Premium
Synthesis of Fluorinated Ketoheptoses as Specific Diagnostic Agents
Author(s) -
Waschke Daniel,
Leshch Yevgeniy,
Thimm Julian,
Himmelreich Uwe,
Thiem Joachim
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101238
Subject(s) - chemistry , in vivo , electrophile , nucleophile , combinatorial chemistry , stereochemistry , biochemistry , catalysis , microbiology and biotechnology , biology
The straightforward syntheses of six regioisomeric mono‐ and difluorinated D ‐ manno ‐heptulose and Kamusol analogues, which use electrophilic or nucleophilic fluorinaton, are reported. D ‐ manno ‐Heptulose shows attractive pharmacological properties in vivo, such as antitumour activity, as well as binding to and accumulating in pancreatic beta cells to induce hyperglycemia. The synthesised analogues represent promising probes for the detection and quantification of beta cells in vivo by 19 F MRI techniques, which could help to investigate disease progression. In addition, they are potential candidates for the inhibition of tumour growth.