Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety
Copyright (c) 2010 Elsevier Masson SAS. All rights reserved..
Treatment of 2-cyano-N-(9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetamide (1) with phenyl isothiocyanate/dimethylsulphate afforded the corresponding ketene N,S-acetal 2 which upon treatment with hydrazine hydrate and 4-aminoantipyrine afforded the pyrazolo derivatives 3 and 4, respectively. 3-aminopyrazole derivative 3 was utilized as key intermediate for the synthesis of pyrazolo[3,4-d]pyrimidine 5, pentaaza-as-indacene 6, triaza-cyclopenta[c]phenanthrene 7, pyrazolo[1,5-a]pyrimidine 8, 9 and (dimethyl-pyrrol-1-yl)pyrazole 10 derivatives. Furthermore, treatment of 1 with DMF/DMA gave the corresponding acrylamide derivative 11 which upon treatment with hydrazine hydrate afforded the corresponding 3-aminopyrazole derivative 12. Moreover, coupling of 1 with 4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-diazonium chloride gave the hydrazone derivative 13 which upon cyclization with acetic acid afforded the corresponding pentaaza-fluorene derivative 14. Representative compounds of the synthesized products were evaluated as antimicrobial agents. Some of these compounds 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), 5 vom: 15. Mai, Seite 1843-8 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Gouda, M A [VerfasserIn] |
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| Links: |
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| Themen: |
3QD5KJZ7ZJ |
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| Anmerkungen: |
Date Completed 21.06.2010 Date Revised 15.11.2012 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.ejmech.2010.01.021 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM194990834 |
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| 245 | 1 | 0 | |a Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety |
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| 500 | |a Date Revised 15.11.2012 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright (c) 2010 Elsevier Masson SAS. All rights reserved. | ||
| 520 | |a Treatment of 2-cyano-N-(9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetamide (1) with phenyl isothiocyanate/dimethylsulphate afforded the corresponding ketene N,S-acetal 2 which upon treatment with hydrazine hydrate and 4-aminoantipyrine afforded the pyrazolo derivatives 3 and 4, respectively. 3-aminopyrazole derivative 3 was utilized as key intermediate for the synthesis of pyrazolo[3,4-d]pyrimidine 5, pentaaza-as-indacene 6, triaza-cyclopenta[c]phenanthrene 7, pyrazolo[1,5-a]pyrimidine 8, 9 and (dimethyl-pyrrol-1-yl)pyrazole 10 derivatives. Furthermore, treatment of 1 with DMF/DMA gave the corresponding acrylamide derivative 11 which upon treatment with hydrazine hydrate afforded the corresponding 3-aminopyrazole derivative 12. Moreover, coupling of 1 with 4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-diazonium chloride gave the hydrazone derivative 13 which upon cyclization with acetic acid afforded the corresponding pentaaza-fluorene derivative 14. Representative compounds of the synthesized products were evaluated as antimicrobial agents. Some of these compounds exhibited promising activities | ||
| 650 | 4 | |a Journal Article | |
| 650 | 7 | |a Anthraquinones |2 NLM | |
| 650 | 7 | |a Anti-Bacterial Agents |2 NLM | |
| 650 | 7 | |a Pyrazoles |2 NLM | |
| 650 | 7 | |a pyrazole |2 NLM | |
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| 700 | 1 | |a Berghot, M A |e verfasserin |4 aut | |
| 700 | 1 | |a Shoeib, A I |e verfasserin |4 aut | |
| 700 | 1 | |a Khalil, A M |e verfasserin |4 aut | |
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