- Docente: Federica Belluti
- Credits: 10
- SSD: CHEM-07/A
- Language: Italian
- Moduli: Federica Belluti (Modulo 1) Elisa Uliassi (Modulo 2) Federica Belluti (Modulo 3) Federica Belluti (Modulo 4) Elisa Uliassi (Modulo 5) Federica Belluti (Modulo 6)
- Teaching Mode: In-person learning (entirely or partially) (Modulo 1); In-person learning (entirely or partially) (Modulo 2); In-person learning (entirely or partially) (Modulo 3); In-person learning (entirely or partially) (Modulo 4); In-person learning (entirely or partially) (Modulo 5); In-person learning (entirely or partially) (Modulo 6)
- Campus: Bologna
-
Corso:
Single cycle degree programme (LMCU) in
Pharmaceutical Chemistry and Technology (cod. 5986)
Also valid for Single cycle degree programme (LMCU) in Pharmaceutical Chemistry and Technology (cod. 5986)
Learning outcomes
At the end of the course, which also includes laboratory exercises, the student knows: the basic concepts related to synthetic and extraction strategies used in research and industrial laboratories for the discovery and development of new drugs; the classical and innovative methodologies for the synthesis of low molecular weight molecules having biological activity and for the extraction of products of natural origin. Moreover the student learns to face an experimental procedure for the synthesis, the extraction and the characterization of a single compound, to consult the scientific literature before the experiment and to report the experimental results obtained.
Course contents
Module 1
Laboratory Safety and Organic Synthesis Techniques
Fundamentals of safety in the chemical laboratory. Laboratory techniques and equipment: glassware and interchangeable-joint apparatus commonly used in preparative organic chemistry; proper use, care and maintenance of laboratory equipment. Cooling and heating of reaction mixtures. Stirring techniques.
Isolation and purification techniques. Purification of solid compounds. Decolorization procedures. Gravity and vacuum filtration using depth and surface filters. Crystallization and reprecipitation techniques. Chromatographic methods, including adsorption chromatography, thin-layer chromatography (TLC), silica gel column chromatography, and flash column chromatography.
Synthesis of molecular libraries, combinatorial chemistry, and solid-phase synthesis.
Preparation and maintenance of the laboratory notebook.
Reactions involving water removal using a Dean–Stark apparatus. Microwave-assisted synthesis. Reactions performed under special conditions. Drying of solids and laboratory equipment. Anhydrous reactions. Drying of organic liquids and solutions using suitable drying agents. Use of the rotary evaporator.
Representative synthetic reactions
Wittig reaction: synthesis of 9-(2-phenylethenyl)anthracene.
Hantzsch reaction: synthesis of nifedipine.
Acetylation reactions: synthesis of p-aminophenol and acetylsalicylic acid.
Claisen–Schmidt aldol condensation: synthesis of a library of chalcone derivatives.
Fischer esterification: synthesis of methyl cinnamate or methyl benzoate.
Grignard reaction.
Reduction reactions and reducing agents.
Module 2
Green and Sustainable Pharmaceutical Manufacturing
Principles of green and sustainable manufacturing in the pharmaceutical industry. Case studies illustrating environmentally sustainable approaches to the production of active pharmaceutical ingredients (APIs).
Module 3
Extraction, Purification and Characterization of Natural Products
Fundamentals of extraction techniques. Solvent extraction. Ternary phase diagrams. Extraction and distribution coefficients. Acid–base liquid-liquid extraction. Counter-current extraction. Extraction using ionic liquids and deep eutectic solvents. Ionic liquid-based aqueous biphasic extraction systems. Continuous solid-liquid extraction (Soxhlet extraction). Solid-phase extraction. Pressurized solvent extraction. Supercritical fluid extraction. Ultrasound-assisted extraction. Microwave-assisted extraction.
Distillation techniques, including steam distillation and fractional distillation under atmospheric and reduced pressure.
Chromatographic techniques applied to natural product extracts, including adsorption chromatography, thin-layer chromatography, and silica gel column chromatography.
Theoretical principles underlying the extraction, purification, and structural characterization of small molecules from plant matrices, including:
Lycopene and β-carotene from Solanum lycopersicum (tomato);
Flavonoids and essential oils from Matricaria chamomilla and Citrus aurantium pericarp;
Curcuminoids and terpenes from Curcuma longa;
Phenylpropanoids from Syzygium aromaticum.
Module 4
Laboratory Practice: Organic Synthesis, Purification and Structural Characterization
Wittig reaction: synthesis of 9-(2-phenylethenyl)anthracene.
Grignard reaction: synthesis of 1-(4-methoxyphenyl)-1-phenylethan-1-ol.
Hantzsch reaction: synthesis of tetrahydropyridine derivatives (nifedipine).
Acetylation reaction: synthesis of p-aminophenol (paracetamol).
Claisen–Schmidt condensation: synthesis of a library of chalcone derivatives.
Fischer esterification: synthesis of methyl cinnamate.
Module 5
Green Synthetic Methodologies
Microwave-assisted green synthesis of aspirin.
Biocatalytic reduction of ethyl acetoacetate.
Module 6
Laboratory Practice: Extraction, Purification and Structural Characterization of Natural Products
Extraction, purification and structural characterization of:
Lycopene and β-carotene from Lycospericon esculentum.
Flavonoids and essential oils from Matricaria chamomilla.
Curcuminoids from Curcuma longa.
Phenylpropanoids from Syzygium aromaticum.
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 LUCIDI, CD, APPUNTI DI LEZIONI, COPIE DI ARTICOLI INERENTI GLI ARGOMENTI DI LEZIONE ADVANCED PRATICAL ORGANIC CHEMISTRY THIRD EDITION LEONARD LYGO PROCTER CRC PRESS
Teaching methods
The course consists of mandatory lectures and laboratory practical sessions and is organized into six teaching modules, three of which include individual laboratory practical activities related to the topics covered in the course.
To ensure effective use of the laboratory facilities, students will be divided into two groups (Group A and Group B), which will attend the laboratory practical sessions in successive shifts.
Attendance requirements are considered fulfilled upon attendance of at least 80% of the laboratory practical sessions and 60% of the lectures. Attendance is recorded through the University's electronic attendance monitoring system.
The lectures are designed to provide students with the theoretical background underlying the various strategies employed for the synthesis, purification, and structural characterization of small organic molecules (Modules 1 and 2), as well as for the extraction, purification, and structural characterization of the major constituents of plant matrices (Module 3).
Laboratory practical sessions are carried out individually. During the laboratory activities, students are supervised by the instructor and teaching assistants to progressively develop practical skills and laboratory autonomy. Each student is required to maintain a personal laboratory notebook, recording the experimental procedures performed and critically discussing the results obtained. For Modules 4 and 6, the laboratory notebook will be reviewed by the instructor, who may provide comments and corrections, and must be presented during the final oral examination.
Laboratory activities are conducted with the assistance of laboratory technicians to promote compliance with good laboratory practice and safety regulations.
Considering the nature of the laboratory activities and the teaching methods adopted, all students, including incoming international students (e.g. Erasmus students), are required to complete the General Health and Safety Training Modules 1 and 2 through the University's e-learning platform, available at:
https://www.unibo.it/it/servizi-e-opportunita/salute-e-assistenza/salute-e-sicurezza/sicurezza-e-salute-nei-luoghi-di-studio-e-tirocinio
Students are also required to attend Module 3 (Specific Health and Safety Training for Study Facilities). Information regarding the schedule and attendance procedures for Module 3 is available in the dedicated section of the Degree Programme website.
Assessment methods
The final assessment is designed to verify the achievement of the following learning outcomes: knowledge of the fundamental concepts underlying the synthetic strategies employed in academic and industrial research laboratories for the discovery and development of new drugs, together with the associated laboratory procedures; knowledge of the fundamental principles of practical medicinal chemistry techniques and both classical and innovative methodologies for the synthesis of biologically active small molecules; knowledge of the methods used for the purification, identification, and structural characterization of synthesized compounds, as well as of the techniques employed for the extraction, purification, and structural characterization of small molecules isolated from plant matrices.
Students are expected to demonstrate a level of knowledge that enables them to integrate the concepts acquired during the course with those developed in previous years, particularly in Organic Chemistry, in order to successfully undertake subsequent courses.
The final assessment for the Synthetic Module (Modules 1, 2, 4 and 5) consists of a single oral examination covering both teaching units and conducted on the same day in the presence of both instructors.
The final assessment for the Extraction Module (Modules 3 and 6) consists of an independent oral examination.
The Synthetic and Extraction Modules may be taken during different examination sessions. No compulsory order is established; therefore, students are free to decide the sequence in which they complete the two examinations.
The oral examination consists of specific questions covering the topics addressed during the course. Particular importance is given to the student's ability to integrate the knowledge acquired during previous courses, especially Organic Chemistry. The final mark also takes into account the successful completion of the laboratory practical activities.
Students are expected to demonstrate their ability to analyse and solve experimental problems and to discuss scientific topics clearly and rigorously, using appropriate scientific terminology.
Module 1. Students will be asked specific questions on the topics covered during the course. The first question, aimed at assessing theoretical knowledge, concerns the theoretical principles and instrumental aspects underlying laboratory activities in Organic and Medicinal Chemistry. This is followed by a question concerning one of the laboratory experiments performed during the course. The discussion is based on the student's laboratory notebook, in which the experimental procedures and the results obtained have been recorded and critically discussed.
Module 2. The oral examination consists of the discussion of a scientific article selected by the student and related to the topics covered during the course.
Module 3. Students will be asked specific questions on the topics covered during the course. The first question assesses the theoretical principles and instrumental aspects of natural product extraction techniques from plant matrices. This is followed by a discussion of one of the laboratory experiments carried out during the course, based on the student's laboratory notebook.
The use of Artificial Intelligence (AI) tools during any assessment is strictly prohibited. Any use of AI tools constitutes a violation of the University's principles of academic integrity.
The final grade for the course is calculated as the weighted average of the marks obtained in the oral examinations, weighted according to the number of credits (CFU) assigned to each module, provided that the student has successfully completed the required laboratory practical activities.
Students must register for the oral examinations exclusively through the AlmaEsami online platform:
https://almaesami.unibo.it/almaesami/welcome.htm
Examination sessions for the Synthetic and Extraction Modules are published separately on AlmaEsami. The two examinations may be taken during different examination sessions and in any order chosen by the student.
Examination sessions are scheduled within the official examination periods for enrolled students. Additional examination dates may be arranged throughout the academic year for students repeating the course, subject to prior agreement with the instructor and registration through AlmaEsami.
Students with temporary or permanent disabilities or Specific Learning Disorders (SLD) are encouraged to contact the University's dedicated support service as early as possible:
https://site.unibo.it/studenti-con-disabilita-e-dsa/it
The support service will propose any appropriate examination accommodations, which must be submitted to the instructor for approval at least 15 days before the examination. The instructor will assess their suitability in relation to the intended learning outcomes of the course.
Teaching tools
Video projector-PC system, laboratory for the practical exercises. The slides presented during the lectures are made available to students on the online teaching platform (Virtuale), username and password are reserved only for Bologna University students.
Office hours
See the website of Federica Belluti
See the website of Elisa Uliassi
See the website of Elisa Uliassi