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Special Issue "Versatile Coumarins"

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

Deadline for manuscript submissions: closed (15 August 2017)

Special Issue Editor

Guest Editor
Emeritus Prof. Perry T. Kaye

Department of Chemistry, Rhodes University, Grahamstown, South Africa
Website | E-Mail
Interests: synthetic methodology: Applications of the Baylis–Hillman reaction in the synthesis of benzannulated heterocyclic systems and their elaboration to biologically active compounds; medicinal chemistry: Design, synthesis and in silico and in vitro evaluation of the medicinal potential of novel compounds as anti-parasitic (anti-malarial and anti-trypanosomal), HIV-1 PR, IN and RT inhibitors and anti-TB agents; physical organic chemistry: Kinetic-mechanistic studies of organic reaction mechanisms using spectroscopic and computational methods

Special Issue Information

Dear Colleagues,

Since the isolation of Daphnin from Daphne alpina in 1812 and of coumarin itself from the Tonka bean (Dipteryx odorata) shortly afterwards in 1820; coumarin derivatives have been discovered in a wide variety of plants. Coupled with the variety of natural sources has been the remarkable range of biological activities that coumarin-containing phytochemicals have been observed to exhibit, and such activities have undoubtedly contributed to their use in herbal remedies. Various classes of coumarin derivatives, including 4-hydroxycoumarins, furanocoumarins, and pyranocoumarins, have been identified and synthetic methods continue to be developed to access both the natural products and structural analogues. The broad medicinal potential of coumarin derivatives as, inter alia, anti-coagulant, anti-inflammatory, anti-oxidant, antibiotic, anti-fungal, anti-cancer, anti-diabetic and anti-HIV agents, makes the coumarin nucleus an attractive platform for the development of novel therapeutic agents.

This Special Issue will focus on recent developments in the synthesis or isolation of new coumarin derivatives and their potential as drug discovery lead compounds. Colleagues are invited to submit contributions to research in this area.

Emeritus Prof. Perry T. Kaye
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 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

  • Coumarin
  • 2H-Chromene-2-one
  • Hydroxycoumarin
  • Furanocoumarin
  • Pyranocoumarin
  • Drug discovery
  • Medicinal Chemistry
  • Phytochemistry

Published Papers (3 papers)

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Research

Open AccessArticle Versatility of 7-Substituted Coumarin Molecules as Antimycobacterial Agents, Neuronal Enzyme Inhibitors and Neuroprotective Agents
Molecules 2017, 22(10), 1644; doi:10.3390/molecules22101644
Received: 15 September 2017 / Revised: 21 September 2017 / Accepted: 27 September 2017 / Published: 30 September 2017
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Abstract
A medium-throughput screen using Mycobacterium tuberculosis H37Rv was employed to screen an in-house library of structurally diverse compounds for antimycobacterial activity. In this initial screen, eleven 7-substituted coumarin derivatives with confirmed monoamine oxidase-B and cholinesterase inhibitory activities, demonstrated growth inhibition of more than
[...] Read more.
A medium-throughput screen using Mycobacterium tuberculosis H37Rv was employed to screen an in-house library of structurally diverse compounds for antimycobacterial activity. In this initial screen, eleven 7-substituted coumarin derivatives with confirmed monoamine oxidase-B and cholinesterase inhibitory activities, demonstrated growth inhibition of more than 50% at 50 µM. This prompted further exploration of all the 7-substituted coumarins in our library. Four compounds showed promising MIC99 values of 8.31–29.70 µM and 44.15–57.17 µM on M. tuberculosis H37Rv in independent assays using GAST-Fe and 7H9+OADC media, respectively. These compounds were found to bind to albumin, which may explain the variations in MIC between the two assays. Preliminary data showed that they were able to maintain their activity in fluoroquinolone resistant mycobacteria. Structure-activity relationships indicated that structural modification on position 4 and/or 7 of the coumarin scaffold could direct the selectivity towards either the inhibition of neuronal enzymes or the antimycobacterial effect. Moderate cytotoxicities were observed for these compounds and slight selectivity towards mycobacteria was indicated. Further neuroprotective assays showed significant neuroprotection for selected compounds irrespective of their neuronal enzyme inhibitory properties. These coumarin molecules are thus interesting lead compounds that may provide insight into the design of new antimicrobacterial and neuroprotective agents. Full article
(This article belongs to the Special Issue Versatile Coumarins)
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Open AccessArticle Kinetics and Molecular Docking Studies of 6-Formyl Umbelliferone Isolated from Angelica decursiva as an Inhibitor of Cholinesterase and BACE1
Molecules 2017, 22(10), 1604; doi:10.3390/molecules22101604
Received: 22 August 2017 / Revised: 21 September 2017 / Accepted: 21 September 2017 / Published: 24 September 2017
PDF Full-text (2215 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Coumarins, which have low toxicity, are present in some natural foods, and are used in various herbal remedies, have attracted interest in recent years because of their potential medicinal properties. In this study, we report the isolation of two natural coumarins, namely umbelliferone
[...] Read more.
Coumarins, which have low toxicity, are present in some natural foods, and are used in various herbal remedies, have attracted interest in recent years because of their potential medicinal properties. In this study, we report the isolation of two natural coumarins, namely umbelliferone (1) and 6-formyl umbelliferone (2), from Angelica decursiva, and the synthesis of 8-formyl umbelliferone (3) from 1. We investigated the anti-Alzheimer disease (anti-AD) potential of these coumarins by assessing their ability to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and β-site amyloid precursor protein (APP) cleaving enzyme 1 (BACE1). Among these coumarins, 2 exhibited poor inhibitory activity against AChE and BChE, and modest activity against BACE1. Structure–activity relationship analysis showed that 2 has an aldehyde group at the C-6 position, and exhibited strong anti-AD activity, whereas the presence or absence of an aldehyde group at the C-8 position reduced the anti-AD activity of 3 and 1, respectively. In addition, 2 exhibited concentration-dependent inhibition of peroxynitrite-mediated protein tyrosine nitration. A kinetic study revealed that 2 and 3 non-competitively inhibited BACE1. To confirm enzyme inhibition, we predicted the 3D structures of AChE and BACE1, and used AutoDock 4.2 to simulate binding of coumarins to these enzymes. The blind docking studies demonstrated that these molecules could interact with both the catalytic active sites and peripheral anionic sites of AChE and BACE1. Together, our results indicate that 2 has an interesting inhibitory activity in vitro, and can be used in further studies to develop therapeutic modalities for the treatment of AD. Full article
(This article belongs to the Special Issue Versatile Coumarins)
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Open AccessArticle Deep Eutectic Solvents as Convenient Media for Synthesis of Novel Coumarinyl Schiff Bases and Their QSAR Studies
Molecules 2017, 22(9), 1482; doi:10.3390/molecules22091482
Received: 8 August 2017 / Revised: 29 August 2017 / Accepted: 2 September 2017 / Published: 5 September 2017
PDF Full-text (2687 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Deep eutectic solvents, as green and environmentally friendly media, were utilized in the synthesis of novel coumarinyl Schiff bases. Novel derivatives were synthesized from 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide and corresponding aldehyde in choline chloride:malonic acid (1:1) based deep eutectic solvent. In these reactions, deep
[...] Read more.
Deep eutectic solvents, as green and environmentally friendly media, were utilized in the synthesis of novel coumarinyl Schiff bases. Novel derivatives were synthesized from 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide and corresponding aldehyde in choline chloride:malonic acid (1:1) based deep eutectic solvent. In these reactions, deep eutectic solvent acted as a solvent and catalyst as well. Novel Schiff bases were synthesized in high yields (65–75%) with no need for further purification, and their structures were confirmed by mass spectra, 1H and 13C NMR. Furthermore, their antioxidant activity was determined and compared to antioxidant activity of previously synthesized derivatives, thus investigating their structure–activity relationship utilizing quantitative structure-activity relationship QSAR studies. Calculation of molecular descriptors has been performed by DRAGON software. The best QSAR model (Rtr = 0.636; Rext = 0.709) obtained with three descriptors (MATS3m, Mor22u, Hy) implies that the pairs of atoms higher mass at the path length 3, three-dimensional arrangement of atoms at scattering parameter s = 21 Å1, and higher number of hydrophilic groups (-OH, -NH) enhanced antioxidant activity. Electrostatic potential surface of the most active compounds showed possible regions for donation of electrons to 1,1-diphenyl-2-picryhydrazyl (DPPH) radicals. Full article
(This article belongs to the Special Issue Versatile Coumarins)
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