Calix[4]arene alpha-aminophosphonic acids: asymmetric synthesis and enantioselective inhibition of an alkaline phosphatase.
[structure: see text] Chiral calix[4]arene alpha-aminophosphonic acids were obtained through diastereoselective Pudovik-type addition of sodium ethyl phosphites to the chiral calixarene imines, removal of chiral auxiliary groups, and mild dealkylation of phosphonate fragments. The diacids obtained show inhibitory activity toward porcine kidney alkaline phosphatase that depends considerably on the absolute configuration of the alpha-carbon atoms.
Cherenok
Sergiy
S
The Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska, 5, 02094, Kyiv-94, Ukraine.
Vovk
Andriy
A
Muravyova
Iryna
I
Shivanyuk
Alexander
A
Kukhar
Valery
V
Lipkowski
Janusz
J
Kalchenko
Vitaly
V
D000469:Alkaline Phosphatase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000818:Animals; D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology*; D007668:Kidney / Q000201:enzymology*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology*; D017905:Phosphites / Q000737:chemistry*; D013237:Stereoisomerism; D013552:Swine
D063065:Organophosphonates; D017905:Phosphites; D047250:Calixarenes; D000469:Alkaline Phosphatase