Sulfur [18F]Fluoride Exchange Click Chemistry Enabled Ultrafast Late-Stage Radiosynthesis

2021 ◽  
Author(s):  
Qinheng Zheng ◽  
Hongtao Xu ◽  
Hua Wang ◽  
Wen-Ge Han Du ◽  
Nan Wang ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Late Stage ◽  
18F Fluoride

scholarly journals Novel late-stage radiosynthesis of 5-[18F]-trifluoromethyl-1,2,4-oxadiazole (TFMO) containing molecules for PET imaging

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Nashaat Turkman ◽  
Daxing Liu ◽  
Isabella Pirola
Keyword(s):  
Late Stage ◽  
Histone Deacetylases ◽  
Radiochemical Purity ◽  
Radiochemical Yield ◽  
Single Step ◽  
The Novel ◽  
Molar Activity ◽  
The Central Nervous System ◽  
Class Iia Hdacs ◽  
18F Fluoride

AbstractSmall molecules that contain the (TFMO) moiety were reported to specifically inhibit the class-IIa histone deacetylases (HDACs), an important target in cancer and the disorders of the central nervous system (CNS). However, radiolabeling methods to incorporate the [18F]fluoride into the TFMO moiety are lacking. Herein, we report a novel late-stage incorporation of [18F]fluoride into the TFMO moiety in a single radiochemical step. In this approach the bromodifluoromethyl-1,2,4-oxadiazole was converted into [18F]TFMO via no-carrier-added bromine-[18F]fluoride exchange in a single step, thus producing the PET tracers with acceptable radiochemical yield (3–5%), high radiochemical purity (> 98%) and moderate molar activity of 0.33–0.49 GBq/umol (8.9–13.4 mCi/umol). We validated the utility of the novel radiochemical design by the radiosynthesis of [18F]TMP195, which is a known TFMO containing potent inhibitor of class-IIa HDACs.

scholarly journals A Model for Late-Stage Modification of Polyurethane Dendrimers Using Thiol-Ene Click Chemistry

2021 ◽  
Author(s):  
Dhruba Poudel ◽  
Richard Taylor
Keyword(s):  
Click Chemistry ◽  
Late Stage ◽  
Click Reaction ◽  
Synthetic Approach ◽  
Protecting Group ◽  
One Pot ◽  
The Core ◽  
Curtius Reaction

Protecting group free, one-pot multicomponent Curtius reaction was utilized to afford diurethane G-1 dendron. In our synthetic approach, G-1 dendron can undergo late-stage modification using thiol-ene click reaction, which was then attached to the core to furnish a dendrimer. In another approach, the G-1 dendron was attached to the core and so formed dendrimer was surface functionalized using thiol-ene click chemistry. Either way, we can synthesize the dendrimer.

scholarly journals SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization

2018 ◽  
Vol 140 (8) ◽  
pp. 2919-2925 ◽  
Author(s):  
Zilei Liu ◽  
Jie Li ◽  
Suhua Li ◽  
Gencheng Li ◽  
K. Barry Sharpless ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Late Stage

CuI NPs Facilitated Click Chemistry for the Late-Stage Diversification of Bioactive Complex Small Molecules

2019 ◽  
Author(s):  
rahul upadhyay ◽  
Rahul Kumar ◽  
Rohit Rana ◽  
Onkar S. Nayal ◽  
Sushil K. Maurya
Keyword(s):  
Small Molecules ◽  
Click Chemistry ◽  
Late Stage

Late Stage Benzylic C–H Fluorination with [18F]Fluoride for PET Imaging

2014 ◽  
Vol 136 (19) ◽  
pp. 6842-6845 ◽  
Author(s):  
Xiongyi Huang ◽  
Wei Liu ◽  
Hong Ren ◽  
Ramesh Neelamegam ◽  
Jacob M. Hooker ◽  
...  
Keyword(s):  
Pet Imaging ◽  
Late Stage ◽  
18F Fluoride

scholarly journals A Model for Late-Stage Modification of Polyurethane Dendrimers Using Thiol-Ene Click Chemistry

2021 ◽  
Author(s):  
Dhruba Poudel ◽  
Richard Taylor
Keyword(s):  
Click Chemistry ◽  
Late Stage ◽  
Click Reaction ◽  
Synthetic Approach ◽  
Protecting Group ◽  
One Pot ◽  
The Core ◽  
Curtius Reaction

Protecting group free, one-pot multicomponent Curtius reaction was utilized to afford diurethane G-1 dendron. In our synthetic approach, G-1 dendron can undergo late-stage modification using thiol-ene click reaction, which was then attached to the core to furnish a dendrimer. In another approach, the G-1 dendron was attached to the core and so formed dendrimer was surface functionalized using thiol-ene click chemistry. Either way, we can synthesize the dendrimer.

scholarly journals A kit-based aluminium-[18F]fluoride approach to radiolabelled microbubbles

2021 ◽  
Author(s):  
Jin Teh ◽  
Marta Costa-Braga ◽  
Louis Allott ◽  
Chris Barnes ◽  
Javier Hernandez-Gil ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Radiochemical Yield ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Electron Demand ◽  
18F Fluoride

The production of 18F-labelled microbubbles (MBs) via the aluminium-[18F]fluoride ([18F]AlF) radiolabelling method and facile inverse-electron-demand Diels-Alder (IEDDA) ‘click’ chemistry is reported. An [18F]AlF-NODA-labelled tetrazine was synthesised in excellent radiochemical yield...

scholarly journals Synthesis and Diels–Alder Reactivity of 4-Fluoro-4-Methyl-4H-Pyrazoles

2020 ◽  
Vol 21 (11) ◽  
pp. 3964
Author(s):  
Nile S. Abularrage ◽  
Brian J. Levandowski ◽  
Ronald T. Raines
Keyword(s):  
Transition State ◽  
Click Chemistry ◽  
Ground State ◽  
Late Stage ◽  
Diels Alder ◽  
Ground State Structure ◽  
Large Decrease ◽  
State Structure ◽  
Large Loss

4H-Pyrazoles are emerging scaffolds for “click” chemistry. Late-stage fluorination with Selectfluor® is found to provide a reliable route to 4-fluoro-4-methyl-4H-pyrazoles. 4-Fluoro-4-methyl-3,5-diphenyl-4H-pyrazole (MFP) manifested 7-fold lower Diels–Alder reactivity than did 4,4-difluoro-3,5-diphenyl-4H-pyrazole (DFP), but higher stability in the presence of biological nucleophiles. Calculations indicate that a large decrease in the hyperconjugative antiaromaticity in MFP relative to DFP does not lead to a large loss in Diels–Alder reactivity because the ground-state structure of MFP avoids hyperconjugative antiaromaticity by distorting into an envelope-like conformation like that in the Diels–Alder transition state. This predistortion enhances the reactivity of MFP and offsets the decrease in reactivity from the diminished hyperconjugative antiaromaticity.

scholarly journals Development of Customized [18F]Fluoride Elution Techniques for the Enhancement of Copper-Mediated Late-Stage Radiofluorination

2017 ◽  
Vol 7 (1) ◽  
Author(s):  
Andrew V. Mossine ◽  
Allen F. Brooks ◽  
Naoko Ichiishi ◽  
Katarina J. Makaravage ◽  
Melanie S. Sanford ◽  
...  
Keyword(s):  
Late Stage ◽  
18F Fluoride
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