Exercises in Organic Synthesis Based on Synthetic Drugs

Marcus Vinícius Nora de Souza

• Publisher: Bentham Science Publishers
• Year: 2020
• eBook ISBN: 9789811487569
• Topic: Ciencias físicas
• Subtopic: Química orgánica

Exercises in Organic Synthesis Based on Synthetic Drugs presents information on topics about the synthesis of biologically active compounds which are used against a range of diseases in both humans and animals. Topics are supplemented by notes and exercises for students to stimulate inquiry and learning in the academic environment. Readers will be equipped with basic knowledge of synthetic techniques used in organic chemistry and pharmaceutical research and development. Key Features: - Presents information about different techniques and strategies for the synthesis of organic compounds- Covers a broad range of biologically active compounds- Easy to read topical presentation- Exercises, with answers, designed for improving concepts in organic synthesis and medicinal chemistry- Wide range of bibliographic references for further reading and exercises presented, Exercises in Organic Synthesis Based on Synthetic Drugs is an essential textbook for students in beginner level courses in organic chemistry, organic synthesis and medicinal chemistry.

Identifying Drug Structure and Completing the Gaps

Marcus Vinícius Nora de Souza

Abstract

In this chapter, the exercises below are also based on two themes. The first has an objective of the identification of the structure of the drugs having information of the starting materials and reagents used. This activity also enables the reader to become familiar with different classical chemical transformations used in medicinal chemistry and with varying types of reagents, reaction conditions, and necessary intermediates. In the second theme, the exercises are based on a series of gaps in the synthesis of different drugs. Therefore, it is up to the reader to complete them. This type of exercise is a combination of the themes previously presented. It is necessary to identify the reagents' use, the reaction conditions employed, and the intermediates formed, besides the use of the concept of retrosynthesis.

Keywords: Bioactive compounds, Chemical transformations, Drugs, Exercises, Medicinal chemistry, Molecules, Reaction conditions, Reagents, Retrosynthetic analysis, Substances, Synthesis, Synthons.

EXERCISE 7 - IDENTIFYING DRUG STRUCTURE

The exercises below have an objective of the identification of the structure of the drugs having information of the starting materials and reagents used.

Examples

a) What is the structure of the drug lubiprostone after heating the intermediate below?

b) What is the structure of the drug below? Can step number two be performed with heating and excess ammonia? Justify.

Answers

a) We can observe that an intramolecular cyclization occurs between the hydroxyl and the carbonyl, with the formation of a six-membered ring (hemiacetal - tautomerism chain-ring).

b) The first two steps are easy because they are classical and widely used transformations, thionyl chloride followed...

Table of contents

• Welcome
• Table of Content
• Title
• BENTHAM SCIENCE PUBLISHERS LTD.
• PREFACE
• How to Build a Drug: Exercises Based on the Concept of Retrosynthetic Analysis
• Identifying Drug Structure and Completing the Gaps
• Organizing Synthetic Routes and Identifying Reagents
• Heteroaromatic Substances
• Hydrazine and its Derivatives
• Nitriles
• Combinatorial Chemistry
• Multicomponent Reaction (MCR)
• Click Chemistry
• Fluorine in Drug Discovery
• LIST OF JOURNALS USED AND THEIR RESPECTIVE ABBREVIATIONS
• LIST OF ABBREVIATIONS