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      Novel triazoles of 3-acetylbetulin and betulone as anticancer agents

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          Abstract

          The CuAAC reaction of azides and acetylenic triterpenes was used for synthesis of new triazoles of 3-acetylbetulin and betulone. The triazole derivatives were evaluated for their anticancer activity in vitro against amelanotic melanoma C-32, ductal carcinoma T47D and glioblastoma SNB-19 cell lines. 28-[1-(3’-Deoxythymidine-5’-yl)-1 H-1,2,3-triazol-4-yl]carbonylbetulone 6e exhibited a significant IC 50 value (0.17 µM) against the human glioblastoma SNB-19 cell line, an almost 5-fold higher potency while compared with reference cisplatin.

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          Medicinal attributes of 1,2,3-triazoles: Current developments.

          Divya Dheer, Virender Singh, Ravi Pathiyil Shankar (2017)
          1,2,3-Triazoles are important five-membered heterocyclic scaffold due to their extensive biological activities. This framework can be readily obtained in good to excellent yields on the multigram scale through click chemistry via reaction of aryl/alkyl halides, alkynes and NaN3 under ambient conditions. It has been an emerging area of interest for many researchers throughout the globe owing to its immense pharmacological scope. The present work aims to summarize the current approaches adopted for the synthesis of the 1,2,3-triazole and medicinal significance of these architectures as a lead structure for the discovery of drug molecules such as COX-1/COX-2 inhibitors (celecoxib, pyrazofurin), HIV protease inhibitors, CB1 cannabinoid receptor antagonist and much more which are in the pipeline of clinical trials. The emphasis has been given on the major advancements in the medicinal prospectus of this pharmacophore for the period during 2008-2016.
          Article 0 comments Cited 121 times – based on 0 reviews     Review now
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            Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities.

            Cheng Zhou, Kun Wan, Xian Wang (2010)
            A series of novel sulfanilamide-derived 1,2,3-triazole compounds were synthesized in excellent yields via 1,3-dipolar cycloaddition and confirmed by MS, IR and NMR spectra as well as elemental analyses. All the compounds were screened in vitro for their antibacterial and antifungal activities. Preliminary results indicated that some target compounds exhibited promising antibacterial potency. Especially, 4-amino-N-((1-dodecyl-1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide, N-((1-(2,4-dichlorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl)-4-aminobenzenesulfonamide and 4-amino-N-((1-(2,4-difluorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide were found to be the most potent compounds against all the tested strains except for Candida albicans (ATCC76615) and Candida mycoderma. Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.
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              New click-chemistry methods for 1,2,3-triazoles synthesis: recent advances and applications

              Jane Totobenazara, Anthony J. Burke (2015)
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                Author and article information

                Contributors
                Ewa Bębenek: ebebenek@sum.edu.pl
                Journal
                Journal ID (nlm-ta): Med Chem Res
                Journal ID (iso-abbrev): Med Chem Res
                Title: Medicinal Chemistry Research
                Publisher: Springer US (New York )
                ISSN (Print): 1054-2523
                ISSN (Electronic): 1554-8120
                Publication date (Electronic): 17 July 2018
                Publication date PMC-release: 17 July 2018
                Publication date (Print): 2018
                Volume: 27
                Issue: 9
                Pages: 2051-2061
                Affiliations
                [1 ]ISNI 0000 0001 2198 0923, GRID grid.411728.9, Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, , Medical University of Silesia in Katowice, ; 4 Jagiellońska Str., 41-200 Sosnowiec, Poland
                [2 ]ISNI 0000 0001 2198 0923, GRID grid.411728.9, Department of Cell Biology, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, , Medical University of Silesia in Katowice, ; 8 Jedności Str., 41-200 Sosnowiec, Poland
                Article
                Publisher ID: 2213
                DOI: 10.1007/s00044-018-2213-x
                PMC ID: 6133159
                PubMed ID: 30220830
                SO-VID: 162af9dd-b559-4a85-bc20-b5e1a32ac298
                Copyright © © The Author(s) 2018
                License:

                Open Access This article is distributed under the terms of the Creative Commons Attribution 4.0 International License ( http://creativecommons.org/licenses/by/4.0/), which permits use, duplication, adaptation, distribution, and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.

                History
                Date received : 13 April 2018
                Date accepted : 27 June 2018
                Categories
                Subject: Review Article
                Custom metadata
                issue-copyright-statement © Springer Science+Business Media, LLC, part of Springer Nature 2018

                ScienceOpen disciplines: Pharmaceutical chemistry
                Keywords: betulin,1,2,3-triazole,cuaac,anticancer activity,lipophilicity
                Data availability:
                ScienceOpen disciplines: Pharmaceutical chemistry
                Keywords: betulin, 1,2,3-triazole, cuaac, anticancer activity, lipophilicity

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