The 2-(2-Azidoethyl)cycloalkanone Strategy for Bridged Amides and Medium-Sized Cyclic Amine Derivatives in the Aubé-Schmidt Reaction

In the presence of a catalytic amount of Fe3O4‐Guanidine acetic acid (GAA) nanoparticles, efficient transamidation of several amides with various amines is described under solvent‐free conditions. Fe3O4‐Guanidine acetic acid nanoparticles provide the first example of a magnetically recoverable organocatalyst for transamidation in the highest catalytic activity. The catalyst could be simply recycled with the assistance of an external magnet and reused for six runs without significant loss of its catalytic activity.

show abstract

Guanidine Acetic Acid Functionalized Magnetic Nanoparticles: Recoverable Green Catalyst for Transamidation

Miraki

Arefi

Yazdani

et al. 2016

ChemistrySelect

View full text Add to dashboard Cite

show abstract

[¹⁸F]Fluoroethyl Triazole Substituted PSMA Inhibitor Exhibiting Rapid Normal Organ Clearance

et al. 2016

View full text Add to dashboard Cite

Prostate-specific membrane antigen (PSMA) is overexpressed in the epithelium of prostate cancer and nonprostate solid tumor neovasculature. PSMA is increasingly utilized as a target for cancer imaging and therapy. Here, we report the synthesis and in vivo biodistribution of a low-molecular-weight PSMA-based imaging agent, 2-[3-(1-carboxy-5-{3-[1-(2-[18F]fluoroethyl)-1H-1,2,3-triazol-yl]propanamido}pentyl)ureido]-pentanedioic acid ([18F]YC-88), containing an [18F]fluoroethyl triazole moiety. [18F]YC-88 was synthesized from 2-[18F]fluoroethyl azide and the corresponding alkyne precursor in two steps using either a one- or two-pot procedure. Biodistribution and positron emission tomography (PET) imaging were performed in immunocompromised mice using isogenic PSMA+ PC3 PIP and PSMA− PC3 flu xenografts. YC-88 exhibited high affinity for PSMA as evidenced by a Ki value of 12.9 nM. The non-decay corrected radiochemical yields of [18F]YC-88 averaged 14 ± 1% (n = 5). Specific radioactivities ranged from 320 to 2,460 Ci/mmol (12–91 GBq/μmol) with an average of 940 Ci/mmol (35 GBq/μmol, n = 5). In an immunocompromised mouse model, [18F]YC-88 clearly delineated PSMA+ PC3 PIP prostate tumor xenografts on imaging with PET. At 1 h postinjection, 47.58 ± 5.19% injected dose per gram of tissue (% ID/g) was evident within the PSMA+ PC3 PIP tumor, with a ratio of 170:1 of uptake within PSMA+ PC3 PIP to PSMA− PC3 flu tumor placed in the opposite flank. The tumor-to-kidney ratio at 2 h postinjection was 4:1. At or after 30 min postinjection, minimal nontarget tissue uptake of [18F]YC-88 was observed. Compared to [18F]DCFPyL, which is currently in clinical trials, the uptake of [18F]YC-88 within the kidney, liver, and spleen was significantly lower at all time-points studied. At 30 min and 1 h postinjection, salivary gland uptake of [18F]YC-88 was significantly less than that of [18F]DCFPyL. [18F]YC-88 is a new PSMA-targeted PET agent synthesized utilizing click chemistry that demonstrates high PSMA+ tumor uptake in a xenograft model. Because of its low uptake in the kidney, rapid clearance from nontarget organs, and relatively simple one-pot, two-step radiosynthesis, [18F]YC-88 is a viable new PET radiotracer for imaging PSMA-expressing lesions.

show abstract

Radiolabeled Selective Matrix Metalloproteinase 13 (MMP-13) Inhibitors: (Radio)Syntheses and in Vitro and First in Vivo Evaluation

et al. 2016

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

The 2-(2-Azidoethyl)cycloalkanone Strategy for Bridged Amides and Medium-Sized Cyclic Amine Derivatives in the Aubé-Schmidt Reaction

Cited by 5 publications

References 7 publications

Guanidine Acetic Acid Functionalized Magnetic Nanoparticles: Recoverable Green Catalyst for Transamidation

Guanidine Acetic Acid Functionalized Magnetic Nanoparticles: Recoverable Green Catalyst for Transamidation

[¹⁸F]Fluoroethyl Triazole Substituted PSMA Inhibitor Exhibiting Rapid Normal Organ Clearance

Radiolabeled Selective Matrix Metalloproteinase 13 (MMP-13) Inhibitors: (Radio)Syntheses and in Vitro and First in Vivo Evaluation

Contact Info

Product

Resources

About

The 2-(2-Azidoethyl)cycloalkanone Strategy for Bridged Amides and Medium-Sized Cyclic Amine Derivatives in the Aubé-Schmidt Reaction

Cited by 5 publications

References 7 publications

Guanidine Acetic Acid Functionalized Magnetic Nanoparticles: Recoverable Green Catalyst for Transamidation

Guanidine Acetic Acid Functionalized Magnetic Nanoparticles: Recoverable Green Catalyst for Transamidation

[18F]Fluoroethyl Triazole Substituted PSMA Inhibitor Exhibiting Rapid Normal Organ Clearance

Radiolabeled Selective Matrix Metalloproteinase 13 (MMP-13) Inhibitors: (Radio)Syntheses and in Vitro and First in Vivo Evaluation

Contact Info

Product

Resources

About

[¹⁸F]Fluoroethyl Triazole Substituted PSMA Inhibitor Exhibiting Rapid Normal Organ Clearance