An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents

Tsoukala, Evangelia; Agelis, George; Dolinšek, Jan; Botić, Tanja; Cencič, Avrelija; Komiotis, Dimitri

doi:10.1016/j.bmc.2007.02.031

Cited by 25 publications

(14 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The high electronegativity of fluorine atom attached to aromatic ring manipulate the magnitude of activity. 36,37) Besides, the hydrazono derivatives 4 and 5a, b showed more potent cytotoxic activity than doxorubicin with IC 50 range 19-27 nM. The cyclohexanedione derivative 4 and the pyrimidinetrione derivative 5a were almost equipotent, however, incorporation of carbonyl group in the position 2 of pyrimidine scaffold by thioxo function, compound 5b, resulted in decline in cytotoxic activity.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Certain 2-Substituted-1<i>H</i>-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents

Taher

Khalil

Ahmed

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

A series of 2-substituted-1H-benzimidazole derivatives were synthesized and evaluated for antimicrobial, antifungal and cytotoxic activities. The results showed that all tested compounds showed potent antimicrobial activity against some species of Gram-negative bacteria (Pseudomonas aeruginosa, Escherichia coli, Salmonella typhi) and fungi (Candida albicans) with minimum inhibitory concentrations (MICs) lower than 0.016 µg/mL. In contrast, all tested compounds were inactive against Staphylococcus aureus (Gram-positive bacterium). The final targets were also tested for their antitumor activity in vitro on cervical carcinoma (HeLa) cell line. Eight of the test compounds displayed more potent cytotoxic effect than doxorubicin at nanomolar concentrations. Compounds 2c and 3c exerted the strongest cytoyoxic effect with IC 50 15 and 13 nM, respectively.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of Certain 2-Substituted-1<i>H</i>-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents

Taher

Khalil

Ahmed

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…164 In their synthesis, the 3 0 b-fluorine atom was introduced via treatment of the tosylate 252 with KF/acetamide (Scheme 47). The resultant fluoride 253 was subjected to periodate oxidation, borohydride reduction and sulfonylation to afford the intermediate 254 in 84% yield.…”

Section: 0 -Monofluorinated Nucleosidesmentioning

confidence: 99%

Recent advances in the synthesis of fluorinated nucleosides

Qiu¹,

Xu²,

Qing³

2010

Tetrahedron

146

View full text Add to dashboard Cite

“…34 Removal of all O-acetyl protecting groups of 5a-c, with saturated methanolic ammonia, 35 gave 6a-c in excellent yields. Specific acetalation of the aforementioned compounds using 2,2-dimethoxypropane 35 in acetone led to the 2 0 ,3 0 -J-isopropylidene derivatives 7a-c, in yields 72%, 75%, and 68%, respectively.…”

Section: Introductionmentioning

confidence: 98%

Efficient synthesis of exomethylene- and keto-exomethylene-d-glucopyranosyl nucleoside analogs as potential cytotoxic agents

Tzioumaki

Tsoukala

Manta

et al. 2011

Carbohydrate Research

Self Cite

View full text Add to dashboard Cite

A novel series of exomethylene- and keto-exomethylene-d-glucopyranonucleosides with thymine, uracil, and 5-fluorouracil as heterocyclic bases have been designed and synthesized. Wittig condensation of the 3-keto glucoside 1 gave the corresponding 1,2:5,6-di-O-isopropylidene-3-deoxy-3-methylene-d-glucofuranose (2), which after hydrolysis and acetylation led to the precursor 1,2,4,6-tetra-O-acetyl-3-deoxy-3-methylene-d-glucopyranose (4). Compound 4 was condensed with silylated thymine, uracil, and 5-fluorouracil, respectively, deacetylated and acetalated to afford 1-(3'-deoxy-4',6'-O-isopropylidene-3'-methylene-β-d-glucopyranosyl)pyrimidines 7a-c. Oxidation of the free hydroxyl group in the 2'-position of the sugar moiety led to the formation of the labile 1-(3'-deoxy-4',6'-O-isopropylidene-3'-methylene-β-d-glucopyranosyl-2'-ulose)pyrimidines 8a-c. Finally, deisopropylidenation of the resulted derivatives 8a-c afforded the diol nucleosides 9a-c. The target keto-exomethylene analogs 9a-c were more cytostatic against a variety of tumor cell lines than the corresponding saturated-hydroxy-exomethylene derivatives 6. In particular, the 5-fluorouracil derivative 9c was highly cytostatic at an IC(50) (50% inhibitory concentration) ranging between 0.56 and 9.4 microg/mL, which was comparable to the free parental 5-fluorouracil base.

show abstract

An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents

Cited by 25 publications

References 38 publications

Synthesis of Certain 2-Substituted-1<i>H</i>-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents

Synthesis of Certain 2-Substituted-1<i>H</i>-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents

Recent advances in the synthesis of fluorinated nucleosides

Efficient synthesis of exomethylene- and keto-exomethylene-d-glucopyranosyl nucleoside analogs as potential cytotoxic agents

Contact Info

Product

Resources

About