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Special Issue "Women in Organic Chemistry"

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

Deadline for manuscript submissions: closed (8 March 2017).

Special Issue Information

Dear Colleagues,

International Women’s Day will be celebrated on 8 March 2017. To mark this important milestone, our journal, Molecules, will launch a Special Issue on “Women in Organic Chemistry” to be published in Molecules (ISSN 1420-3049, https://www.mdpi.com/journal/molecules) in 2017. This Special Issue will include high quality papers and review articles in all areas of chemistry. We encourage all research groups (led by men or women) to contribute original research papers or an up-to-date, comprehensive review, highlighting recent developments in any area of chemistry.

Prof. Dr. Margaret A. Brimble
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 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 2000 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.

Published Papers (16 papers)

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Research

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Open AccessCommunication
Optimizing the Readout of Lanthanide-DOTA Complexes for the Detection of Ligand-Bound Copper(I)
Molecules 2017, 22(5), 802; https://doi.org/10.3390/molecules22050802 - 14 May 2017
Cited by 9 | Viewed by 3715
Abstract
The CuAAC ‘click’ reaction was used to couple alkyne-functionalized lanthanide-DOTA complexes to a range of fluorescent antennae. Screening of the antenna components was aided by comparison of the luminescent output of the resultant sensors using data normalized to account for reaction conversion as [...] Read more.
The CuAAC ‘click’ reaction was used to couple alkyne-functionalized lanthanide-DOTA complexes to a range of fluorescent antennae. Screening of the antenna components was aided by comparison of the luminescent output of the resultant sensors using data normalized to account for reaction conversion as assessed by IR. A maximum 82-fold enhanced signal:background luminescence output was achieved using a Eu(III)-DOTA complex coupled to a coumarin-azide, in a reaction which is specific to the presence of copper(I). This optimized complex provides a new lead design for lanthanide-DOTA complexes which can act as irreversible ‘turn-on’ catalytic sensors for the detection of ligand-bound copper(I). Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessArticle
C-C Coupling Reactions between Benzofurazan Derivatives and 1,3-Diaminobenzenes
Molecules 2017, 22(5), 684; https://doi.org/10.3390/molecules22050684 - 26 Apr 2017
Cited by 3 | Viewed by 2364
Abstract
Aromatic substitution reactions between 1,3-diaminobenzene and chloronitrobenzofurazan derivatives have never been reported so far. The aim of the current study was to synthesize novel electron-donor and -acceptor architectures of interest in applied fields and to provide new insights on the nucleophilic behavior of [...] Read more.
Aromatic substitution reactions between 1,3-diaminobenzene and chloronitrobenzofurazan derivatives have never been reported so far. The aim of the current study was to synthesize novel electron-donor and -acceptor architectures of interest in applied fields and to provide new insights on the nucleophilic behavior of 1,3-diaminobenzenes. The reaction of 1,3-dipiperidinyl-, 1,3-dimorpholinyl-, 1,3-dipyrrolidinyl-, or 1,3-dimethylamino-benzene with 7-chloro-4,6-dinitrobenzofuroxan or with a series of chloro-nitrobenzofurazans has been carried out in mild conditions. The partners reactivity has been investigated by monitoring the reaction course through 1H-NMR spectroscopy. The reaction occurred in a regioselective way, providing in good yields the novel C-C coupling compounds. Indications on the reactivity behavior for the studied nucleophiles have been relieved. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessArticle
One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors
Molecules 2017, 22(4), 626; https://doi.org/10.3390/molecules22040626 - 12 Apr 2017
Cited by 3 | Viewed by 2195
Abstract
Polysubstituted pyridinium salts are valuable pharmacophores found in many biologically active molecules. Their synthesis typically involves the use of multistep procedures or harsh reaction conditions. Here, we report water-based phosphate mediated reaction conditions that promote the condensation of arylacetaldehydes with amines to give [...] Read more.
Polysubstituted pyridinium salts are valuable pharmacophores found in many biologically active molecules. Their synthesis typically involves the use of multistep procedures or harsh reaction conditions. Here, we report water-based phosphate mediated reaction conditions that promote the condensation of arylacetaldehydes with amines to give 1,3,5-pyridinium salts. The reaction, carried out at pH 6, provides conditions suitable for the use of less stable aldehydes and amines in this Chichibabin pyridine condensation. The evaluation of selected 1,3,5-trisubstituted pyridinium salts highlighted that they can inhibit the growth of S. aureus in the low μg/mL range. The synthetic accessibility of these compounds and preliminary growth inhibition data may pave the way towards the discovery of new anti-bacterials based on the 1,3,5-trisubstituted pyridinium scaffold. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessCommunication
Chemical Synthesis and Characterization of an Equinatoxin II(1–85) Analogue
Molecules 2017, 22(4), 559; https://doi.org/10.3390/molecules22040559 - 30 Mar 2017
Cited by 2 | Viewed by 1994
Abstract
The chemical synthesis of an 85 residue analogue of the pore-forming protein, Equinatoxin II (EqtII), was achieved. Peptide precursors with over 40 residues were assembled by solid phase synthesis. The EqtII(1–46) fragment was modified to the reactive C-terminal thioester and native chemical ligation [...] Read more.
The chemical synthesis of an 85 residue analogue of the pore-forming protein, Equinatoxin II (EqtII), was achieved. Peptide precursors with over 40 residues were assembled by solid phase synthesis. The EqtII(1–46) fragment was modified to the reactive C-terminal thioester and native chemical ligation was performed with the A47C mutated EqtII(47–85) peptide to form the EqtII(1–85) analogue. Circular dichroism spectroscopy indicated that the N-terminal domain of EqtII(1–46) and EqtII(1–85) maintains predominantly an α-helical structure in solution and also in the presence of lipid micelles. This demonstrates the feasibility of assembling the full 179 residue protein EqtII via chemical means. Site-specific isotopic labels could be incorporated for structural studies in membranes by solid-state NMR spectroscopy. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessCommunication
Revision of the Structure of Acremine P from a Marine-Derived Strain of Acremonium persicinum
Molecules 2017, 22(4), 521; https://doi.org/10.3390/molecules22040521 - 24 Mar 2017
Cited by 10 | Viewed by 2272
Abstract
The previously published structure of the fungal metabolite acremine P is revised by re-evaluation of chemical shift values and NOESY data, and by DFT calculations. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessArticle
Synthesis of Novel Saccharin Derivatives
Molecules 2017, 22(4), 516; https://doi.org/10.3390/molecules22040516 - 23 Mar 2017
Cited by 1 | Viewed by 2365
Abstract
The synthesis of saccharin (1,2-benzisothiazol-3-one-1,1-dioxide) derivatives substituted on the benzene ring has seen limited development despite the longevity of this compound’s use as an artificial sweetener. This type of saccharin derivative would however present attractive properties for the development of new bioactive, drug-like [...] Read more.
The synthesis of saccharin (1,2-benzisothiazol-3-one-1,1-dioxide) derivatives substituted on the benzene ring has seen limited development despite the longevity of this compound’s use as an artificial sweetener. This type of saccharin derivative would however present attractive properties for the development of new bioactive, drug-like small molecule compounds. Here we report the derivatisation of the benzene ring of saccharin using Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC) to synthesise a diverse library of novel saccharin-1,2,3-triazole conjugates. All library compounds retain the capability for interactions with biomolecules via the unmodified sulfonamide and lactam groups of the parent saccharin core heterocycle. The compounds also encompass alternate orientations of the 1,2,3-triazole heterocycle, thus further adding diversity to the potential hydrogen bonding interactions of these compounds with biomolecules of therapeutic interest. Our findings demonstrate that specifically functionalized derivatives of saccharin may be prepared from either saccharin azide or saccharin alkyne building blocks in high yield using CuAAC. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessArticle
Three-Component Reaction of Benzylamines, Diethyl Phosphite and Triethyl Orthoformate: Dependence of the Reaction Course on the Structural Features of the Substrates and Reaction Conditions
Molecules 2017, 22(3), 450; https://doi.org/10.3390/molecules22030450 - 11 Mar 2017
Cited by 3 | Viewed by 2652
Abstract
The reaction between benzyl amines, triethyl orthoformate, and diethyl phosphite affords either bisphosphonic (compound 1) or N-benzylaminobenzylphosphonic (compound 2) acid depending on the reaction conditions. The final output of the reaction can be manipulated by the choice of reaction conditions, [...] Read more.
The reaction between benzyl amines, triethyl orthoformate, and diethyl phosphite affords either bisphosphonic (compound 1) or N-benzylaminobenzylphosphonic (compound 2) acid depending on the reaction conditions. The final output of the reaction can be manipulated by the choice of reaction conditions, particularly the molar ratio of substrates. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessArticle
Antiproliferative, Cytotoxic, and Apoptotic Activity of Steroidal Oximes in Cervicouterine Cell Lines
Molecules 2016, 21(11), 1533; https://doi.org/10.3390/molecules21111533 - 14 Nov 2016
Cited by 8 | Viewed by 2790
Abstract
Steroidal sapogenins have shown antiproliferative effects against several tumor cell lines; and their effects on human cancer cells are currently under study. Changes in the functionality on the steroidal structure make it possible to modify the biological activity of compounds. Herein, we report [...] Read more.
Steroidal sapogenins have shown antiproliferative effects against several tumor cell lines; and their effects on human cancer cells are currently under study. Changes in the functionality on the steroidal structure make it possible to modify the biological activity of compounds. Herein, we report the synthesis and in vitro antitumor activity of two steroidal oxime compounds on cervical cancer cells. These derivatives were synthesized from the steroidal sapogenin diosgenin in good yields. The in vitro assays show that the steroidal oximes show significant antiproliferative activity compared to the one observed for diosgenin. Cell proliferation, cell death, and the cytotoxic effects were determined in both cervical cancer cells and human lymphocytes. The cancer cells showed apoptotic morphology and an increased presence of active caspase-3, providing the notion of a death pathway in the cell. Significantly, the steroidal oximes did not exert a cytotoxic effect on lymphocytes. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Review

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Open AccessFeature PaperReview
β-Formyl- and β-Vinylporphyrins: Magic Building Blocks for Novel Porphyrin Derivatives
Molecules 2017, 22(8), 1269; https://doi.org/10.3390/molecules22081269 - 29 Jul 2017
Cited by 14 | Viewed by 3830
Abstract
Porphyrins bearing formyl or vinyl groups have been explored as starting materials to prepare new compounds with adequate features for different applications. In this review it is discussed mainly synthetic strategies based on the reaction of meso-tetraarylporphyrins bearing those groups at β-pyrrolic [...] Read more.
Porphyrins bearing formyl or vinyl groups have been explored as starting materials to prepare new compounds with adequate features for different applications. In this review it is discussed mainly synthetic strategies based on the reaction of meso-tetraarylporphyrins bearing those groups at β-pyrrolic positions. The use of some of the obtained porphyrin derivatives for further transformations, namely via pericyclic reactions, is also highlighted. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessReview
Chemical Methods to Knock Down the Amyloid Proteins
Molecules 2017, 22(6), 916; https://doi.org/10.3390/molecules22060916 - 01 Jun 2017
Cited by 7 | Viewed by 3273
Abstract
Amyloid proteins are closely related with amyloid diseases and do tremendous harm to human health. However, there is still a lack of effective strategies to treat these amyloid diseases, so it is important to develop novel methods. Accelerating the clearance of amyloid proteins [...] Read more.
Amyloid proteins are closely related with amyloid diseases and do tremendous harm to human health. However, there is still a lack of effective strategies to treat these amyloid diseases, so it is important to develop novel methods. Accelerating the clearance of amyloid proteins is a favorable method for amyloid disease treatment. Recently, chemical methods for protein reduction have been developed and have attracted much attention. In this review, we focus on the latest progress of chemical methods that knock down amyloid proteins, including the proteolysis-targeting chimera (PROTAC) strategy, the “recognition-cleavage” strategy, the chaperone-mediated autophagy (CMA) strategy, the selectively light-activatable organic and inorganic molecules strategy and other chemical strategies. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessReview
Exploring Anti-Prion Glyco-Based and Aromatic Scaffolds: A Chemical Strategy for the Quality of Life
Molecules 2017, 22(6), 864; https://doi.org/10.3390/molecules22060864 - 24 May 2017
Cited by 3 | Viewed by 2940
Abstract
Prion diseases are fatal neurodegenerative disorders caused by protein misfolding and aggregation, affecting the brain progressively and consequently the quality of life. Alzheimer’s is also a protein misfolding disease, causing dementia in over 40 million people worldwide. There are no therapeutics able to [...] Read more.
Prion diseases are fatal neurodegenerative disorders caused by protein misfolding and aggregation, affecting the brain progressively and consequently the quality of life. Alzheimer’s is also a protein misfolding disease, causing dementia in over 40 million people worldwide. There are no therapeutics able to cure these diseases. Cellular prion protein is a high-affinity binding partner of amyloid β (Aβ) oligomers, the most toxic species in Alzheimer’s pathology. These findings motivate the development of new chemicals for a better understanding of the events involved. Disease control is far from being reached by the presently known therapeutics. In this review we describe the synthesis and mode of action of molecular entities with intervention in prion diseases’ biological processes and, if known, their role in Alzheimer’s. A diversity of structures is covered, based on glycans, steroids and terpenes, heterocycles, polyphenols, most of them embodying aromatics and a structural complexity. These molecules may be regarded as chemical tools to foster the understanding of the complex mechanisms involved, and to encourage the scientific community towards further developments for the cure of these devastating diseases. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessReview
Applications of Gold Nanoparticles in Nanomedicine: Recent Advances in Vaccines
Molecules 2017, 22(5), 857; https://doi.org/10.3390/molecules22050857 - 22 May 2017
Cited by 53 | Viewed by 5155
Abstract
Nowadays, gold is used in (nano-)medicine, usually in the form of nanoparticles, due to the solid proofs given of its therapeutic effects on several diseases. Gold also plays an important role in the vaccine field as an adjuvant and a carrier, reducing toxicity, [...] Read more.
Nowadays, gold is used in (nano-)medicine, usually in the form of nanoparticles, due to the solid proofs given of its therapeutic effects on several diseases. Gold also plays an important role in the vaccine field as an adjuvant and a carrier, reducing toxicity, enhancing immunogenic activity, and providing stability in storage. An even brighter golden future is expected for gold applications in this area. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessReview
Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry
Molecules 2017, 22(5), 780; https://doi.org/10.3390/molecules22050780 - 12 May 2017
Cited by 23 | Viewed by 5540
Abstract
Over the last 20 years, high valent metal complexes have evolved from mere curiosities to being at the forefront of modern catalytic method development. This approach has enabled transformations complimentary to those possible via traditional manifolds, most prominently carbon-heteroatom bond formation. Key to [...] Read more.
Over the last 20 years, high valent metal complexes have evolved from mere curiosities to being at the forefront of modern catalytic method development. This approach has enabled transformations complimentary to those possible via traditional manifolds, most prominently carbon-heteroatom bond formation. Key to the advancement of this chemistry has been the identification of oxidants that are capable of accessing these high oxidation state complexes. The oxidant has to be both powerful enough to achieve the desired oxidation as well as provide heteroatom ligands for transfer to the metal center; these heteroatoms are often subsequently transferred to the substrate via reductive elimination. Herein we will review the central role that hypervalent iodine reagents have played in this aspect, providing an ideal balance of versatile reactivity, heteroatom ligands, and mild reaction conditions. Furthermore, these reagents are environmentally benign, non-toxic, and relatively inexpensive compared to other inorganic oxidants. We will cover advancements in both catalysis and high valent complex isolation with a key focus on the subtle effects that oxidant choice can have on reaction outcome, as well as limitations of current reagents. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessReview
Recent Advances in Cyanamide Chemistry: Synthesis and Applications
Molecules 2017, 22(4), 615; https://doi.org/10.3390/molecules22040615 - 12 Apr 2017
Cited by 29 | Viewed by 4620
Abstract
The application of alkyl and aryl substituted cyanamides in synthetic chemistry has diversified multi-fold in recent years. In this review, we discuss recent advances (since 2012) in the chemistry of cyanamides and detail their application in cycloaddition chemistry, aminocyanation reactions, as well as [...] Read more.
The application of alkyl and aryl substituted cyanamides in synthetic chemistry has diversified multi-fold in recent years. In this review, we discuss recent advances (since 2012) in the chemistry of cyanamides and detail their application in cycloaddition chemistry, aminocyanation reactions, as well as electrophilic cyanide-transfer agents and their unique radical and coordination chemistry. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessFeature PaperReview
Direct Substitution of Alcohols in Pure Water by Brønsted Acid Catalysis
Molecules 2017, 22(4), 574; https://doi.org/10.3390/molecules22040574 - 01 Apr 2017
Cited by 16 | Viewed by 3317
Abstract
With the increasing concern for sustainability, the use of environmentally friendly media to perform chemical processes has attracted the attention of many research groups. Among them, the use of water, as the unique solvent for reactions, is currently an active area of research. [...] Read more.
With the increasing concern for sustainability, the use of environmentally friendly media to perform chemical processes has attracted the attention of many research groups. Among them, the use of water, as the unique solvent for reactions, is currently an active area of research. One process of particular interest is the direct nucleophilic substitution of an alcohol avoiding its preliminary transformation into a good leaving group, since one of the by-products in this approach would be water. The direct substitution of allylic, benzylic, and tertiary alcohols has been achieved through SN1-type reactions with catalytic amounts of Brønsted or Lewis acids; however, organic solvents are often required. In this review, the pioneering SN1 approaches performed in pure water and in the absence of a metal based Lewis acid are compiled and discussed. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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Open AccessFeature PaperReview
Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives
Molecules 2017, 22(3), 483; https://doi.org/10.3390/molecules22030483 - 19 Mar 2017
Cited by 4 | Viewed by 2681
Abstract
A comprehensive survey of pathways leading to the generation of α-trifluoromethyl monocyclic piperidinic derivatives is provided (65 references). These compounds have been synthesized either from 6-membered rings e.g., pipecolic acid or lactam derivatives by introduction a trifluoromethyl group, from pyridine or pyridinone derivatives [...] Read more.
A comprehensive survey of pathways leading to the generation of α-trifluoromethyl monocyclic piperidinic derivatives is provided (65 references). These compounds have been synthesized either from 6-membered rings e.g., pipecolic acid or lactam derivatives by introduction a trifluoromethyl group, from pyridine or pyridinone derivatives by reduction, and from 5-membered rings e.g., prolinol derivatives by ring expansion, from linear amines by cyclization or from dienes/dienophiles by [4 + 2]-cycloaddition. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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