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Organic Synthesis and Application of Bioactive Molecules
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Organic Synthesis and Application of Bioactive Molecules

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

Deadline for manuscript submissions: 31 May 2024 | Viewed by 5165

Special Issue Editor

Dr. Lorenzo Botta

E-Mail Website
Guest Editor
Department of Biological and Ecological Sciences, University of Tuscia, 01100 Viterbo, Italy
Interests: medicinal chemistry; organic syntheisis; prebiotic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Plants are a source of bioactive, structurally complex natural products, classified as secondary metabolites, that are useful for protective reasons against herbivores and microbes. Modern drug discovery is focused on the identification and characterization of the biologically relevant constituents of plant extracts that, once isolated, could represent drug candidates or prototypes for a future therapeutic agent. At this stage, organic synthesis has become very important for the synthesis of natural products or their analogs. For this purpose, many approaches have been developed, such as total and semi-synthesis, privileged scaffold manipulation, hybridization and dimerization strategies, scaffold morphing and scaffold decoration approaches. The Special Issue “Organic Synthesis and Application of Bioactive Molecules” aims to present the most recent advances in the identification of natural products and semi-synthetic and fully synthetic derivatives endowed with biological activity obtained through the use of modern organic synthesis approaches. This Special Issue will include manuscripts and review articles that focus on the latest synthetic strategies in the achievement of bioactive molecules.

Dr. Lorenzo Botta
Guest Editor

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 submissions that pass pre-check are 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 semimonthly 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 2700 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

  • bioactive molecules
  • total synthesis
  • semi-synthesis
  • privileged scaffold
  • hybridization
  • dimerization
  • scaffold morphing
  • scaffold decoration

Published Papers (6 papers)

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Research

12 pages, 1786 KiB  
Communication
Photoredox-Catalyzed Decarboxylative Cross-Coupling Reaction to Synthesis Unsymmetrical Diarylmethanes
by Guozhe Guo, Yuquan Zhang, Yanchun Li and Zhijun Li
Molecules 2024, 29(9), 2156; https://doi.org/10.3390/molecules29092156 - 06 May 2024
Viewed by 235
Abstract
The photoredox-catalyzed decarboxylative cross-coupling reaction of aryl acetic acids and aryl nitriles has been achieved under an argon atmosphere in high yields. This method provides a fast way to obtain prevalent aryl acetic acids from an abundant natural source. A tentative radical mechanism [...] Read more.
The photoredox-catalyzed decarboxylative cross-coupling reaction of aryl acetic acids and aryl nitriles has been achieved under an argon atmosphere in high yields. This method provides a fast way to obtain prevalent aryl acetic acids from an abundant natural source. A tentative radical mechanism has been proposed. Full article
(This article belongs to the Special Issue Organic Synthesis and Application of Bioactive Molecules)
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20 pages, 2131 KiB  
Article
Serendipitous Identification of Azine Anticancer Agents Using a Privileged Scaffold Morphing Strategy
by Silvia Cesarini, Ilaria Vicenti, Federica Poggialini, Silvia Filippi, Eleonora Mancin, Lia Fiaschi, Elisa De Marchi, Federica Giammarino, Chiara Vagaggini, Bruno Mattia Bizzarri, Raffaele Saladino, Elena Dreassi, Maurizio Zazzi and Lorenzo Botta
Molecules 2024, 29(7), 1452; https://doi.org/10.3390/molecules29071452 - 24 Mar 2024
Viewed by 566
Abstract
The use of privileged scaffolds as a starting point for the construction of libraries of bioactive compounds is a widely used strategy in drug discovery and development. Scaffold decoration, morphing and hopping are additional techniques that enable the modification of the chosen privileged [...] Read more.
The use of privileged scaffolds as a starting point for the construction of libraries of bioactive compounds is a widely used strategy in drug discovery and development. Scaffold decoration, morphing and hopping are additional techniques that enable the modification of the chosen privileged framework and better explore the chemical space around it. In this study, two series of highly functionalized pyrimidine and pyridine derivatives were synthesized using a scaffold morphing approach consisting of triazine compounds obtained previously as antiviral agents. Newly synthesized azines were evaluated against lymphoma, hepatocarcinoma, and colon epithelial carcinoma cells, showing in five cases acceptable to good anticancer activity associated with low cytotoxicity on healthy fibroblasts. Finally, ADME in vitro studies were conducted on the best derivatives of the two series showing good passive permeability and resistance to metabolic degradation. Full article
(This article belongs to the Special Issue Organic Synthesis and Application of Bioactive Molecules)
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17 pages, 11522 KiB  
Article
Dimethyl Bisphenolate Ameliorates Carbon Tetrachloride-Induced Liver Injury by Regulating Oxidative Stress-Related Genes
by Rong Wang, Huanhuan Shen, Jiaxiang Zhang, Xiyan Li, Yang Guo, Zhenjun Zhao, Pingyu Wang, Ning Xie, Youjie Li, Guiwu Qu and Shuyang Xie
Molecules 2023, 28(24), 7989; https://doi.org/10.3390/molecules28247989 - 07 Dec 2023
Viewed by 840
Abstract
Liver disease accounts for millions of deaths per year all over the world due to complications from cirrhosis and liver injury. In this study, a novel compound, dimethyl bisphenolate (DMB), was synthesized to investigate its role in ameliorating carbon tetrachloride (CCl4)-induced [...] Read more.
Liver disease accounts for millions of deaths per year all over the world due to complications from cirrhosis and liver injury. In this study, a novel compound, dimethyl bisphenolate (DMB), was synthesized to investigate its role in ameliorating carbon tetrachloride (CCl4)-induced liver injury through the regulation of oxidative stress-related genes. The structure of DMB was confirmed based on its hydrogen spectrum and mass spectrometry. DMB significantly reduced the high levels of ALT, AST, DBIL, TBIL, ALP, and LDH in a dose-dependent manner in the sera of CCl4-treated rats. The protective effects of DMB on biochemical indicators were similar to those of silymarin. The ROS fluorescence intensity increased in CCl4-treated cells but significantly weakened in DMB-treated cells compared with the controls. DMB significantly increased the content of oxidative stress-related GSH, Nrf2, and GCLC dose-dependently but reduced MDA levels in CCl4-treated cells or the liver tissues of CCl4-treated rats. Moreover, DMB treatment decreased the expression levels of P53 and Bax but increased those of Bcl2. In summary, DMB demonstrated protective effects on CCl4-induced liver injury by regulating oxidative stress-related genes. Full article
(This article belongs to the Special Issue Organic Synthesis and Application of Bioactive Molecules)
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28 pages, 8182 KiB  
Article
Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity
by Diter Miranda-Sánchez, Carlos H. Escalante, Dulce Andrade-Pavón, Omar Gómez-García, Edson Barrera, Lourdes Villa-Tanaca, Francisco Delgado and Joaquín Tamariz
Molecules 2023, 28(20), 7223; https://doi.org/10.3390/molecules28207223 - 23 Oct 2023
Viewed by 1037
Abstract
As a new approach, pyrrolo[1,2-a]pyrazines were synthesized through the cyclization of 2-formylpyrrole-based enaminones in the presence of ammonium acetate. The enaminones were prepared with a straightforward method, reacting the corresponding alkyl 2-(2-formyl-1H-pyrrol-1-yl)acetates, 2-(2-formyl-1H-pyrrol-1-yl)acetonitrile, and 2-(2-formyl-1H-pyrrol-1-yl)acetophenones [...] Read more.
As a new approach, pyrrolo[1,2-a]pyrazines were synthesized through the cyclization of 2-formylpyrrole-based enaminones in the presence of ammonium acetate. The enaminones were prepared with a straightforward method, reacting the corresponding alkyl 2-(2-formyl-1H-pyrrol-1-yl)acetates, 2-(2-formyl-1H-pyrrol-1-yl)acetonitrile, and 2-(2-formyl-1H-pyrrol-1-yl)acetophenones with DMFDMA. Analogous enaminones elaborated from alkyl (E)-3-(1H-pyrrol-2-yl)acrylates were treated with a Lewis acid to afford indolizines. The antifungal activity of the series of substituted pyrroles, pyrrole-based enaminones, pyrrolo[1,2-a]pyrazines, and indolizines was evaluated on six Candida spp., including two multidrug-resistant ones. Compared to the reference drugs, most test compounds produced a more robust antifungal effect. Docking analysis suggests that the inhibition of yeast growth was probably mediated by the interaction of the compounds with the catalytic site of HMGR of the Candida species. Full article
(This article belongs to the Special Issue Organic Synthesis and Application of Bioactive Molecules)
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17 pages, 6578 KiB  
Article
3-Ferrocenyl-estra-1,3,5 (10)-triene-17-one: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Studies, and Its Binding to Human Serum Albumin Studied through Fluorescence Quenching and In Silico Docking Studies
by Mariola M. Flores-Rivera, José A. Carmona-Negrón, Arnold L. Rheingold and Enrique Meléndez
Molecules 2023, 28(16), 6147; https://doi.org/10.3390/molecules28166147 - 20 Aug 2023
Viewed by 888
Abstract
3-ferrocenyl-estra-1,3,5 (10)-triene-17-one (2), [Fe(C5H5)(C24H25O3)], crystallizes in the monoclinic space group C2. The cyclopentadienyl (Cp) rings adopt a nearly eclipsed conformation, and the Cp plane is tilted by 87.66° with respect to [...] Read more.
3-ferrocenyl-estra-1,3,5 (10)-triene-17-one (2), [Fe(C5H5)(C24H25O3)], crystallizes in the monoclinic space group C2. The cyclopentadienyl (Cp) rings adopt a nearly eclipsed conformation, and the Cp plane is tilted by 87.66° with respect to the substituted phenyl plane. An average Fe-C(Cp) bond length of 2.040(13) Å was determined, similar to the one reported for ferrocene. Hirshfeld surfaces and two-dimensional fingerprint plots were generated to analyze weak intermolecular C-H···π and C-H···O interactions. Density functional theory studies revealed a 1.15 kcal/mol rotational barrier for the C3-O1 single bound. Fluorescence quenching studies and in silico docking studies suggest that human serum albumin forms a complex with 2 via a static mechanism dominated by van der Waals interactions and hydrogen bonding interactions. Full article
(This article belongs to the Special Issue Organic Synthesis and Application of Bioactive Molecules)
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9 pages, 838 KiB  
Article
Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes
by Denis S. Baranov, Anna S. Kashnik, Anastasiya N. Atnyukova and Sergei A. Dzuba
Molecules 2023, 28(16), 5991; https://doi.org/10.3390/molecules28165991 - 10 Aug 2023
Viewed by 1030
Abstract
Diclofenac is a non-steroidal anti-inflammatory drug (NSAID) from the group of phenylacetic acid derivatives, which has analgesic, anti-inflammatory and antipyretic properties. The interaction of non-steroidal anti-inflammatory drugs with cell membranes can affect their physicochemical properties, which, in turn, can cause a number of [...] Read more.
Diclofenac is a non-steroidal anti-inflammatory drug (NSAID) from the group of phenylacetic acid derivatives, which has analgesic, anti-inflammatory and antipyretic properties. The interaction of non-steroidal anti-inflammatory drugs with cell membranes can affect their physicochemical properties, which, in turn, can cause a number of side effects in the use of these drugs. Electron paramagnetic resonance (EPR) spectroscopy could be used to study the interaction of diclofenac with a membrane, if its spin-labeled analogs existed. This paper describes the synthesis of spin-labeled diclofenac (diclofenac-SL), which consists of a simple sequence of transformations such as iodination, esterification, Sonogashira cross-coupling, oxidation and saponification. EPR spectra showed that diclofenac-SL binds to a lipid membrane composed of palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC). 2H electron spin echo spectroscopy (ESEEM) was used to determine the position of the diclofenac-SL relative to the membrane surface. It was established that its average depth of immersion corresponds to the 5th position of the carbon atom in the lipid chain. Full article
(This article belongs to the Special Issue Organic Synthesis and Application of Bioactive Molecules)
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