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Special Issue "Design and Synthesis of Organic Molecules as Antineoplastic Agents"

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

Deadline for manuscript submissions: 30 September 2019

Special Issue Editors

Guest Editor
Prof. Dr. Carla Boga

Department of Industrial Chemistry “Toso Montanari”, University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy
Website | E-Mail
Phone: +39 051 2093616
Interests: organic synthesis; bioorganic chemistry; NMR spectroscopy; small molecule synthesis; mechanisms elucidation
Guest Editor
Dr. Gabriele Micheletti

Department of Industrial Chemistry “Toso Montanari”, University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy
Website | E-Mail
Interests: organic synthesis; organophosphorus chemistry; heterocyclic chemistry; NMR spectroscopy

Special Issue Information

Dear Colleagues,

The fight against cancer can be dealt with, among different approaches, by synthetizing new compounds with high effectiveness and selectivity to the targeting cancer cells by concomitantly reducing side effects.

In this context, synthetic organic chemistry plays a key role and constitutes a flexible tool since it gives access to a great number of compounds, including antitumoral molecules present in nature, but which are not readily available, as well as novel drugs exhibiting anticancer actions. Through the variation of functional groups or motifs within the organic architecture, it is possible to find and modulate structure–activity relationships and, once the molecular target has been identified, to design new molecules or structural hybrids. Original articles, as well as reviews, regarding recent advancements in the design and synthesis of organic molecules of interest as antineoplastic agents are greatly welcome for inclusion in this Special Issue of Molecules.

Prof. Dr. Carla Boga
Dr. Gabriele Micheletti
Guest Editors

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 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

  • antineoplastic
  • cancer
  • organic compounds
  • organic synthesis
  • drug design
  • biochemistry
  • medicinal chemistry
  • biological activity

Published Papers (3 papers)

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Research

Open AccessArticle Synthesis of Novel Pyrazole Derivatives and Their Tumor Cell Growth Inhibitory Activity
Molecules 2019, 24(2), 279; https://doi.org/10.3390/molecules24020279
Received: 31 October 2018 / Revised: 6 January 2019 / Accepted: 10 January 2019 / Published: 13 January 2019
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Abstract
To find novel antitumor agents, a series of 1H-benzofuro[3,2-c]pyrazole derivatives 4a-e were designed and synthesized. The treatment of 6-methoxybenzofuran-3(2H)-one 3 with LiHMDS in anhydrous tetrahydrofuran (THF) followed by reaction with 3-substitued phenyl isothiocyanate gave the thioamide intermediates, [...] Read more.
To find novel antitumor agents, a series of 1H-benzofuro[3,2-c]pyrazole derivatives 4a-e were designed and synthesized. The treatment of 6-methoxybenzofuran-3(2H)-one 3 with LiHMDS in anhydrous tetrahydrofuran (THF) followed by reaction with 3-substitued phenyl isothiocyanate gave the thioamide intermediates, which underwent condensation with hydrazine monohydrate in dioxane/EtOH (1:1) to provide the benzofuropyrazole derivatives 4ae as well as the unexpected pyrazole derivatives 5ae. In tumor cell growth inhibitory assay, all the benzofuropyrazole derivatives were not active against the breast tumor MCF-7 cell, only 4a was highly active and more potent than ABT-751 against the leukemia K562 (GI50 = 0.26 μM) and lung tumor A549 cells (GI50 = 0.19 μM), while other benzofuropyrazoles showed very weak inhibitory activity. In contrast, the pyrazoles 5a-e were in general more potent than the benzofuropyrazoles 4ae. Compound 5a exhibited a similar tendency to that of 4a with high potency against K562 and A549 cells but weak effects on MCF-7 cell. Both pyrazoles 5b and 5e exhibited high inhibitory activities against K562, MCF-7 and A549 cells. The most active compound 5b was much more potent than ABT-751 against K562 and A549 cells with GI50 values of 0.021 and 0.69 μM, respectively. Moreover, 5b was identified as a novel tubulin polymerization inhibitor with an IC50 of 7.30 μM. Full article
(This article belongs to the Special Issue Design and Synthesis of Organic Molecules as Antineoplastic Agents)
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Open AccessArticle Synthesis and Evaluation of Anticancer Activities of Novel C-28 Guanidine-Functionalized Triterpene Acid Derivatives
Molecules 2018, 23(11), 3000; https://doi.org/10.3390/molecules23113000
Received: 8 October 2018 / Revised: 5 November 2018 / Accepted: 13 November 2018 / Published: 16 November 2018
PDF Full-text (1608 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Triterpene acids, namely, 20,29-dihydrobetulinic acid (BA), ursolic acid (UA) and oleanolic acid (OA) were converted into C-28-amino-functionalized triterpenoids 47, 8a, 15, 18 and 20. These compounds served as precursors for the synthesis of novel guanidine-functionalized triterpene acid [...] Read more.
Triterpene acids, namely, 20,29-dihydrobetulinic acid (BA), ursolic acid (UA) and oleanolic acid (OA) were converted into C-28-amino-functionalized triterpenoids 47, 8a, 15, 18 and 20. These compounds served as precursors for the synthesis of novel guanidine-functionalized triterpene acid derivatives 9b12b, 15c, 18c and 20c. The influence of the guanidine group on the antitumor properties of triterpenoids was investigated. The cytotoxicity was tested on five human tumor cell lines (Jurkat, K562, U937, HEK, and Hela), and compared with the tests on normal human fibroblasts. The antitumor activities of the most tested guanidine derivatives was lower, than that of corresponding amines, but triterpenoids with the guanidine group were less toxic towards human fibroblasts. The introduction of the tris(hydroxymethyl)aminomethane moiety into the molecules of triterpene acids markedly enhanced the cytotoxic activity of the resulting conjugates 15, 15c, 18b,c and 20b,c irrespective of the triterpene skeleton type. The dihydrobetulinic acid amine 15, its guanidinium derivative 15c and guanidinium derivatives of ursolic and oleanolic acids 18c and 20c were selected for extended biological investigations in Jurkat cells, which demonstrated that the antitumor activity of these compounds is mediated by induction of cell cycle arrest at the S-phase and apoptosis. Full article
(This article belongs to the Special Issue Design and Synthesis of Organic Molecules as Antineoplastic Agents)
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Open AccessArticle Design, Synthesis and Biological Evaluation of Novel 4-Substituted Coumarin Derivatives as Antitumor Agents
Molecules 2018, 23(9), 2281; https://doi.org/10.3390/molecules23092281
Received: 17 August 2018 / Revised: 1 September 2018 / Accepted: 4 September 2018 / Published: 6 September 2018
Cited by 1 | PDF Full-text (6818 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Herein, fifteen new compounds containing coumarin, 1,2,3-triazole and benzoyl- substituted arylamine moieties were designed, synthesized and tested in vitro for their anticancer activity. The results showed that all tested compounds had moderate antiproliferative activity against MDA-MB-231, a human breast cancer cell line, under [...] Read more.
Herein, fifteen new compounds containing coumarin, 1,2,3-triazole and benzoyl- substituted arylamine moieties were designed, synthesized and tested in vitro for their anticancer activity. The results showed that all tested compounds had moderate antiproliferative activity against MDA-MB-231, a human breast cancer cell line, under both normoxic and hypoxic conditions. Furthermore, the 4-substituted coumarin linked with benzoyl 3,4-dimethoxyaniline through 1,2,3-triazole (compound 5e) displayed the most prominent antiproliferative activities with an IC50 value of 0.03 μM, about 5000 times stronger than 4-hydroxycoumarin (IC50 > 100 μM) and 20 times stronger than doxorubicin (IC50 = 0.60 μM). Meanwhile, almost all compounds revealed general enhancement of proliferation-inhibiting activity under hypoxia, contrasted with normoxia. A docking analysis showed that compound 5e had potential to inhibit carbonic anhydrase IX (CA IX). Full article
(This article belongs to the Special Issue Design and Synthesis of Organic Molecules as Antineoplastic Agents)
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Graphical abstract

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