Thiazole and Oxazole Alkaloids: Isolation and Synthesis

Davyt, Danilo; Serra, Gloria

doi:10.3390/md8112755

Cited by 168 publications

(75 citation statements)

References 89 publications

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“…Oxazole and its natural product-related derivatives, especially those from marine environments (Davyt and Serra 2010), have been shown to possess significant biological activities, including anti-tumor, anti-bacterial, anti-viral, antimalaria, and anthelmintic activities (Jin 2011). Furthermore, several oxazole-based pharmaceutical agents, such as virginiamycin (Wu and Panek 2010) and linezolid (Barbachyn and Ford 2003), are currently in clinical trials for the prevention and treatment of infectious diseases.…”

Section: Electronic Supplementary Materialsmentioning

confidence: 99%

Inhibition of Streptococcus mutans biofilm formation, extracellular polysaccharide production, and virulence by an oxazole derivative

Chen

Ren

Zhou

et al. 2015

Appl Microbiol Biotechnol

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Dental caries, a biofilm-related oral disease, is a result of disruption of the microbial ecological balance in the oral environment. Streptococcus mutans, which is one of the primary cariogenic bacteria, produces glucosyltransferases (Gtfs) that synthesize extracellular polysaccharides (EPSs). The EPSs, especially water-insoluble glucans, contribute to the formation of dental plaque, biofilm stability, and structural integrity, by allowing bacteria to adhere to tooth surfaces and supplying the bacteria with protection against noxious stimuli and other environmental attacks. The identification of novel alternatives that selectively inhibit cariogenic organisms without suppressing oral microbial residents is required. The goal of the current study is to investigate the influence of an oxazole derivative on S. mutans biofilm formation and the development of dental caries in rats, given that oxazole and its derivatives often exhibit extensive and pharmacologically important biological activities. Our data shows that one particular oxazole derivative, named 5H6, inhibited the formation of S. mutans biofilms and prevented synthesis of extracellular polysaccharides by antagonizing Gtfs in vitro, without affecting the growth of the bacteria. In addition, topical applications with the inhibitor resulted in diminished incidence and severity of both smooth and sulcal surface caries in vivo with a lower percentage of S. mutans in the animals' dental plaque compared to the control group (P<0.05). Our results showed that this oxazole derivative has the capacity to inhibit biofilm formation and cariogenicity of S. mutans.

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Section: Electronic Supplementary Materialsmentioning

confidence: 99%

Inhibition of Streptococcus mutans biofilm formation, extracellular polysaccharide production, and virulence by an oxazole derivative

Chen

Ren

Zhou

et al. 2015

Appl Microbiol Biotechnol

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“…They are present in some of the natural resources and found to possess moderate to good pharmacological value [1]. Many researchers have made considerable progress on the synthesis of novel Thiazole derivatives and reported their important medicinal properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bio-Evaluation of Novel N-(4-(8-Methoxy-2-Oxo-2<i>H</i>-Chromen-3-Yl) Thiazol-2-Yl) Amide Derivatives

Shah

Patel²,

Rajani³

et al. 2016

ILCPA

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Abstract. In present work novel derivatives of substituted N-(4-(8-methoxy-2-oxo-2H-chromen-3-yl) thiazol-2-yl) amide have been synthesized. The solvent free reaction of 2-Hydroxy-3-methoxybenzaldehyde with Ethyl acetoacetate in presence of Piperidine catalyst produces 3-acetyl-8-methoxy-2H-chromen-2-one (C). Compound C was α-brominated using CuBr 2 and subsequently cyclized using Thiourea to produce 3-(2-aminothiazol-4-yl)-8-methoxy-2H-chromen-2-one as main scaffold (E). This scaffold E was finally reacted with different Acid chloride to isolate title compound derivatives. The chemical structures of synthesized compounds were confirmed by 1 H-NMR, FT-IR and Mass spectral/LCMS analysis. The synthesized compounds were screened for potential Antimicrobial, Antifungal and Antimalerial activity.

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“…Since their isolation from marine products in the late 1980s, oxazole-containing peptidomimetics have been studied extensively by synthetic organic and medicinal chemists [1][2][3][4][5]. It is believed that many of these natural products are derived from enzymatic post-translational modifications of peptide-based precursors containing serine or threonine moieties [2].…”

Section: Introductionmentioning

confidence: 99%

A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles

Slobodyanyuk

Artamonov

Kulik

et al. 2018

Heterocyclic Communications

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A convenient four-step approach to the synthesis of (S)-4-alkyl-2-(pyrrolidin-2-yl)oxazoles starting from l-Boc-proline inspired by naturally occurring oxazolecontaining peptidomimetics is described. The key step is the cyclization of 1-Boc-N-(1-oxoalkan-2-yl)pyrrolidine-2-carboxamides -aldehyde intermediates which demonstrate low to moderate stability -under Appel reaction conditions. This method furnishes the target compounds with more than 98% ee and in a 17-51% overall yield and has been used at up to a 45-g scale.

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Thiazole and Oxazole Alkaloids: Isolation and Synthesis

Cited by 168 publications

References 89 publications

Inhibition of Streptococcus mutans biofilm formation, extracellular polysaccharide production, and virulence by an oxazole derivative

Inhibition of Streptococcus mutans biofilm formation, extracellular polysaccharide production, and virulence by an oxazole derivative

Synthesis and Bio-Evaluation of Novel N-(4-(8-Methoxy-2-Oxo-2<i>H</i>-Chromen-3-Yl) Thiazol-2-Yl) Amide Derivatives

A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles

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