Synthesis of Novel Chiral Sulfonamide‐Bearing 1,2,4‐Triazole‐3‐thione Analogs Derived from D‐ and L‐Phenylalanine Esters as Potential Anti‐Influenza Agents
Identifieur interne : 001020 ( Main/Exploration ); précédent : 001019; suivant : 001021Synthesis of Novel Chiral Sulfonamide‐Bearing 1,2,4‐Triazole‐3‐thione Analogs Derived from D‐ and L‐Phenylalanine Esters as Potential Anti‐Influenza Agents
Auteurs : Eyüp Ba Aran [Turquie] ; Ay Egül Karaküçük-Iyido An [Turquie] ; Dominique Schols [Belgique] ; Emine Elçin Oruç-Emre [Turquie]Source :
- Chirality [ 0899-0042 ] ; 2016-06.
Abstract
Novel enantiopure 1,2,4‐trizole‐3‐thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D‐phenylalanine methyl ester and L‐phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR, 1H NMR, 13C NMR, 2D NMR (HETCOR), and mass spectral data. All compounds were tested in vitro antiviral activity against a broad variety of DNA and RNA viruses and in vitro cytostatic activity against murine leukemia (L1210), human T‐lymphocyte (CEM) and human cervix carcinoma (HeLa) cell lines. Although enantiopure 1,2,4‐triazole‐3‐thione analogs in (R) configuration emerged as promising anti‐influenza A H1N1 subtype in Madin Darby canine kidney cell cultures (MDCK), their enantiomers exhibited no activity. Especially compounds , , , , and (EC50: 6.5, 6.1, 2.4, 1.6, 1.7 μM, respectively) had excellent activity against influenza A H1N1 subtype compared to the reference drug ribavirin (EC50: 8.0 μM). Several compounds have been found to inhibit proliferation of L1210, CEM and HeLa cell cultures with IC50 in the 12–53 μM range. Compound and in (R) configuration were the most active compounds (IC50: 12–22 μM for and IC50: 19–23 μM for ). Chirality 28:495–513, 2016. © 2016 Wiley Periodicals, Inc.
Url:
DOI: 10.1002/chir.22607
Affiliations:
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The chemical structures of all compounds were characterized by elemental analysis, UV, IR, 1H NMR, 13C NMR, 2D NMR (HETCOR), and mass spectral data. All compounds were tested in vitro antiviral activity against a broad variety of DNA and RNA viruses and in vitro cytostatic activity against murine leukemia (L1210), human T‐lymphocyte (CEM) and human cervix carcinoma (HeLa) cell lines. Although enantiopure 1,2,4‐triazole‐3‐thione analogs in (R) configuration emerged as promising anti‐influenza A H1N1 subtype in Madin Darby canine kidney cell cultures (MDCK), their enantiomers exhibited no activity. Especially compounds , , , , and (EC50: 6.5, 6.1, 2.4, 1.6, 1.7 μM, respectively) had excellent activity against influenza A H1N1 subtype compared to the reference drug ribavirin (EC50: 8.0 μM). Several compounds have been found to inhibit proliferation of L1210, CEM and HeLa cell cultures with IC50 in the 12–53 μM range. Compound and in (R) configuration were the most active compounds (IC50: 12–22 μM for and IC50: 19–23 μM for ). Chirality 28:495–513, 2016. © 2016 Wiley Periodicals, Inc.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>Turquie</li></country></list><tree><country name="Turquie"><noRegion><name sortKey="Ba Aran, Eyup" sort="Ba Aran, Eyup" uniqKey="Ba Aran E" first="Eyüp" last="Ba Aran">Eyüp Ba Aran</name></noRegion><name sortKey="Karakucuk Yido An, Ay Egul" sort="Karakucuk Yido An, Ay Egul" uniqKey="Karakucuk Yido An A" first="Ay Egül" last="Karaküçük-Iyido An">Ay Egül Karaküçük-Iyido An</name><name sortKey="Karakucuk Yido An, Ay Egul" sort="Karakucuk Yido An, Ay Egul" uniqKey="Karakucuk Yido An A" first="Ay Egül" last="Karaküçük-Iyido An">Ay Egül Karaküçük-Iyido An</name><name sortKey="Oruc Mre, Emine Elcin" sort="Oruc Mre, Emine Elcin" uniqKey="Oruc Mre E" first="Emine Elçin" last="Oruç-Emre">Emine Elçin Oruç-Emre</name></country><country name="Belgique"><noRegion><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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