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Labelling of Carbaboranyl Compounds with a Selenium Atom with a View to Applications in Boron‐Neutron‐Capture Therapy (BNCT) and Positron‐Emission Tomography (PET)
Author(s) -
dos Santos Deborah F.,
Argentini Mario,
Weinreich Regin,
Hansen HansJürgen
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20001108)83:11<2926::aid-hlca2926>3.0.co;2-6
Subject(s) - chemistry , benzimidazole , positron emission tomography , neutron capture , structural isomer , radiochemistry , in vivo , pet imaging , boron , positron , nuclear chemistry , nuclear medicine , stereochemistry , organic chemistry , nuclear physics , microbiology and biotechnology , biology , physics , electron , medicine
We synthesized 2′‐carbaboranyl‐2,5′‐bi‐1 H ‐benzimidazoles containing 10 B‐atoms and labeled with Se or the positron‐emitting radionuclide 73 Se ( t 1/2 =7.1 h), with a view to their application to cancer treatment by boron‐neutron‐capture therapy (BNCT) and to compound‐distribution measurements in vivo by positron‐emission tomography (PET). Thus, 2,2′‐{{2′‐{4‐[1,2‐dicarba‐ closo ‐dodecaboran(12)‐2‐ylmethoxy]phenyl}‐[2,5′‐bi‐1 H ‐benzimidazol]‐5‐yl}imino}bis[ethanol] ( 26c ) was obtained by the reaction of 2,2′‐[(3,4‐diaminophenyl)imino]bis[ethanol] ( 19 ) with ethyl 2‐{4‐[1,2‐dicarba‐ closo ‐dodecaboran(12)‐2‐ylmethoxy]phenyl}‐1 H ‐benzimidazole‐5‐carboximidate hydrochloride ( 25 ), as well as the analogues 26a and 26b ( Scheme 6 ). Tosylation of compound 26c gave 4 regioisomers 27a – d , which, after selenation, produced 2′‐{4‐[1,2‐dicarba‐ closo ‐dodecaboran(12)‐2‐ylmethoxy]phenyl}‐5‐(tetrahydro‐2 H ‐1,4‐selenazin‐4‐yl)‐2,5′‐bi‐1 H ‐benzimidazole ( 29 ) in 42% yield ( Scheme 7 ).