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Synthesis of Compounds with Cytotoxic Activity
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Synthesis of Compounds with Cytotoxic Activity

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

Deadline for manuscript submissions: closed (20 May 2021) | Viewed by 5547

Special Issue Editor

Prof. Dr. Tomasz Janecki

E-Mail Website
Guest Editor
Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Łódz, Poland
Interests: organic synthesis; diastereo- and enantioselective reactions; aza-/oxaheterocycles; sesquiterpene lactones and related compounds; cytotoxic activity; structure–activity relationship

Special Issue Information

Dear Colleagues,

Cancer is one of the leading causes of mortality worldwide, and the limited success of currently used anticancer drugs is a driving force for the search of new compounds with anticancer potential. A great number of such compounds are being synthesized in laboratories all over the world. The main challenge is to find a relatively simple, efficient, and generally synthetic method which enables preparation of libraries of compounds containing one or more pharmacophoric groups (hybrid molecules) with hope for new, effective anticancer agents. In addition, great attention is given to the diastereo- and enantioselective synthesis of these compounds.

This Special Issue is devoted to all aspects of synthetic methodologies which enable preparation of compounds with known or potential cytotoxic activity, including new synthetic protocols and improvement of the existing ones, as well as catalytic or multicomponent syntheses. Further, evaluation of the cytotoxicity of novel compounds, their structure–activity relationship, and molecular mechanisms of action is welcomed.

Prof. Dr. Tomasz Janecki
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 submissions that pass pre-check are 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 2700 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

  • Organic synthesis
  • Stereoselective synthesis
  • Total synthesis
  • Catalysis
  • Cytotoxic activity
  • Structure–activity relationship
  • Molecular mechanism of action

Published Papers (2 papers)

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Research

13 pages, 3031 KiB  
Communication
Synthesis and Antiproliferative Evaluation of 2-Deoxy-N-glycosylbenzotriazoles/imidazoles
by Caleigh S. Garton, Noelle K. DeRose, Dylan Dominguez, Maria L. Turbi-Henderson, Ashley L. Lehr, Ashley D. Padilla, Scott D. Twining, Stephanie Casas, Chidozie O. Alozie, Azad L. Gucwa, Mohammed R. Elshaer and Michael De Castro
Molecules 2021, 26(12), 3742; https://doi.org/10.3390/molecules26123742 - 19 Jun 2021
Cited by 2 | Viewed by 2699
Abstract
A series of 2-deoxy-2-iodo-α-d-mannopyranosylbenzotriazoles was synthesized using the benzyl, 4,6-benzylidene and acetyl protected D-glucal in the presence of N-iodosuccinimide (NIS). Subsequent removal of the iodine at the C-2 position using tributyltin hydride under free radical conditions afforded the 2-deoxy-α-d [...] Read more.
A series of 2-deoxy-2-iodo-α-d-mannopyranosylbenzotriazoles was synthesized using the benzyl, 4,6-benzylidene and acetyl protected D-glucal in the presence of N-iodosuccinimide (NIS). Subsequent removal of the iodine at the C-2 position using tributyltin hydride under free radical conditions afforded the 2-deoxy-α-d-glucopyranosylbenzotriazoles in moderate to high yields. This method was extended to the preparation of substituted 2-deoxy-β-d-glucopyranosylimidazoles as well. The stereoselectivity of the addition reaction and the effect of the protecting group and temperature on anomer distribution of the benzotriazole series were also investigated. The anticancer properties of the newly synthesized compounds were evaluated in a series of viability studies using HeLa (human cervical adenocarcinoma), human breast and lung cancer cell lines. The N-[3,4,6-tri-O-benzyl-2-deoxy-α-d-glucopyranosyl]-1H-benzotriazole and the N-[3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl]-2H-benzotriazole were found to be the most potent cancer cell inhibitors at 20 µM concentrations across all four cell lines. Full article
(This article belongs to the Special Issue Synthesis of Compounds with Cytotoxic Activity)
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12 pages, 2151 KiB  
Article
Synthesis of 2,2,6-Trisubstituted 5-Methylidene-tetrahydropyran-4-ones with Anticancer Activity
by Tomasz Bartosik, Jacek Kędzia, Joanna Drogosz-Stachowicz, Anna Janecka, Urszula Krajewska, Marek Mirowski and Tomasz Janecki
Molecules 2020, 25(3), 611; https://doi.org/10.3390/molecules25030611 - 30 Jan 2020
Cited by 3 | Viewed by 2338
Abstract
In our continuous search for new, relatively simple 2-alkylidene-1-oxoheterocycles as promising anticancer drug candidates, herein we report an efficient synthesis of 2,2,6-trisubstituted 5-methylidenetetrahydropyran-4-ones. These compounds were obtained in a four step reaction sequence, in which starting diethyl 2-oxopropylphosphonate was transformed into 2,2-disubstituted 5-diethoxyphosphoryldihydropyran-4-ones, [...] Read more.
In our continuous search for new, relatively simple 2-alkylidene-1-oxoheterocycles as promising anticancer drug candidates, herein we report an efficient synthesis of 2,2,6-trisubstituted 5-methylidenetetrahydropyran-4-ones. These compounds were obtained in a four step reaction sequence, in which starting diethyl 2-oxopropylphosphonate was transformed into 2,2-disubstituted 5-diethoxyphosphoryldihydropyran-4-ones, followed by Michael addition of various Grignard reagents and Horner-Wadsworth-Emmons reaction of the obtained adducts with formaldehyde. Stereochemistry of the intermediate Michael adducts is also discussed. Final 5-methylidenetetrahydropyran-4-ones were tested for their possible antiproliferative effect against three cancer cell lines and 6-isopropyl-2,2-dimethyl-5-methylidenetetrahydropyran-4-one (11c), which showed very high cytotoxic activity against HL-60 human leukemia cells and was three times more active than known anticancer drug carboplatin, was selected for further biological evaluation, in order to disclose its mechanism of action. The obtained results indicated that 11c induced apoptosis in HL-60 cells and caused the arrest of the cell cycle in the G2/M phase, which may suggest its cytotoxic and cytostatic activity. Full article
(This article belongs to the Special Issue Synthesis of Compounds with Cytotoxic Activity)
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