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Special Issue "Chalcone: A Privileged Structure in Medicinal Chemistry"

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

Deadline for manuscript submissions: 31 May 2018

Special Issue Editors

Guest Editor
Prof. Dr. Angela Rampa

Department of Pharmacy and Biotechnology, Alma Mater Studiorum—University of Bologna,Via Belmeloro 6, 40126 Bologna, Italy
Website | E-Mail
Interests: drug design; hybrid molecules; Alzheimer’s disease; AChE inhibitors; FAAH inhibitors; CB receptors ligands; flavonoids
Guest Editor
Prof. Dr. Alessandra Bisi

Department of Pharmacy and Biotechnology, Alma Mater Studiorum—University of Bologna,Via Belmeloro 6, 40126 Bologna, Italy
Website | E-Mail
Interests: flavonoids; hybrid molecules; privileged structures; MDR reversal; cytochromes P-450 inhibitors; Alzheimer’s disease

Special Issue Information

Dear Colleagues,

Chalcones belong to the flavonoid family and are widely distributed in edible plants. Naturally-occurring chalcones are endowed with a broad spectrum of biological activities and have been used in traditional medicine for many years. These natural products can be defined “privileged structures” and, as such, they can be properly exploited to develop effective strategies in drug discovery. The design and synthetic feasibility of chalcone-based compounds provides a new world of possibilities to find novel biological activities and unexplored therapeutic applications. Indeed, the peculiar electrophilic trans-α,β-unsaturated carbonyl framework of chalcone allows the molecule to interact with cysteine residues of different biological targets. Furthermore, because of their conjugated system, chalcones can be fluorescent, making them potential chemical probes for mechanistic investigations and imaging/diagnosis. This Special Issue aims to provide an overview of the latest applications of this intriguing class of natural/synthetic compounds in medicinal chemistry.

Prof. Dr. Angela Rampa
Prof. Dr. Alessandra Bisi
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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. Molecules 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 1800 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
  • antioxidant
  • anticancer
  • anti-inflammatory
  • antibacterial
  • antimicrobial
  • neuroprotective effects
  • antimalarial
  • antidiabetic
  • Probes

Published Papers (4 papers)

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Research

Open AccessArticle Synthesis and Anticandidal Activity of New Imidazole-Chalcones
Molecules 2018, 23(4), 831; doi:10.3390/molecules23040831
Received: 23 March 2018 / Revised: 28 March 2018 / Accepted: 29 March 2018 / Published: 4 April 2018
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Abstract
In the present work, 15 new 1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-substituedphenyl)prop-2-en-1-one derivatives (3a3o) were synthesized to evaluate their antifungal activity. Structures of newly synthesized imidazole derivatives (3a3o) were characterized by IR, 1H-NMR, 13C-NMR, and LCMSMS
[...] Read more.
In the present work, 15 new 1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-substituedphenyl)prop-2-en-1-one derivatives (3a3o) were synthesized to evaluate their antifungal activity. Structures of newly synthesized imidazole derivatives (3a3o) were characterized by IR, 1H-NMR, 13C-NMR, and LCMSMS spectroscopic methods. The anticandidal activity of compounds (3a3o) against C. albicans (ATCC 24433), C. krusei (ATCC 6258), C. parapsilosis (ATCC 22019), and C. glabrata (ATCC 90030) was elucidated according to the EUCAST definitive (EDef 7.1) method. Consistent with the activity studies, 3a3d were found to be more potent derivatives with their MIC50 values (0.78 µg/mL–3.125 µg/mL) against Candida strains. Compound 3c indicated similar antifungal activity to ketoconazole against all Candida species and was evaluated as the most active derivative in the series. Effects of the most potent derivatives 3a3d on ergosterol biosynthesis were observed by LC-MS-MS method, which is based on quantification of the ergosterol level in C. krusei. Moreover, these compounds were subjected to a cytotoxicity test for the preliminary toxicological profiles and were found as non-cytotoxic. Furthermore, docking studies for the most active derivative 3c were performed to evaluate its binding modes on lanosterol 14-α-demethylase. In addition to in vitro tests, docking studies also revealed that Compound 3c is a potential ergosterol biosynthesis inhibitor. Full article
(This article belongs to the Special Issue Chalcone: A Privileged Structure in Medicinal Chemistry)
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Open AccessArticle Synthesis and Antiproliferative Activity of Minor Hops Prenylflavonoids and New Insights on Prenyl Group Cyclization
Molecules 2018, 23(4), 776; doi:10.3390/molecules23040776
Received: 7 March 2018 / Revised: 22 March 2018 / Accepted: 27 March 2018 / Published: 28 March 2018
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Abstract
Synthesis of minor prenylflavonoids found in hops and their non-natural derivatives were performed. The antiproliferative activity of the obtained compounds against some human cancer cell lines was investigated. Using xanthohumol isolated from spent hops as a lead compound, a series of minor hop
[...] Read more.
Synthesis of minor prenylflavonoids found in hops and their non-natural derivatives were performed. The antiproliferative activity of the obtained compounds against some human cancer cell lines was investigated. Using xanthohumol isolated from spent hops as a lead compound, a series of minor hop prenylflavonoids and synthetic derivatives were obtained by isomerization, cyclisation, oxidative-cyclisation, oxidation, reduction and demethylation reactions. Three human cancer cell lines—breast (MCF-7), prostate (PC-3) and colon (HT-29)—were used in antiproliferative assays, with cisplatin as a control compound. Five minor hop prenyl flavonoids and nine non-natural derivatives of xanthohumol have been synthetized. Syntheses of xanthohumol K, its dihydro- and tetrahydro-derivatives and 1″,2″,α,β-tetrahydroxanthohumol C were described for the first time. All of the minor hops prenyl flavonoids exhibited strong to moderate antiproliferative activity in vitro. The minor hops flavonoids xanthohumol C and 1″,2″-dihydroxanthohumol K and non-natural 2,3-dehydroisoxanthohumol exhibited the activity comparable to cisplatin. Results described in the article suggest that flavonoids containing chromane- and chromene-like moieties, especially chalcones, are potent antiproliferative agents. The developed new efficient, regioselective cyclisation reaction of the xanthohumol prenyl group to 1″,2″-dihydroxantohumol K may be used in the synthesis of other compounds with the chromane moiety. Full article
(This article belongs to the Special Issue Chalcone: A Privileged Structure in Medicinal Chemistry)
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Open AccessArticle A New Series of Pyrrole-Based Chalcones: Synthesis and Evaluation of Antimicrobial Activity, Cytotoxicity, and Genotoxicity
Molecules 2017, 22(12), 2112; doi:10.3390/molecules22122112
Received: 3 November 2017 / Revised: 27 November 2017 / Accepted: 28 November 2017 / Published: 30 November 2017
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Abstract
In an effort to develop new potent antimicrobial and anticancer agents, new pyrrole-based chalcones were designed and synthesized via the base-catalyzed Claisen-Schmidt condensation of 2-acetyl-1-methylpyrrole with 5-(aryl)furfural derivatives. The compounds were evaluated for their in vitro antimicrobial effects on pathogenic bacteria and Candida
[...] Read more.
In an effort to develop new potent antimicrobial and anticancer agents, new pyrrole-based chalcones were designed and synthesized via the base-catalyzed Claisen-Schmidt condensation of 2-acetyl-1-methylpyrrole with 5-(aryl)furfural derivatives. The compounds were evaluated for their in vitro antimicrobial effects on pathogenic bacteria and Candida species using microdilution and ATP luminescence microbial cell viability assays. MTT assay was performed to determine the cytotoxic effects of the compounds on A549 human lung adenocarcinoma, HepG2 human hepatocellular carcinoma, C6 rat glioma, and NIH/3T3 mouse embryonic fibroblast cell lines. 1-(1-Methyl-1H-pyrrol-2-yl)-3-(5-(4-chlorophenyl)furan-2-yl)prop-2-en-1-one (7) and 1-(1-methyl-1H-pyrrol-2-yl)-3-(5-(2,5-dichlorophenyl)furan-2-yl)prop-2-en-1-one (9) were found to be the most potent antifungal agents against Candida krusei and therefore these compounds were chosen for flow cytometry analysis and Ames MPF assay. ATP bioluminescence assay indicated that the antifungal activity of compounds 7 and 9 against C. krusei was significantly higher than that of other compounds and the reference drug (ketoconazole), whereas flow cytometry analysis revealed that the percentage of dead cells treated with compound 7 was more than that treated with compound 9 and ketoconazole. According to Ames MPF assay, compounds 7 and 9 were found to be non-genotoxic against TA98 and TA100 with/without metabolic activation. MTT assay indicated that 1-(1-methyl-1H-pyrrol-2-yl)-3-(5-(2-nitrophenyl)furan-2-yl)prop-2-en-1-one (3) showed more selective anticancer activity than cisplatin against the HepG2 cell line. On the other hand, 1-(1-methyl-1H-pyrrol-2-yl)-3-(5-(4-nitrophenyl)furan-2-yl)prop-2-en-1-one (1) was found to be more effective and selective on the A549 cell line than cisplatin. Full article
(This article belongs to the Special Issue Chalcone: A Privileged Structure in Medicinal Chemistry)
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Open AccessArticle Practical Synthesis of Chalcone Derivatives and Their Biological Activities
Molecules 2017, 22(11), 1872; doi:10.3390/molecules22111872
Received: 30 September 2017 / Revised: 21 October 2017 / Accepted: 24 October 2017 / Published: 1 November 2017
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Abstract
Practical synthesis and biological activities of 4-hydroxy-3-methoxy-2-propene derivatives are described. The novel chalcone derivatives were prepared by acid catalysed one-step condensation of 1,3- or 1,4-diacetylbenzene and 1,3,5-triacetylbenzene with 4-hydroxy-3-methoxybenzaldehyde. They were then evaluated for free radical scavenging activity, suppression of lipopolysaccharides (LPS)-induced NO
[...] Read more.
Practical synthesis and biological activities of 4-hydroxy-3-methoxy-2-propene derivatives are described. The novel chalcone derivatives were prepared by acid catalysed one-step condensation of 1,3- or 1,4-diacetylbenzene and 1,3,5-triacetylbenzene with 4-hydroxy-3-methoxybenzaldehyde. They were then evaluated for free radical scavenging activity, suppression of lipopolysaccharides (LPS)-induced NO generation, and anti-excitotoxicity in vitro. It was found that all compounds showed good effects for 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging, LPS-induced NO generation, and anti-neurotoxicity. Compounds 6 and 7 were potent suppressor of NO generation with the concentration range 10 µM and especially compound 8 showed very potent anti-inflammatory activity with 1 µM. In addition, the di- and tri-acetylbenzyl derivatives 6, 7, and 8 showed enhanced anti-neurotoxicity activity in cultured cortical neurons. Molecular modelling studies to investigate the chemical structural characteristics required for the enhanced biological activities interestingly revealed that compound 8 has the smallest highest occupied molecular orbital-lowest energy unoccupied molecular orbital (HOMO-LUMO) gap, which signifies easy electron and radical transfer between HOMO and LUMO in model studies. Full article
(This article belongs to the Special Issue Chalcone: A Privileged Structure in Medicinal Chemistry)
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