Scheda programma d'esame
Anno accademico2023/24
PeriodoPrimo semestre

Programma non disponibile nella lingua selezionata
Learning outcomes

Introduction to Medicinal Chemistry will give to the students an overview of the issues and methods related with the synthesis and screening of new biological active molecules. Drug Design, Combinatorial approaches and Bioconjugation methods will be discussed from an organic chemistry point of view. The language of the course is English, while the exams will be held in any language understood by the instructor.

Assessment criteria of knowledge

Current research-related issues will be proposed to the students, to discuss possible solutions.


At the end of the course:

  • the students will be able to propose mimetics and analogs of natural molecules and biological active compounds
  • the students will be able to propose strategies for the design of combinatorial experiments
  • the students will be able to propose  synthetic methods of designed drugs
  • the students will learn the most common challenges for a medicinal chemist and will have some knowledge of recent advances in medicinal chemistry
Assessment criteria of skills

Current research-related issues will be proposed to the students, to discuss possible solutions.


At this point of their career, students should already possess all the soft skills they will need in the future, like managing their time, collaborate with their collegues and discuss their ideas. This course could be an opportunity to train those skills.

Assessment criteria of behaviors
  • Didactic project has been proposed. Through the creation of a Science divulgation Journal "Il Piccolo Cimento", students will have the opportunity to train their skills and behaviours, collaborating with each other in writing minireviews about particular topics of the course.

Good knowledge of Organic Chemistry are required, particularly regarding, synthetic methods, reactions mechanisms, and stereochemistry.

Teaching methods
  • The course consists of direct lectures, but open debate is appreciated
  • PowerPoint presentations (in English) are used for the lessons
  • Meetings can be fixed directly e-mailing the teacher

- Introduction on the contents and objectives of the course. Books suggested, and mode of examination. - Nomenclature in Med Chem - Drug activity phases into the body - Drug Classification Systems - Strategies in the search for new lead compounds: Analog Design, Systematic screening, Explotaion of biological informations, Planned research and rational design

- Primary Structure Activity - Topological exploration of lead compounds - Reasoning by functionalities - Application Rules - Isosterism: Hystory & Definitions - Ring equivalents - Bioisosters of Pyridine, Pyridazine, Oxazolidinone, Carboxylic acid derivatives, carboxiamides, Urea and Thiourea derivatives, phenol functions and halogens

- Ring Transormations using: Analogical approach, Disjunctive or Conjunctive approach. - Imprtance of Macrocycles in Med Chem - History, Importance and Use of Combinatorial Chemistry in the discovery and development of new drugs - Methods and Techniques: Splity and Mix libraries; Houghton's Tea bag method;Parallel Synthesis - Reading and Interpretation of Combi libraries: Deconvolution methods; Encoding and Tagging methods. - Multicomponent Reactions: Strecker, Bigginelli, Passerini Ugi reactions - Bioconjugation methods useful for Combi Chem: Reductive amination; Morita-Baylis-Hillman reaction; S-alkylation; Native Chemical Ligation; Click Chemistry - Bio-orthogonal reactions; Copper-free click chemistry

-  Dynamic Combinatorial Chemistry: Hystory and application in Med Chem. - Exchange reactions used in DCLs - Development of synthetic receptors and ligands for biomolecules using DCLs - Different strategies to find ligands for biomolecules in DCLs: Stoichiometric DCLs, Post-modified DCLs, Pre-equilibrated and itered DCLs, Tethering approach, In situ Click approach

- Optical isomerism in drugs, three-point contact model, definition of Eutomers, Distomers and Eudismic quotient/index. Pfeiffer's rule and practical considerations on chirality on drugs. - Solubilizing moieties: acidic solubilizing chains, basic solubilizing chains, non-ionizible solubilizing chains. - Short overview on System Chemistry to conclude the discussion on Combi Chem. Self-replicator systems, Asymmetric Autocatalysis.

- QSAR Quantitative Structure-Activity Relationship; - Electronic effects: The Hammett equation - Lipophilic effects: The Hansch equation - Steric effects: The Taft equation; Molar refractivity and Verloop parameters - Influence of Substituent groups on Lead molecules: Methyl substitution effects on solubility, lipophilicity, crystal lattice cohesion, conformational constrain, metabolism Effects of Vinyl and Allylic substituent groups, N-Allyl derivatives, Acetylenic groups - Effects of Halogenation - Effects of Hydroxylation

- Drug Delivery Systems General techniques of Pharmaceutical preparations: Passive, pre-regulated delivery sysyems. Active self-regulated delivery systems. - Main mechanisms to control drug the drug release: Dissolution, Partitioning, Diffusion, Osmosis, Swelling, Erosion, Targeting.

- Introduction to Nanomedicine 

- Exercises in the class-room based on real case studies. Students proposed solutions for Drug-Design issues, Med Chem strategies. SAR studies.

  • Slides and notes of the lectures
  • Literature cited during lecture (all references will be given)
  • The Practice of Medicinal Chemistry (C. G. Wermuth et al, Elsevier)
  • The Organic Chemistry of Drug Design and Drug Action (Silverman and Holladay, Elsevier)
  • Chemistry of Bioconjugates, (Narain, Wiley)
Non-attending students info
  • An oral examination will be used as assessment method
  • the oral examination is normally 30-40 minutes long
  • the examination consists of questions concerning the course
  • candidates will be initially asked to propose design and synthesis of analogs of given molecules, as a starting point for exam questions
  • At the end of the examination, the teacher will assign a score (from 18/18 to a max of 30/30 cum laude) reflecting student's degree of preparation.


Additional web pages


For the academic year 2022/2023 the course of Medicinal Chemistry will be involved in the didactic project "Il Piccolo Cimento", in collaboration with other 2 courses. More informations will be given the first day of lesson.

Ultimo aggiornamento 31/07/2023 14:28