Synthesis and anticholinesterase properties of some S-benzhydryl esters of phosphorus monothio acids

  • T. A. Mastryukova
  • R. S. Agabekyan
  • A. B. Uryupin
  • M. I. Kabachnik
Organic Chemistry

Conclusions

  1. 1.

    Alkylation of salts of phosphorus monothio acids with diphenylbromomethane in benzene forms S-benzhydryl esters of the corresponding phosphorus monothio acids with concomitant formation of the O-benzhydryl esters (<5–7%).

     
  2. 2.

    We have examined the anticholinesterase activity of S-benzhydryl esters of phosphorus monothio acids toward human erythrocyte acetylcholinesterase (ACE) and horse serum butyrylcholinesterase (BuCE).

     
  3. 3.

    S-Benzhydryl O,O-diethyl phosphorothiolate, O-ethyl methylphosphonothiolate, and O-ethyl phenylphosphonothiolate, and diethylphosphinothiolate belong among mixed inhibitors, whereas esters of diisopropylphosphinothioic acid inhibit both enzymes only reversibly. We demonstrate that purely reversible inhibition of CE by thiolates of phorphorus acids is possible.

     
  4. 4.

    We examine the influence of the substituents on the phosphorus atom on the rate constants for ACE and BuCE inhibition.

     

Keywords

Enzyme Ester Phosphorus Benzene Alkylation 

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Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • T. A. Mastryukova
    • 1
  • R. S. Agabekyan
    • 1
  • A. B. Uryupin
    • 1
  • M. I. Kabachnik
    • 1
  1. 1.Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

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