HETEROCYCLES IN MEDICINAL CHEMISTRY AND ENVIRONMENTAL IMPACT

Università degli Studi
"G. d'Annunzio"

Chieti - Pescara

Single discipline educational activity

Course Sheet

Course code:

CEF010

Academic Year of enrolment:

2020

Year of supply:

2022/2023

Type of Course:

Elective Course

Degree:

Course of 1st Cycle Degree in SUSTAINABLE TECHNOLOGIES AND ENVIRONMENTAL TOXICOLOGY

Disciplinary Sector:

Pharmaceutical Chemistry

Language:

Italian

Location:

CHIETI

Credits:

Programme Year:

Professor and Collaborators:

DE FILIPPIS Barbara

Cycle:

First semester

Obligatory attendance:

Yes

Minimum hours of attendance:

Hours of classroom activity:

Individual study hours:

Prerequisites:

The study requires a good knowledge of Organic Chemistry and the fundamental concepts of Biochemistry.
In order to understand and be able to apply most of the topics described in the course it is necessary to have successfully taken the exam of Organic Chemistry and Biochemistry.

The topics covered in the course require a good knowledge of protein structures, the main types of inter and intramolecular interaction, the main chemical-physical parameters that characterize a drug. Good knowledge of these issues is an important prerequisite for the student who wants to follow the course profitably.
Preparatory examinations: Organic chemistry

Objectives

The course is aimed at acquiring knowledge and understanding the classification, nomenclature, structural properties, reactivity of the main simple and condensed heterocyclic compounds of pharmaceutical interest; provide a general knowledge of synthetic strategies and functionalization of heterocyclic systems, with particular attention to the intermediates involved in reactions.

Contents

definition and classification of heterocyclic compounds; nomenclature of heterocyclic compounds; main methods of synthesis with a focus on green chemistry; examples of natural molecules and of pharmaceutical interest with heterocyclic nucleus

Extended Syllabus

Generalità: Definizione, caratteristiche chimiche, diffusione in natura, utilizzo pratico.
Introduzione ai composti eterociclici: Classificazione e nomenclatura italiana ed inglese dei principali composti eterociclici e policiclici. Sistema Hantzsch-Widman, nomi d'uso, nomenclatura dei tautomeri; sistemi eterociclici condensati, nomenclatura sistematica alternativa, composti eterociclici spiranici. Basicità dei sistemi eterociclici azotati.
Utilizzo del programma ChemDraw (online e offline) per assegnare e controllare la nomenclatura.
Parte specifica: La trattazione di ogni anello eterociclico consiste in ciascuna delle parti che seguono: struttura e proprietà fisiche; proprietà chimiche e metodi di sintesi; derivati principali, prodotti naturali, farmaci correlati, intermedi industriali; uso come reagenti, building-blocks o ausiliari in sintesi.
- Reattività dei sistemi eterociclici. Reattività dei sistemi eteroaromatici: comportamento di fronte agli elettrofili, reazioni di sostituzione nucleofila, comportamento di fronte ai riducenti e agli ossidanti. Idrossiderivati di sistemi eteroaromatici: tautomeria cheto-enolica, reattività nucleofila. Amminoderivati di sistemi eteroaromatici: basicità, reazione di diazotazione.
- Classi farmaceutiche di derivati eterociclici: Benzodiazepine, barbiturici, chinoloni, piridine, piperidine, pirimidine, fenotiazine, cumarine.
General section: Definition, chemical characteristics, diffusion in nature, practical use.
Introduction to heterocyclic compounds: Italian and English classification and nomenclature of the main heterocyclic and polycyclic compounds. Hantzsch-Widman system, use of names, nomenclature of tautomers; condensed heterocyclic systems, alternative systematic nomenclature, spiranic heterocyclic compounds. Basicity of nitrogenous heterocyclic systems. Using the ChemDraw program (online and offline) to assign and control nomenclature.
Special part: The treatment of each heterocyclic ring consists of each of the following parts: structure and physical properties; chemical properties and methods of synthesis; main derivatives, natural products, related drugs, industrial intermediates; use as reagents, building-blocks or auxiliaries in synthesis.
- Reactivity of heterocyclic systems. Reactivity of heteroaromatic systems: behavior in front of electrophiles, nucleophilic substitution reactions, behavior in the face of reducing agents and oxidants. Hydroxyderivatives of heteroaromatic systems: keto-enolic tautomerism, nucleophilic reactivity. Amino derivatives of heteroaromatic systems: basicity, nitrogen reaction.
- Pharmaceutical classes of heterocyclic derivatives: Benzodiazepines, barbiturates, quinolones, pyridines, piperidines, pyrimidines, phenothiazines, coumarins.

Recommended Bibliography

- Sica, Zollo. CHIMICA DEI COMPOSTI ETEROCICLI FARMACOLOGICAMENTE ATTIVI
- teaching material from the teacher

Methods of Provision

Conventional

Teaching Methods

Lectures with the help of multimedia supports. During the course, the teacher verifies the students' ability to know the proposed topics through self-assessment tests to be carried out independently or in a group comparison. This has no impact on the final evaluation of the student but aims to monitor and accompany the student to a methodical and continuous study throughout the course.

Evaluation methods

Verification of learning:

The final evaluation consists of an oral exam. The type of talk aims to cover the entire program carried out and verify the level of learning achieved, the ability to correctly apply the knowledge acquired, the ability to develop solutions in autonomous judgment.

The exam aims to verify the level of learning of the student and the ability to argue on topics related to the entire program in an appropriate manner. The student must demonstrate their knowledge of the chemical structures and chemical properties of drugs, the pharmacological target and the pathology for which the drugs are used as well as the summaries proposed during the course.

Università degli Studi
"G. d'Annunzio"

Chieti - Pescara

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