Derivatives and Analogues of Resveratrol: Recent Advances in Structural Modification

2019 ◽  
Vol 19 (10) ◽  
pp. 809-825 ◽  
Author(s):  
Qing-Shan Li ◽  
Yao Li ◽  
Girdhar Singh Deora ◽  
Ban-Feng Ruan
Keyword(s):  
Structural Modification ◽  
Biological Activities ◽  
Biological Properties ◽  
Synthetic Analogues ◽  
Pharmacological Activities ◽  
The Past ◽  
Structure Activity ◽  
Clinical Drugs ◽  
New Compounds ◽  
Reliable Basis

Resveratrol is a non-flavonoid polyphenol containing a terpenoid backbone. It has been intensively studied because of its various promising biological properties, such as anticancer, antioxidant, antibacterial, neuroprotective and anti-inflammatory activities. However, the medicinal application of resveratrol is constrained by its poor bioavailability and stability. In the past decade, more attention has been focused on making resveratrol derivatives to improve its pharmacological activities and pharmacokinetics. This review covers the literature published over the past 15 years on synthetic analogues of resveratrol. The emphasis is on the chemistry of new compounds and relevant biological activities along with structure-activity relationship. This review aims to provide a scientific and reliable basis for the development of resveratrol-based clinical drugs.

scholarly journals Potential of Steroidal Alkaloids in Cancer: Perspective Insight Into Structure–Activity Relationships

2021 ◽  
Vol 11 ◽  
Author(s):  
Ying Huang ◽  
Gen Li ◽  
Chong Hong ◽  
Xia Zheng ◽  
Haiyang Yu ◽  
...  
Keyword(s):  
Chemical Structure ◽  
Structural Modification ◽  
Biological Activities ◽  
Chemical Properties ◽  
Steroidal Alkaloids ◽  
Pharmacological Activities ◽  
Structure Activity Relationships ◽  
Lead Compounds ◽  
Structure Activity ◽  
Insight Into

Steroidal alkaloids contain both steroidal and alkaloid properties in terms of chemical properties and pharmacological activities. Due to outstanding biological activities such as alkaloids and similar pharmacological effects to other steroids, steroidal alkaloids have received special attention in anticancer activity recently. Substituted groups in chemical structure play markedly important roles in biological activities. Therefore, the effective way to obtain lead compounds quickly is structural modification, which is guided by structure–activity relationships (SARs). This review presents the SAR of steroidal alkaloids and anticancer, including pregnane alkaloids, cyclopregnane alkaloids, cholestane alkaloids, C-nor-D-homosteroidal alkaloids, and bis-steroidal pyrazine. A summary of SAR can powerfully help to design and synthesize more lead compounds.

Recent Development of Oridonin Derivatives with Diverse Pharmacological Activities

2018 ◽  
Vol 19 (2) ◽  
pp. 114-124 ◽  
Author(s):  
Weiyan Cheng ◽  
Chuanhui Huang ◽  
Weifeng Ma ◽  
Xin Tian ◽  
Xiaojian Zhang
Keyword(s):  
Chinese Medicine ◽  
Traditional Chinese Medicine ◽  
Biological Activities ◽  
Biological Properties ◽  
Clinical Applications ◽  
Structure Modification ◽  
Pharmacological Activities ◽  
The Poor ◽  
Structure Activity ◽  
Anti Inflammation

Oridonin is one of the major components isolated from Isodon rubescens, a traditional Chinese medicine, and it has been confirmed to exhibit many kinds of biological activities including anticancer, anti-inflammation, antibacterial and so on. However, the poor pharmaceutical property limits the clinical applications of oridonin. So many strategies have been explored in the purpose of improving the potencies of oridonin, and structure modification is one thus way. This review outlines the landscape of the recent development of oridonin derivatives with diverse pharmacological activities, mainly focusing on the biological properties, structure-activity relationships, and mechanism of actions.

scholarly journals Bioactivities and Structure–Activity Relationships of Fusidic Acid Derivatives: A Review

2021 ◽  
Vol 12 ◽  
Author(s):  
Junjun Long ◽  
Wentao Ji ◽  
Doudou Zhang ◽  
Yifei Zhu ◽  
Yi Bi
Keyword(s):  
Fusidic Acid ◽  
Structural Modification ◽  
Biological Activities ◽  
Pharmacological Activities ◽  
Structure Activity ◽  
Wide Range ◽  
Resistance Reversal ◽  
Anti Inflammation

Fusidic acid (FA) is a natural tetracyclic triterpene isolated from fungi, which is clinically used for systemic and local staphylococcal infections, including methicillin-resistant Staphylococcus aureus and coagulase-negative staphylococci infections. FA and its derivatives have been shown to possess a wide range of pharmacological activities, including antibacterial, antimalarial, antituberculosis, anticancer, tumor multidrug resistance reversal, anti-inflammation, antifungal, and antiviral activity in vivo and in vitro. The semisynthesis, structural modification and biological activities of FA derivatives have been extensively studied in recent years. This review summarized the biological activities and structure–activity relationship (SAR) of FA in the last two decades. This summary can prove useful information for drug exploration of FA derivatives.

A common mechanism links activities of butyrate in the colon

2017 ◽  
Author(s):  
Mohit S. Verma ◽  
Michael J. Fink ◽  
Gabriel L Salmon ◽  
Nadine Fornelos ◽  
Takahiro E. Ohara ◽  
...  
Keyword(s):  
Stem Cells ◽  
Histone Deacetylases ◽  
Biological Activities ◽  
Short Chain Fatty Acids ◽  
Common Mechanism ◽  
Epithelial Stem Cells ◽  
Degree Of Unsaturation ◽  
Structure Activity ◽  
Starting Point ◽  
New Compounds

Two biological activities of butyrate in the colon (suppression of proliferation of colonic epithelial stem cells and inflammation) correlate with inhibition of histone deacetylases. Cellular and biochemical studies of molecules similar in structure to butyrate, but different in molecular details (functional groups, chain-length, deuteration, oxidation level, fluorination, or degree of unsaturation) demonstrated that these activities were sensitive to molecular structure, and were compatible with the hypothesis that butyrate acts by binding to the Zn<sup>2+</sup> in the catalytic site of histone deacetylases. Structure-activity relationships drawn from a set of 36 compounds offer a starting point for the design of new compounds targeting the inhibition of histone deacetylases. The observation that butyrate was more potent than other short-chain fatty acids is compatible with the hypothesis that crypts evolved (at least in part), to separate stem cells at the base of crypts from butyrate produced by commensal bacteria.

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.

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.

scholarly journals New Sesterterpenes from Marine  Sponges from the Tropical Waters of the  Kingdom of Tonga

2021 ◽  
Author(s):  
◽  
Taitusi Taufa
Keyword(s):  
Biological Activities ◽  
Screening Method ◽  
Biological Properties ◽  
Geometric Isomer ◽  
Marine Sponges ◽  
Ring Closure ◽  
Substitution Pattern ◽  
Methyl Group ◽  
Structure Activity ◽  
Insight Into

<p>Over the course of this study, various species of Tongan marine sponges were investigated using an NMR-based screening method and has resulted in the discovery of three new sesterterpenes and 11 known compounds. Examination of the sponge Fascaplysinopsis sp. resulted in the isolation of two novel sesterterpenes, isoluffariellolide (46) and 1-O-methylisoluffariellolide (47). Compounds 46 and 47 share the same backbone pattern as the known luffariellolide (45) and 25-Omethylluffariellolide (107) respectively, and differ only in the substitution pattern of the butenolide rings. Isoluffariellolide (46) was found to be approximately six times less cytotoxic than 1-O-methylisoluffariellolide (47). Interestingly, these results suggested that the 1-O-methyl group in compound 47 plays an important role in the cytotoxicity of the compound. Secothorectolide (49), a new ring-opened and geometric isomer of the known compound thorectolide (48), was obtained from a sponge of the order Dictyoceratida. This ring closure and opening relationship was also observed between manoalide (109) and secomanoalide (110), as well as luffariellins A (141) and B (142). Despite the different carbon skeleton, the functional groups in 141 and 142 are similar with those in 109 and 110, respectively, and not surprisingly the biological properties are almost identical. The biological activities of compounds 48 and 49 were almost the same, which would give an insight into the structure-activity relationship (SAR) between these types of compounds.</p>

scholarly journals New Sesterterpenes from Marine  Sponges from the Tropical Waters of the  Kingdom of Tonga

2021 ◽  
Author(s):  
◽  
Taitusi Taufa
Keyword(s):  
Biological Activities ◽  
Screening Method ◽  
Biological Properties ◽  
Geometric Isomer ◽  
Marine Sponges ◽  
Ring Closure ◽  
Substitution Pattern ◽  
Methyl Group ◽  
Structure Activity ◽  
Insight Into

<p>Over the course of this study, various species of Tongan marine sponges were investigated using an NMR-based screening method and has resulted in the discovery of three new sesterterpenes and 11 known compounds. Examination of the sponge Fascaplysinopsis sp. resulted in the isolation of two novel sesterterpenes, isoluffariellolide (46) and 1-O-methylisoluffariellolide (47). Compounds 46 and 47 share the same backbone pattern as the known luffariellolide (45) and 25-Omethylluffariellolide (107) respectively, and differ only in the substitution pattern of the butenolide rings. Isoluffariellolide (46) was found to be approximately six times less cytotoxic than 1-O-methylisoluffariellolide (47). Interestingly, these results suggested that the 1-O-methyl group in compound 47 plays an important role in the cytotoxicity of the compound. Secothorectolide (49), a new ring-opened and geometric isomer of the known compound thorectolide (48), was obtained from a sponge of the order Dictyoceratida. This ring closure and opening relationship was also observed between manoalide (109) and secomanoalide (110), as well as luffariellins A (141) and B (142). Despite the different carbon skeleton, the functional groups in 141 and 142 are similar with those in 109 and 110, respectively, and not surprisingly the biological properties are almost identical. The biological activities of compounds 48 and 49 were almost the same, which would give an insight into the structure-activity relationship (SAR) between these types of compounds.</p>

scholarly journals Advances in Phenazines over the Past Decade: Review of Their Pharmacological Activities, Mechanisms of Action, Biosynthetic Pathways and Synthetic Strategies

Marine Drugs ◽  
2021 ◽  
Vol 19 (11) ◽  
pp. 610
Author(s):  
Junjie Yan ◽  
Weiwei Liu ◽  
Jiatong Cai ◽  
Yiming Wang ◽  
Dahong Li ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Pharmacological Activity ◽  
Biological Activities ◽  
Natural Compounds ◽  
Mechanisms Of Action ◽  
Biosynthetic Pathways ◽  
Pharmacological Activities ◽  
Chemical Structures ◽  
The Past ◽  
Synthetic Derivatives

Phenazines are a large group of nitrogen-containing heterocycles, providing diverse chemical structures and various biological activities. Natural phenazines are mainly isolated from marine and terrestrial microorganisms. So far, more than 100 different natural compounds and over 6000 synthetic derivatives have been found and investigated. Many phenazines show great pharmacological activity in various fields, such as antimicrobial, antiparasitic, neuroprotective, insecticidal, anti-inflammatory and anticancer activity. Researchers continued to investigate these compounds and hope to develop them as medicines. Cimmino et al. published a significant review about anticancer activity of phenazines, containing articles from 2000 to 2011. Here, we mainly summarize articles from 2012 to 2021. According to sources of compounds, phenazines were categorized into natural phenazines and synthetic phenazine derivatives in this review. Their pharmacological activities, mechanisms of action, biosynthetic pathways and synthetic strategies were summarized. These may provide guidance for the investigation on phenazines in the future.

Approaches for the synthesis, chemical modification and biological properties of N-acylphenothiazines

2021 ◽  
Vol 10 (4) ◽  
pp. 377-392 ◽  
Author(s):  
Iryna Myrko ◽  
Taras Chaban ◽  
Yulia Matiichuk ◽  
Mohammad Arshad ◽  
Vasyl Matiychuk
Keyword(s):  
Experimental Data ◽  
Chemical Modification ◽  
Medicinal Chemistry ◽  
Biological Properties ◽  
Chemotherapeutic Agents ◽  
Present Review ◽  
The Novel ◽  
Pharmacological Activities ◽  
The Past ◽  
Biological Potential

In this review we systematized the theoretical and experimental data concerning the versatile approaches for the synthesis of N-acylphenothiazines. The aim of the study was to compile the literature reported worldwide in the past 20 years. This article also reviewed the analysis of pharmacological activities of these heterocycles as one of the promising chemotherapeutic objects for the modern bioorganic and medicinal chemistry. It has been hypothesized that the enormous biological potential of these moieties is due to the radical nature in the acyl moiety. Therefore, the present review will be a good contribution to the literature and will provide the platform for the medicinal chemistry researchers to carry out more studies aiming the N-acylphenothiazine moieties as the novel chemotherapeutic agents.

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