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The synthesis and medicinal applications of pyrogallol4arenes

Carey, Stephen (2006) The synthesis and medicinal applications of pyrogallol4arenes. PhD thesis, Dublin City University.

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Abstract

To date almost all pyrogallol[4]arenes reported in the literature have been prepared from alkyl aldehydes. We were interested in preparing more pyrogallol[4]arenes from commercially available benzaldehydes. On synthesising these compounds we discovered that they are structurally unique, compared to previously reported pyrogallol[4]arenes, as they exist in a rctt chair conformation as determined by X-ray crystallography and 1HNMR. We also discovered from our synthetic studies that the yields for the pyrogallol[4]arenes depend strongly on the electron donating/withdrawing ability of substituents placed in the benzaldehyde, the more electron withdrawing the higher the yield. We also discovered a unique metal salt effect on the condensation of pyrogallol with 4-fluorobenzaldehyde that doubled the yields o f the resulting macrocycle. Interestingly, this effect is absent with the condensation of pyrogallol with alkyl aldehydes. The role of steric effects, using bulky substituted benzaldehydes was also investigated to determine whether the stereochemical outcome for these condensation reactions could be controlled. The further derivatisation of the pyrogallol[4]arenes was also investigated. The preparation of partially and completely alkylated derivatives of these macrocycles was of interest to us. We found that the introduction of acetate groups could be readily accomplished, however other alkyl groups could not be efficiently introduced into the pyrogallol[4]arenes. The partially and completely alkylated acetate derivatives of pyrogallol[4]arene were screened for biological activity against HIV-1. It was discovered that the partially alkylated derivatives possessed higher selectivity indexes than the completely alkylated derivatives indicating that biological activity may not be dependent on charge.

Item Type:Thesis (PhD)
Date of Award:2006
Refereed:No
Supervisor(s):Nolan, Kieran
Uncontrolled Keywords:synthesis; medicinal chemistry; pyrogallol[4]arenes; benzaldehydes
Subjects:Physical Sciences > Chemistry
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 3.0 License. View License
ID Code:17419
Deposited On:06 Sep 2012 14:51 by Fran Callaghan. Last Modified 06 Sep 2012 14:51

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