Thiazoles in glycosylation reactions: Novel synthesis of thiazole thioglycosides

Abu-Zaied, Mamdouh A.; Elgemeie, Galal H.

doi:10.1002/hc.21404

Cited by 13 publications

(9 citation statements)

References 16 publications

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“…The 1 H NMR spectrum revealed an imine group (D 2 O exchangeable) and two different methyl protons, demonstrating that the methyl group at C-5 did not participate in the cyclization. A similar intramolecular cyclization reaction of this type was reported by us 40. In another experiment, compound 4 reacted with α-acetobromoxylose 5a and α-acetobromoarabinose 5b in acetone at room temperature to give the corresponding S-xyloside 7a or S-arabinoside 7b, respectively.…”

Section: Resultssupporting

confidence: 74%

<p>Novel purine thioglycoside analogs: synthesis, nanoformulation and biological evaluation in in vitro human liver and breast cancer models</p>

Abu-Zaied

Loutfy

Hassan

et al. 2019

DDDT

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Background: A series of novel pyrazolopyrimidine and pyrazololpyridine thioglycosides were synthesized and conﬁrmed via their spectral analyses. Purpose: To evaluate the effect of these anti-metabolic compounds against proliferation of Huh-7 and Mcf-7 as in vitro models of human liver and breast cancers, respectively. Vero cells were used as an example of normal green monkey kidney cells. Methods: The most promising compound was subjected to a nanoformulation by its encapsulation into chitosan nanoparticles to increase its anti-cancerous activity. Nanoformulation was confirmed by TEM and FT-IR to ensure encapsulation and screened for their cytotoxicity against Huh-7 and Mcf-7 cells using MTT colorimetric assay and morphological examination. Genotoxic effect was performed by cellular DNA fragmentation assay. Simulated CompuSyn software (linear interaction effect) was conducted to predict the possible synergistic effect of nanocomposite as anticancerous activity. Apoptotic effect was further analyzed by detection of apoptotic proteins using ELISA assay. Results: The nano preparation was successfully prepared by encapsulation of compound 14 into chitosan nanoparticles, controlled to a size at 105 nm and zeta charges at 40.2 mV. Treatment of Huh-7 and Mcf-7 showed that compound 14 was the most cytotoxic compound on both cancer cell lines where IC 50 was 24.59 (9.836 μg/mL) and 12.203 (4.8812 μg/mL) on Huh-7 and Mcf-7 respectively. But IC 50 of the nano preparation was 37.19 and 30.68 μg/mL on Huh-7 and Mcf-7, respectively, indicating its aggressiveness on human breast cancer cells as confirmed by DNA fragmentation assay and theoretically by CompuSyn tool. Conclusion: A novel series of pyrazolopyrimidine thioglycosides and pyrazolopyridine thioglycosides were synthesized. Nanoformulation of compound 14 into chitosan nanoparticles demonstrated anticancer activity and can be used as a drug delivery system, but further studies are still required.

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Section: Resultssupporting

confidence: 74%

<p>Novel purine thioglycoside analogs: synthesis, nanoformulation and biological evaluation in in vitro human liver and breast cancer models</p>

Abu-Zaied

Loutfy

Hassan

et al. 2019

DDDT

Self Cite

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“…[58] Abu-Zaied et al synthesized thiazole 131 by condensation of cyanamide 126 and carbon disulfide in a solution of ethanol and potassium hydroxide to give compound 127, which reacts easily with phenacyl bromide and ethyl bromoacetate to produce potassium 4-amino-5-substituted-thiazole-2-thiolates derivatives 128. [59] Adding acid on 128 gives 3-mercaptothiazole derivatives 129 while adding tetra-Oacetyl-a-D-glucopyranosyl bromide and tetra-O-acetyl-a-D-galactopyranosyl bromide 130 in DMF gives thiazole S-glycosides 131 in a good yield (Scheme 34). [59] Farag et al used the potassium salts method to prepare thiazole compound 136.…”

Section: Scheme 25 Synthesis Of Thiazole Derivatives 88mentioning

confidence: 99%

“…[59] Adding acid on 128 gives 3-mercaptothiazole derivatives 129 while adding tetra-Oacetyl-a-D-glucopyranosyl bromide and tetra-O-acetyl-a-D-galactopyranosyl bromide 130 in DMF gives thiazole S-glycosides 131 in a good yield (Scheme 34). [59] Farag et al used the potassium salts method to prepare thiazole compound 136. The initial materials were 3-oxo-N-(pyridin-2-yl)butanamide 132 and phenyl isothiocyanate, which reacted with KOH in DMF to give the corresponding salt 133.…”

Section: Scheme 25 Synthesis Of Thiazole Derivatives 88mentioning

confidence: 99%

Review of the synthesis and biological activity of thiazoles

Ali

Sayed

2020

Synthetic Communications

113

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“…Zaied and Elgemeie reported a method for synthesizing thiazole thioglycosides ( 254 ). Potassium 4‐amino‐5‐substituted‐thiazole‐2‐thiolates ( 250 a and b) were initially prepared in good yield by the reaction of potassium cyanocarbonimidodithioate ( 242 ) with benzoyl acetonitrile and ethyl bromoacetate ( 249 ) in the presence of ethanol in potassium hydroxide.…”

Section: Synthesis Of Thiazolesmentioning

confidence: 99%

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

et al. 2020

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Thiazole frame work represents a vital pharmacophore in several areas of chemistry. Consequently, several synthetic protocols to construct and functionalize this core, in an attempt to generate diverse thiazole containing architectures have been developed by various researchers across the globe. These wide range of methodologies developed will allow the access to fully decorated thiazole containing new chemical entities that can find various application in the field of medicinal chemistry, agrochemicals and material science. This review will provide an insight in to the various synthons used in construction and diversification of this core. Diversely functionalized thiazole analogs are considered as a vital azole framework present in many natural products. This prominent heterocycle also constitutes an important pharmacophore in medicinal chemistry, in agrochemicals and in molecules for material science applications. All these above‐mentioned features of thiazole necessitates the continuous development of efficient methods to access this heterocycle. Accordingly, various researchers across the globe have come up with efficient synthetic protocols in an attempt functionalize different positions of this important scaffold. This review aims at highlighting some of the latest synthetic approaches to di/tri‐substituted thiazole analogs which are known to possess a wide spectrum of biological activities.

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Thiazoles in glycosylation reactions: Novel synthesis of thiazole thioglycosides

Abstract: This research reports a novel method for synthesizing new thiazole thioglycosides.This series of thiazole thioglycosides were designed by the reaction of potassium

Cited by 13 publications

References 16 publications

<p>Novel purine thioglycoside analogs: synthesis, nanoformulation and biological evaluation in in vitro human liver and breast cancer models</p>

<p>Novel purine thioglycoside analogs: synthesis, nanoformulation and biological evaluation in in vitro human liver and breast cancer models</p>

Review of the synthesis and biological activity of thiazoles

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

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