Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety
Copyright (c) 2009 Elsevier Masson SAS. All rights reserved..
2-(5-oxothiazolidinone)-cyanoacetamido derivative 3 was prepared in two steps by reaction of 2-(2-cyano-acetylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxamide (1) with phenyl isothiocyanate and chloroacetyl chloride, which diazocoupled with p-tolyldiazonium chloride in pyridine to afford the corresponding hydrazono derivative 4. Also, condensation of 3 with p-anisaldehyde gave the corresponding arylidine derivative 5. Treatment of 2 with dimethyl sulfate afforded the ketene N,S-acetal 9 which give 5-amino pyrazole derivative 10 upon treatment with hydrazine hydrate. Compound 10 was used as key intermediate for synthesis of pyrazolo[5,1-c][1,2,4]triazine 13a, b, pyrazolo[5,1-a]pyrimidine 14-17 and pyrolo pyrazole 18 derivatives. Finally, condensation of 1 with DMF-DMA afforded the corresponding acryloamide derivative 19, which afforded the corresponding pyrazole derivative 20 upon heating with hydrazine hydrate. All new synthesized compounds were evaluated as antimicrobial agents; some of them exhibited promising activities.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2010 |
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| Erschienen: |
2010 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:45 |
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| Enthalten in: |
European journal of medicinal chemistry - 45(2010), 4 vom: 17. Apr., Seite 1338-45 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Gouda, M A [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 02.08.2010 Date Revised 08.03.2010 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.ejmech.2009.12.020 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM194268039 |
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| 245 | 1 | 0 | |a Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety |
| 264 | 1 | |c 2010 | |
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| 500 | |a Date Completed 02.08.2010 | ||
| 500 | |a Date Revised 08.03.2010 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright (c) 2009 Elsevier Masson SAS. All rights reserved. | ||
| 520 | |a 2-(5-oxothiazolidinone)-cyanoacetamido derivative 3 was prepared in two steps by reaction of 2-(2-cyano-acetylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxamide (1) with phenyl isothiocyanate and chloroacetyl chloride, which diazocoupled with p-tolyldiazonium chloride in pyridine to afford the corresponding hydrazono derivative 4. Also, condensation of 3 with p-anisaldehyde gave the corresponding arylidine derivative 5. Treatment of 2 with dimethyl sulfate afforded the ketene N,S-acetal 9 which give 5-amino pyrazole derivative 10 upon treatment with hydrazine hydrate. Compound 10 was used as key intermediate for synthesis of pyrazolo[5,1-c][1,2,4]triazine 13a, b, pyrazolo[5,1-a]pyrimidine 14-17 and pyrolo pyrazole 18 derivatives. Finally, condensation of 1 with DMF-DMA afforded the corresponding acryloamide derivative 19, which afforded the corresponding pyrazole derivative 20 upon heating with hydrazine hydrate. All new synthesized compounds were evaluated as antimicrobial agents; some of them exhibited promising activities | ||
| 650 | 4 | |a Journal Article | |
| 650 | 7 | |a Anti-Infective Agents |2 NLM | |
| 650 | 7 | |a Pyrazoles |2 NLM | |
| 650 | 7 | |a Thiazoles |2 NLM | |
| 700 | 1 | |a Berghot, M A |e verfasserin |4 aut | |
| 700 | 1 | |a Abd El-Ghani, Ghada E |e verfasserin |4 aut | |
| 700 | 1 | |a Khalil, A M |e verfasserin |4 aut | |
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