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Pharmaceuticals
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Recent Developments of Chalcones and Their Derivatives in Medicinal Chemistry
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Recent Developments of Chalcones and Their Derivatives in Medicinal Chemistry

A special issue of Pharmaceuticals (ISSN 1424-8247). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (25 July 2024) | Viewed by 7780

Special Issue Editor

Dr. Luis Octavio Regasini

E-Mail Website1 Website2
Guest Editor
Laboratory of Antibiotics and Chemotherapeutics, Department of Chemistry and Environmental Sciences, Institute of Biosciences, Humanities and Exact Sciences, São Paulo State University, São José do Rio Preto 15054-000, SP, Brazil
Interests: antiviral; helicase; polymerase; protease; arbovirus; influenza and HCV
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Chalcones are recognized as privileged scaffolds in drug discovery due to their concise synthesis and versatile skeleton to derive structure–activity relationships. In addition, their therapeutic potential has been confirmed by a series of successful preclinical and clinical trials. Thus, medicinal chemists continue to be fascinated and inspired by the chemical and biological properties of chalcones and their derivatives and hybrids. I would like to invite you to celebrate the marvelous biological activities of synthetic and natural chalcones in this Special Issue. 

Dr. Luis Octavio Regasini
Guest Editor

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Pharmaceuticals is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 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

  • chalcone
  • antibacterial
  • antifungal
  • antimicrobial
  • anticancer
  • antiprotozoal
  • anthelmintic

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Published Papers (5 papers)

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Research

24 pages, 9864 KiB  
Article
Synthesis and Antiproliferative Effect of 3,4,5-Trimethoxylated Chalcones on Colorectal and Prostatic Cancer Cells
by Cécile Letulle, François-Xavier Toublet, Aline Pinon, Soufyane Hba, Aurélie Laurent, Vincent Sol, Catherine Fagnère, Benjamin Rioux, Florent Allais, Sophie Michallet, Laurence Lafanechère, Youness Limami, Mounia Oudghiri, Mohamed Othman, Adam Daïch, Bertrand Liagre, Ata Martin Lawson and Christelle Pouget
Pharmaceuticals 2024, 17(9), 1207; https://doi.org/10.3390/ph17091207 - 13 Sep 2024
Viewed by 924
Abstract
In the context of designing innovative anticancer agents, the synthesis of a series of chalcones bearing a 3,4,5-trimethoxylated A ring and a variety of B rings, including phenols and original heterocycles such as chromones, was conducted. For this end, Claisen–Schmidt condensation was performed [...] Read more.
In the context of designing innovative anticancer agents, the synthesis of a series of chalcones bearing a 3,4,5-trimethoxylated A ring and a variety of B rings, including phenols and original heterocycles such as chromones, was conducted. For this end, Claisen–Schmidt condensation was performed in basic or acidic conditions between the common starting material 3,4,5-trimethoxyacetophenone and appropriate aldehydes; this allowed the recovery of fifteen chalcones in moderate–good yields. The synthesized compounds were screened for their antiproliferative activity against colorectal and prostatic cancer cells, using a colorimetric MTT assay. Among the new chromonyl series, chalcone 13 demonstrates an interesting antiproliferative effect, with IC50 values in the range of 2.6–5.1 µM at 48 h. Then, our study evidenced that indolyl chalcone 10 exhibits excellent activity towards the selected cell lines (with IC50 less than 50 nM). This compound has already been described and has been shown to be a potent anticancer agent against other cancer cell lines. Our investigations highlighted apoptosis induction, through several pro-apoptotic markers, of these two heterocyclic chalcones. Considering phenolic chalcones, compounds 2 and 8 were found to be the most active against cell proliferation, exerting their effect by inducing the depolymerization of cell microtubules. The most promising compounds in this series will be selected for application in a strategy of vectorization by either active or passive targeting. Full article
(This article belongs to the Special Issue Recent Developments of Chalcones and Their Derivatives in Medicinal Chemistry)
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15 pages, 2478 KiB  
Article
Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C
by Patrick Rômbola Ozanique, Alvaro Luiz Helena, Ralciane de Paula Menezes, Daniela Silva Gonçalves, Mariana Brentini Santiago, Guilherme Dilarri, Janaína de Cássia Orlandi Sardi, Henrique Ferreira, Carlos Henrique Gomes Martins and Luis Octávio Regasini
Pharmaceuticals 2024, 17(5), 634; https://doi.org/10.3390/ph17050634 - 14 May 2024
Viewed by 1329
Abstract
Drug-resistant bacteria constitute a big barrier against current pharmacotherapy. Efforts are urgent to discover antibacterial drugs with novel chemical and biological features. Our work aimed at the synthesis, evaluation of antibacterial effects, and toxicity of licochalcone C (LCC), a naturally occurring chalcone. The [...] Read more.
Drug-resistant bacteria constitute a big barrier against current pharmacotherapy. Efforts are urgent to discover antibacterial drugs with novel chemical and biological features. Our work aimed at the synthesis, evaluation of antibacterial effects, and toxicity of licochalcone C (LCC), a naturally occurring chalcone. The synthetic route included six steps, affording a 10% overall yield. LCC showed effects against Gram-positive bacteria (MIC = 6.2–50.0 µg/mL), Mycobacterium species (MIC = 36.2–125 µg/mL), and Helicobacter pylori (MIC = 25 µg/mL). LCC inhibited the biofilm formation of MSSA and MRSA, demonstrating MBIC50 values of 6.25 μg/mL for both strains. The investigations by fluorescence microscopy, using PI and SYTO9 as fluorophores, indicated that LCC was able to disrupt the S. aureus membrane, similarly to nisin. Systemic toxicity assays using Galleria mellonella larvae showed that LCC was not lethal at 100 µg/mL after 80 h treatment. These data suggest new uses for LCC as a compound with potential applications in antibacterial drug discovery and medical device coating. Full article
(This article belongs to the Special Issue Recent Developments of Chalcones and Their Derivatives in Medicinal Chemistry)
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19 pages, 7282 KiB  
Article
Synthesis and Biological Evaluation of Chalconesulfonamides: En Route to Proapoptotic Agents with Antiestrogenic Potency
by Stepan K. Krymov, Diana I. Salnikova, Lyubov G. Dezhenkova, Fedor B. Bogdanov, Alexander A. Korlyukov, Alexander M. Scherbakov and Andrey E. Shchekotikhin
Pharmaceuticals 2024, 17(1), 32; https://doi.org/10.3390/ph17010032 - 25 Dec 2023
Viewed by 1312
Abstract
Breast and other estrogen receptor α-positive cancers tend to develop resistance to existing drugs. Chalcone derivatives possess anticancer activity based on their ability to form covalent bonds with targets acting as Michael acceptors. This study aimed to evaluate the anticancer properties of a [...] Read more.
Breast and other estrogen receptor α-positive cancers tend to develop resistance to existing drugs. Chalcone derivatives possess anticancer activity based on their ability to form covalent bonds with targets acting as Michael acceptors. This study aimed to evaluate the anticancer properties of a series of chalcones (7a–l) with a sulfonamide group attached to the vinyl ketone moiety. Chalconesulfonamides showed a potent antiproliferative effect at low micromolar concentrations against several cancer cell lines, including ERα-positive 4-hydroxytamoxifen-resistant MCF7/HT2. Immunoblotting of samples treated with the lead compound 7e revealed its potent antiestrogenic activity (ERα/GREB1 axis) and induction of PARP cleavage (an apoptosis marker) in breast cancer cells. The obtained compounds represent a promising basis for further development of targeted drugs blocking hormone pathways in cancer cells. Full article
(This article belongs to the Special Issue Recent Developments of Chalcones and Their Derivatives in Medicinal Chemistry)
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28 pages, 7360 KiB  
Article
Curcuminoid Chalcones: Synthesis, Stability, and New Neuroprotective and Sonosensitising Activities
by Dorota Olender, Małgorzata Józkowiak, Hanna Piotrowska-Kempisty, Katarzyna Sowa-Kasprzak, Lucjusz Zaprutko, Izabela Muszalska-Kolos, Ewa Baranowska-Wójcik and Dominik Szwajgier
Pharmaceuticals 2023, 16(9), 1331; https://doi.org/10.3390/ph16091331 - 21 Sep 2023
Cited by 5 | Viewed by 1494
Abstract
The primary purpose of this work was to design and obtain a series of curcuminoid chalcone–NSAID hybrid derivatives. The ester-type hybrid compounds with ibuprofen (i), ketoprofen (ii), and naproxen (iii) were obtained in two ways, using the [...] Read more.
The primary purpose of this work was to design and obtain a series of curcuminoid chalcone–NSAID hybrid derivatives. The ester-type hybrid compounds with ibuprofen (i), ketoprofen (ii), and naproxen (iii) were obtained in two ways, using the Claisen–Schmidt reaction and the Steglich esterification reaction. The designed molecules were successfully synthesised, and FT-IR, MS, and NMR spectroscopy confirmed their structures. Moreover, the cytotoxic effect of the sonodynamic therapy and the anti-inflammatory, antioxidant, and anticholinergic properties of some curcuminoid chalcones and curcuminoid chalcones hybrids were evaluated. The curcuminoid chalcone derivatives showed promising neuroprotective activity as sonosensitisers for sonodynamic therapy in the studied cell lines. Additionally, the stability of the ester-type hybrid compounds with promising activity was determined. The RP-HPLC method was used to observe the degradation of the tested compounds. Studies have shown that structural isomers of ester-type hybrid compounds (3ai, 3bi) are characterised by a similar susceptibility to degradation factors, i.e., they are extremely unstable in alkaline environments, very unstable in acidic environments, unstable in neutral environments, practically stable in oxidising environments, and photolabile in solutions and in the solid phase. These compounds maintain adequate stability in environment at pH 1.2 and 6.8, which may make them good candidates for developing formulations for oral administration. Full article
(This article belongs to the Special Issue Recent Developments of Chalcones and Their Derivatives in Medicinal Chemistry)
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24 pages, 3259 KiB  
Article
Discovery of a New Chalcone-Trimethoxycinnamide Hybrid with Antimitotic Effect: Design, Synthesis, and Structure—Activity Relationship Studies
by Joana Moreira, Patrícia M. A. Silva, Matilde Barros, Lucília Saraiva, Madalena Pinto, Hassan Bousbaa and Honorina Cidade
Pharmaceuticals 2023, 16(6), 879; https://doi.org/10.3390/ph16060879 - 14 Jun 2023
Viewed by 1937
Abstract
In this work, the design and synthesis of a new chalcone-trimethoxycinnamide hybrid (7) based on the combination of subunits of two promising antiproliferative compounds (CM-M345 (1) and BP-M345 (2)), previously obtained by our research group, are [...] Read more.
In this work, the design and synthesis of a new chalcone-trimethoxycinnamide hybrid (7) based on the combination of subunits of two promising antiproliferative compounds (CM-M345 (1) and BP-M345 (2)), previously obtained by our research group, are reported. In order to expand the structure–activity relationship (SAR) knowledge, a new series of 7-analogues was also designed and synthetized. All the compounds were evaluated for their antitumor activity against melanoma (A375-C5), breast adenocarcinoma (MCF-7), and colorectal carcinoma (HCT116) cell lines, as well as non-tumor HPAEpiC cells. Three of the newly synthesized compounds (6, 7, and 13) exhibited potent antiproliferative activity, mainly on colorectal tumor cells (GI50 = 2.66–3.26 μM), showing hybrid 7 selectivity for tumor cells. We performed molecular mechanism studies to evaluate the potential interference of compounds with the p53 pathway, namely, p53–MDM2 interaction and mitosis in HCT116 cells. The antiproliferative activities of compounds were shown to be p53-independent. Compound 7 emerged as an antimitotic agent by inducing the mitotic arrest of colorectal tumor cells, and subsequently, cell death. Full article
(This article belongs to the Special Issue Recent Developments of Chalcones and Their Derivatives in Medicinal Chemistry)
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