TY - JOUR
T1 - Syntheses and electrochemical properties of novel aminopyrimidinone derivatives as a new class of abasic-site binders
AU - Chiba, Junya
AU - Doi, Yasuhiro
AU - Inouye, Masahiko
PY - 2013/1
Y1 - 2013/1
N2 - We describe syntheses and electrochemical properties of a new class of aminopyrimidinone derivatives: 2-amino-4-(3',4'-dimethoxyphenyl)-6-pyrimidinone, 2-amino-4-(3',4'-dihydroxyphenyl)-6-pyrimidinone, 2,4-diamino-5-(3',4'- dimethoxyphenyl)-6-pyrimidinone, 2,4-diamino-5-(3',4'-dihydroxyphenyl)-6- pyrimidinone, and 4-amino-5-(3',4'-dihydroxyphenyl)-2,6-pyrimidinione, three of which possess a catechol unit as an oxidation-active moiety for developing electrochemically detectable abasic-site binders. These compounds were synthesized via a pyrimidine-ring forming reaction with guanidine. Cyclic voltammetry measurements revealed that the catechol-bearing derivatives showed oxidation potentials lower than that of DNA, indicating that they satisfied the requirements for the purpose. Graphical Abstract: [Figure not available: see fulltext.]
AB - We describe syntheses and electrochemical properties of a new class of aminopyrimidinone derivatives: 2-amino-4-(3',4'-dimethoxyphenyl)-6-pyrimidinone, 2-amino-4-(3',4'-dihydroxyphenyl)-6-pyrimidinone, 2,4-diamino-5-(3',4'- dimethoxyphenyl)-6-pyrimidinone, 2,4-diamino-5-(3',4'-dihydroxyphenyl)-6- pyrimidinone, and 4-amino-5-(3',4'-dihydroxyphenyl)-2,6-pyrimidinione, three of which possess a catechol unit as an oxidation-active moiety for developing electrochemically detectable abasic-site binders. These compounds were synthesized via a pyrimidine-ring forming reaction with guanidine. Cyclic voltammetry measurements revealed that the catechol-bearing derivatives showed oxidation potentials lower than that of DNA, indicating that they satisfied the requirements for the purpose. Graphical Abstract: [Figure not available: see fulltext.]
KW - Abasic site
KW - Aminopyrimidinone
KW - Catechol
KW - Electrochemistry
UR - http://www.scopus.com/inward/record.url?scp=84871779926&partnerID=8YFLogxK
U2 - 10.1007/s11164-012-0641-7
DO - 10.1007/s11164-012-0641-7
M3 - 学術論文
AN - SCOPUS:84871779926
SN - 0922-6168
VL - 39
SP - 177
EP - 183
JO - Research on Chemical Intermediates
JF - Research on Chemical Intermediates
IS - 1
ER -