scholarly journals Indolylboronic Acids: Preparation and Applications

Molecules ◽  
2019 ◽  
Vol 24 (19) ◽  
pp. 3523
Author(s):  
Marek Čubiňák ◽  
Tereza Edlová ◽  
Peter Polák ◽  
Tomáš Tobrman
Keyword(s):  
Biological Activities ◽  
Chemical Transformations ◽  
Indole Derivatives ◽  
Material Chemistry

Indole derivatives are associated with a variety of both biological activities and applications in the field of material chemistry. A number of different strategies for synthesizing substituted indoles by means of the reactions of indolylboronic acids with electrophilic compounds are considered the methods of choice for modifying indoles because indolylboronic acids are easily available, stable, non-toxic and new reactions using indolylboronic acids have been described in the literature. Thus, the aim of this review is to summarize the methods available for the preparation of indolylboronic acids as well as their chemical transformations. The review covers the period 2010–2019.

Recent Developments on Synthesis of Indole Derivatives Through Green Approaches and Their Pharmaceutical Applications

2020 ◽  
Vol 24 (22) ◽  
pp. 2665-2693
Author(s):  
Dipayan Mondal ◽  
Pankaj Lal Kalar ◽  
Shivam Kori ◽  
Shovanlal Gayen ◽  
Kalpataru Das
Keyword(s):  
Biological Activities ◽  
Synthetic Methods ◽  
Pharmaceutical Chemistry ◽  
Indole Derivatives ◽  
Biological Studies ◽  
Recent Developments ◽  
Pharmaceutical Industries ◽  
Green Methodology ◽  
Conventional Methods ◽  
High Yields

Indole moiety is often found in different classes of pharmaceutically active molecules having various biological activities including anticancer, anti-viral, anti-psychotic, antihypertensive, anti-migraine, anti-arthritis and analgesic activities. Due to enormous applications of indole derivatives in pharmaceutical chemistry, a number of conventional synthetic methods as well as green methodology have been developed for their synthesis. Green methodology has many advantages including high yields, short reaction time, and inexpensive reagents, highly efficient and environmentally benign over conventional methods. Currently, the researchers in academia as well as in pharmaceutical industries have been developing various methods for the chemical synthesis of indole based compounds via green approaches to overcome the drawbacks of conventional methods. This review reflects the last ten years developments of the various greener methods for the synthesis of indole derivatives by using microwave, ionic liquids, water, ultrasound, nanocatalyst, green catalyst, multicomponent reaction and solvent-free reactions etc. (please see the scheme below). Furthermore, the applications of green chemistry towards developments of indole containing pharmaceuticals and their biological studies have been represented in this review.

An Overview on Steroids and Microwave Energy in Multi-Component Reactions towards the Synthesis of Novel Hybrid Molecules

2020 ◽  
Vol 17 (8) ◽  
pp. 594-609
Author(s):  
Preetismita Borah ◽  
Vhatkar Dattatraya Shivling ◽  
Bimal Krishna Banik ◽  
Biswa Mohan Sahoo
Keyword(s):  
Energy Consumption ◽  
Multicomponent Reactions ◽  
Biological Activities ◽  
Vital Role ◽  
Microwave Energy ◽  
Biosynthetic Pathways ◽  
Chemical Transformations ◽  
Carbon Carbon Bond ◽  
Hybrid Molecules ◽  
Time Required

In recent years, hybrid systems are gaining considerable attention owing to their various biological applications in drug development. Generally, hybrid molecules are constructed from different molecular entities to generate a new functional molecule with improved biological activities. There already exist a large number of naturally occurring hybrid molecules based on both non-steroid and steroid frameworks synthesized by nature through mixed biosynthetic pathways such as, a) integration of the different biosynthetic pathways or b) Carbon- Carbon bond formation between different components derived through different biosynthetic pathways. Multicomponent reactions are a great way to generate efficient libraries of hybrid compounds with high diversity. Throughout the scientific history, the most common factors developing technologies are less energy consumption and avoiding the use of hazardous reagents. In this case, microwave energy plays a vital role in chemical transformations since it involves two very essential criteria of synthesis, minimizing energy consumption required for heating and time required for the reaction. This review summarizes the use of microwave energy in the synthesis of steroidal and non-steroidal hybrid molecules and the use of multicomponent reactions.

Biotransformation of Coumarins by Filamentous Fungi: An Alternative Way for Achievement of Bioactive Analogs

2019 ◽  
Vol 16 (6) ◽  
pp. 568-577 ◽  
Author(s):  
Jainara Santos do Nascimento ◽  
João Carlos Silva Conceição ◽  
Eliane de Oliveira Silva
Keyword(s):  
Filamentous Fungi ◽  
Chemical Reactions ◽  
Biological Activities ◽  
Chemical Transformations ◽  
Chemical Structures ◽  
Pattern Structures ◽  
Pharmacological Interest ◽  
Aspergillus Sp ◽  
The Impact ◽  
Related Compounds

Coumarins are natural 1,2-benzopyrones, present in remarkable amounts as secondary metabolites in edible and medicinal plants. The low yield in the coumarins isolation from natural sources, along with the difficulties faced by the total synthesis, make them attractive for biotechnological studies. The current literature contains several reports on the biotransformation of coumarins by fungi, which can generate chemical analogs with high selectivity, using mild and eco-friendly conditions. Prompted by the enormous pharmacological interest in the coumarin-related compounds, their alimentary and chemical applications, this review covers the biotransformation of coumarins by filamentous fungi. The chemical structures of the analogs were presented and compared with those from the pattern structures. The main chemical reactions catalyzed the insertion of functional groups, and the impact on the biological activities caused by the chemical transformations were discussed. Several chemical reactions can be catalyzed by filamentous fungi in the coumarin scores, mainly lactone ring opening, C3-C4 reduction and hydroxylation. Chunninghamella sp. and Aspergillus sp. are the most common fungi used in these transformations. Concerning the substrates, the biotransformation of pyranocoumarins is a rarer process. Sometimes, the bioactivities were improved by the chemical modifications and coincidences with the mammalian metabolism were pointed out.

Secondary Metabolites of Plant Origin containing Carbazole as Lead Molecule: A Review

2019 ◽  
Vol 05 ◽  
Author(s):  
Atul Sharma ◽  
Devender Pathak
Keyword(s):  
Drug Discovery ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Chemical Compounds ◽  
Lethal Effect ◽  
Chemical Diversity ◽  
Chemical Transformations ◽  
Pharmacological Effects ◽  
Structural Class ◽  
Biological Targets

Keeping this fact that study of a body is biology but life is all about chemicals and chemical transformations, many medicinal chemist start research in finding new and novel chemical compounds which having pharmacological activities. Most of those chemical compounds which are having active pharmacological effects are heterocyclic compounds. Heterocyclic compounds clutch a particular place among pharmaceutically active natural and synthetic compounds. The ability to serve both as biomimetics and reactive pharmacophores of heterocyclic nuclei is incredible and it has principally contributed to their unique value as traditional key elements of numerous drugs. These heterocyclic nuclei offer a huge area for new lead molecules for drug discovery and for generation of activity relationships with biological targets to enhance pharmacological effects. For these reasons, it is not surprising that this structural class has received special attention in drug discovery. The hydrogen bond acceptors and donors arranged in a manner of a semi-rigid skeleton in heterocyclic rings and therefore they can present a varied display of significant pharmacophores. Lead identification and optimization of drug target probable can be achieved by generation of chemical diversity produced by derivatization of heterocyclic pharmacophores with different groups or substituents. A tricyclic carbazole nucleus is an integral part of naturally occurring alkaloids and synthetic derivatives, possessing various potential biological activities such as anticancer, antimicrobial and antiviral. Binding mechanism of carbazole with target receptor as a molecule or fused molecule exhibits the potential lethal effect.

scholarly journals Recent Developments in the Functionalization of Betulinic Acid and Its Natural Analogues: A Route to New Bioactive Compounds

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 355 ◽  
Author(s):  
Joana L. C. Sousa ◽  
Carmen S. R. Freire ◽  
Armando J. D. Silvestre ◽  
Artur M. S. Silva
Keyword(s):  
Betulinic Acid ◽  
Antitumor Agents ◽  
Aldol Condensation ◽  
Antimalarial Activity ◽  
Biological Activities ◽  
Chemical Transformations ◽  
Pentacyclic Triterpenoids ◽  
Natural Analogues ◽  
Palladium Catalyzed ◽  
Aldol Condensation Reactions

Betulinic acid (BA) and its natural analogues betulin (BN), betulonic (BoA), and 23-hydroxybetulinic (HBA) acids are lupane-type pentacyclic triterpenoids. They are present in many plants and display important biological activities. This review focuses on the chemical transformations used to functionalize BA/BN/BoA/HBA in order to obtain new derivatives with improved biological activity, covering the period since 2013 to 2018. It is divided by the main chemical transformations reported in the literature, including amination, esterification, alkylation, sulfonation, copper(I)-catalyzed alkyne-azide cycloaddition, palladium-catalyzed cross-coupling, hydroxylation, and aldol condensation reactions. In addition, the synthesis of heterocycle-fused BA/HBA derivatives and polymer‒BA conjugates are also addressed. The new derivatives are mainly used as antitumor agents, but there are other biological applications such as antimalarial activity, drug delivery, bioimaging, among others.

scholarly journals Alkaloids Produced by Endophytic Fungi: A Review

2012 ◽  
Vol 7 (7) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Yanyan Zhang ◽  
Ting Han ◽  
Qianliang Ming ◽  
Lingshang Wu ◽  
Khalid Rahman ◽  
...  
Keyword(s):  
Endophytic Fungi ◽  
Host Plants ◽  
Biological Activities ◽  
Biological Properties ◽  
Research Progress ◽  
Indole Derivatives ◽  
Anticancer Activities ◽  
Action Mechanisms ◽  
The Future ◽  
Potential Applications

In recent years, a number of alkaloids have been discovered from endophytic fungi in plants, which exhibited excellent biological properties such as antimicrobial, insecticidal, cytotoxic, and anticancer activities. This review mainly deals with the research progress on endophytic fungi for producing bioactive alkaloids such as quinoline and isoquinoline, amines and amides, indole derivatives, pyridines, and quinazolines. The biological activities and action mechanisms of these alkaloids from endophytic fungi are also introduced. Furthermore, the relationships between alkaloid-producing endophytes and their host plants, as well as their potential applications in the future are discussed.

ChemInform Abstract: Synthesis of Some N-Substituted Indole Derivatives and Their Biological Activities.

ChemInform ◽  
2010 ◽  
Vol 23 (43) ◽  
pp. no-no
Author(s):  
H. EL-DIWANI ◽  
S. S. NAKKADY ◽  
O. H. HISHMAT ◽  
O. A. EL-SHABRAWY ◽  
S. S. MAHMOUD
Keyword(s):  
Biological Activities ◽  
Indole Derivatives

Synthetic Approaches for Building Tricyclic Cage-like Motifs Found in Indoxamycins

2020 ◽  
Vol 24 ◽  
Author(s):  
Saqlain Haider ◽  
Ikhlas A. Khan ◽  
Hanfeng Ding ◽  
Amar G. Chittiboyina
Keyword(s):  
Natural Products ◽  
Michael Addition ◽  
Claisen Rearrangement ◽  
Biological Activities ◽  
Cascade Reactions ◽  
Biological Properties ◽  
Starting Material ◽  
Central Core ◽  
Chemical Transformations ◽  
One Pot

Abstract:: Indoxamycins A-F, a novel class of polyketides, were isolated from the saline culture of marine-derived actinomyces by Sato et al. in 2009. Intriguing stereochemical complexity involving tricyclic [5.5.6] cage-like structures with six consecutive chiral centers challenged many organic chemists. Chemical ingenuity, implementation of pioneered reactions along with fine chemical transformations allowed not only the rapid construction of the central core but also allowed minor structural revision and paved the information to delineate the absolute stereostructures of these complex polyketide marine natural products. To achieve the central core structure in indoxamycins A-F, reactions like the Ireland- Claisen rearrangement, an enantioselective 1,6-enyne reductive cyclization, and one-pot cascade reactions of 1,2- addition/oxa-Michael/methylenation were employed. Using the chiral pool approach, the readily available R-carvone was employed as a cost-effective starting material to achieve the concise total syntheses of (-)-indoxamycins A and B, in which Pauson-Khand, Cu-catalyzed Michael addition and tandem retro-oxa-Michael addition/1,2-addition/oxa-Michael addition reactions were employed. The antipodes, (+)-indoxamycins can be easily accessed by simply switching to S-carvone as the starting material. Synthetically prepared indoxamycins A-F are devoid of antiproliferative properties which disagrees with the work reported by Sato and co-workers for (-)-indoxamycins A and F. Nevertheless, ready access to such complex natural products allows probing the untapped potential biological activities of these polyketides including cytotoxicity. A concise overview of interesting, key chemical transformations including named reactions in establishing the architecture of indoxamycins was compiled to inspire organic chemists and help reinvigorate the development of novel strategies for the asymmetric synthesis as well as the development of novel derivatives of indoxamycins with unique physicochemical and biological properties.

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