of Fused Thiazolo[3,2-a]Pyrimidines as New Acetylcholinesterase Inhibitors

et al. 2019

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“…All arylmethylidenethiazolopyrimidines 7-15 were synthesized following the scheme presented on Figure 2. In the first stage, a three-component Biginelli condensation involving appropriate aldehyde (benzaldehyde, 2-methoxybenzaldehyde, 4-methoxybenzaldehyde, 3-nitrobenzaldehyde, or 4-brombenzaldehyde), thiourea, and 1,3-dicarbonyl compound (acetoacetic ether or benzoylacetone) in a molar ratio 1:1.5:1 led to the preparation of 1,2,3,4-tetrahydropyrimidine-2-thions in the presence of a catalytic amount of molecular iodine (0.03 mmol) under refluxing conditions in acetonitrile as described earlier [18][19][20][21][22]. Then the obtained compounds were used as precursors for the synthesis of targeted 2-and 4-hydroxybenzylidene thiazolo[3,2-a]pyrimidine 7-15 by reaction with corresponding 2-or 4-hydroxybenzaldehydes.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-a]pyrimidines

et al. 2022

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A series of new thiazolo[3,2-a]pyrimidines different by aryl substituents in 2 and 5 positions are synthesized and characterized in solution as well as in the crystalline phase using 1H and 13C NMR-, IR-spectroscopies, mass-spectrometry methods, and single crystal X-ray diffraction (SCXRD). The SCXRD study revealed the role of intermolecular H-bonding in the formation of supramolecular architectures (racemic monomers, centrosymmetric racematic dimers, or homochiral 1D chains) of obtained thiazolo[3,2-a]pyrimidines derivatives depending on solvents (aprotic DMSO or protic EtOH) used upon the crystallization process. Moreover, the in vitro study of cytotoxicity toward different tumor cells showed their high or moderate efficiency with moderate cytotoxicity against normal liver cells which allows to consider the obtained thiazolo[3,2-a]pyrimidine derivatives as promising candidates for application as antitumor agents.

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“…Shiryaev's group reported a very interesting protocol of oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-one 116 with DMSO and LR at room temperature to provide 2,2 / -dimer 117. [65] They proposed DMSO reacted with the active monomer 2 to generate reactive species 118 which initiated the reaction via capturing the acidic proton of 116. Then nucleophilic substitution at the sulfur atom provided the formation of 119 which further interacted with 118 to explore the dimer 117 (Scheme 34).…”

Section: Dimerization Of Certain Motifsmentioning

confidence: 99%

“…Shiryaev's group reported a very interesting protocol of oxidation of thiazolo[3,2‐ a ]pyrimidin‐3(2 H )‐one 116 with DMSO and LR at room temperature to provide 2,2 / ‐dimer 117 . They proposed DMSO reacted with the active monomer 2 to generate reactive species 118 which initiated the reaction via capturing the acidic proton of 116 .…”

Section: Dimerization Of Certain Motifsmentioning

confidence: 99%

Diversity of Lawesson's Reagent: Advances and Scope

Gayen

Chatterjee

2020

Asian J Org Chem

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Lawesson's reagent is a classic example of a compound having a remarkable construction and also a distinctive chemical behaviour that can challenge stereotype conceptual explanations. At the very beginning, it was mainly known for its use in the thionation of various types of carbonyl groups. However, over the last few years chemists reported some appealing examples which can nurture the chemistry community to perceive innovative ideas. These include the construction of valuable heterocycles, important coupling reactions, and the decoration of metal‐based attractive cores. Several important reports provided comprehensive theoretical studies regarding mechanistic classification. This article gives an overview of the recent insights and synthetic applications of this famous reagent from 2013 to 2019.

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Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent

Cited by 12 publications

References 42 publications

Synthesis, Crystal Structure, and Biological Evaluation of Fused Thiazolo[3,2-a]Pyrimidines as New Acetylcholinesterase Inhibitors

Synthesis, Crystal Structure, and Biological Evaluation of Fused Thiazolo[3,2-a]Pyrimidines as New Acetylcholinesterase Inhibitors

Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-a]pyrimidines

Diversity of Lawesson's Reagent: Advances and Scope

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