Synthesis and antitumour activity of new tiazofurin analogues bearing a 2,3-anhydro functionality in the furanose ring

Popsavin, Mirjana; Spaić, Saša; Svirčev, Miloš; Kojić, Vesna; Bogdanovic, Gordana; Popsavin, Velimir

doi:10.1016/j.bmcl.2007.05.050

Cited by 35 publications

(12 citation statements)

References 31 publications

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“…[1] Tiazofurin (2-(β-d-ribofuranosyl)thiazole) is a well-known synthetic C-nucleoside with interesting anticancer activity in a variety of tumor systems ( Figure 1). [2] The Tiazofurin biological activity is rendered to its potential to inhibit inosine monophosphate dehydrogenase which will lead to shutdown of guanine nucleotide synthesis. [3] In spite of the known efficacy of Tiazofurin, its high toxicity and lack of specificity represent a problem for its clinical use.…”

Section: Introductionmentioning

confidence: 99%

Thiazoles in glycosylation reactions: Novel synthesis of thiazole thioglycosides

Abu-Zaied

Elgemeie

2017

Heteroatom Chemistry

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Section: Introductionmentioning

confidence: 99%

Thiazoles in glycosylation reactions: Novel synthesis of thiazole thioglycosides

Abu-Zaied

Elgemeie

2017

Heteroatom Chemistry

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“…5) exhibited the most significant cytotoxicity against K562 cells, being approximately 100-fold more potent than tiazofurin. Popsavin et al (2007) reported the synthesis of 2-(2,3-anhydrofuranosyl) thiazole-4-carboxamide (2 0 ,3 0 -anhydro tiazofurin) derivatives and screened them for their antitumor activity against K562 malignant cells. The compound ( Fig.…”

Section: Biological Activitiesmentioning

confidence: 99%

Thiazoles: having diverse biological activities

Kashyap¹,

Garg²,

Sharma³

et al. 2011

Med Chem Res

218

114

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In the last few decades, a lot of work has been done on thiazole ring to find new compounds related to this scaffold to act as antioxidant, analgesic, anti-inflammatory, antimicrobial, antifungal, antiviral, diuretic, anticonvulsant, neuroprotective, and antitumor or cytotoxic drug molecules with lesser side effects. This review presents the up to date development on the design and development of different thiazole derivatives.

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“…[ 18–20 ] Heterocyclic compounds incorporating the thiazole moiety show fascinating antitumor and cytotoxic activities. [ 21,22 ] Moreover, it has been reported that the presence of thioether moiety in the tested derivatives increases their bioactivities such as in‐vitro antimicrobial activity. [ 23–25 ]…”

Section: Introductionmentioning

confidence: 99%

“…[18][19][20] Heterocyclic compounds incorporating the thiazole moiety show fascinating antitumor and cytotoxic activities. [21,22] Moreover, it has been reported that the presence of thioether moiety in the tested derivatives increases their bioactivities such as in-vitro antimicrobial activity. [23][24][25] In connection with the fascinating bioactivities of thiazoles and our efforts regarding the preparation and characterization of heterocyclic derivatives incorporating the sulfur atom, [26][27][28][29][30][31][32] the work in this study was aimed to design a facile protocol for the synthesis of hybrid arylazo-4-methylthiazoles and thiazol-4(5H)ones, bearing thioether moieties, as potent antibacterial agents against both Gram-positive and -negative bacterial strains.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in‐vitro and in‐silico study of novel thiazoles as potent antibacterial agents and MurB inhibitors

Sanad

Ahmed

Mekky

2020

Archiv der Pharmazie

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Efficient procedures are herein reported for the synthesis of novel hybrid thiazoles via a one‐pot three‐component protocol. The protocol involves the reaction of novel aldehyde, thiosemicarbazide and halogen‐containing reagents in solvent‐ and catalyst‐free conditions. The structures of the new thiazoles were elucidated by elemental analyses and spectroscopic data. The in‐vitro antibacterial screening and MurB enzyme inhibition assays were performed for the novel thiazoles. The thiazol‐4(5H)‐one derivative 6d, with p‐MeO, exhibits the best antibacterial activities with minimum inhibitory concentration values of 3.9, 3.9, 7.8, and 15.6 μg/ml against Staphylococcus aureus, Klebsiella pneumoniae, Streptococcus mutans, and Escherichia coli, respectively, as compared to the reference antibiotic drugs. It also exhibits the highest inhibition of the MurB enzyme with an IC50 of 8.1 μM. The structure–activity relationship was studied to determine the effect of the structures of the newly prepared molecules on the strength of the antibacterial activities. Molecular docking was also performed to predict the binding modes of the new thiazoles in the active sites of the E. coli MurB enzyme.

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Synthesis and antitumour activity of new tiazofurin analogues bearing a 2,3-anhydro functionality in the furanose ring

Cited by 35 publications

References 31 publications

Thiazoles in glycosylation reactions: Novel synthesis of thiazole thioglycosides

Thiazoles in glycosylation reactions: Novel synthesis of thiazole thioglycosides

Thiazoles: having diverse biological activities

Synthesis, in‐vitro and in‐silico study of novel thiazoles as potent antibacterial agents and MurB inhibitors

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