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Nitrogen-Containing Heterocycles as Significant Molecular Scaffolds for Medicinal and Other Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (15 November 2020) | Viewed by 50935

Special Issue Editors


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Guest Editor
Stereochemistry Research Group of the Hungarian Academy of Sciences, University of Szeged, H-6720 Szeged, Hungary
Interests: asymmetric catalysis; organocatalysis; N-heterocycles; multicomponent reactions; green chemistry
Department of Organic Chemistry, University of Szeged, Dóm tér 8., H-6720 Szeged, Hungary
Interests: organic chemistry; synthesis; steroids; heterocycles; stereoselectivity; microwave; anticancer agents

Special Issue Information

Dear Colleagues,

Aza-heterocyclic compounds that contain at least one nitrogen atom, including monocyclic and fused bicyclic ring systems, represent the largest and most diverse family of organic compounds. These versatile structural motifs differing in the number of ring members and functionalization, as well as the number, nature, and relative position of heteroatoms constituting the rings, are present in several biologically active natural compounds and in a large number of marketed small molecule drugs. The binding ability via coordinative or hydrogen bonding interactions seems to be an important factor in the development of biological effects, whereas certain physicochemical and pharmacokinetic properties of the molecules, such as aqueous solubility, intestinal absorption, and stability against metabolic degradation may also be modulated by the incorporation of these scaffolds. Besides their medicinal importance, nitrogen-containing heterocycles also find applications as corrosion inhibitors, preservatives, surface modifiers, copolymers, dyes, antistatic agents, agrochemicals, etc.

The diversity of the structures involved, as well as their practical relevance, have motivated research aimed at the development of efficient, selective, and environmentally friendly synthetic strategies. The present Special Issue is dedicated to the preparation of aromatic and non-aromatic nitrogen-containing heterocycles possessing any biological action or suitable for other potential applications in material science and catalysis. Contributions (original research articles and reviews) are expected primarily on the state of the art of green chemistry approaches as sustainable alternatives to conventional methodologies.

Dr. Eva Frank
Dr. György Szöllösi
Guest Editors

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Keywords

  • N-containing heterocycles
  • 1,3-dipolar cycloadditions
  • heterocyclization
  • heteroannulation
  • ring-closing metathesis
  • cross-coupling reactions
  • one-pot multicomponent reactions
  • organocatalysis
  • photocatalysis
  • ultrasonic irradiation
  • microwave-assisted synthesis
  • green solvents
  • green and sustainable chemistry
  • application
  • biological activity
  • target-based design
  • structure-activity relationship
  • docking studies

Published Papers (14 papers)

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Editorial

Jump to: Research, Review

3 pages, 205 KiB  
Editorial
Nitrogen-Containing Heterocycles as Significant Molecular Scaffolds for Medicinal and Other Applications
by Éva Frank and György Szőllősi
Molecules 2021, 26(15), 4617; https://doi.org/10.3390/molecules26154617 - 30 Jul 2021
Cited by 14 | Viewed by 2057
Abstract
Most of the organic compounds applied as pharmaceuticals or intermediates utilized in their synthesis contain heterocyclic motifs [...] Full article

Research

Jump to: Editorial, Review

9 pages, 6412 KiB  
Communication
Synthesis and Properties of Pentafluorosulfanyl Group (SF5)-Containing Meta-Diamide Insecticides
by Jae Gon Kim, On-Yu Kang, Sang Mee Kim, Guldana Issabayeva, In Seok Oh, Yaeji Lee, Won Hyung Lee, Hwan Jung Lim and Seong Jun Park
Molecules 2020, 25(23), 5536; https://doi.org/10.3390/molecules25235536 - 25 Nov 2020
Cited by 9 | Viewed by 3809
Abstract
Herein, we describe novel pentafluorosulfanyl (SF5) group-containing meta-diamide insecticides. For the facile preparation of the SF5-based compounds 4ad, practical synthetic methods were applied. Among newly synthesized compounds, 3-benzamido-N-(2,6-dimethyl-4-(pentafluoro-λ6-sulfanyl)phenyl)-2-fluorobenzamide 4d showed (i) a [...] Read more.
Herein, we describe novel pentafluorosulfanyl (SF5) group-containing meta-diamide insecticides. For the facile preparation of the SF5-based compounds 4ad, practical synthetic methods were applied. Among newly synthesized compounds, 3-benzamido-N-(2,6-dimethyl-4-(pentafluoro-λ6-sulfanyl)phenyl)-2-fluorobenzamide 4d showed (i) a high insecticidal activity, (ii) an excellent selectivity to insects, and (iii) good levels of water solubility and log P values. In this study, we demonstrated that the pentafluorosulfanyl moiety could serve as an attractive functionality for the discovery of a new scope of crop-protecting agents. Full article
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15 pages, 2816 KiB  
Article
Synthesis and Antibacterial Evaluation of New Pyrazolo[3,4-d]pyrimidines Kinase Inhibitors
by Chiara Greco, Rosa Catania, Dario Leonardo Balacco, Vincenzo Taresco, Francesca Musumeci, Cameron Alexander, Alan Huett and Silvia Schenone
Molecules 2020, 25(22), 5354; https://doi.org/10.3390/molecules25225354 - 16 Nov 2020
Cited by 10 | Viewed by 2692
Abstract
Pyrazolo[3,4-d]pyrimidines represent an important class of heterocyclic compounds well-known for their anticancer activity exerted by the inhibition of eukaryotic protein kinases. Recently, pyrazolo[3,4-d]pyrimidines have become increasingly attractive for their potential antimicrobial properties. Here, we explored the activity of a [...] Read more.
Pyrazolo[3,4-d]pyrimidines represent an important class of heterocyclic compounds well-known for their anticancer activity exerted by the inhibition of eukaryotic protein kinases. Recently, pyrazolo[3,4-d]pyrimidines have become increasingly attractive for their potential antimicrobial properties. Here, we explored the activity of a library of in-house pyrazolo[3,4-d]pyrimidines, targeting human protein kinases, against Staphylococcus aureus and Escherichia coli and their interaction with ampicillin and kanamycin, representing important classes of clinically used antibiotics. Our results represent a first step towards the potential application of dual active pyrazolo[3,4-d]pyrimidine kinase inhibitors in the prevention and treatment of bacterial infections in cancer patients. Full article
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18 pages, 3992 KiB  
Article
Design of Anticancer 2,4-Diaminopyrimidines as Novel Anoctamin 1 (ANO1) Ion Channel Blockers
by Taewoo Kim, Sinyoung Cho, Haejun Oh, Joonseong Hur, Haedong Kim, Young-Ho Choi, Seongho Jeon, Young Duk Yang and Seok-Ho Kim
Molecules 2020, 25(21), 5180; https://doi.org/10.3390/molecules25215180 - 06 Nov 2020
Cited by 6 | Viewed by 2195
Abstract
Pyrimidine is a privileged scaffold in many synthetic compounds exhibiting diverse pharmacological activities, and is used for therapeutic applications in a broad spectrum of human diseases. In this study, we prepared a small set of pyrimidine libraries based on the structure of two [...] Read more.
Pyrimidine is a privileged scaffold in many synthetic compounds exhibiting diverse pharmacological activities, and is used for therapeutic applications in a broad spectrum of human diseases. In this study, we prepared a small set of pyrimidine libraries based on the structure of two hit compounds that were identified through the screening of an in-house library in order to identify an inhibitor of anoctamin 1 (ANO1). ANO1 is amplified in various types of human malignant tumors, such as head and neck, parathyroid, and gastrointestinal stromal tumors, as well as in breast, lung, and prostate cancers. After initial screening and further structure optimization, we identified Aa3 as a dose-dependent ANO1 blocker. This compound exhibited more potent anti-cancer activity in the NCI-H460 cell line, expressing high levels of ANO1 compared with that in A549 cells that express low levels of ANO1. Our results open a new direction for the development of small-molecule ANO1 blockers composed of a pyrimidine scaffold and a nitrogen-containing heterocyclic moiety, with drug-like properties. Full article
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17 pages, 1117 KiB  
Article
Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System
by Ernestine Nicaise Djuidje, Elisa Durini, Sabrina Sciabica, Elena Serra, Jan Balzarini, Sandra Liekens, Stefano Manfredini, Silvia Vertuani and Anna Baldisserotto
Molecules 2020, 25(18), 4324; https://doi.org/10.3390/molecules25184324 - 21 Sep 2020
Cited by 13 | Viewed by 2785
Abstract
In the search for scaffolds for multifunctional compounds we investigated the structure activity relationship of a class of benzimidazole derivatives bearing 5-membered ring. The newly synthesized and the already known compounds were divided into three classes that present different substituent at 5 position [...] Read more.
In the search for scaffolds for multifunctional compounds we investigated the structure activity relationship of a class of benzimidazole derivatives bearing 5-membered ring. The newly synthesized and the already known compounds were divided into three classes that present different substituent at 5 position of the benzimidazole ring (-H, -COOH or –SO3H) and different heterocycle at position 2 (thiophene, furan or pyrrole). All the derivatives were synthesized and tested to determine their photoprotective profile against UV rays, in vitro antioxidant capacity against different radicals (DPPH and FRAP test), antifungal inhibitory activity (dermatophytes and Candida albicans), antiviral and antiproliferative activity. A Structure-Activity Relationship study indicated compound 10, bearing a pyrrole heterocycle on the benzimidazole ring, as the best multifunctional derivative of the series and as potential candidate for the development of drugs especially in case of melanoma. Full article
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20 pages, 2116 KiB  
Article
Multistep Synthesis and In Vitro Anticancer Evaluation of 2-Pyrazolyl-Estradiol Derivatives, Pyrazolocoumarin-Estradiol Hybrids and Analogous Compounds
by Barnabás Molnár, Mohana Krishna Gopisetty, Dóra Izabella Adamecz, Mónika Kiricsi and Éva Frank
Molecules 2020, 25(18), 4039; https://doi.org/10.3390/molecules25184039 - 04 Sep 2020
Cited by 12 | Viewed by 2710
Abstract
Although the hormone independent cytotoxic activity of several estradiol derivatives endowed with a simple substituent at C-2 has been reported so far, 2-heterocyclic and 2,3-condensed analogs are less investigated from both synthetic and pharmacological points of view. Therefore, novel A-ring-connected 2-pyrazoles of estradiol [...] Read more.
Although the hormone independent cytotoxic activity of several estradiol derivatives endowed with a simple substituent at C-2 has been reported so far, 2-heterocyclic and 2,3-condensed analogs are less investigated from both synthetic and pharmacological points of view. Therefore, novel A-ring-connected 2-pyrazoles of estradiol and, for comparison, their structurally simplified non-steroidal pairs were synthesized from estradiol 3-methyl ether and 6-methoxy-1,2,3,4-tetrahydronaphthalene. Friedel-Crafts acetylation of the protected phenolic compounds and subsequent O-demethylation led to ortho-substituted derivatives regioselectively, which were converted to arylhydrazones with phenylhydrazine, 4-tolylhydrazine and 4-chloro-phenylhydrazine, respectively, under microwave conditions. The hydrazones were subjected to cyclization with the Vilsmeier-Haack reagent immediately after preparation and the ring closure/formylation sequence resulted in steroidal and non-steroidal 4′-formylpyrazoles in moderate to good yields. During reductive transformations, 4-hydroxymethyl-pyrazoles were obtained, while oxidative lactonization of the 4-formylpyrazole moiety with the phenolic OH in the presence of the Jones reagent afforded A-ring-integrated pyrazolocoumarin hybrids and related analogs. Steroidal pyrazoles, which were produced as C-17 acetates due to acetylation of C-17 OH during the primary Friedel-Crafts reaction, underwent deacetylation in alkaline methanol to furnish 2-heterocyclic estradiol derivatives. Pharmacological studies revealed the overall and cancer cell-specific cytotoxicity of the derivatives and the half maximal inhibitory concentrations were obtained for the most promising compounds. Full article
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20 pages, 9637 KiB  
Article
Stabilisation of Exotic Tribromide (Br3) Anions via Supramolecular Interaction with a Tosylated Macrocyclic Pyridinophane. A Serendipitous Case
by Álvaro Martínez-Camarena, Matteo Savastano, Carla Bazzicalupi, Antonio Bianchi and Enrique García-España
Molecules 2020, 25(14), 3155; https://doi.org/10.3390/molecules25143155 - 10 Jul 2020
Cited by 13 | Viewed by 2608
Abstract
Tetraaza-macrocyclic pyridinophane L-Ts, decorated with a p-toluenesulfonyl (tosyl; Ts) group, appear to be a useful tool to provide evidence on how the interplay of various supramolecular forces can help stabilise exotic anionic species such as tribromide (Br3) anions. Indeed, [...] Read more.
Tetraaza-macrocyclic pyridinophane L-Ts, decorated with a p-toluenesulfonyl (tosyl; Ts) group, appear to be a useful tool to provide evidence on how the interplay of various supramolecular forces can help stabilise exotic anionic species such as tribromide (Br3) anions. Indeed, crystals of (H2L-Ts)(Br3)1.5(NO3)0.5 unexpectedly grew from an acidic (HNO3) aqueous solution of L-Ts in the presence of Br anions. The crystal structure of this compound was determined by single crystal XRD analysis. Hydrogen bonds, salt-bridges, anion-π, π-π stacking, and van der Waals interactions contribute to stabilising the crystal lattice. The observation of two independent Br3 anions stuck over the π-electron densities of pyridine and tosyl ligand groups, one of them being sandwiched between two pyridine rings, corroborates the significance of anion-π interactions for N-containing heterocycles. We show herein the possibility of detecting anion-π contacts from fingerprint plots generated by Hirshfeld surface analysis, demonstrating the effective usage of this structural investigation technique to further dissect individual contributions of stabilising supramolecular forces. Full article
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30 pages, 12393 KiB  
Article
New Paracyclophanylthiazoles with Anti-Leukemia Activity: Design, Synthesis, Molecular Docking, and Mechanistic Studies
by Ashraf A Aly, Stefan Bräse, Alaa A. Hassan, Nasr K. Mohamed, Lamiaa E. Abd El-Haleem, Martin Nieger, Nesrin M. Morsy and Elshimaa M. N. Abdelhafez
Molecules 2020, 25(13), 3089; https://doi.org/10.3390/molecules25133089 - 07 Jul 2020
Cited by 13 | Viewed by 2677
Abstract
A new series of methyl 2-(2-(4′-[2.2]paracyclophanyl)-hydrazinylidene)-3-substituted-4-oxothiazolidin-5-ylidene)acetates 3af were synthesized from the reaction of paracyclophanyl-acylthiosemicarbazides 2af with dimethyl acetylenedicarboxylate. Based upon nuclear magnetic resonance (NMR), infrared (IR), and mass spectra (HRMS), the structure of the obtained products was elucidated. X-ray [...] Read more.
A new series of methyl 2-(2-(4′-[2.2]paracyclophanyl)-hydrazinylidene)-3-substituted-4-oxothiazolidin-5-ylidene)acetates 3af were synthesized from the reaction of paracyclophanyl-acylthiosemicarbazides 2af with dimethyl acetylenedicarboxylate. Based upon nuclear magnetic resonance (NMR), infrared (IR), and mass spectra (HRMS), the structure of the obtained products was elucidated. X-ray structure analysis was also used as unambiguous tool to elucidate the structure of the products. The target compounds 3af were screened against 60 cancer cell lines. They displayed anticancer activity against a leukemia subpanel, namely, RPMI-8226 and SR cell lines. The activity of compound 3a was found as the most cytotoxic potency against 60 cancer cell lines. Consequently, it was selected for further five doses analysis according to National Cancer Institute (NCI) protocol. The cytotoxic effect showed selectivity ratios ranging between 0.63 and 1.28 and between 0.58 and 5.89 at the GI50 and total growth inhibition (TGI) levels, respectively. Accordingly, compound 3a underwent further mechanistic study against the most sensitive leukemia RPMI-8226 and SR cell lines. It showed antiproliferation with IC50 = 1.61 ± 0.04 and 1.11 ± 0.03 µM against RPMI-8226 and SR cell lines, respectively. It also revealed a remarkable tubulin inhibitory activity, compared to colchicine with IC50 = 4.97 µM/mL. Caspase-3, BAX, and Bcl-2 assays for 3a using annexin V-FITC staining revealed significant pro-apoptotic activity. Furthermore, multidrug-resistant leukemia SR cells were used to show better resistance indices (1.285 ng/mL, 1.15-fold) than the reference. Docking studies with β-tubulin indicate that most of the tested compounds illustrated good binding at the colchicine binding site of the enzyme, especially for compound 3a, which made several interactions better than that of the reference colchicine. Full article
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11 pages, 695 KiB  
Article
Synthesis and Characterization of New Series of 1,3-5-Triazine Hydrazone Derivatives with Promising Antiproliferative Activity
by Hessa H. Al H. Al Rasheed, Azizah M. M. Malebari, Kholood A. A. Dahlous and Ayman El-Faham
Molecules 2020, 25(11), 2708; https://doi.org/10.3390/molecules25112708 - 11 Jun 2020
Cited by 10 | Viewed by 3076
Abstract
A new series of s-triazine hydrazone derivatives was prepared based on the reaction of 6-hydrazino-2,4-disubstituted-s-triazine with p-substituted benzaldehyde derivatives using a straightforward synthetic pathway. The antiproliferative activity of all synthesized compounds was evaluated against two human cancer cell lines; [...] Read more.
A new series of s-triazine hydrazone derivatives was prepared based on the reaction of 6-hydrazino-2,4-disubstituted-s-triazine with p-substituted benzaldehyde derivatives using a straightforward synthetic pathway. The antiproliferative activity of all synthesized compounds was evaluated against two human cancer cell lines; breast cancer MCF-7 and colon carcinoma HCT-116 using MTT assay. Among all, 11 compounds have shown strong to moderate antiproliferative activity with IC50 values in the range 1.01–18.20 µM in MCF-7 and 0.97–19.51 µM in HCT-116. The best results were obtained with 4,4’-(6-(2-(pyridin-2-ylmethylene)hydrazinyl)-1,3,5-triazine-2,4-diyl) dimorpholine 11 (IC50 = 1.0 µM and 0.98 µM in MCF-7 and HCT-116 cell lines, respectively). The substituents on the s-triazine core as well as the substituent at the benzylidene moiety have a great effect on the antiproliferative activity. Whereas compounds containing dimorpholino-s-triazine derivatives 8a–e showed more potent antiproliferative in MCF-7 compared to their analogs 7a–f (compounds containing two-piperidine rings), compounds containing one piperidine and one morpholine ring 9a–f showed better IC50 values in the range 10.4–22.2 µM. On the other hand, compounds containing two-piperidine rings 7a–f showed more potent antiproliferative in HCT-116 (IC50 values in the range 8.8–19.5 µM) than their analogs 8a–e and 9a–f. Full article
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23 pages, 5714 KiB  
Article
Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers
by Ádám Golcs, Bálint Árpád Ádám, Viola Horváth, Tünde Tóth and Péter Huszthy
Molecules 2020, 25(11), 2571; https://doi.org/10.3390/molecules25112571 - 31 May 2020
Cited by 10 | Viewed by 3136
Abstract
New highly lipophilic enantiopure crown ethers containing a heterocyclic unit have been synthesized. Phase transport, UV-Vis- and fluorescence spectrophotometric investigations as well as electrochemical studies on the complexation of the new macrocycles with several amine and amino acid derivatives were also carried out. [...] Read more.
New highly lipophilic enantiopure crown ethers containing a heterocyclic unit have been synthesized. Phase transport, UV-Vis- and fluorescence spectrophotometric investigations as well as electrochemical studies on the complexation of the new macrocycles with several amine and amino acid derivatives were also carried out. Achiral amines were used for studying the structural preference of the new macrocycles. Among the studied structural features of the guest molecules, the intermolecular π-π interaction showed the most significant effect on complexation, which made the aralkylamine-type compounds the most preferable guest molecules. The studied liquid membrane-based applications and photophysical investigations showed appreciable enantiomeric recognition toward some aralkylamine model compounds with homochiral preferences. New crown ether derivatives (R,R)-2 and (S,S)-2 were successfully applied as enantioselective carrier and sensor molecules. Full article
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25 pages, 16563 KiB  
Article
Discovery of New Apoptosis-Inducing Agents for Breast Cancer Based on Ethyl 2-Amino-4,5,6,7-Tetra Hydrobenzo[b]Thiophene-3-Carboxylate: Synthesis, In Vitro, and In Vivo Activity Evaluation
by Emad M. Gad, Mohamed S. Nafie, Elsayed H. Eltamany, Magdy S. A. G. Hammad, Assem Barakat and Ahmed T. A. Boraei
Molecules 2020, 25(11), 2523; https://doi.org/10.3390/molecules25112523 - 28 May 2020
Cited by 62 | Viewed by 3695
Abstract
A multicomponent synthesis was empolyed for the synthesis of ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 1. An interesting cyclization was obtained when the amino-ester 1 reacted with ethyl isothiocyanate to give the benzo[4,5]thieno[2,3-d][1,3]thiazin-4-one 3. Acylation of the amino-ester 1 with chloroacetyl [...] Read more.
A multicomponent synthesis was empolyed for the synthesis of ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 1. An interesting cyclization was obtained when the amino-ester 1 reacted with ethyl isothiocyanate to give the benzo[4,5]thieno[2,3-d][1,3]thiazin-4-one 3. Acylation of the amino-ester 1 with chloroacetyl chloride in DCM and Et3N afforded the acylated ester 4. The amino-ester 1 was cyclized to benzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 8, which was reacted with some alkylating agents leading to alkylation at nitrogen 9–13. Hydrazide 14 was utilized as a synthon for the synthesis of the derivatives 1519. Chloro-thieno[2,3-d]pyrimidine 20 was synthesized and reacted with the hydrazine hydrate to afford the hydrazino derivative 21, which was used as a scaffold for getting the derivatives 2228. Nucleophilic substitution reactions were used for getting the compounds 2935 from chloro-thieno[2,3-d]pyrimidine 20. In the way of anticancer therapeutics development, the requisite compounds were assessed for their cytotoxicity in vitro against MCF-7 and HepG-2 cancer cell lines. Twelve compounds showed an interesting antiproliferative potential with IC50 from 23.2 to 95.9 µM. The flow cytometric analysis results showed that hit 4 induces the apoptosis in MCF-7 cells with a significant 26.86% reduction in cell viability. The in vivo study revealed a significant decrease in the solid tumor mass (26.6%) upon treatment with compound 4. Moreover, in silico study as an agonist for inhibitors of JAK2 and prediction study determined their binding energies and predicted their physicochemical properties and drug-likeness scores. Full article
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Review

Jump to: Editorial, Research

25 pages, 6192 KiB  
Review
Pentacyclic Triterpenoids with Nitrogen-Containing Heterocyclic Moiety, Privileged Hybrids in Anticancer Drug Discovery
by Vuyolwethu Khwaza, Sithenkosi Mlala, Opeoluwa O. Oyedeji and Blessing A. Aderibigbe
Molecules 2021, 26(9), 2401; https://doi.org/10.3390/molecules26092401 - 21 Apr 2021
Cited by 34 | Viewed by 3688
Abstract
Pentacyclic triterpenoids are well-known phytochemicals with various biological activities commonly found in plants as secondary metabolites. The wide range of biological activities exhibited by triterpenoids has made them the most valuable sources of pharmacological agents. A number of novel triterpenoid derivatives with many [...] Read more.
Pentacyclic triterpenoids are well-known phytochemicals with various biological activities commonly found in plants as secondary metabolites. The wide range of biological activities exhibited by triterpenoids has made them the most valuable sources of pharmacological agents. A number of novel triterpenoid derivatives with many skeletal modifications have been developed. The most important modifications are the formation of analogues or derivatives with nitrogen-containing heterocyclic scaffolds. The derivatives with nitrogen-containing heterocyclic compounds are among the most promising candidate for the development of novel therapeutic drugs. About 75% of FDA-approved drugs are nitrogen-containing heterocyclic moieties. The unique properties of heterocyclic compounds have encouraged many researchers to develop new triterpenoid analogous with pharmacological activities. In this review, we discuss recent advances of nitrogen-containing heterocyclic triterpenoids as potential therapeutic agents. This comprehensive review will assist medicinal chemists to understand new strategies that can result in the development of compounds with potential therapeutic efficacy. Full article
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54 pages, 37321 KiB  
Review
Recent Advances in the Synthesis of β-Carboline Alkaloids
by Tímea Szabó, Balázs Volk and Mátyás Milen
Molecules 2021, 26(3), 663; https://doi.org/10.3390/molecules26030663 - 27 Jan 2021
Cited by 45 | Viewed by 8949
Abstract
β-Carboline alkaloids are a remarkable family of natural and synthetic indole-containing heterocyclic compounds and they are widely distributed in nature. Recently, these alkaloids have been in the focus of interest, thanks to their diverse biological activities. Their pharmacological activity makes them desirable as [...] Read more.
β-Carboline alkaloids are a remarkable family of natural and synthetic indole-containing heterocyclic compounds and they are widely distributed in nature. Recently, these alkaloids have been in the focus of interest, thanks to their diverse biological activities. Their pharmacological activity makes them desirable as sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic or antimicrobial drug candidates. The growing potential inherent in them encourages many researchers to address the challenges of the synthesis of natural products containing complex β-carboline frameworks. In this review, we describe the recent developments in the synthesis of β-carboline alkaloids and closely related derivatives through selected examples from the last 5 years. The focus is on the key steps with improved procedures and synthetic approaches. Furthermore the pharmacological potential of the alkaloids is also highlighted. Full article
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41 pages, 20200 KiB  
Review
Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review
by Sara Janowska, Agata Paneth and Monika Wujec
Molecules 2020, 25(18), 4309; https://doi.org/10.3390/molecules25184309 - 20 Sep 2020
Cited by 43 | Viewed by 5607
Abstract
During recent years, small molecules containing five-member heterocyclic moieties have become the subject of considerable growing interest for designing new antitumor agents. One of them is 1,3,4-thiadiazole. This study is an attempt to collect the 1,3,4-thiadiazole and its derivatives, which can be considered [...] Read more.
During recent years, small molecules containing five-member heterocyclic moieties have become the subject of considerable growing interest for designing new antitumor agents. One of them is 1,3,4-thiadiazole. This study is an attempt to collect the 1,3,4-thiadiazole and its derivatives, which can be considered as potential anticancer agents, reported in the literature in the last ten years. Full article
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