Extractive and Synthetic Preparation of Drugs and Laboratory of Extractive and Synthetic Preparation of Drugs

A.Y. 2020/2021
6
Max ECTS
72
Overall hours
SSD
CHIM/08
Language
Italian
Learning objectives
The course aims at teaching, both from a theoretical and a practical point of view, the basic operations carried out in a medicinal chemistry laboratory, in order to obtain biologically active compounds by extraction from natural sources, or by organic synthesis exploiting classical methods as well as innovative methodologies.
After reviewing some basic techniques already studied in the Organic Chemistry laboratory (extraction, crystallization, chromatography), some simple syntheses of pharmacologically active products and some extractions of natural compounds from vegetable matrices are proposed.
Expected learning outcomes
At the end of the course, the student should know the basic notions regarding the organic synthesis of substances of pharmaceutical interest and the extraction of active ingredients from vegetable matrices. Furthermore, the student will be able to apply in the laboratory the extraction and synthesis techniques treated in the course. The student will also be able to fill in the personal lab book and critically analyze the obtained results. In the learning verification phase, the student should be able to understand the questions and critically process the knowledge acquired during the lectures and the practical training.
Course syllabus and organization

Linea AK

Responsible
Lesson period
Second semester
Didactic methods
The lessons scheduled for the second semester will be held synchronously using the Microsoft Teams platform. If the regulations concerning social distancing will allow it and if classrooms will be available, part of the lessons will be held in person. All lessons will be also simultaneously available remotely through the Microsoft Teams Platform. The rules for participation to the lessons on site will be published on the Ariel Platform, as well as all updates related to the evolution of the legislation imposed by Covid-19.
The recording of the lessons will be accessible on MS-Teams within the class Team. The pdf files of the slides used during the lessons will be made available through the Ariel Platform.
At least 30% of the practical training will be held in person in the lab. The remaining 70% will be held in a virtual lab. If it is not possible, all the practical training will be will be held synchronously using the Microsoft Teams platform.

Program and reference material
The program and reference material will not be modified.

Methods for verification of learning and evaluation criteria.
The examination will take place in written form in person. Students unable to reach the University due to reasons related to the Covid-19 emergency, will still be allowed to take the exam remotely.
The characteristics of the test and the evaluation criteria will not be modified.
Remote exams will be carried out using the Microsoft Teams Platform and exam.net, as illustrated on the University portal (https://www.unimi.it/it/studiare/frequentare-un-corso-di-laurea/segui -the-course-of-studies / exams / distance-exams-faq-the-students). Students enrolled in the exam will receive by e-mail all the necessary information.
Course syllabus
Program of the frontal lessons
1) Laboratory Techniques
2) Extractive and synthetic methodologies useful in the identification, optimization and production of a drug.
a-Extractive techniques (distillation in steam current; extraction with solvents; Soxhlet and percolators; extraction with supercritical fluids, extraction with microwave, extraction with ultrasound, extraction with pressurized liquids, extraction with Extractor Naviglio)
b-Bioguided fractionation and Craig's countercurrent distribution. Examples: camptotecine and Taxol isolation
c- Solution Phase synthesis
d- Peptide synthesis
e- High-efficiency synthetic methodologies: microwave-assisted synthesis, solid-phase synthesis, flow chemistry, synthesis with immobilized reagents, parallel and combinatorial synthesis.
f- Preparation of drugs by fermentation and modifications through semisynthetic approaches, precursor-driven biosynthesis and mutasynthesis.
g- Biotechnology to solve the problem of the supply of drugs of natural origin

Practical training
- Synthesis of paracetamol, bleaching, purification by recrystallization
- Synthesis of lidocaine and purification by recrystallization
- Extraction of trimyristin with solvents from nutmeg and purification by recrystallization
- Extraction of eugenol from cloves by distillation under steam current
- Extraction of caffeine with solvents from tea leaves and purification by recrystallization
- Synthesis of the dipeptide N-Boc-Phe-Phe-COOEt (protection of Phe with Boc, obtainment of Phe-COOEt free base, coupling reaction the DCC/DMAP).
Prerequisites for admission
Background in Organic Chemistry
Teaching methods
Frontal lessons and practical training
Teaching Resources
- Power point presentations of the lessons, as PDF file, are available on the Ariel platform.
- Additional educational material may be suggested by the teacher during the lessons and made available through the Ariel platform.
Assessment methods and Criteria
The exam is a written test (90 minute time limit) including 3 questions on the topics of the theoretical course and 2 questions aimed at evaluating the comprehension of the practical training. The evaluation will take into consideration the student's ability to correctly understand the questions and chose, elaborate and interconnect the information and knowledge acquired during the course, using an appropriate scientific language. The evaluation obtained in the written test is added to a maximum of 3 points, based on the evaluation of the laboratory activity.
Extractive and Synthetic Preparation of Drugs
CHIM/08 - PHARMACEUTICAL CHEMISTRY - University credits: 3
Lessons: 24 hours
Professor: Tamborini Lucia
Laboratory of Extractive and Synthetic Preparation of Drugs
CHIM/08 - PHARMACEUTICAL CHEMISTRY - University credits: 3
Single bench laboratory practical: 48 hours
Professor: Tamborini Lucia
Shifts:
Turno 1
Professor: Tamborini Lucia
Turno 2
Professor: Tamborini Lucia

Linea LZ

Responsible
Lesson period
Second semester
Didactic methods
The lessons scheduled for the second semester will be held synchronously using the Microsoft Teams platform. If the regulations concerning social distancing will allow it and if classrooms will be available, part of the lessons will be held in person. All lessons will be also simultaneously available remotely through the Microsoft Teams Platform. The rules for participation to the lessons on-site will be published on the Ariel Platform, as well as all updates related to the evolution of the legislation imposed by Covid-19.
The recording of the lessons will be accessible on MS-Teams within the class Team. The pdf files of the slides used during the lessons will be made available through the Ariel Platform.
At least 30% of the practical training will be held in person in the lab. The remaining 70% will be held in a virtual lab. If it is not possible, all the practical training will be held synchronously using the Microsoft Teams platform.

Program and reference material
The program and reference material will not be modified.

Methods for verification of learning and evaluation criteria.
As in the past, the examination will take place in written form remotely or, if the regulations will allow it, in person. In the latter case, students unable to reach the University due to reasons related to the Covid-19 emergency will still be allowed to take the exam remotely.
The characteristics of the test and the evaluation criteria will not be modified.
Remote exams will be carried out using the Microsoft Teams Platform and exam.net, as illustrated on the University portal (https://www.unimi.it/it/studiare/frequentare-un-corso-di-laurea/segui -the-course-of-studies / exams / distance-exams-faq-the-students). Students enrolled in the exam will receive by e-mail all the necessary information.
Course syllabus
Program of the frontal lessons:
1) Laboratory Techniques
2) Extractive and synthetic methodologies useful in the identification, optimization, and production of a drug.
a-Extractive techniques (distillation in the steam current; extraction with solvents; Soxhlet and percolators; extraction with supercritical fluids, extraction with microwave, extraction with ultrasound, extraction with pressurized liquids, extraction with Extractor Naviglio)
b-Bioguided fractionation and Craig's countercurrent distribution. Examples: camptothecin and Taxol isolation
c- Solution Phase synthesis
d- Peptide synthesis
e- High-efficiency synthetic methodologies: microwave-assisted synthesis, solid-phase synthesis, flow chemistry, synthesis with immobilized reagents, parallel and combinatorial synthesis.
f- Preparation of drugs by fermentation and modifications through semisynthetic approaches, precursor-driven biosynthesis, and mutasynthesis.
g- Biotechnology to solve the problem of the supply of drugs of natural origin.

Program of practical training:
- Synthesis of paracetamol, bleaching, purification by recrystallization
- Synthesis of lidocaine and purification by recrystallization
- Extraction of trimyristin with solvents from nutmeg and purification by recrystallization
- Extraction of eugenol from cloves by distillation under steam current
- Extraction of caffeine with solvents from tea leaves and purification by recrystallization
- Synthesis of the dipeptide N-Boc-Phe-Phe-COOEt (protection of Phe with Boc, obtainment of Phe-COOEt free base, coupling reaction the DCC/DMAP).
Prerequisites for admission
Background in Organic Chemistry, e.g., safety in an organic laboratory.
Teaching methods
Frontal lessons and practical training.
Teaching Resources
Powerpoint presentations of the lessons, as PDF files, are available on the Ariel platform. Additional educational material may be suggested by the teacher during the lessons and made available through the Ariel platform.
Assessment methods and Criteria
The exam is a written test (90 minute time limit) including 3 questions on the topics of the theoretical course and 2 questions aimed at evaluating the comprehension of the practical training. The evaluation will take into consideration the student's ability to correctly understand the questions and chose, elaborate and interconnect the information and knowledge acquired during the course, using an appropriate scientific language. The evaluation obtained in the written test is added to a maximum of 3 points, based on the evaluation of the laboratory activity.
Extractive and Synthetic Preparation of Drugs
CHIM/08 - PHARMACEUTICAL CHEMISTRY - University credits: 3
Lessons: 24 hours
Professor: Grazioso Giovanni
Laboratory of Extractive and Synthetic Preparation of Drugs
CHIM/08 - PHARMACEUTICAL CHEMISTRY - University credits: 3
Single bench laboratory practical: 48 hours
Professor: Fumagalli Laura
Professor(s)
Reception:
Friday 10.30 -12.30, fixing an appointment by email
Office 2015 - Lab. 2053 - Via Mangiagalli 25