Naphthoquinone 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 (15 February 2023) | Viewed by 4777

Special Issue Editors


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Guest Editor
Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Rua Outeiro São João Batista, Niterói 24020-141, RJ, Brazil
Interests: organic synthesis; medicinal chemistry; naphthoquinones; triazoles; heterocycles
Special Issues, Collections and Topics in MDPI journals

E-Mail Website
Guest Editor
Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Niterói 24020-141, RJ, Brazil
Interests: organic synthesis; medicinal chemistry; naphthoquinones; triazoles
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Quinones represent a class of natural products of great structural diversity with a wide distribution in nature and can be found in various plants, fungi, bacteria, and insects. Among this family, the class of naphthoquinones has significant prominence, both for its great versatility of application in organic synthesis and for its remarkable applications in medicinal chemistry. This biological diversity is closely related to its good synthetic accessibility, since many substances can be obtained from the base structure of naphthoquinones. In addition to the discovery of new natural products, the synthesis of new molecules through innovative methodologies has also contributed to the great expansion of this subgroup in recent decades. Among the protocols used to obtain new compounds are carbonyl additions and the introduction of groups on the benzene ring and the quinonoid ring.

Currently, a large number of original scientific articles have been presented on this topic, exploring reactions using naphthoquinones as starting material and biological applications such as antitumor, leishmanicidal, antibacterial, antifungal, antimalarial, and trypanocidal. 

The journal Pharmaceuticals invites both reviews and original articles presenting the historical importance of naphthoquinones in medicinal chemistry and the latest findings published. The collection of manuscripts will be published as a Special Issue of the journal.

Prof. Dr. David Rodrigues da Rocha
Prof. Dr. Fernando de Carvalho da Silva
Guest Editors

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

  • naphthoquinones
  • medicinal chemistry
  • organic synthesis
  • natural products
  • cancer
  • malaria
  • neglected diseases

Published Papers (2 papers)

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Research

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18 pages, 4798 KiB  
Article
Interactions of Antibacterial Naphthoquinones with Mesoporous Silica Surfaces: A Physicochemical and Theoretical Approach
by César Iván Corpus-Mendoza, Denisse de Loera, Lluvia Itzel López-López, Brenda Acosta, Sarai Vega-Rodríguez and Gabriela Navarro-Tovar
Pharmaceuticals 2022, 15(12), 1464; https://doi.org/10.3390/ph15121464 - 25 Nov 2022
Cited by 1 | Viewed by 1264
Abstract
1,4−naftoquinone (NQ) molecules have been extensively evaluated as potent antibacterial compounds; however, their use is limited, since they have low water solubility and exhibit toxicities in healthy eukaryotic cells. A possible path to overcoming these challenges is the use of particulate vehicles, such [...] Read more.
1,4−naftoquinone (NQ) molecules have been extensively evaluated as potent antibacterial compounds; however, their use is limited, since they have low water solubility and exhibit toxicities in healthy eukaryotic cells. A possible path to overcoming these challenges is the use of particulate vehicles, such as SBA-15, which is a biocompatible and biodegradable mesoporous silica material, that may enhance drug delivery and decrease dosages. In this work, an isotherm model-based adsorption of three NQs into SBA-15 microparticles was evaluated. Interactions between NQs and SBA-15 microparticles were modeled at the B3LYP/6-31+G(d,p) level of theory to understand the nature of such interactions. The results demonstrated that the adsorption of NQ, 2NQ, and 5NQ into SBA-15 fit the Freundlich adsorption model. According to theorical studies, physisorption is mediated by hydrogen bonds, while the most stable interactions occur between the carbonyl group of NQ and silica surfaces. Both experimental and theoretical results contribute to a deeper understanding of the use of SBA-15 or similar particles as nanovehicles in such a way that NQs can be modified in carbonyl or C3 to enhance adsorptions. The theoretical and experimental results were in accordance and contribute to a deeper understanding of how interactions between NQ-type molecules and SiO2 materials occur. Full article
(This article belongs to the Special Issue Naphthoquinone in Medicinal Chemistry)
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Review

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34 pages, 19804 KiB  
Review
The Relevance and Insights on 1,4-Naphthoquinones as Antimicrobial and Antitumoral Molecules: A Systematic Review
by Gabriela Navarro-Tovar, Sarai Vega-Rodríguez, Elisa Leyva, Silvia Loredo-Carrillo, Denisse de Loera and Lluvia Itzel López-López
Pharmaceuticals 2023, 16(4), 496; https://doi.org/10.3390/ph16040496 - 27 Mar 2023
Cited by 5 | Viewed by 2984
Abstract
Natural product derivatives are essential in searching for compounds with important chemical, biological, and medical applications. Naphthoquinones are secondary metabolites found in plants and are used in traditional medicine to treat diverse human diseases. Considering this, the synthesis of naphthoquinone derivatives has been [...] Read more.
Natural product derivatives are essential in searching for compounds with important chemical, biological, and medical applications. Naphthoquinones are secondary metabolites found in plants and are used in traditional medicine to treat diverse human diseases. Considering this, the synthesis of naphthoquinone derivatives has been explored to contain compounds with potential biological activity. It has been reported that the chemical modification of naphthoquinones improves their pharmacological properties by introducing amines, amino acids, furan, pyran, pyrazole, triazole, indole, among other chemical groups. In this systematic review, we summarized the preparation of nitrogen naphthoquinones derivatives and discussed their biological effect associated with redox properties and other mechanisms. Preclinical evaluation of antibacterial and/or antitumoral naphthoquinones derivatives is included because cancer is a worldwide health problem, and there is a lack of effective drugs against multidrug-resistant bacteria. The information presented herein indicates that naphthoquinone derivatives could be considered for further studies to provide drugs efficient in treating cancer and multidrug-resistant bacteria. Full article
(This article belongs to the Special Issue Naphthoquinone in Medicinal Chemistry)
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