Δα,β-Butenolides [Furan-2(5H)-ones]: Ring Construction Approaches and Biological Aspects - A Mini-Review

2020 ◽  
Vol 17 (8) ◽  
pp. 922-945
Author(s):  
Andrés-Felipe Villamizar-Mogotocoro ◽  
Andrés-Felipe León-Rojas ◽  
Juan-Manuel Urbina-González
Keyword(s):  
Biological Activities ◽  
Ring Formation ◽  
High Interest ◽  
The Past ◽  
Biological Aspects ◽  
Synthetic Methodologies ◽  
New Procedures

The five-membered oxacyclic system of furan-2(5H)-ones, commonly named as γ- butenolides or appropriately as Δα,β-butenolides, is of high interest since many studies have proven its bioactivity. During the past few years, Δα,β-butenolides have been important synthetic targets, with several reports of new procedures for their construction. A short compendium of the main different synthetic methodologies focused on the Δα,β-butenolide ring formation, along with selected examples of compounds with relevant biological activities of these promising pharmaceutical entities is presented.

Enzymatic Synthesis of Glycosphingolipids: A Review

Synthesis ◽  
2021 ◽  
Author(s):  
Qingjiang Li ◽  
Zhongwu Guo
Keyword(s):  
Signal Transduction ◽  
Enzymatic Synthesis ◽  
Biological Activities ◽  
Cell Interaction ◽  
Glycosidic Linkage ◽  
The Past ◽  
Biological Studies ◽  
Hydrophobic Lipid ◽  
Synthetic Methodologies ◽  
And Function

Glycosphingolipids (GSLs) are the major vertebrate glycolipids, which contain two distinctive moieties, a glycan and a ceramide, stitched together by a β-glycosidic linkage. The hydrophobic lipid chains of ceramide can insert into the cell membrane to form “lipid rafts” and anchor the hydrophilic glycan onto the cell surface to generate microdomains and function as signaling molecules. GSLs mediate signal transduction, cell interaction, and many other biological activities, and are also related to many diseases. To meet the need of biological studies, chemists have developed various synthetic methodologies to access GSLs. Among them, the application of enzymes to GSL synthesis has witnessed significant advancements in the past decades. This review summarizes briefly the history and progress of enzymatic GSL synthesis.

Click Reactions in Chemistry of Triterpenes - Advances Towards Development of Potential Therapeutics

2018 ◽  
Vol 25 (5) ◽  
pp. 636-658 ◽  
Author(s):  
Jan Pokorny ◽  
Lucie Borkova ◽  
Milan Urban
Keyword(s):  
Biological Activities ◽  
Synthetic Approach ◽  
Clinical Use ◽  
New Approach ◽  
Click Reactions ◽  
Drug Candidates ◽  
The Past ◽  
Low Toxicity ◽  
New Compounds ◽  
Potential Therapeutics

Triterpenoids are natural compounds with a large variety of biological activities such as anticancer, antiviral, antibacterial, antifungal, antiparazitic, antiinflammatory and others. Despite their low toxicity and simple availability from the natural resources, their clinical use is still severely limited by their higher IC50 and worse pharmacological properties than in the currently used therapeutics. This fact encouraged a number of researchers to develop new terpenic derivatives more suitable for the potential clinical use. This review summarizes a new approach to improve both, the activity and ADME-Tox properties by connecting active terpenes to another modifying molecules using click reactions. Within the past few years, this synthetic approach was well explored yielding a lot of great improvements of the parent compounds along with some less successful attempts. A large quantity of the new compounds presented here are superior in both activity and ADME-Tox properties to their parents. This review should serve the researchers who need to promote their hit triterpenic structures towards their clinical use and it is intended as a guide for the chemical synthesis of better drug candidates.

Structural and Bioactive Studies of Halogenated Constituents from Sponges

2020 ◽  
Vol 27 (14) ◽  
pp. 2335-2360 ◽  
Author(s):  
Chao Li ◽  
Dayong Shi
Keyword(s):  
Microbial Communities ◽  
Organic Compounds ◽  
Biological Activities ◽  
Marine Sponges ◽  
Nitrogen Compounds ◽  
Halogenated Organic Compounds ◽  
Bioactive Natural Products ◽  
The Past ◽  
Tyrosine Derivatives ◽  
Polyunsaturated Lipids

: Marine organisms are abundant sources of bioactive natural products. Among metabolites produced by sponges and their associated microbial communities, halogenated natural compounds accounted for an important part due to their potent biological activities. The present review updates and compiles a total of 258 halogenated organic compounds isolated in the past three decades, especially brominated derivatives derived from 31 genera of marine sponges. These compounds can be classified as the following classes: brominated polyunsaturated lipids, nitrogen compounds, brominated tyrosine derivatives and other halogenated compounds. These substances were listed together with their source organisms, structures and bioactivities. For this purpose, 84 references were consulted.

Single Heterocyclic Compounds as Monoamine Oxidase Inhibitors: From Past to Present

2020 ◽  
Vol 20 (10) ◽  
pp. 908-920 ◽  
Author(s):  
Su-Min Wu ◽  
Xiao-Yang Qiu ◽  
Shu-Juan Liu ◽  
Juan Sun
Keyword(s):  
Monoamine Oxidase ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
The Past ◽  
Structure Activity ◽  
Receptor Interactions ◽  
Heterocyclic Derivatives ◽  
Inhibitory Activities ◽  
Leading Compounds ◽  
Heterocyclic Moiety

Inhibitors of monoamine oxidase (MAO) have shown therapeutic values in a variety of neurodegenerative diseases such as depression, Parkinson’s disease and Alzheimer’s disease. Heterocyclic compounds exhibit a broad spectrum of biological activities and vital leading compounds for the development of chemical drugs. Herein, we focus on the synthesis and screening of novel single heterocyclic derivatives with MAO inhibitory activities during the past decade. This review covers recent pharmacological advancements of single heterocyclic moiety along with structure- activity relationship to provide better correlation among different structures and their receptor interactions.

Metal and Non-Metal Catalysts in the Synthesis of Five-Membered S-Heterocycles

2019 ◽  
Vol 16 (2) ◽  
pp. 258-275 ◽  
Author(s):  
Navjeet Kaur
Keyword(s):  
Organic Synthesis ◽  
Biological Activities ◽  
Reaction Times ◽  
Research Field ◽  
Environmentally Benign ◽  
Metal Catalyst ◽  
Efficient Synthesis ◽  
Heterocyclic Molecules ◽  
The Past ◽  
Harsh Conditions

Background:A wide variety of biological activities are exhibited by N, O and S containing heterocycles and recently, many reports appeared for the synthesis of these heterocycles. The synthesis of heterocycles with the help of metal and non-metal catalyst has become a highly rewarding and important method in organic synthesis. This review article concentrated on the synthesis of S-heterocylces in the presence of metal and non-metal catalyst. The synthesis of five-membered S-heterocycles is described here.Objective:There is a need for the development of rapid, efficient and versatile strategy for the synthesis of heterocyclic rings. Metal, non-metal and organocatalysis involving methods have gained prominence because traditional conditions have disadvantages such as long reaction times, harsh conditions and limited substrate scope.Conclusion:The metal-, non-metal-, and organocatalyst assisted organic synthesis is a highly dynamic research field. For ßthe chemoselective and efficient synthesis of heterocyclic molecules, this protocol has emerged as a powerful route. Various methodologies in the past few years have been pointed out to pursue more sustainable, efficient and environmentally benign procedures and products. Among these processes, the development of new protocols (catalysis), which avoided the use of toxic reagents, are the focus of intense research.

1,4-Diazepines: A Review on Synthesis, Reactions and Biological Significance

2019 ◽  
Vol 16 (5) ◽  
pp. 709-729 ◽  
Author(s):  
Muhammad A. Rashid ◽  
Aisha Ashraf ◽  
Sahibzada S. Rehman ◽  
Shaukat A. Shahid ◽  
Adeel Mahmood ◽  
...  
Keyword(s):  
Biological Activities ◽  
Biological Significance ◽  
Biological Evaluation ◽  
Wide Range ◽  
Pharmaceutical Industries ◽  
Biological Aspects ◽  
Synthetic Routes ◽  
Biological Attributes ◽  
Synthesis Reactions ◽  
Potential Use

Background:1,4-Diazepines are two nitrogen containing seven membered heterocyclic compounds and associated with a wide range of biological activities. Due to its medicinal importance, scientists are actively involved in the synthesis, reactions and biological evaluation of 1,4-diazepines since number of decades.Objective:The primary purpose of this review is to discuss the synthetic schemes and reactivity of 1,4- diazepines. This article also describes biological aspects of 1,4-diazepine derivatives, that can be usefully exploited for the pharmaceutical sector.Conclusion:This review summarizes the abundant literature on synthetic routes, chemical reactions and biological attributes of 1,4-diazepine derivatives. We concluded that 1,4-diazepines have significant importance due to their biological activities like antipsychotic, anxiolytic, anthelmintic, anticonvulsant, antibacterial, antifungal and anticancer. 1,4-diazepine derivatives with significant biological activities could be explored for potential use in the pharmaceutical industries.

scholarly journals Cytokinin N-glucosides: Occurrence, Metabolism and Biological Activities in Plants

Biomolecules ◽  
2020 ◽  
Vol 11 (1) ◽  
pp. 24
Author(s):  
Eva Pokorná ◽  
Tomáš Hluska ◽  
Petr Galuszka ◽  
H. Tucker Hallmark ◽  
Petre I. Dobrev ◽  
...  
Keyword(s):  
Metabolic Pathways ◽  
Growth And Development ◽  
Biological Activities ◽  
Physiological Effects ◽  
Inhibitory Effects ◽  
Plant Growth And Development ◽  
The Past ◽  
Complex Process ◽  
Considerable Impact ◽  
Physiological Impact

Cytokinins (CKs) are a class of phytohormones affecting many aspects of plant growth and development. In the complex process of CK homeostasis in plants, N-glucosylation represents one of the essential metabolic pathways. Its products, CK N7- and N9-glucosides, have been largely overlooked in the past as irreversible and inactive CK products lacking any relevant physiological impact. In this work, we report a widespread distribution of CK N-glucosides across the plant kingdom proceeding from evolutionary older to younger plants with different proportions between N7- and N9-glucosides in the total CK pool. We show dramatic changes in their profiles as well as in expression levels of the UGT76C1 and UGT76C2 genes during Arabidopsis ontogenesis. We also demonstrate specific physiological effects of CK N-glucosides in CK bioassays including their antisenescent activities, inhibitory effects on root development, and activation of the CK signaling pathway visualized by the CK-responsive YFP reporter line, TCSv2::3XVENUS. Last but not least, we present the considerable impact of CK N7- and N9-glucosides on the expression of CK-related genes in maize and their stimulatory effects on CK oxidase/dehydrogenase activity in oats. Our findings revise the apparent irreversibility and inactivity of CK N7- and N9-glucosides and indicate their involvement in CK evolution while suggesting their unique function(s) in plants.

scholarly journals Sphingolipids of Asteroidea and Holothuroidea: Structures and Biological Activities

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 330
Author(s):  
Timofey V. Malyarenko ◽  
Alla A. Kicha ◽  
Valentin A. Stonik ◽  
Natalia V. Ivanchina
Keyword(s):  
Marine Invertebrates ◽  
Biological Activities ◽  
Complete Information ◽  
Structural Features ◽  
Marine Organisms ◽  
Structural Components ◽  
Chemical Structures ◽  
The Past ◽  
Complex Lipids ◽  
Complex Sphingolipids

Sphingolipids are complex lipids widespread in nature as structural components of biomembranes. Commonly, the sphingolipids of marine organisms differ from those of terrestrial animals and plants. The gangliosides are the most complex sphingolipids characteristic of vertebrates that have been found in only the Echinodermata (echinoderms) phylum of invertebrates. Sphingolipids of the representatives of the Asteroidea and Holothuroidea classes are the most studied among all echinoderms. In this review, we have summarized the data on sphingolipids of these two classes of marine invertebrates over the past two decades. Recently established structures, properties, and peculiarities of biogenesis of ceramides, cerebrosides, and gangliosides from starfishes and holothurians are discussed. The purpose of this review is to provide the most complete information on the chemical structures, structural features, and biological activities of sphingolipids of the Asteroidea and Holothuroidea classes.

scholarly journals Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 249
Author(s):  
Raquel G. Soengas ◽  
Humberto Rodríguez-Solla
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Functional Group ◽  
Biological Activities ◽  
Synthetic Methods ◽  
Bond Forming ◽  
Drug Candidates ◽  
The Past ◽  
Wide Range

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.

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