Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives
The reaction of 5-(1-adamantyl)-4-amino-3-mercapto-1,2,4-triazole (5) with various aromatic aldehydes in ethanol or acetic acid yielded the corresponding 4-arylideneamino derivatives 6a–v. Treatment of the 4-(2,6-difluoro- and dichlorobenzylideneamino) derivatives 6o and 6q with 1-substituted pipera...
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MDPI AG
2010-04-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/15/4/2526/ |
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| author | Mohamed A. Al-Omar Ebtehal S. Al-Abdullah Ihsan A. Shehata Elsayed E. Habib Tarek M. Ibrahim Ali A. El-Emam |
| author_facet | Mohamed A. Al-Omar Ebtehal S. Al-Abdullah Ihsan A. Shehata Elsayed E. Habib Tarek M. Ibrahim Ali A. El-Emam |
| author_sort | Mohamed A. Al-Omar |
| collection | DOAJ |
| description | The reaction of 5-(1-adamantyl)-4-amino-3-mercapto-1,2,4-triazole (5) with various aromatic aldehydes in ethanol or acetic acid yielded the corresponding 4-arylideneamino derivatives 6a–v. Treatment of the 4-(2,6-difluoro- and dichlorobenzylideneamino) derivatives 6o and 6q with 1-substituted piperazines, and formaldehyde solution in ethanol afforded good yields of the corresponding 5-(1-adamantyl)-4-(2,6-dihalobenzylideneamino-2-(4-substituted-1-piperazinylmethyl)-1,2,4-triazoline-3-thiones 7a–p. 5-(1-Adamantyl)-4-arylideneamino-2-(4-ethoxycarbonyl-1-piperidylmethyl)-1,2,4-triazoline-3-thiones 8a–n, were similarly prepared via the reaction of the corresponding arylideneamino derivative with ethyl 4-piperidinecarboxylate and formaldehyde solution in ethanol. Compounds 6a–v, 7a–p and 8a–n were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several derivatives showed good or moderate activities, particularly against the tested Gram-positive bacteria. In addition, the in vivo anti-inflammatory activity of 21 compounds was determined using the carrageenan-induced paw oedema method in rats. Compounds 7d, 7g, 7i, 7j, 7l, 8c, 8e and 8l showed good or moderate dose-dependent activity in this area. |
| first_indexed | 2024-04-13T12:23:34Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T12:23:34Z |
| publishDate | 2010-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9dd13154a4c44d33908604e1b085f29d2022-12-22T02:47:07ZengMDPI AGMolecules1420-30492010-04-011542526255010.3390/molecules15042526Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related DerivativesMohamed A. Al-OmarEbtehal S. Al-AbdullahIhsan A. ShehataElsayed E. HabibTarek M. IbrahimAli A. El-EmamThe reaction of 5-(1-adamantyl)-4-amino-3-mercapto-1,2,4-triazole (5) with various aromatic aldehydes in ethanol or acetic acid yielded the corresponding 4-arylideneamino derivatives 6a–v. Treatment of the 4-(2,6-difluoro- and dichlorobenzylideneamino) derivatives 6o and 6q with 1-substituted piperazines, and formaldehyde solution in ethanol afforded good yields of the corresponding 5-(1-adamantyl)-4-(2,6-dihalobenzylideneamino-2-(4-substituted-1-piperazinylmethyl)-1,2,4-triazoline-3-thiones 7a–p. 5-(1-Adamantyl)-4-arylideneamino-2-(4-ethoxycarbonyl-1-piperidylmethyl)-1,2,4-triazoline-3-thiones 8a–n, were similarly prepared via the reaction of the corresponding arylideneamino derivative with ethyl 4-piperidinecarboxylate and formaldehyde solution in ethanol. Compounds 6a–v, 7a–p and 8a–n were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several derivatives showed good or moderate activities, particularly against the tested Gram-positive bacteria. In addition, the in vivo anti-inflammatory activity of 21 compounds was determined using the carrageenan-induced paw oedema method in rats. Compounds 7d, 7g, 7i, 7j, 7l, 8c, 8e and 8l showed good or moderate dose-dependent activity in this area.http://www.mdpi.com/1420-3049/15/4/2526/1-adamantyl derivatives1,2,4-triazolesantimicrobial activityanti-inflammatory activity |
| spellingShingle | Mohamed A. Al-Omar Ebtehal S. Al-Abdullah Ihsan A. Shehata Elsayed E. Habib Tarek M. Ibrahim Ali A. El-Emam Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives Molecules 1-adamantyl derivatives 1,2,4-triazoles antimicrobial activity anti-inflammatory activity |
| title | Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives |
| title_full | Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives |
| title_fullStr | Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives |
| title_full_unstemmed | Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives |
| title_short | Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives |
| title_sort | synthesis antimicrobial and anti inflammatory activities of novel 5 1 adamantyl 4 arylideneamino 3 mercapto 1 2 4 triazoles and related derivatives |
| topic | 1-adamantyl derivatives 1,2,4-triazoles antimicrobial activity anti-inflammatory activity |
| url | http://www.mdpi.com/1420-3049/15/4/2526/ |
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