LABORATORY OF EXTRACTIVE AND SYNTHETIC PREPARATIONS OF DRUGS (LESPD)
Academic year and teacher
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- Versione italiana
- Academic year
- 2022/2023
- Teacher
- DELIA PRETI
- Credits
- 9
- Didactic period
- Primo Semestre
- SSD
- CHIM/08
Training objectives
- KNOWLEDGE AND UNDERSTANDING
The main objective of this course is to provide students with the basic theoretical and practical knowledge allowing them to obtain a drug either synthetically or through 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 basic principles of the retrosynthetic approach.
APPLYING KNOWLEDGE AND UNDERSTANDING
Students will acquire the following skills:
_ Ability to understand, discuss with an appropriate language and critically apply synthetic/extractive procedures reported in the literature.
_ Ability to set up and monitor organic reactions.
_ Ability to isolate a product from reaction mixtures through crystallization, distillation, filtration, extraction and chromatography procedures.
_ Ability to use the basic equipment of a synthetic laboratory.
_ Ability to design with a critical approach the synthesis of a biologically active molecule by retrosynthetic analysis and through appropriate disconnections. Prerequisites
- It is essential to have acquired the knowledge provided by the courses of General and Inorganic Chemistry, Organic Chemistry and Advanced Organic Chemistry. In order to fully achieve the educational objectives, it is also recommended that you have attended the courses of Pharmaceutical and Toxicological Chemistry I, Pharmaceutical and Toxicological Chemistry II, Physical Methods in Organic Chemistry and Drug Design. Finally, the practical laboratory skills gained in the courses of Organic Chemistry, Advanced Organic Chemistry, Qualitative and Quantitative Drug Analysis are highly recommended.
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; 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), the first 13 of which will be delivered in video-recorded mode through the teaching classroom before the beginning of the laboratories. 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
- 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.
