Saligenin Cyclic Alkyl Phosphates and Phosphorothionates with Insecticidal Activity

Alkylfurans: effects of alkyl side-chain length on insecticidal activity.

The insecticidal activity of five alkylfurans against the generalist insect herbivore beet armyworm, Spodoptera exigua, was examined. Two naturally occurring compounds, the avocadofurans 2-(pentadecyl)furan (1) and 2-(heptadecyl)furan (2), previously isolated from specialized avocado idioblast oil cells, and three homologues, 2-(tetradecyl)furan (3), 2-(hexadecyl)furan (4), and 2-(octadecyl)fur...

Biologic activity of cyclic and caged phosphates: a review.

The recognition in the early 1960s by Morifusa Eto that tri-o-cresyl phosphate (TOCP) is hydroxylated by the cytochrome P450 system to an intermediate that spontaneously cyclizes to a neurotoxic phosphate (saligenin phosphate ester) ignited the interest in this group of compounds. Only the ortho isomer can cyclize and clinically cause Organo Phosphate Induced Delayed Neurotoxicity (OPIDN); the ...

Alkaline phosphatase revisited: hydrolysis of alkyl phosphates.

Escherichia coli alkaline phosphatase (AP) is the prototypical two metal ion catalyst with two divalent zinc ions bound approximately 4 A apart in the active site. Studies spanning half a century have elucidated many structural and mechanistic features of this enzyme, rendering it an attractive model for investigating the potent catalytic power of bimetallic centers. Unfortunately, fundamental ...

CHANGES IN SERUM CHOLINESTERASE ACTIVITY DURING ADMINISTRATION OF SUBTOXIC DOSAGES OF ALKYL PHOSPHATES By Pharmacist Major

Synthesis of inositol glycan cyclic phosphates.

An efficient synthesis of tri-, tetra-, and pentasaccharide cyclic phosphates 1-5, structurally related to natural inositol phosphate glycans, is reported. The title compounds were assembled by PhSeOTf-promoted glycosylation of the known glucosamine precursor, t-butyldimethylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside (8) with protected 1-methylthio mono-, di-, and trimannoside...