Date of Publication

1-4-1997

Document Type

Master's Thesis

Degree Name

Master of Science in Chemistry

Subject Categories

Chemistry

College

College of Science

Department/Unit

Chemistry

Thesis Adviser

Martin C. Ilao

Defense Panel Chair

Gerardo C. Janairo

Defense Panel Member

Jaime Raul O. Janairo
Wyona C. Patalinghug

Abstract/Summary

Empirical forcefield calculations are performed on the diasteriomeric a- amd B- azabicyclanes (3-methyl-9-methoxy-9-phenyl-3-azabicyclo[3.3.3] nonames), which are prototypical phenyl-axial and phenyl-equatorial opiates. After energy minimization, optimized structures of both compounds and protonated analogs are found to prefer a chair-chair-conformation of the piperidine and cyclohexane rings with two mirror image orientations of the phenyl and methoxyl groups. Comparison of the protonated a- and B- azabicyclanes for the same conformation revealed very similar orientations of the pharmacophoric groups (phenyl, methoxyl and tertiary N) which suggest that interchange of piperidine and cyclohexane rings has minimal effect on the relative conformation of the pharcophoric groups. These may account for the observed similarity of their opiate activities. A detailed comparison is also made between the optimized models and those obtained by X-ray crystallography with satisfactory agreement in geometries despite the different molecular environments of the two methods calculations were done in the gas phase while X-ray data were obtained from the solid phase.

Abstract Format

html

Language

English

Format

Print

Accession Number

TG02518

Shelf Location

Archives, The Learning Commons, 12F Henry Sy Sr. Hall

Physical Description

66 leaves

Keywords

Molecular structure; Force and energy; Mechanics; Alkaloids--Spectra

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