4.06 - Thiazoles

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This chapter is a review of the scientific literature from 1995 to 2007. In conjunction with the corresponding chapters in CHEC(1984) and CHEC-II(1996), it constitutes a thorough review of the chemistry of thiazoles. Structures discussed include thiazoles, thiazolines, thiazolidines, thiazolium salts, benzothiazoles, and benzothiazolines as well as more complex structures and/or fused systems bearing substituents on the ring carbons and heteroatoms. The chapter’s subsections describe theoretical methods (including molecular orbital calculations, bond lengths and angles, electronic density and aromaticity), experimental measurements (covering various techniques such as X-ray diffraction, and IR and UV spectroscopies, mass spectrometry, and NMR spectroscopy), a survey of the reactivity of thiazole systems (covering reactivity of the ring carbons, heteratoms, and attached functional groups), approaches to ring synthesis (organized by the number of atoms in each component used), a comparison of the various routes to classes of compounds containing thiazoles (including biosynthesis and solid-phase approaches), and important thiazole compounds and their applications (including naturally occurring thiazole systems, thiazole peptides, lactones and alkaloids, and synthetic tools such as thiazole as a formyl equivalent, thiazolidine thiones as chiral auxiliaries, and thiazolium catalysts). Other applications of thiazoles such as fluorescence PNA probes for DNA determination, synthetic fluorophores, and DNA nucleases are also discussed.

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Beining Chen graduated from China Pharmaceutical University with a B.Sc., in 1984 and an M.Sc. in 1987, both in medicinal chemistry. She obtained a Ph.D in organic chemistry in 1991 from University of Glasgow under the supervision of Professor Gordon Kirby. After spending three years working for Professor Sir Jack Baldwin at University of Oxford and seven years of employment by Cranfield, she joined Department of Chemistry at University of Sheffield as a lecturer in medicinal chemistry in 2003.

The main focus of her research is on the design, synthesis, and screening of biologically active heterocyclic compounds including thiazoles. Over the last three years, she has been intensively involved in the development of therapeutic compounds against acquired variant Creutzfeldt–Jakob disease (vCJD, the human form of mad cow disease), a member of a family of fatal neurodegenerative diseases called transmissible spongiform encephalopathies (TSEs) or prion diseases for which there are no therapeutic drugs currently available. The project was funded by the Department of Health (DoH).

William Heal was born in Norwich, UK, in 1976. He was awarded a B.Sc. with honors in chemistry in 1998 and an M.Sc. in chemical process (research and development) the following year from the University of Liverpool (UK). He stayed on in Liverpool to complete a Ph.D. in 2003, studying the polyleucine-catalyzed asymmetric epoxidation of α,β-unsaturated ketones under the supervision of Professor Stan Roberts, funded by the EPSRC and a CASE award from Novartis. He then carried out postdoctoral research in medicinal chemistry at the University of Sheffield (UK), designing and synthesizing small molecule inhibitors of prion disease funded by the Department of Health. He is presently at Imperial College London (UK), carrying out MRC-funded postdoctoral research in the field of chemical proteomics directed toward malaria. His research is carried out at the biology–chemistry interface and he is particularly interested in the design and synthesis of small molecules for use in studying biological systems.

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