Three-dimensional structural analysis of avian-teratogenic pyrimidine dialkyl phosphate esters and their analogs by molecular orbital calculations.
The most stable structures of avian-teratogenic pyrimidinyl dialkyl phosphates and phosphorothionates at semi-empirical molecular orbital (MO) AM1 method level were obtained to get net charges of nitrogen (N) and phosphorus (P), distances between 1-N and P, and twist angles between plane of the heterocycle and that made by C-O-P. These geometries of typical compounds were optimized by ab initio MO calculations at level of HF/6-31 G*. In the most potent teratogens, distances between 1-N and P were 4.3-5.4 A. Compounds of about 3 A has no teratogenicity.
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Laboratory of Food Chemistry, Himeji College of Hyogo, Japan.
D000818:Animals; D002642:Chick Embryo / Q000187:drug effects; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009946:Organothiophosphorus Compounds / Q000737:chemistry* / Q000633:toxicity; D011743:Pyrimidines / Q000737:chemistry* / Q000633:toxicity; D013329:Structure-Activity Relationship; D013723:Teratogens / Q000737:chemistry* / Q000633:toxicity
D009946:Organothiophosphorus Compounds; D011743:Pyrimidines; D013723:Teratogens