Journal article
Cu-Free 1,3-Dipolar Cycloaddition Click Reactions To Form Isoxazole Linkers in Chelating Ligands for fac-[MI(CO)3]+ Centers (M = Re, 99mTc)
Inorganic chemistry, Vol.53(4), pp.1943-1945
02/17/2014
DOI: 10.1021/ic402825t
PMCID: PMC3993946
PMID: 24483834
Abstract
Isoxazole ring formation was examined
as a potential Cu-free alternative click reaction to Cu
I
-catalyzed alkyne/azide cycloaddition. The isoxazole reaction was
explored at macroscopic and radiotracer concentrations with the
fac
-[M
I
(CO)
3
]
+
(M = Re,
99m
Tc) core for use as a noncoordinating linker strategy between
covalently linked molecules. Two click assembly methods (
click,
then chelate
and
chelate, then click
) were
examined to determine the feasibility of isoxazole ring formation
with either alkyne-functionalized tridentate chelates or their respective
fac
-[M
I
(CO)
3
]
+
complexes
with a model nitrile oxide generator. Macroscale experiments, alkyne-functionalized
chelates, or Re complexes indicate facile formation of the isoxazole
ring.
99m
Tc experiments demonstrate efficient radiolabeling
with
click, then chelate
; however, the
chelate,
then click
approach led to faster product formation, but
lower yields compared to the Re analogues.
Isoxazole ring formation was examined as a potential Cu-free alternative
click scheme to CuAAC reactions at macroscopic and radiotracer concentrations
with
fac
-[M
I
(CO)
3
]
+
(M = Re,
99m
Tc) for use as a noncoordinating linker between
covalently linked molecules. Two click assembly methods (
click,
then chelate
and
chelate, then click
) were
examined to determine the feasibility of isoxazole ring formation
with either alkyne-functionalized tridentate chelates or their respective
fac
-[M
I
(CO)
3
]
+
complexes
with a model nitrile oxide generator.
Details
- Title: Subtitle
- Cu-Free 1,3-Dipolar Cycloaddition Click Reactions To Form Isoxazole Linkers in Chelating Ligands for fac-[MI(CO)3]+ Centers (M = Re, 99mTc)
- Creators
- Shalina C Bottorff - Washington State UniversityBenjamin B Kasten - Washington State UniversityJelena Stojakovic - University of IowaAdam L Moore - Washington State UniversityLeonard R MacGillivray - University of IowaPaul D Benny - Washington State University
- Resource Type
- Journal article
- Publication Details
- Inorganic chemistry, Vol.53(4), pp.1943-1945
- DOI
- 10.1021/ic402825t
- PMID
- 24483834
- PMCID
- PMC3993946
- NLM abbreviation
- Inorg Chem
- ISSN
- 0020-1669
- eISSN
- 1520-510X
- Publisher
- American Chemical Society
- Grant note
- DOI: 10.13039/100000052, name: NIH Office of the Director, award: T32-GM008336
- Language
- English
- Date published
- 02/17/2014
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216674402771
Metrics
11 Record Views