The aim of the course is to provide the student with specific and in-depth knowledge about the role of chirality in the biological activity of chiral drugs. Methodologies of preparation, purification, and analysis of chiral compounds will be trated during the course, with a particular focus on compounds of pharmaceutical interest. At the end of the course Students must be confident with the main techniques useful for prepration and characterization of chiral drugs, as well as with the key role that chirality plays in the drug discovery and development process.
Course Prerequisites
The students should possess adequate basic knowledge in organic chemistry, with particular reference to the nature and reactivity of functional groups, and to the general aspects of the medicinal chemistry.
Teaching Methods
The lessons will be performed in a mixed form, in presence and remote, using multimedia platforms suitable for streaming and video conferences (e.g. zoom).
Assessment Methods
Oral examination. It consists in delivering a seminar, followed by discussion, about deepening the knowledge on a topic to be chosen among those ones listed in the programme, plus verifying a general knowledge of the other topics.
Texts
Chirality in Drug Research (Methods and Principles in Medicinal Chemistry) di Eric Francotte, Wolfgang Lindner, Raimund Mannhold,Hugo Kubinyi, Gerd Folkers, Wiley.
La stereochimica attraverso esercizi di Maria Valeria D'Auria, Orazio Taglialatela Scafati, Angela Zampella.
Scientific papers and review.
Contents
Chirality and stereogenicity. Importance of the chirality in biological systems. Preparation of chiral compounds (asymmetric synthesis, bio-transformation, crystallization, enantioselective chromatography, combined methodologies). Characterization of the chiroptic properties through polarimetry and circular dichroism. Determination of the absolute and relative configuration (chemical correlation and X-ray diffraction, circular dichroism, NMR). Chirality in drug discovery and development. Racemic switch. Analysis and comment of specialized aspects on chirality reported in the recent literature.
