Ateneo - UPO

The course examines the structure-activity relationship (SAR) of secondary metabolites and toxins of animal and plant origin, analyzing their toxicity profiles and therapeutic potential. The course will explore organic synthesis strategies and structural chemical modifications (semisynthesis, bioisosterics, and functionalization) necessary to reduce the toxicity of these molecules and optimize their pharmacokinetic and pharmacodynamic properties, as lead compounds for the development of new drugs.

Lecture slides will be provided, along with articles focusing on the total synthesis or semisynthesis of the molecules covered. Recommended software: Students are encouraged to use open-source chemical drawing software for independent practice with structures.

Module B (1 CFU) aims to provide a scientific overview of the dual nature of chemistry, highlighting how the intrinsic properties of naturally occurring substances—initially discovered as poisons—can be utilized and transformed into compounds of pharmacological interest.
The module introduces students to a critical evaluation of the chemical and physical properties, reactivity, and methods of use of naturally occurring substances, providing them with a comprehensive overview of the role of these substances as active ingredients in the development of safe and effective therapeutic agents.

Students should have mastered the topics covered in the Organic Chemistry courses

Lectures with multimedia support. Students will be provided with the slides used during the lectures via the D.I.R. platform. The concepts covered in the course will be discussed collaboratively in class to foster students’ critical thinking and independent judgment. Communication skills will be developed through the use of terminology appropriate to the subject matter. Learning skills will be promoted through materials provided by the teacher and case study literature.

The teacher is available to students for any clarifications or explanations regarding the topics covered during the course. Assessment: Classroom discussion of the topics covered in the course. Students with disabilities, Specific Learning Disorders (SLD), or Special Educational Needs (SEN) may request specific services and resources designed for them by contacting the Career Development and Coordination and Student Services Staff and consulting the dedicated page on the University website: https://uniupo.it/it/servizi/servizi-studentidisabili-e-dsa. Students with disabilities, SLDs, or SEN, after contacting the University staff, may contact the course instructor regarding the specific arrangements for the exam and any teaching-related matters.

The final grade will take into account the proficiency of scientific language, the rigor in describing chemical mechanisms, the ability to synthesize information, and the degree of independent judgment demonstrated. The assessment of learning for the module takes place through a written test which includes: 7 multiple-choice questions, each evaluated 1 point, for a total of 7 points; 1 open-ended question, evaluated up to 3 points. The maximum score that can be achieved is 10 points. To pass the module of the course, it is necessary to achieve an evaluation of not less than 6/10.
The final grade of the course will be determined by the sum of the scores obtained in the three modules, for a maximum overall score of 30 points, corresponding to 30/30.

Definition of poison and drug. Definition of a pharmacophore. The evolution of natural toxins into therapeutic agents through structure-activity relationships (SAR). The program introduces the concepts of pharmacophores and modern industrial extraction techniques, and then maps the main naturally occurring scaffolds (flavonoids, coumarins, alkaloids, terpenoids, steroids, and glycosides) from a chemical and biological perspective. The monographic portion of the course is structured around the analysis of five case studies—taxanes, atropine, digoxin, coumarins, and captopril.

By the end of the module, students will be able to: Knowledge and understanding: Identify the main classes of secondary metabolites (alkaloids, glycosides, terpenes, coumarins) with toxic activity; understand the importance of functional groups in determining chemical reactivity and interaction with biological receptors.Ability to apply knowledge: Predict the chemical modifications (e.g., esterifications, alkylations, functional group conversions) requiredIndependence of judgment: Evaluate the chemical stability and reactivity of a toxic moleculeCommunication skills: Describe the mechanisms of molecular interaction with organic chemistry rigor (hydrogen bonds, hydrophobic interactions, reversible/irreversible covalent bonds).