Synthesis and anticholinesterase activity of some benzo-1,3,2-dioxaphospholene, oxazaphospholine and diazaphospholine 2-ones containing 2-amino acid substitution

Article abstract of DOI:10.1080/10426509908044979

Synthesis of the titled compounds has been described. ¹H NMR, IR band frequencies and MS fragmentation and rearrangement peaks were analyzed and discussed in detail. Studying the inhibitory effect of these compounds on acetylcholinesterase (AChE) showed that dioxaphospholenes were stronger inhibitors than oxazaphospholines and diazaphospholines. This was explained by increasing the number of nitrogen atoms around the phosphorus atom in the later two series, which reduces the electrophilic character of the phosphorus atom by the overlapping between the dπ - pπ orbitals of the phosphorus and the neighboring nitrogen atoms, and hence reducing the electrophilic attack of the phosphorus atom on a nucleophilic center at the esteratic site of the enzyme. Steric factor of the amino acid moiety showed stronger effect than the electronic factor on the inhibition activity, the observed order was glycine > glutamic > methaionine > phenylalanine > alanine.

Full text of DOI:10.1080/10426509908044979

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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SYNTHESIS AND
ANTICHOLINESTERASE ACTIVITY
OF SOME OXAZAPHOSPHOLINE
AND BENZO-1,3,2-
DIOXAPHOSPHOLENE,
DIAZAPHOSPHOLINE 2-ONES
CONTAINING 2-AMINO ACID
SUBSTITUTION
a
Hussein M. Ali
a
Agricultural Biochemistry Department, Faculty
of Agriculture, Ain Shams University, Cairo, Egypt,
11241
Version of record first published: 04 Oct 2006.
To cite this article: Hussein M. Ali (1999): SYNTHESIS AND ANTICHOLINESTERASE
ACTIVITY OF SOME OXAZAPHOSPHOLINE AND BENZO-1,3,2-DIOXAPHOSPHOLENE,
DIAZAPHOSPHOLINE 2-ONES CONTAINING 2-AMINO ACID SUBSTITUTION, Phosphorus,
Sulfur, and Silicon and the Related Elements, 155:1, 157-166
To link to this article: http://dx.doi.org/10.1080/10426509908044979
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