Nowoczesne metody pozyskiwania substancji biologicznie aktywnych przy zastosowaniu reakcji wieloskładnikowych ze szczególnym uwzględnieniem reakcji Ugi
Journal Title: Wiadomości Chemiczne - Year 2017, Vol 71, Issue 1
Abstract
In the last decade a change of thought has taken place in the pharmaceutical industry which has led to a renaissance of the Multicomponent reactions (MCRs) [1]. Under the inspiration of diversity-oriented-synthesis (DOS), numerous efforts have been devoted to find powerful synthetic tools for rapidly accessing maximum molecular diversity with minimum cost. In the toolbox enabling DOS for generating molecular libraries, MCRs are now recognized as one of the most useful and powerful strategies [2], which provide the highest number of compounds for the least synthetic effort [3]. Following the rapid progress in the research area of MCRs, widespread application has been found in many different areas such as chemical biology, natural product synthesis, pharmaceuticals as well as agrochemistry [2]. The overall aim of a DOS is to generate a small-molecule collection with a high degree of structural, and thus functional, diversity that interrogates large areas of chemical space simultaneously [4]. In Targed-Oriented Synthesis (TOS) a complex target is transformed into a sequence of progressively simpler structures by formally performing chemical reactions in the reverse-synthetic direction [3]. Special subclasses are isocyanide based MCRs (IMCRs). They are particularly interesting because they are more versatile and diverse than the remaining MCRs. Today most MCRs chemistry performed with isocyanides relates to the classical reactions of Passerini and Ugi (Scheme 1)[5]. In Ugi four-component reaction (U-4CR), carboxylic acids, primary amines and oxo components (aldehydes or ketones) react with isocyanides in polar solvents to obtain -amino carboxamides (Schemes 2 and 3). Occasionally however, selective conversion of amide groups into other functional groups is desirable for an increase of diversity of the IMCR-derived compounds [6]. In this reaction two substituted amide groups are formed under release of one equivalent of water. Thus, the U-4CR is an atom-economic and environmentally friendly reaction. It was also shown that water can be used as the solvent. This reaction is typically performed by stirrling the components for approximately 1 day in small quantities of a protic solvent (e.g. methanol or trifluoroethanol) [7]. The examples of Ugi reactions are described in the Schemes 4–10. Multicomponent reactions have become attractive tools in modern synthetic organic chemistry. Among their many advantages, they allow the creation of large chemical libraries of diverse, complex molecular structures, starting from simple materials within a short time frame. Not surprisingly, these particular features have made MCRs especially appealing to medicinal chemists [8].
Authors and Affiliations
Stanisław Ryng, Izabela Jęśkowiak
Keywords
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