Green Chemistry Approaches to the Synthesis of Coumarin Derivatives

2020 ◽  
Vol 24 (1) ◽  
pp. 4-43 ◽  
Author(s):  
Maja Molnar ◽  
Melita Lončarić ◽  
Marija Kovač

This review is a compilation of the green synthetic methods used in the synthesis of coumarin derivatives. Coumarins are a class of compounds with a pronounced wide range of biological activities, which have found their application in medicine, pharmacology, cosmetics and food industry. Their biological activity and potential application are highly dependent on their structure. Therefore, many researchers have been performing the synthesis of coumarin derivatives on a daily basis. High demands for their synthesis often result in an increased generation of different waste chemicals. In order to minimize the utilization and generation of toxic organic substances, green synthetic methods are applied in this manner. These methods are getting more attention in the last few decades. Green chemistry methods cover a wide range of methods, including the application of ultrasound and microwaves, ionic liquids and deep eutectic solvents, solvent-free synthesis, mechanosynthesis and multicomponent reactions. All typical condensation reactions for coumarin synthesis like Knoevenagel, Perkin, Kostanecki-Robinson, Pechmann and Reformansky reactions, have been successfully performed using these green synthetic methods. According to the authors mentioned in this review, not only these methods reduce the utilization and generation of toxic chemicals, but they can also enhance the reaction performance in terms of product yields, purity, energy consumption and post-synthetic procedures when compared to the conventional methods. Due to the significance of coumarins as biologically active systems and the recent demands of reducing toxic solvents, catalysts and energy consumption, this review provides a first full literature overview on the application of green synthetic methods in the coumarin synthesis. It covers a literature search over the period from 1995-2019. The importance of this work is its comprehensive literature survey on a specific class of heterocyclic compounds, and those researchers working on the coumarin synthesis can find very useful information on the green synthetic approaches to their synthesis. There are some reviews on the coumarin synthesis, but most of them cover only specific reactions on coumarin synthesis and none of them the whole range of green chemistry methods.

2020 ◽  
Vol 16 (6) ◽  
pp. 837-852 ◽  
Author(s):  
Hanan M. Alshibl ◽  
Ebtehal S. Al-Abdullah ◽  
Hamad M. Alkahtani

Background: As coumarin derivatives are known to prevent and treat various diseases, they have attracted the attention of medicinal chemists. They have strong potential as drugs because their benzopyrone structure can interact noncovalently with numerous enzymes and receptors. Methods: The aim of this review was to summarize the most recently published literature on coumarin derivatives in terms of their antioxidant, antimicrobial, anti-inflammatory, anticancer, and other miscellaneous properties. Results: Coumarin derivatives have a wide range of biological activities. They exhibit antioxidant, antimicrobial, anti-inflammatory, anticancer, anti-coagulant, and anti-Alzheimer effects. Conclusion: The coumarin nucleus is an interesting starting point for the design and development of novel bioactive agents. The present review may help medicinal chemists design biologically active molecules based on the coumarin nucleus.


2022 ◽  
Vol 0 (0) ◽  
Author(s):  
Arvind Singh ◽  
Amartya Basu ◽  
Aditi Sharma ◽  
Anu Priya ◽  
Manmmet Kaur ◽  
...  

Abstract 2-Hydroxy-1,4-naphthaquinone, commonly known as lawsone, represents an extremely important biologically active naturally occurring compound. It can easily be isolated from Lawsonia inermis (henna) tree leaf extract. Last decade has seen tremendous applications of lawsone as a starting component for the preparation of various organic scaffolds. Many of these synthesized scaffolds showed a wide range of biological activities including potential activities towards several cancer cell lines. This review deals with diverse synthetic methods of lawsone derived scaffolds and their screening against different anti-cancer cell lines along with promising results.


2019 ◽  
Author(s):  
Chem Int

Coumarin and its derivatives are widely spread in nature. Coumarin goes to agroup as benzopyrones, which consists of a benzene ring connected to a pyronemoiety. Coumarins displayed a broad range of pharmacologically useful profile.Coumarins are considered as a promising group of bioactive compounds thatexhibited a wide range of biological activities like anti-microbial, anti-viral,antiparasitic, anti-helmintic, analgesic, anti-inflammatory, anti-diabetic, anticancer,anti-oxidant, anti-proliferative, anti-convulsant, and antihypertensiveactivities etc. The coumarin compounds have immense interest due to theirdiverse pharmacological properties. In particular, these biological activities makecoumarin compounds more attractive and testing as novel therapeuticcompounds.


2020 ◽  
Vol 16 (3) ◽  
pp. 272-306
Author(s):  
Ioannis Fotopoulos ◽  
Dimitra Hadjipavlou-Litina

Background: Coumarins exhibit a plethora of biological activities, e.g. antiinflammatory and anti-tumor. Molecular hybridization technique has been implemented in the design of novel coumarin hybrids with several bioactive groups in order to obtain molecules with better pharmacological activity and improved pharmacokinetic profile. Objective: Therefore, we tried to gather as many as possible biologically active coumarin hybrids referred in the literature till now, to delineate the structural characteristics in relation to the activities and to have a survey that might help the medicinal chemists to design new coumarin hybrids with drug-likeness and varied bioactivities. Results: The biological activities of the hybrids in most of the cases were found to be different from the biological activities presented by the parent coumarins. The results showed that the hybrid molecules are more potent compared to the standard drugs used in the evaluation experiments. Conclusion: Conjugation of coumarin with varied pharmacophore groups/druglike molecules responsible for different biological activities led to many novel hybrid molecules, with a multitarget behavior and improved pharmacokinetic properties.


Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 249
Author(s):  
Raquel G. Soengas ◽  
Humberto Rodríguez-Solla

The 1,3-butadiene motif is widely found in many natural products and drug candidates with relevant biological activities. Moreover, dienes are important targets for synthetic chemists, due to their ability to give access to a wide range of functional group transformations, including a broad range of C-C bond-forming processes. Therefore, the stereoselective preparation of dienes have attracted much attention over the past decades, and the search for new synthetic protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged in the last decade, with a focus on the synthetic processes that meet the requirements of efficiency and sustainability of modern organic chemistry.


Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3166
Author(s):  
Anthi Petrou ◽  
Maria Fesatidou ◽  
Athina Geronikaki

Background: Thiazole is a good pharmacophore nucleus due to its various pharmaceutical applications. Its derivatives have a wide range of biological activities such as antioxidant, analgesic, and antimicrobial including antibacterial, antifungal, antimalarial, anticancer, antiallergic, antihypertensive, anti-inflammatory, and antipsychotic. Indeed, the thiazole scaffold is contained in more than 18 FDA-approved drugs as well as in numerous experimental drugs. Objective: To summarize recent literature on the biological activities of thiazole ring-containing compounds Methods: A literature survey regarding the topics from the year 2015 up to now was carried out. Older publications were not included, since they were previously analyzed in available peer reviews. Results: Nearly 124 research articles were found, critically analyzed, and arranged regarding the synthesis and biological activities of thiazoles derivatives in the last 5 years.


2012 ◽  
Vol 7 (3) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Zhanjie Xu ◽  
Peng Du ◽  
Peter Meiser ◽  
Claus Jacob

Proanthocyanidins represent a unique class of oligomeric and polymeric secondary metabolites found ubiquitously and in considerable amounts in plants and some algae. These substances exhibit a range of rather surprising physical and chemical properties which, once applied to living organisms, are translated into a multitude of biological activities. The latter include antioxidant properties, cancer chemoprevention, anti-inflammatory and anti-diabetic effects as well as some exceptional, yet highly interesting activities, such as anti-nutritional and antimicrobial activity. Despite the wide range of activities and possible medical/agricultural applications of proanthocyanidins, many questions still remain, including issues related to bioavailability, metabolism and the precise biochemical, extra- and intracellular targets and mode(s) of action of these highly potent materials. Among the various physical and chemical interactions of such substances, strong binding to proteins appears to form the basis of many of their biological activities. Once easy-to-use synthetic methods to produce appropriate quantities of pure proanthocyanidins are available, it will be possible to identify the prime biological targets of these oligomers, study oligomer-protein interactions in more detail and develop possible practical applications in medicine and agriculture.


Author(s):  
Mahathy Vanguru ◽  
Ramchander Merugu ◽  
Swetha Garimella ◽  
Laxminarayana E

Chromones group of compounds and their derivatives form the essential component of pharmacophores in many biologically active molecules. They exhibit a wide range of biological activities such as antibiotic, antitumor, antiviral, antioxidant, antipsychotic, and antihypoxic activities. These applications have stimulated a continuous search for the synthesis of new compounds in this field and are being extensively investigated. The various methodologies so far reported for the synthesis of these compounds with the compounds biological applications are discussed in this communication


Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1178
Author(s):  
Guillermo Otárola ◽  
Juan J. Vaquero ◽  
Estíbaliz Merino ◽  
Manuel A. Fernández-Rodríguez

Four carbon ring systems are frequently present in natural products with remarkable biological activities such as terpenoids, alkaloids, and steroids. The development of new strategies for the assembly of these structures in a rapid and efficient manner has attracted the interest of synthetic chemists for a long time. The current research is focused mainly on the development of synthetic methods that can be performed under mild reaction conditions with a high tolerance to functional groups. In recent years, gold complexes have turned into excellent candidates for this aim, owing to their high reactivity, and are thus capable of promoting a wide range of transformations under mild conditions. Their remarkable efficiency has been thoroughly demonstrated in the synthesis of complex organic molecules from simple starting materials. This review summarizes the main synthetic strategies described for gold-catalyzed four-carbon ring formation, as well as their application in the synthesis of natural products.


2018 ◽  
Vol 18 (2) ◽  
pp. 124-148 ◽  
Author(s):  
Thiago Moreira Pereira ◽  
Daiana Portella Franco ◽  
Felipe Vitorio ◽  
Arthur Eugen Kummerle

Coumarins are natural products characterized as 1,2 benzopyrones widely distributed in plants, as well as, in many species of fungi and bacteria. Nowadays, many synthetic procedures allow the discovery of coumarins with expanded chemical space. The ability to exert noncovalent interactions with many enzymes and receptors in live organisms lead the coumarins to exhibit a wide range of biological activities and applications. Then, this manuscript provides an overview of the use of coumarins compounds in medicinal chemistry in treating many diseases. Important examples of the last years have been selected concerning the activities of coumarins as anticoagulant, anticancer, antioxidant, antiviral, anti-diabetics, anti-inflammatory, antibacterial, antifungal and anti-neurodegerative agents. Additionally, it also includes applications of coumarins as fluorescent sensors for biological systems. Thus, this work aims to contribute to the development of new rational research projects for the treatment and diagnosis of pathologies using coumarin derivatives.


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