LABORATORY OF EXTRACTIVE AND SYNTHETIC PREPARATIONS OF DRUGS (LESPD)
Academic year and teacher
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- Versione italiana
- Academic year
- 2020/2021
- Teacher
- DELIA PRETI
- Credits
- 9
- Didactic period
- Primo Semestre
- SSD
- CHIM/08
Training objectives
- The main educational objective of this course is to provide students with the basic theoretical and practical knowledge that allows them to obtain a drug either synthetically or for extraction from vegetable raw materials. Laboratory experiences are an essential part of the training program and will be aimed at developing the necessary manual skills for the synthesis / extraction of compounds of pharmaceutical interest. The course also aims to train students on the ability to identify the optimal synthetic path for the realization of an organic molecule using a retrosynthetic approach.
The main skills acquired by the student at the end of the course will be:
_Understanding, discussing with appropriate language, and critically applying synthetic / extractive procedures reported in the literature.
_Set up and monitor organic reactions.
_Isolate a product from reaction mixtures through crystallization, distillation, filtration, extraction and chromatography procedures.
_Use the basic equipment of a synthetic laboratory.
_Designing with a critical approach the synthesis of a biologically active molecule by retrosynthetic analysis and through appropriate disconnections. Prerequisites
- In view of the course contents it is essential to have acquired the knowledge provided by General and inorganic chemistry, Organic chemistry and Advanced organic chemistry. The knowledge from the courses of Pharmaceutical and Toxicological Chemistry I, Pharmaceutical and Toxicological Chemistry II, Physical methods in organic chemistry and Drug Design are recommended. Lastly, the practical laboratory skills acquired in the courses of Organic Chemistry, Advanced Organic Chemistry, Qualitative and Quantitative Analysis of Drugs are necessary prerequisites.
Course programme
- THEORETICAL LESSONS (32 hours, 4 CFU):
Starting notes: general safety directions in a synthetic laboratory; Laboratory notebook: his compilation and care.
Techniques of a synthetic laboratory (equipment and procedures): Solid separation techniques from liquids: filtration systems; Extraction with solvents and use of the separating funnel; Column chromatography; Thin layer chromatography (TLC); Purification of liquids: distillation; Purification of solids: crystallization; Heating, cooling and stirring techniques; Drying of liquids and solids; Reactions in inert atmosphere.
Advanced synthetic methodologies: Principles of green chemistry; Use of alternative solvents: ionic liquids, supercritical fluids; Domino reactions and multicomponent reactions. Oxidizing and reducing agents; Coupling reactions mediated by Palladium (reactions of Stille, Heck, Sonogashira, Suzuki). Design of a synthetic pathway with the disconnection approach.
PRACTICAL EXERCISES (60 hours, 5 CFU):
Separation of a mixture of compounds by extraction; Synthesis of isoniazid; Synthesis of acetyl salicylic acid; Paracetamol synthesis; Extraction of limonene from orange peels; Enzymatic reduction of a beta keto ester with Baker's yeast; Chemical reduction of a beta keto ester with NaBH4. Reduction of methyl paranitrobenzoate; Saponification of methyl paranitrobenzoate; Extraction of eugenol from the cloves; extraction of limonene from orange peel; Synthesis of Phenacetin. Synthesis of an isoxazole derivative. Didactic methods
- The course will be given in lectures for a total of 32 hours (4 CFU). These will be accompanied by practical laboratory exercises that will require a total commitment of 60 hours (15 experiences of 4 hours each for a total of 5 CFU). The theoretical lessons will take advantage of computer aids and will provide students with the prerequisites of the methods to be applied on a practical level during the experiences of synthesis and extraction of bioactive molecules.
Learning assessment procedures
- Learning assessment will take into account the skills acquired from both a practical and a theoretical point of view and will be structured as follows:
1) An oral exam that includes three questions: a) a question concerning one of the experiences faced in the laboratory aimed at ascertaining the achievement of adequate knowledge of the basic techniques to be applied to the synthesis and extraction of organic molecules; b) a question concerning one of the reaction classes addressed during the theoretical course; c) the last question is the retrosynthetic analysis of a molecule. (from 0 to 22 points).
2) Evaluation of the laboratory notebook during the oral exam (from 0 to 3 points, the student is required to deliver the notebook at least one week before the date scheduled for the oral exam, a necessary condition for taking the final exam).
3) The teacher and the teaching support staff will constantly monitor and evaluate the autonomy and attitudes shown by the student during practical laboratory activities (from 0 to 8 points, the frequency of the laboratory is a necessary condition for the oral exam).
An overall score of 33 corresponds to the final evaluation of 30/30 cum laude. A score between 30 and 32 leads to a final evaluation of 30/30. A score above 18 is necessary for passing the exam. Reference texts
- Slides and notes provided by the teacher.
For any further information, the following texts are recommended:
1) Costantino L, Barlocco D. Laboratory for the extractive and synthetic drug preparation. Aracne publishing house 2017.
2) Stuart Warren, Paul Wyatt. Organic synthesis: The disconnection approach. Second edition. Wiley 2008.
3) Jonathan Clayden, Nick Greeves, Stuart Warren. Organic Chemistry.
