Reusability report: Learning the language of synthetic methods used in medicinal chemistry

Author(s):  
Jon Paul Janet ◽  
Anna Tomberg ◽  
Jonas Boström
2021 ◽  
Vol 25 ◽  
Author(s):  
Dhaval B. Patel ◽  
Jagruti A. Parmar ◽  
Siddharth S. Patel ◽  
Unnati J. Naik ◽  
Hitesh D. Patel

: The synthesis of ester containing heterocyclic compounds via multicomponent reaction is one of the most preferable process in the synthetic organic chemistry and medicinal chemistry. Compounds containing ester linkage have a wide range of biological application in the pharmaceutical field. Therefore, many method have been developed for the synthesis of these type of derivatives. However, some of them are carried out in the presence of toxic solvents and catalysts, with lower yields, longer reaction times, low selectivities and by-products. Thus, the development of new synthetic methods for the ester synthesis is required in the medicinal chemistry. As we know, multicomponent reactions (MCRs) are a powerful tool towards the one-pot ester synthesis, so in this article we have reviewed the recent developments in ester synthesis. This work covers selected explanation of methods via multicomponent reactions to explore the methodological development in ester synthesis.


Molecules ◽  
2019 ◽  
Vol 25 (1) ◽  
pp. 42 ◽  
Author(s):  
Alina Secrieru ◽  
Paul Michael O’Neill ◽  
Maria Lurdes Santos Cristiano

Pyrazoles are known as versatile scaffolds in organic synthesis and medicinal chemistry, often used as starting materials for the preparation of more complex heterocyclic systems with relevance in the pharmaceutical field. Pyrazoles are also interesting compounds from a structural viewpoint, mainly because they exhibit tautomerism. This phenomenon may influence their reactivity, with possible impact on the synthetic strategies where pyrazoles take part, as well as on the biological activities of targets bearing a pyrazole moiety, since a change in structure translates into changes in properties. Investigations of the structure of pyrazoles that unravel the tautomeric and conformational preferences are therefore of upmost relevance. 3(5)-Aminopyrazoles are largely explored as precursors in the synthesis of condensed heterocyclic systems, namely pyrazolo[1,5-a]pyrimidines. However, the information available in the literature concerning the structure and chemistry of 3(5)-aminopyrazoles is scarce and disperse. We provide a revision of data on the present subject, based on investigations using theoretical and experimental methods, together with the applications of the compounds in synthesis. It is expected that the combined information will contribute to a deeper understanding of structure/reactivity relationships in this class of heterocycles, with a positive impact in the design of synthetic methods, where they take part.


2019 ◽  
Author(s):  
Marc R. Becker ◽  
Alistair D. Richardson ◽  
Corinna S. Schindler

<p>Azetidines are four-membered nitrogen-containing heterocycles that hold great promise in current medicinal chemistry due to their desirable pharmacokinetic effects. However, a lack of efficient synthetic methods to access functionalized azetidines has hampered their incorporation into pharmaceutical lead structures. As [2+2] cycloaddition reaction between imines and alkenes, the aza Paternò-Büchi reaction arguably represents the most direct approach to functionalized azetidines. Currently, competing reaction paths accessible upon photochemical excitation of the substrates greatly restrict the synthetic utility of these transformations. We herein report the development of a visible light-enabled aza Paternò-Büchi reaction that surmounts existing limitations and represents a general solution for the direct formation of functionalized azetidines from imine and alkene containing precursors.<br></p><br><p></p>


2018 ◽  
Vol 18 (17) ◽  
pp. 1428-1453 ◽  
Author(s):  
Luana da S.M. Forezi ◽  
Mariana F.C. Cardoso ◽  
Daniel T.G. Gonzaga ◽  
Fernando de C. da Silva ◽  
Vitor F. Ferreira

Heterocyclic rings having nitrogen atoms are the molecular fragments most used in drug design by using the tools of medicinal chemistry. The 1,2,4-triazole rings are part of an extensive family of drugs that are in use in the pharmaceutical market. More recently, 1,2,3-triazole rings have begun to arouse the great interest of scientists and therefore, many researches have been developed seeking the synthesis of new substances and their possible biological activities. A number of articles have been published by us and others highlighting the synthetic and biological aspects of 1,2,3-triazoles. The growth of new substances of this class was largely due to the simple and selective synthetic method of 1,2,3- triazole ring developed by Sharpless et al. However, some 1,2,3-triazole cannot be synthesized by this method. This review focuses on other synthetic methods that give access to other variations around the 1,2,3-triazole core. The systematic arrangement in this review explores the possibility of providing practical guidance to alternatives of this heterocycle. It has been divided into sections according to the types of starting materials and reactions.


2017 ◽  
Vol 15 (14) ◽  
pp. 2906-2909 ◽  
Author(s):  
Alexander Sapegin ◽  
Angelina Osipyan ◽  
Mikhail Krasavin

A facile approach to hitherto unknown ten-membered ring systems via a hydrolytic imidazoline ring expansion (HIRE) is described. Medium-sized rings are scarce in the contemporary medicinal chemistry toolbox. The new HIRE strategy broadens the arsenal of synthetic methods to obtain such scaffolds.


2021 ◽  
Vol 25 ◽  
Author(s):  
Paolo Ronchi ◽  
Sara Guariento ◽  
Daniele Pala ◽  
Daniela Pizzirani ◽  
Claudio Fiorelli ◽  
...  

: The use of F-based decorations in drug discovery started from the development of fluorocorticoids and fluorochinolones (1950s and 1980s, respectively), and has resulted in about 20% of approved drugs on the Market containing fluorine. From a medicinal chemistry perspective, the installation of F-based small groups (e.g., CF3, -CF2H, -OCF3, -OCF2H, -SCF3, -SCF2H) necessarily impacts on physicochemical, pharmacokinetics, pharmacodynamics and toxicological properties of small molecules. Accordingly, a huge interest in this topic is constantly arising in the medicinal chemistry community. Focusing on heteroarenes, the synthetic access to these substitutions is guaranteed by a number of effective reactions such as Minisci-type reaction, photochemistry or electrochemistry C-H activation. The aim of this work is to analyze the rationale in using these groups in medicinal chemistry and highlight the currently available synthetic toolbox of C-H activation for their introduction on heteroarenes of pharmaceutical interest. A particular focus has been given to those procedures amenable to the late-stage functionalisation process.


2019 ◽  
Author(s):  
Marc R. Becker ◽  
Alistair D. Richardson ◽  
Corinna S. Schindler

<p>Azetidines are four-membered nitrogen-containing heterocycles that hold great promise in current medicinal chemistry due to their desirable pharmacokinetic effects. However, a lack of efficient synthetic methods to access functionalized azetidines has hampered their incorporation into pharmaceutical lead structures. As [2+2] cycloaddition reaction between imines and alkenes, the aza Paternò-Büchi reaction arguably represents the most direct approach to functionalized azetidines. Currently, competing reaction paths accessible upon photochemical excitation of the substrates greatly restrict the synthetic utility of these transformations. We herein report the development of a visible light-enabled aza Paternò-Büchi reaction that surmounts existing limitations and represents a general solution for the direct formation of functionalized azetidines from imine and alkene containing precursors.<br></p><br><p></p>


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