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A theoretical investigation of some novel pilocarpine prodrugs
Author(s) -
Ek holm Michaela,
Konschin Henrik
Publication year - 1994
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560510106
Subject(s) - van der waals force , chemistry , prodrug , force field (fiction) , context (archaeology) , computational chemistry , organic chemistry , molecule , physics , quantum mechanics , biochemistry , paleontology , biology
A new class of pilocarpine double prodrugs of the bispilocarpic acid diester type has been investigated. Molecular orbital and molecular mechanics calculations have been done to obtain information about the conformational preferences and general physicochemical properties. Geometries of the structures were obtained with the force field implemented in the CHEM‐X program and using the semiempirical quantum chemical program AMPAC and the AM 1 method. A correlation between the van der Waals volume, van der Waals area, and log P of the bispilocarpic acid diester structures is observed. The structures of these biscompounds are compared with the structures of the corresponding monopilocarpic acid diesters. Electrostatic and electronic properties of the compounds will be discussed in the context of the interaction between the prodrugs and the hydrolyzing esterase enzymes. © 1994 John Wiley & Sons, Inc.