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  • 1
    ISSN: 1520-5126
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    ISSN: 0020-7608
    Keywords: Computational Chemistry and Molecular Modeling ; Atomic, Molecular and Optical Physics
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 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 AM1 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.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 0020-7608
    Keywords: Computational Chemistry and Molecular Modeling ; Atomic, Molecular and Optical Physics
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pilocarpine is used as a topical miotic to control elevated intraocular pressure in the glaucoma-afflicted eye. However, its ocular availability is low, it is subject to difficult delivery problems, and it is rapidly lost from the preferred site of action. Therefore, the prodrug approach has been used to design suitable pilocarpine derivatives. Possible pilocarpine prodrugs are pilocarpic acid esters of which little structural and molecular level information is available. Molecular modeling studies of a series of pilocarpic acid mono- and diester prodrugs have been done to gain an understanding of their general physicochemical properties. Molecular structures and conformers have been determined with molecular mechanics and quantum chemical AM1 calculations. Both the molecular mechanics and the AM1 methods yield similar molecular equilibrium structures. Calculations on the protonated forms of the molecules show that protonating introduces variations at the ester linkages prone to enzymatic attack. The calculations indicate, however, that spatial requirements may be more important than electrostatic characteristics for effective enzymatic hydrolysis of the pilocarpic acid diesters. Preliminary calculations on chosen examples of a new class of pilocarpine prodrugs of the bispilocarpic acid ester type are also reported.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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