Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents
Başlık çevirisi mevcut değil.
- Tez No: 402384
- Danışmanlar: PROF. ROGER HUNTER, PROF. MINO R. CAIRA
- Tez Türü: Doktora
- Konular: Kimya, Chemistry
- Anahtar Kelimeler: Belirtilmemiş.
- Yıl: 2008
- Dil: İngilizce
- Üniversite: University of Cape Town
- Enstitü: Yurtdışı Enstitü
- Ana Bilim Dalı: Kimya Ana Bilim Dalı
- Bilim Dalı: Belirtilmemiş.
- Sayfa Sayısı: 212
Özet
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Özet (Çeviri)
Allicin, a known constituent of garlic, is a potent but unstable antimicrobial agent. Consideration of the underlying features responsible for allicin's activity, as well as its instability, prompted an investigation into substituted S-aryl alkylthiosulfinates as a class of potential allicin mimics with enhanced stability. Synthesis of the targets also inspired development of a novel unsymmetrical disulfide synthesis. This thesis describes the development of a new methodology for synthesizing unsymmetrical disulfides. The synthesis involves converting a thiol to a sulfenylating agent by 1-chlorobenzotriazole (BtCl) in the presence of 1,2,3-benzotriazole (BtH). Addition of a second thiol affords unsymmetrical disulfides in excellent yields. In addition to being a one-pot methodology, the approach offers attractive environmentally friendly and cost-saving aspects. The methodology proved to be versatile, producing all types of unsymmetrical disulfides; aromatic-aliphatic disulfides, aromatic-aromatic disulfides as well as aliphatic-aliphatic disulfides including unsymmetrical cysteine disulfides. A class of unsymmetrical disulfides (alkyl p-methoxyphenyl disulfides), with an activated aromatic ring, were oxidized to the corresponding thiosulfinates (S-alkyl p-methoxyphenylthiosulfinates) using m-CPBA, and were established to be markedly more stable than allicin itself with only ~5% structural change after 1 month at room temperature. This was in contrast to the same class of thiosulfinates with deactivated rings, which were found to be unstable. A family of relatively stable thiosulfinates was thus prepared by varying the length and fluorine content of the alkyl chain. Such compounds were subjected to a preliminary antibacterial study, which revealed that the S-p-methoxyphenyl alkylthiosulfinates exhibit activity against Gram-positive (Mycobacterium aurum and Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria, qualifying them as allicin mimics at a preliminary level. Lastly, the thesis describes the preparation and characterization of inclusion complexes formed between selected cyclodextrins and S-aryl alkylthiosulfinates. The complexes were investigated by thermal techniques, IR spectroscopy, powder X-ray diffraction and in three cases, single crystal X-ray diffraction. Such complexes may also offer the included molecules valuable stability and biological characteristics.
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