Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 9, Pages 1655-1659Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600137
Keywords
Isosteres; Guanidinium; Cyclopropenium; Aromaticity; Medicinal chemistry
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Funding
- National Institute of General Medical Sciences (NIGMS) [R01 GM102611]
- National Institutes of Health (NIH) [R01 EB020892]
- Japan Society for the Promotion of Science (JSPS)
- Uehara Memorial Foundation Research Fellowship
- Kyoto University Foundation Fellowship for Research Abroad
- Columbia University
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The deltic guanidinium ion is described here as a macrostere of the guanidinium ion. The use of the 2,4-dimethoxybenzyl protecting group allows for the synthesis of the fully unsubstituted parent compound and a variety of derivatives bearing multiple N-H functions for the first time. Deltic urea, deltic thiourea, and deltic benzamidine are also synthesized. A comparison of the physical properties of guanidinium and deltic guanidinium ions is provided. The use of a deltic guanidinium dendrimer for cell transport is demonstrated.
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