SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW (Z)-2-(BENZYLIDENE)-3,4-DIHYDRO-2H-[1,4]-BENZOTHIAZIN-3-ONE D-GLUCOSE DERIVATIVES
In this work, we are interested in the synthesis of new N-glucosyl 1,4-benzothiazin-3-ones by grafting 5,6-anhydro-3-O-alkyl-1,2-O-isopropylidene-α-D-glucofuranoses onto (Z)-2-benzylidene-3,4-dihydro-2H-1,4-benzothiazin-3-one 1. Deprotection of compounds 3a-c was performed in the mixture CF3COOH-H2O...
Saved in:
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Alma Mater Publishing House "Vasile Alecsandri" University of Bacau
2019-12-01
|
| Series: | Scientific Study & Research: Chemistry & Chemical Engineering, Biotechnology, Food Industry |
| Subjects: | |
| Online Access: | http://pubs.ub.ro/?pg=revues&rev=cscc6&num=201904&vol=4&aid=4956 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849324663632560128 |
|---|---|
| author | MOHAMED ELLOUZ NADA KHEIRA SEBBAR HICHAM ELMSELLEM BRAHIM LAKHRISSI ZAKARIA MENNANE REDA CHAROF MARTINE URRUTIGOÎTY EL MOKHTAR ESSASSI |
| author_facet | MOHAMED ELLOUZ NADA KHEIRA SEBBAR HICHAM ELMSELLEM BRAHIM LAKHRISSI ZAKARIA MENNANE REDA CHAROF MARTINE URRUTIGOÎTY EL MOKHTAR ESSASSI |
| author_sort | MOHAMED ELLOUZ |
| collection | DOAJ |
| description | In this work, we are interested in the synthesis of new N-glucosyl 1,4-benzothiazin-3-ones by grafting 5,6-anhydro-3-O-alkyl-1,2-O-isopropylidene-α-D-glucofuranoses onto (Z)-2-benzylidene-3,4-dihydro-2H-1,4-benzothiazin-3-one 1. Deprotection of compounds 3a-c was performed in the mixture CF3COOH-H2O (9/1: v/v) leading to the corresponding compounds 4a-c with good yields. The structures of the synthesized compounds have been characterized using 1H NMR and 13C NMR. Compounds 3a-c and 4a-c were subjected to the evaluation of antibacterial activity. Some compounds tested showed significant activity. |
| format | Article |
| id | doaj-art-f50aeb3491ce4e8295e092a894b25a02 |
| institution | Kabale University |
| issn | 1582-540X 1582-540X |
| language | English |
| publishDate | 2019-12-01 |
| publisher | Alma Mater Publishing House "Vasile Alecsandri" University of Bacau |
| record_format | Article |
| series | Scientific Study & Research: Chemistry & Chemical Engineering, Biotechnology, Food Industry |
| spelling | doaj-art-f50aeb3491ce4e8295e092a894b25a022025-08-20T03:48:37ZengAlma Mater Publishing House "Vasile Alecsandri" University of BacauScientific Study & Research: Chemistry & Chemical Engineering, Biotechnology, Food Industry1582-540X1582-540X2019-12-01204563574SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW (Z)-2-(BENZYLIDENE)-3,4-DIHYDRO-2H-[1,4]-BENZOTHIAZIN-3-ONE D-GLUCOSE DERIVATIVESMOHAMED ELLOUZ 0NADA KHEIRA SEBBAR 1HICHAM ELMSELLEM 2BRAHIM LAKHRISSI 3ZAKARIA MENNANE 4REDA CHAROF 5MARTINE URRUTIGOÎTY 6 EL MOKHTAR ESSASSI 71. Université Mohammed V de Rabat, Faculté des Sciences, Pôle de Compétences Pharmacochimie, Centre de Recherche des Sciences des Médicaments, Laboratoire de Chimie Organique Hétérocyclique, Av. Ibn Battouta, BP 10140 Rabat, Maroc1. Université Mohammed V de Rabat, Faculté des Sciences, Pôle de Compétences Pharmacochimie, Centre de Recherche des Sciences des Médicaments, Laboratoire de Chimie Organique Hétérocyclique, Av. Ibn Battouta, BP 10140 Rabat, Maroc 2. Université Ibn Zohr, Faculté des sciences, Laboratoire de Chimie Appliquée et Environnement, Equipe de Chimie Bioorganique Appliquée, Agadir, Maroc3. Université Mohammed Premier, Faculté des Sciences, Laboratoire de Chimie Appliquée et Environnement (LCAE-URAC18), Oujda, Maroc4. Université Ibn Tofail, Laboratoire de Chimie des Agroressources, Kénitra, Maroc5. Institut National d’Hygiène, Département de Bactériologie, avenue Ibn Batouta, B.P. 769, Agdal, Rabat, 11000, Maroc5. Institut National d’Hygiène, Département de Bactériologie, avenue Ibn Batouta, B.P. 769, Agdal, Rabat, 11000, Maroc6. Ecole Nationale Supérieure des Ingénieurs en Arts Chimiques et Technologiques, Laboratoire de Catalyse, Chimie Fine et Polymères, 118 route de Narbonne, 31077 Toulouse Cedex 04, France1. Université Mohammed V de Rabat, Faculté des Sciences, Pôle de Compétences Pharmacochimie, Centre de Recherche des Sciences des Médicaments, Laboratoire de Chimie Organique Hétérocyclique, Av. Ibn Battouta, BP 10140 Rabat, MarocIn this work, we are interested in the synthesis of new N-glucosyl 1,4-benzothiazin-3-ones by grafting 5,6-anhydro-3-O-alkyl-1,2-O-isopropylidene-α-D-glucofuranoses onto (Z)-2-benzylidene-3,4-dihydro-2H-1,4-benzothiazin-3-one 1. Deprotection of compounds 3a-c was performed in the mixture CF3COOH-H2O (9/1: v/v) leading to the corresponding compounds 4a-c with good yields. The structures of the synthesized compounds have been characterized using 1H NMR and 13C NMR. Compounds 3a-c and 4a-c were subjected to the evaluation of antibacterial activity. Some compounds tested showed significant activity.http://pubs.ub.ro/?pg=revues&rev=cscc6&num=201904&vol=4&aid=4956alkylationanti-bacterial activities14-benzothiazin-3-oned-glucofuranosed-glucose |
| spellingShingle | MOHAMED ELLOUZ NADA KHEIRA SEBBAR HICHAM ELMSELLEM BRAHIM LAKHRISSI ZAKARIA MENNANE REDA CHAROF MARTINE URRUTIGOÎTY EL MOKHTAR ESSASSI SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW (Z)-2-(BENZYLIDENE)-3,4-DIHYDRO-2H-[1,4]-BENZOTHIAZIN-3-ONE D-GLUCOSE DERIVATIVES Scientific Study & Research: Chemistry & Chemical Engineering, Biotechnology, Food Industry alkylation anti-bacterial activities 1 4-benzothiazin-3-one d-glucofuranose d-glucose |
| title | SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW (Z)-2-(BENZYLIDENE)-3,4-DIHYDRO-2H-[1,4]-BENZOTHIAZIN-3-ONE D-GLUCOSE DERIVATIVES |
| title_full | SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW (Z)-2-(BENZYLIDENE)-3,4-DIHYDRO-2H-[1,4]-BENZOTHIAZIN-3-ONE D-GLUCOSE DERIVATIVES |
| title_fullStr | SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW (Z)-2-(BENZYLIDENE)-3,4-DIHYDRO-2H-[1,4]-BENZOTHIAZIN-3-ONE D-GLUCOSE DERIVATIVES |
| title_full_unstemmed | SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW (Z)-2-(BENZYLIDENE)-3,4-DIHYDRO-2H-[1,4]-BENZOTHIAZIN-3-ONE D-GLUCOSE DERIVATIVES |
| title_short | SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW (Z)-2-(BENZYLIDENE)-3,4-DIHYDRO-2H-[1,4]-BENZOTHIAZIN-3-ONE D-GLUCOSE DERIVATIVES |
| title_sort | synthesis and antibacterial activity of new z 2 benzylidene 3 4 dihydro 2h 1 4 benzothiazin 3 one d glucose derivatives |
| topic | alkylation anti-bacterial activities 1 4-benzothiazin-3-one d-glucofuranose d-glucose |
| url | http://pubs.ub.ro/?pg=revues&rev=cscc6&num=201904&vol=4&aid=4956 |
| work_keys_str_mv | AT mohamedellouz synthesisandantibacterialactivityofnewz2benzylidene34dihydro2h14benzothiazin3onedglucosederivatives AT nadakheirasebbar synthesisandantibacterialactivityofnewz2benzylidene34dihydro2h14benzothiazin3onedglucosederivatives AT hichamelmsellem synthesisandantibacterialactivityofnewz2benzylidene34dihydro2h14benzothiazin3onedglucosederivatives AT brahimlakhrissi synthesisandantibacterialactivityofnewz2benzylidene34dihydro2h14benzothiazin3onedglucosederivatives AT zakariamennane synthesisandantibacterialactivityofnewz2benzylidene34dihydro2h14benzothiazin3onedglucosederivatives AT redacharof synthesisandantibacterialactivityofnewz2benzylidene34dihydro2h14benzothiazin3onedglucosederivatives AT martineurrutigoity synthesisandantibacterialactivityofnewz2benzylidene34dihydro2h14benzothiazin3onedglucosederivatives AT elmokhtaressassi synthesisandantibacterialactivityofnewz2benzylidene34dihydro2h14benzothiazin3onedglucosederivatives |