2'-deoxyadenosine bearing hydrophobic carborane pharmacophore.
Modification of 2'-deoxyadenosine at position 8 with para-carborane boron cluster is described. Incorporation of boron cluster into nucleic base has been accomplished using Sonogashira palladium-catalyzed cross-coupling reaction or, alternatively, Huisgen "click" type reaction. These are the first examples of adenosine derivatives with hydrophobic carborane pharmacophore attached to purine base.
Olejniczak
Agnieszka
A
Laboratory of Molecular Virology and Biological Chemistry, Center of Medical Biology, Polish Academy of Sciences, 106 Lodowa Street, 93 232 Lodz, Poland.
Wojtczak
Blazej
B
Lesnikowski
Zbigniew J
ZJ
D001880:Boranes / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D010165:Palladium / Q000737:chemistry
C527158:8-ethynyl-(2-para-carboran)-2'-deoxyadenosine; D001880:Boranes; D001896:Boron Compounds; D003839:Deoxyadenosines; D010165:Palladium; C058118:2'-deoxyadenosine