- Docente: Alberto Leoni
- Credits: 10
- Language: Italian
- Teaching Mode: In-person learning (entirely or partially)
- Campus: Bologna
- Corso: Single cycle degree programme (LMCU) in Chemistry and Pharmaceutical Technologies (cod. 8412)
Learning outcomes
THE COURSE PROVIDES AN INTRODUCTION TO
VARIOUS TECHNIQUES OF SYNTHESIS AND EXTRACTION OF COMPOUNDS OF
PHARMACEUTICAL INTEREST. MAJOR OBJECTIVES OF COURSE ARE IMPROVEMENT
OF SKILL IN THE TECHNICAL ASPECTS OF LABORATORY WORK (I.E. SAFE
HANDLING OF CHEMICALS, APPARATUS MANIPULATION) AND INTRODUCTION TO
TECHNIQUES AND PROCEDURES IMPORTANT TO THE SUCCESSFUL PRACTICE OF
EXPERIMENTS
Course contents
Theoretical lessons
General instructions for safe working in organical chemical
laboratories.
Apparatus and reaction procedures: glassware, apparatus with
interchangeable ground glass joints suitable for general use in
preparative organic chemistry: care and maintenance. Cooling and
heating of reaction mixtures. Mechanical agitation.
Isolation and purification processes: Solids purification.
Decolouration. Filtration techniques: filter funnels and membrane
filters. Recrystallisation tecniques. Extraction theory. Solvent
extraction. Countercurrent extraction: Craig apparatus. Solid phase
extraction. Drying of solids and apparatus. Anhydrous reactions.
Drying of liquids or of solutions of organic compounds in organic
solvents: drying agents. Distillation. Rotary evaporator. Steam
distillation. Fractional distillation at atmospheric and diminished
pressure. Molecular distillation. Purification of common organic
solvents. Silica gel column chromatography: flash chromatography.
Microwave-assisted synthesis of pharmaceutical compounds
Combinatorial chemistry in drug discovery. Solid phase
synthesis.
Some novel and common oxidizing and reducing agents.
Extraction, biosynthesis, and chemical synthesis of
pharmaceutical compounds: taxol, camptothecin,
erythromycine, epibatidine, philanthotoxins.
Guidelines for Keeping a Laboratory Record.
Practical laboratory:
- Enantioselective enzymatic reduction of methylacetoacetate
and purification by gravity-flow column chromatography.
-N-BOC protection of proline.
-Synthesis of tacrine.
-Synthesis of trans-9-(2-phenylethenyl)anthracene.
-Synthesis of nifedipine.
-Oxidation of isoborneol to camphor by potassium chromate.
-Reduction of camphor to isoborneol by sodium borohydride.
-Synthesis of p-nitroacetanilide and purification by flash
chromatography.
-Synthesis of acetylsalicylic acid.
-Resolution of racemic 1-phenylethylamine by fractional
crystallization.
-Extraction, purification and quantitative determination of
beta-carotene from Lycospericon Esculentum
-Extraction and separation of hibiscus acid, hibiscin and
caffeic acid from dried calyces of Hibiscus Sabdariffa by
Extralut column.
-Extraction of trimyristine from Myristica Fragrans.
-Extraction of eugenol by steam distillation from Syzygium
Aromaticum.
- Extraction of flavonoids and essential oil from dried flowers
of Matricaria Camomilla.
- Extraction and quantitative determination of nicotine fron
dried leaves of Nicotiana Tabaccum.
- Solid phase extraction and quantitative determination of
xanthines from dried leaves of Thea Sinensis.
Readings/Bibliography
1) VOGEL. CHIMICA ORGANICA PRATICA. CASA EDITRICE AMBROSIANA, SECONDA EDIZIONE, MILANO 1988 2) R. M. ROBERTS, J.C. GILBERT, S. F. MARTIN. CHIMICA ORGANICA SPERIMENTALE. ZANICHELLI, BOLOGNA 2003 3) A.J. HANDELY. EXTRACTION METHODS IN ORGANIC ANALYSIS. SHEFFIELD ACADEMIC PRESS, CANADA 1999 4) D.L. PAVIA, G. M. LAMPMAN, G.S. KRIZ. IL LABORATORIO DI CHIMICA ORGANICA, EDIZIONI SORBONA , MILANO 1994 5) P.M. DEWICK. CHIMICA, BIOSINTESI E BIOATTIVITA' DELLE SOSTANZE NATURALI. PICCIN, PADOVA 2000 6) MARCO D'ISCHIA LA CHIMICA ORGANICA IN LABORATORIO PICCIN PADOVA 2002
Teaching methods
The course will be supported by laboratory exercises. The
laboratory exercises will be individual and will aim to
provide each student the opportunity to apply the various
methods of preparing extracts of herbal drugs outlined
in theoretical form in class.
Assessment methods
FINAL EXAMINATION:
A comprehensive final exam is given at the end of the semester. The
final test will tend to determine the knowledge of the topics
presented during the lessons.
Teaching tools
PC, LABORATORY OF CHEMISTRY,
TRASPARENCIES, VIDEOPROJECTORS
Office hours
See the website of Alberto Leoni