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Molecules
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Strategies toward Bioactive Natural Product Like-Compounds
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Strategies toward Bioactive Natural Product Like-Compounds

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

Deadline for manuscript submissions: closed (31 January 2021) | Viewed by 20392

Special Issue Editors

Prof. Dr. Ana Estévez-Braun

E-Mail Website
Guest Editor
Organic Chemistry Department, Instituto Universitario de Bio-Orgánica, Universidad de La Laguna, San Cristóbal de La Laguna, Spain
Interests: medicinal chemistry; synthesis of heterocyclic quinones; domino and multicomponent reactions using privileged structures; natural products chemistry
Dr. Ángel Amesty

E-Mail Website
Co-Guest Editor
Instituto Universitario de Bio-Orgánica, Universidad de La Laguna, San Cristóbal de La Laguna, Spain
Interests: medicinal chemistry, molecular modelling, design and synthesis of bioactive compounds, domino and multicomponent reactions using privileged structures, and natural products chemistry

Special Issue Information

Dear Colleagues,

Natural products remain an important source of therapeutic drug leads and continue to inspire new synthetic approaches. In this sense, it is encouraging to see that there is renewed interest in using natural product building blocks or privileged structures to access novel drug-like chemical spaces. Creative chemistry performed on privileged structures together target biological strategies, which has the potential to lead to novel chemical entities with pharmacological potential.

This Special Issue aims to collect original papers and/or review papers focused on strategies that provide natural product-like and natural product-inspired biologically relevant compound collections.

Prof. Ana Estévez-Braun
Dr. Ángel Amesty
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

  • Privileged structures
  • Natural product building blocks
  • Multicomponent reactions (MCR)
  • Domino reactions
  • Diversity-oriented synthesis (DOS)
  • Priviliged substructure-based DOS (pDOS)
  • Biologically oriented synthesis (BIOS)
  • Diverted total synthesis (DTS)
  • Complexity to Diversity (CtD)
  • Function-oriented synthesis (FOS)
  • Analogues of a bioactive natural product (focused libraries)
  • Diversity-enhanced extracts
  • Hybrid compounds
  • Biological activity
  • Molecular modelling.

Published Papers (5 papers)

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Research

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13 pages, 1555 KiB  
Article
N-Phenyl Cinnamamide Derivatives Protect Hepatocytes against Oxidative Stress by Inducing Cellular Glutathione Synthesis via Nuclear Factor (Erythroid-Derived 2)-Like 2 Activation
by Sou Hyun Kim, Minwoo Kim, Doyoung Kwon, Jae Sung Pyo, Joo Hyun Kim, Jae-Hwan Kwak and Young-Suk Jung
Molecules 2021, 26(4), 1027; https://doi.org/10.3390/molecules26041027 - 15 Feb 2021
Cited by 2 | Viewed by 2482
Abstract
Substituted N-phenyl cinnamamide derivatives were designed and synthesized to confirm activation of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway by the electronic effect on beta-position of Michael acceptor according to introducing the R1 and R2 group. Compounds were screened using [...] Read more.
Substituted N-phenyl cinnamamide derivatives were designed and synthesized to confirm activation of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway by the electronic effect on beta-position of Michael acceptor according to introducing the R1 and R2 group. Compounds were screened using the Nrf2/antioxidant response element (ARE)-driven luciferase reporter assay. Compound 1g showed desirable luciferase activity in HepG2 cells without cell toxicity. mRNA and protein expression of Nrf2/ARE target genes such as NAD(P)H quinone oxidoreductase 1, hemeoxygenase-1, and glutamate-cysteine ligase catalytic subunit (GCLC) were upregulated by compound 1g in a concentration-dependent manner. Treatment with 1g resulted in increased endogenous antioxidant glutathione, showing strong correlation with enhanced GCLC expression for synthesis of glutathione. In addition, tert-butyl hydroperoxide (t-BHP)-generated reactive oxygen species were significantly removed by 1g, and the results of a cell survival assay in a t-BHP-induced oxidative cell injury model showed a cytoprotective effect of 1g in a concentration dependent manner. In conclusion, the novel compound 1g can be utilized as an Nrf2/ARE activator in antioxidative therapy. Full article
(This article belongs to the Special Issue Strategies toward Bioactive Natural Product Like-Compounds)
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22 pages, 17069 KiB  
Article
Efficient Multicomponent Synthesis of Diverse Antibacterial Embelin-Privileged Structure Conjugates
by Pedro Martín-Acosta, Rosalyn Peña, Gabriela Feresin, Alejandro Tapia, Isabel Lorenzo-Castrillejo, Félix Machín, Ángel Amesty and Ana Estévez-Braun
Molecules 2020, 25(14), 3290; https://doi.org/10.3390/molecules25143290 - 20 Jul 2020
Cited by 3 | Viewed by 2784
Abstract
A library of embelin derivatives has been synthesized through a multicomponent reaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin, 4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl3 as catalyst. This multicomponent reaction implies Knoevenagel condensation, [...] Read more.
A library of embelin derivatives has been synthesized through a multicomponent reaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin, 4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl3 as catalyst. This multicomponent reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. Many of the synthesized compounds were active and selective against Gram-positive bacteria, including one important multiresistant Staphylococcus aureus clinical isolate. It was found how the conjugation of diverse privileged substructure with embelin led to adducts having enhanced antibacterial activities. Full article
(This article belongs to the Special Issue Strategies toward Bioactive Natural Product Like-Compounds)
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12 pages, 765 KiB  
Article
Synthesis and Antimicrobial Activity of Novel 4-Hydroxy-2-quinolone Analogs
by Thitiphong Khamkhenshorngphanuch, Kittipat Kulkraisri, Alongkorn Janjamratsaeng, Napasawan Plabutong, Arsa Thammahong, Kanitta Manadee, Sarisa Na Pombejra and Tanatorn Khotavivattana
Molecules 2020, 25(13), 3059; https://doi.org/10.3390/molecules25133059 - 04 Jul 2020
Cited by 17 | Viewed by 4289
Abstract
Alkyl quinolone has been proven to be a privileged scaffold in the antimicrobial drug discovery pipeline. In this study, a series of new 4-hydroxy-2-quinolinone analogs containing a long alkyl side chain at C-3 and a broad range of substituents on the C-6 and [...] Read more.
Alkyl quinolone has been proven to be a privileged scaffold in the antimicrobial drug discovery pipeline. In this study, a series of new 4-hydroxy-2-quinolinone analogs containing a long alkyl side chain at C-3 and a broad range of substituents on the C-6 and C-7 positions were synthesized. The antibacterial and antifungal activities of these analogs against Staphylococcus aureus, Escherichia coli, and Aspergillus flavus were investigated. The structure-activity relationship study revealed that the length of the alkyl chain, as well as the type of substituent, has a dramatic impact on the antimicrobial activities. Particularly, the brominated analogs 3j with a nonyl side chain exhibited exceptional antifungal activities against A. flavus (half maximal inhibitory concentration (IC50) = 1.05 µg/mL), which surpassed that of the amphotericin B used as a positive control. The antibacterial activity against S. aureus, although not as potent, showed a similar trend to the antifungal activity. The data suggest that the 4-hydroxy-2-quinolone is a promising framework for the further development of new antimicrobial agents, especially for antifungal treatment. Full article
(This article belongs to the Special Issue Strategies toward Bioactive Natural Product Like-Compounds)
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15 pages, 1994 KiB  
Article
Innovative Bio-Based Organic UV-A and Blue Light Filters from Meldrum’s Acid
by Cédric Peyrot, Matthieu M. Mention, Fanny Brunissen, Patrick Balaguer and Florent Allais
Molecules 2020, 25(9), 2178; https://doi.org/10.3390/molecules25092178 - 06 May 2020
Cited by 18 | Viewed by 5053
Abstract
Faced with the ban of some organic UV filters such as octinoxate or avobenzone, especially in Hawaii, it became essential to offer new alternatives that are both renewable and safe for humans and the environment. In this context, a class of bio-based molecules [...] Read more.
Faced with the ban of some organic UV filters such as octinoxate or avobenzone, especially in Hawaii, it became essential to offer new alternatives that are both renewable and safe for humans and the environment. In this context, a class of bio-based molecules displaying interesting UV filter properties and great (photo)stability has been developed from Meldrum’s acid and bio-based and synthetic p-hydroxycinnamic acids, furans and pyrroles. Moreover, p-hydroxycinnamic acid-based Meldrum’s derivatives possess valuable secondary activities sought by the cosmetic industry such as antioxidant and anti-tyrosinase properties. The evaluation of the properties of mixture of judiciously chosen Meldrum’s acid derivatives highlighted the possibility to modulate secondary activity while maintaining excellent UV protection. Meldrum’s acid derivatives are not only competitive when benchmarked against organic filters currently on the market (i.e., avobenzone), but they also do not exhibit any endocrine disruption activity. Full article
(This article belongs to the Special Issue Strategies toward Bioactive Natural Product Like-Compounds)
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Review

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40 pages, 11972 KiB  
Review
Overcoming Multidrug Resistance: Flavonoid and Terpenoid Nitrogen-Containing Derivatives as ABC Transporter Modulators
by Bruno M. F. Gonçalves, David S. P. Cardoso and Maria-José U. Ferreira
Molecules 2020, 25(15), 3364; https://doi.org/10.3390/molecules25153364 - 24 Jul 2020
Cited by 46 | Viewed by 5177
Abstract
Multidrug resistance (MDR) in cancer is one of the main limitations for chemotherapy success. Numerous mechanisms are behind the MDR phenomenon wherein the overexpression of the ATP-binding cassette (ABC) transporter proteins P-glycoprotein (P-gp), breast cancer resistance protein (BCRP) and multidrug resistance protein 1 [...] Read more.
Multidrug resistance (MDR) in cancer is one of the main limitations for chemotherapy success. Numerous mechanisms are behind the MDR phenomenon wherein the overexpression of the ATP-binding cassette (ABC) transporter proteins P-glycoprotein (P-gp), breast cancer resistance protein (BCRP) and multidrug resistance protein 1 (MRP1) is highlighted as a prime factor. Natural product-derived compounds are being addressed as promising ABC transporter modulators to tackle MDR. Flavonoids and terpenoids have been extensively explored in this field as mono or dual modulators of these efflux pumps. Nitrogen-bearing moieties on these scaffolds were proved to influence the modulation of ABC transporters efflux function. This review highlights the potential of semisynthetic nitrogen-containing flavonoid and terpenoid derivatives as candidates for the design of effective MDR reversers. A brief introduction concerning the major role of efflux pumps in multidrug resistance, the potential of natural product-derived compounds in MDR reversal, namely natural flavonoid and terpenoids, and the effect of the introduction of nitrogen-containing groups are provided. The main modifications that have been performed during last few years to generate flavonoid and terpenoid derivatives, bearing nitrogen moieties, such as aliphatic, aromatic and heterocycle amine, amide, and related functional groups, as well as their P-gp, MRP1 and BCRP inhibitory activities are reviewed and discussed. Full article
(This article belongs to the Special Issue Strategies toward Bioactive Natural Product Like-Compounds)
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