Structure-activity study of phosphoramido acid esters as acetylcholinesterase inhibitors.
Phosphoramido acid esters (CH(3))(2)NP(O)X(p-OC(6)H(4)-CH(3)) (containing P-Cl (1), P-O (2), P-F (3), P-CN (5), and P-N (4,6) bonds, X for 2, 4 and 6 is OCH(3), (C(2)H(5))(2)N and morpholin) have been synthesized to investigate the structure-activity study of AChE enzyme inhibition, through the parameters logP, delta(31)P and IC(50). After their characterization by (31)P, (31)P{(1)H}, (13)C, (1)H NMR, IR and mass spectroscopy, the parameters logP and delta(31)P ((31)P chemical shift in NMR) were used to evaluated the lipophilicity and electronical properties. The ability of compounds to inhibit human AChE was predicted by PASS software (version 1.193), and experimentally evaluated by a modified Ellman's assay.
Ghadimi
Saied
S
Department of Chemistry, Imam Hossein University, Tehran, Iran. Ghadimi_Saied@yahoo.com
Valmoozi
Ali Asghar Ebrahimi
AA
Pourayoubi
Mehrdad
M
Samani
Keyvan Asad
KA
D000110:Acetylcholinesterase / Q000737:chemistry / Q000378:metabolism*; D002800:Cholinesterase Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004952:Esters / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D007700:Kinetics; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013329:Structure-Activity Relationship
D002800:Cholinesterase Inhibitors; D004952:Esters; D009943:Organophosphorus Compounds; D000110:Acetylcholinesterase