A fluorous and click approach for screening potential PET probes: Evaluation of potential hypoxia biomarkers

Béjot, Romain; Carroll, Laurence; Bhakoo, Kishore; Declerck, Jérôme; Gouverneur, Véronique

doi:10.1016/j.bmc.2011.10.084

Cited by 29 publications

(24 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Intermediate 11 was obtained as yellow oil in 86% yield, and its chemical structure was confirmed by liquid chromatography‐mass spectrometry (LC‐MS) and infrared (IR) and 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopies. The results of the analyses were compared with the literature data as this intermediate is already described …”

Section: Resultsmentioning

confidence: 99%

New 1,2,3‐triazole‐based analogues of benznidazole for use against Trypanosoma cruzi infection: In vitro and in vivo evaluations

et al. 2018

View full text Add to dashboard Cite

Chagas disease has spread throughout the world mainly because of the migration of infected individuals. In Brazil, only benznidazole (Bnz) is used; however, it is toxic and not active in the chronic phase, and cases of resistance are described. This work aimed at the synthesis and the trypanocidal evaluation in vitro and in vivo of six new Bnz analogues (3-8). They were designed by exploring the bioisosteric substitution between the amide group contained in Bnz and the 1,2,3-triazole ring. All the compounds were synthesized in good yields. With the exception of compound 7, the in vitro biological evaluation shows that all Bnz analogues were active against the amastigote form, whereas only compounds 3, 4, 5, and 8 were active against trypomastigote. Compounds 4 and 5 showed the most promising activities in vitro against the form of trypomastigote, being more active than Bnz. In vivo evaluation of compounds, 3-8 showed lower potency and higher toxicity than Bnz. Although the 1,2,3-triazole ring has been described in the literature as an amide bioisostere, its substitution here has reduced the activity of the compounds and made them more toxic. Thus, further molecular optimization could provide novel therapeutic agents for Chagas' disease.

show abstract

Section: Resultsmentioning

confidence: 99%

New 1,2,3‐triazole‐based analogues of benznidazole for use against Trypanosoma cruzi infection: In vitro and in vivo evaluations

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Reactants or catalyzers are temporarily tagged with F-chains (e.g. using tagging reagents such as C 8 F 17 C 2-H 4 SO 2 Cl) (Bejot et al, 2012), allowing preferential partition in fluorous media (e.g. a fluorocarbon) or on highly fluorinated substrates (Dinh and Gladysz, 2005).…”

Section: Research Toolsmentioning

confidence: 99%

Selected physicochemical aspects of poly- and perfluoroalkylated substances relevant to performance, environment and sustainability—Part one

Krafft

Riess²

2015

Chemosphere

215

119

View full text Add to dashboard Cite

“…Synthesis of N-propargyl substituted heterocycles and development of available and technologically simulated processes for their preparation are among the goals of organic chemistry due to the fact that these compounds are starting materials for producing polyconjugated polymer compounds with semiconductor properties and components used for the synthesis of radio-pharmaceuticals [1].…”

mentioning

confidence: 99%

“…IR spectrum, ν, cm -1 : 2100 (C≡CH), 1500 (ring). 1 3,5-Dimethyl-1-propargylpyrazole (IVd) was prepared similarly from 9.6 g (0.1 mol) of 3,5-dimethylpyrazole IIIc and 21 mL (0.24 mol) of propargyl bromide. Yield 10.5 g (78%), bp 59°C (1 mmHg), n D 20 1.4990.…”

mentioning

confidence: 99%

“…1 Н NMR spectrum (DMSO-d 6 ), δ, ppm (J, Hz): 2.12 s (3H, 3-CH 3 ), 2.29 d (3H, 5-CH 3 , J 0.8), 2.76 t (1H, ≡CH, J 2.6), 4.75 d (2H, NCH 2 , J 2.6), 5.73 q (1H, H 4 , J 0.8). 1 H and 13 C NMR spectra (DMSO-d 6 -CCl 4 , 1 : 3, 300 K) were obtained on a Varian Mercury-300VX spectrometer operating at 300.05 and 75.46 MHz, respectively, internal reference TMS. IR spectra (thin layer) were recorded on a Specord 75 IR instrument.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Alternative reaction medium for the synthesis of 1-propargylpyrazoles

et al. 2015

View full text Add to dashboard Cite

A fluorous and click approach for screening potential PET probes: Evaluation of potential hypoxia biomarkers

Cited by 29 publications

References 26 publications

New 1,2,3‐triazole‐based analogues of benznidazole for use against Trypanosoma cruzi infection: In vitro and in vivo evaluations

New 1,2,3‐triazole‐based analogues of benznidazole for use against Trypanosoma cruzi infection: In vitro and in vivo evaluations

Selected physicochemical aspects of poly- and perfluoroalkylated substances relevant to performance, environment and sustainability—Part one

Alternative reaction medium for the synthesis of 1-propargylpyrazoles

Contact Info

Product

Resources

About