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Heterocyclic Compounds with Potential Biological Activity: From Synthesis to Application

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A special issue of Applied Sciences (ISSN 2076-3417). This special issue belongs to the section "Chemical and Molecular Sciences".

Deadline for manuscript submissions: closed (30 May 2021) | Viewed by 23933

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Special Issue Editor

Prof. Dr. Mariusz Mojzych

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Guest Editor

Department of Chemistry, Siedlce University of Natural Sciences and Humanities, 08-110 Siedlce, Poland
Interests: medicinal chemistry; medicinal and pharmaceutical chemistry; synthetic organic chemistry; heterocyclic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The fact that heterocyclic compounds play very important functions in living organisms and have found many practical applications makes this group of derivatives a continuously interesting material for further research and new publications. They constitute a structural element of nucleic acids i.e. chemical substances that carry the genetic information controlling inheritance. Some of the naturally occurring products, e.g. pigments, vitamins, alkaloids and antibiotics, possess a heterocyclic core. Modern society is dependent on synthetic heterocycles that are predominantly used as pharmaceuticals, agrochemicals and veterinary products. They also find applications as sanitizers, antioxidants, copolymers, dyes, and plastics. They are used as vehicles in the synthesis of other organic compounds. Due to the variety of modern methods for the synthesis, the chemistry of heterocyclic compounds has developed rapidly and dynamically recently. This is evidenced by the growing trend towards the design and synthesis of a very large number of new heterocycles.The aim of this Special Issue is to spot recent advances in "Heterocyclic Compounds with Potential Biological Activity”, including original research papers or up-to-date, comprehensive reviews, highlighting the recent identification of synthetic and natural molecules with potential biological activity and possible applications.

We believe that this Special Issue is a relevant and timely one, and we look forward to receiving your contributions.

Prof. Dr. Mariusz Mojzych
Guest Editor

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2400 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

Heterocyclic compounds
Drug discovery and synthesis
Design and synthesis
Bioactive compounds
Total synthesis of natural products
Modern methods synthesis
Theoretical evaluation
In silico drug design
Fused heterocycles
Reactivity of heterocyclic compounds

Published Papers (6 papers)

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Research

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12 pages, 3070 KiB

Open AccessFeature PaperArticle

Theoretical and Experimental Insights into the Tandem Mannich—Electrophilic Amination Reaction: Synthesis of Safirinium Dyes

by Jarosław Sączewski, Joanna Fedorowicz, Paulina Wiśniewska and Maria Gdaniec

Appl. Sci. 2021, 11(12), 5498; https://0-doi-org.brum.beds.ac.uk/10.3390/app11125498 - 14 Jun 2021

Cited by 1 | Viewed by 2295

Abstract

Isoxazolo[3,4-b]pyridin-3(1H)-ones are ‘spring-loaded’ compounds that quantitatively react with iminium salts derived from formaldehyde and secondary amines to yield fluorescent Safirinium dyes. The mechanism and energetics of the above tandem Mannich–electrophilic amination reaction have been investigated experimentally and using theoretical methods. The hybrid B3LYP functional with GD3 empirical dispersion and range-separated hybrid functional ωB97XD, both combined with a PCM model, were applied to acquire the energetic profiles of the studied reaction with respect to the structure of secondary amine and isoxazolone used. Diastereoselectivity of the tandem reactions involving iminium salt derived from L-proline has been rationalized theoretically by means of density functional theory calculations. Full article

(This article belongs to the Special Issue Heterocyclic Compounds with Potential Biological Activity: From Synthesis to Application)

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12 pages, 4045 KiB

Open AccessArticle

Isatin-Hydrazones with Multiple Receptor Tyrosine Kinases (RTKs) Inhibitory Activity and In-Silico Binding Mechanism

by Huda S. Al-Salem, Md Arifuzzaman, Iman S. Issa and A. F. M. Motiur Rahman

Appl. Sci. 2021, 11(9), 3746; https://0-doi-org.brum.beds.ac.uk/10.3390/app11093746 - 21 Apr 2021

Cited by 14 | Viewed by 2410

Abstract

Recently, we have reported a series of isatin hydrazone, two of them, namely, 3-((2,6-dichlorobenzylidene)hydrazono)indolin-2-one (1) and 3-((2-chloro-6-fluorobenzylidene)hydrazono)indolin-2-one (2) having potent cytotoxicity, showing cyclin-dependent kinases (CDK2) inhibitory activity and bearing recommended drug likeness properties. Since both compounds (1 and 2) showed inhibitory activity against CDK2, we assumed it would also have multiple receptor tyrosine kinases (RTKs) inhibitory activity. Considering those points, here, above-mentioned two isatin hydrazone 1 and 2 were synthesized using previously reported method for further investigation of their potency on RTKs (EGFR, VEGFR-2 and FLT-3) inhibitory activity. As expected, Compound 1 exhibited excellent inhibitory activity against epidermal growth factor receptor (EGFR, IC₅₀ = 0.269 µM), vascular epidermal growth factor receptor 2 (VEGFR-2, IC₅₀ = 0.232 µM) and FMS-like tyrosine kinase-3 (FLT-3, IC₅₀ = 1.535 µM) tyrosine kinases. On the other hand, Compound 2 also exhibited excellent inhibitory activity against EGFR (IC₅₀ = 0.369 µM), VEGFR-2 (IC₅₀ = 0.266 µM) and FLT-3 (IC₅₀ = 0.546 µM) tyrosine kinases. A molecular docking study with EGFR, VEGFR-2 and FLT-3 kinase suggested that both compounds act as type I ATP competitive inhibitors against EGFR and VEGFR-2, and type II ATP non-competitive inhibitors against FLT-3. Full article

(This article belongs to the Special Issue Heterocyclic Compounds with Potential Biological Activity: From Synthesis to Application)

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22 pages, 5402 KiB

Open AccessArticle

Chiral Pyrazolo[4,3-e][1,2,4]triazine Sulfonamides—Their Biological Activity, Lipophilicity, Protein Affinity, and Metabolic Transformations

by Zofia Bernat, Anna Mieszkowska, Zofia Mazerska, Joanna Matysiak, Zbigniew Karczmarzyk, Katarzyna Kotwica-Mojzych and Mariusz Mojzych

Appl. Sci. 2021, 11(6), 2660; https://0-doi-org.brum.beds.ac.uk/10.3390/app11062660 - 16 Mar 2021

Cited by 2 | Viewed by 1840

Abstract

Referring to our previous laboratory results related to the tyrosinase and urease inhibition by pyrazolo[4,3-e][1,2,4]triazine sulfonamides, we examined here in silico the mechanism of action at the molecular level of the investigated pyrazolotriazine sulfonamides by the molecular docking method. The studied compounds being evaluated for their cytotoxic effect against cancer cell lines (MCF-7, K-562) and for recombinant Abl and CDK2/E kinase inhibitory potency turned out to be inactive in these tests. The pyrazolotriazines were also investigated with respect to their lipophilicity and plasma protein binding using HPLC chromatography in isocratic conditions. The observed small affinity for plasma proteins could be advantageous in the potential in vivo studies. Moreover, the compounds were sensitive to metabolic transformations with phase I enzymes, which led to the hydroxylation and dealkylation products, whereas phase II transformations did not occur. Full article

(This article belongs to the Special Issue Heterocyclic Compounds with Potential Biological Activity: From Synthesis to Application)

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Review

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29 pages, 9910 KiB

Open AccessFeature PaperReview

Synthetic Transformations and Medicinal Significance of 1,2,3-Thiadiazoles Derivatives: An Update

by Ali Irfan, Sami Ullah, Ayesha Anum, Nazish Jabeen, Ameer Fawad Zahoor, Hafza Kanwal, Katarzyna Kotwica-Mojzych and Mariusz Mojzych

Appl. Sci. 2021, 11(12), 5742; https://0-doi-org.brum.beds.ac.uk/10.3390/app11125742 - 21 Jun 2021

Cited by 10 | Viewed by 3602

Abstract

The 1,2,3-thiadiazole moiety occupies a significant and prominent position among privileged heterocyclic templates in the field of medicine, pharmacology and pharmaceutics due to its broad spectrum of biological activities. The 1,2,3-thiadiazole hybrid structures showed myriad biomedical activities such as antifungal, antiviral, insecticidal, antiamoebic, anticancer and plant activators, etc. In the present review, various synthetic transformations and approaches are highlighted to furnish 1,2,3-thiadiazole scaffolds along with different pharmaceutical and pharmacological activities by virtue of the presence of the 1,2,3-thiadiazole framework on the basis of structure–activity relationship (SAR). The discussion in this review article will attract the attention of synthetic and medicinal researchers to explore 1,2,3-thiadiazole structural motifs for future therapeutic agents. Full article

(This article belongs to the Special Issue Heterocyclic Compounds with Potential Biological Activity: From Synthesis to Application)

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24 pages, 5656 KiB

Open AccessReview

Recent Updates on the Synthesis of Bioactive Quinoxaline-Containing Sulfonamides

by Ali Irfan, Sajjad Ahmad, Saddam Hussain, Fozia Batool, Haseeba Riaz, Rehman Zafar, Katarzyna Kotwica-Mojzych and Mariusz Mojzych

Appl. Sci. 2021, 11(12), 5702; https://0-doi-org.brum.beds.ac.uk/10.3390/app11125702 - 19 Jun 2021

Cited by 24 | Viewed by 3599

Abstract

Quinoxaline is a privileged pharmacophore that has broad-spectrum applications in the fields of medicine, pharmacology and pharmaceutics. Similarly, the sulfonamide moiety is of considerable interest in medicinal chemistry, as it exhibits a wide range of pharmacological activities. Therefore, the therapeutic potential and biomedical applications of quinoxalines have been enhanced by incorporation of the sulfonamide group into their chemical framework. The present review surveyed the literature on the preparation, biological activities and structure-activity relationship (SAR) of quinoxaline sulfonamide derivatives due to their broad range of biomedical activities, such as diuretic, antibacterial, antifungal, neuropharmacological, antileishmanial, anti-inflammatory, anti-tumor and anticancer action. The current biological diagnostic findings in this literature review suggest that quinoxaline-linked sulfonamide hybrids are capable of being established as lead compounds; modifications on quinoxaline sulfonamide derivatives may give rise to advanced therapeutic agents against a wide variety of diseases. Full article

(This article belongs to the Special Issue Heterocyclic Compounds with Potential Biological Activity: From Synthesis to Application)

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21 pages, 1997 KiB

Open AccessFeature PaperReview

Current View on Green Tea Catechins Formulations, Their Interactions with Selected Drugs, and Prospective Applications for Various Health Conditions

by Magdalena Cerbin-Koczorowska, Magdalena Waszyk-Nowaczyk, Paweł Bakun, Tomasz Goslinski and Tomasz Koczorowski

Appl. Sci. 2021, 11(11), 4905; https://0-doi-org.brum.beds.ac.uk/10.3390/app11114905 - 26 May 2021

Cited by 557 | Viewed by 8554

Abstract

Green tea extract (GTE) is one of the most popular beverages globally, traditionally prepared from Camelia sinensis leaves. Therefore, it is beneficial to define the impact of GTE and its ingredients on the human organism. Epigallocatechin-3-O-gallate (EGCG) is the most abundant catechin in green tea leaves, belonging to the group of tannins and flavonoids, demonstrating pharmacological activity, but so far, it has not been applied as a drug. This is because EGCG does not present sufficient stability and quickly decomposes through epimerization or autooxidation mechanisms under the influence of light, temperature, changes in pH, or the presence of oxygen. Another limiting factor is EGCG’s low bioavailability after oral administration. Nevertheless, the growing market of dietary supplements together with increasing growing consumption of green tea extracts should prompt us to pay more attention to the safety of both EGCG itself, as well as its influence on other simultaneously used drugs. Previously published data confirm the relationship between healthcare professionals’ access to professional knowledge and their willingness to engage in patient education. For this reason, in this review article, we report the formulations of EGCG and GTE, discuss the data on the safety of EGCG and its possible interactions with drugs, as well as gather various recommendations from medical specialists. Particular attention should be paid to the consumption of green tea during pregnancy and breastfeeding, as well as in the elderly. Patients taking clozapine, digoxin, and warfarin should avoid consuming GTE extracts and dietary supplements containing EGCG. Professional consultation seems especially important for patients treated with statins, calcium channel blockers, or sildenafil. Full article

(This article belongs to the Special Issue Heterocyclic Compounds with Potential Biological Activity: From Synthesis to Application)

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