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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 Synthesis".

Deadline for manuscript submissions: closed (8 March 2017)

Special Issue Editor

Guest Editor
Prof. Dr. Margaret A. Brimble CNZM, FRSNZ

President IUPAC Organic and Biomolecular Division III University Distinguished Professor, Chair of Organic Chemistry and Director of Medicinal Chemistry, School of Chemical Sciences and School of Biological Sciences, The University of Auckland, 23 Symonds St, Auckland 1142, New Zealand
Website | E-Mail
Fax: +64 9 3737422
Interests: synthesis of bioactive natural products and traditional Chinese medicines; alkaloids as neuroprotective agents; peptidomimetics; antimicrobial peptides; cell penetrating peptides; glycopeptides; lipopeptides; antifreeze peptides; cancer vaccines; organocatalysts; proteins, glycopolymers, hydrogels

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, http://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 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.

Published Papers (10 papers)

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Research

Jump to: Review

Open AccessArticle C-C Coupling Reactions between Benzofurazan Derivatives and 1,3-Diaminobenzenes
Molecules 2017, 22(5), 684; doi:10.3390/molecules22050684
Received: 23 February 2017 / Revised: 19 April 2017 / Accepted: 20 April 2017 / Published: 26 April 2017
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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; doi:10.3390/molecules22040626
Received: 17 March 2017 / Revised: 7 April 2017 / Accepted: 9 April 2017 / Published: 12 April 2017
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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; doi:10.3390/molecules22040559
Received: 10 March 2017 / Revised: 29 March 2017 / Accepted: 29 March 2017 / Published: 30 March 2017
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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; doi:10.3390/molecules22040521
Received: 28 February 2017 / Revised: 23 March 2017 / Accepted: 23 March 2017 / Published: 24 March 2017
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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; doi:10.3390/molecules22040516
Received: 3 March 2017 / Revised: 20 March 2017 / Accepted: 20 March 2017 / Published: 23 March 2017
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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; doi:10.3390/molecules22030450
Received: 23 February 2017 / Revised: 8 March 2017 / Accepted: 9 March 2017 / Published: 11 March 2017
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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; doi:10.3390/molecules21111533
Received: 17 September 2016 / Revised: 4 November 2016 / Accepted: 7 November 2016 / Published: 14 November 2016
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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

Jump to: Research

Open AccessReview Recent Advances in Cyanamide Chemistry: Synthesis and Applications
Molecules 2017, 22(4), 615; doi:10.3390/molecules22040615
Received: 9 March 2017 / Revised: 6 April 2017 / Accepted: 7 April 2017 / Published: 12 April 2017
PDF Full-text (6174 KB) | HTML Full-text | XML Full-text | Supplementary Files
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; doi:10.3390/molecules22040574
Received: 8 March 2017 / Revised: 29 March 2017 / Accepted: 30 March 2017 / Published: 1 April 2017
PDF Full-text (4732 KB) | HTML Full-text | XML Full-text
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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Scheme 1

Open AccessFeature PaperReview Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives
Molecules 2017, 22(3), 483; doi:10.3390/molecules22030483
Received: 2 March 2017 / Revised: 9 March 2017 / Accepted: 14 March 2017 / Published: 19 March 2017
PDF Full-text (817 KB) | HTML Full-text | XML Full-text
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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Figure 1

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