A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity
Reaction of the quinolones 6-8 with hydrazine afforded the hydrazide 9-11 in moderate yields. Condensation of 9 and 11 with CS2 /KOH furnished the potassium salts 13 and 14, respectively, which spontaneously afforded the 3-(1,2,4-triazolyl)-quinolones 15 and 16, respectively, on treatment with hydra...
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
2003-01-01
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| Series: | Journal of the Brazilian Chemical Society |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000500014 |
| _version_ | 1818200129392345088 |
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| author | Al-Soud Yaseen A. Al-Masoudi Najim A. |
| author_facet | Al-Soud Yaseen A. Al-Masoudi Najim A. |
| author_sort | Al-Soud Yaseen A. |
| collection | DOAJ |
| description | Reaction of the quinolones 6-8 with hydrazine afforded the hydrazide 9-11 in moderate yields. Condensation of 9 and 11 with CS2 /KOH furnished the potassium salts 13 and 14, respectively, which spontaneously afforded the 3-(1,2,4-triazolyl)-quinolones 15 and 16, respectively, on treatment with hydrazine. Reaction of 9 in refluxing CS2 /KOH gave the 3-(1,2,4-oxadiazolyl)-quinolone 17. Alternatively, 15 was prepared from 17. The azide derivative 12, obtained from 10, furnished the a-amino ester derivative 18, on reaction with the glycine ethyl ester. Coupling of 10 with various sugars gave the N'-aldehydoglycosyl-quinolone-3-yl)carbohydrazides 19a-e. The newly synthesized compounds were screened for their antibacterial activity. |
| first_indexed | 2024-12-12T02:32:45Z |
| format | Article |
| id | doaj.art-24ba3939f57f4e21b827606ef677d034 |
| institution | Directory Open Access Journal |
| issn | 0103-5053 |
| language | English |
| last_indexed | 2024-12-12T02:32:45Z |
| publishDate | 2003-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Journal of the Brazilian Chemical Society |
| spelling | doaj.art-24ba3939f57f4e21b827606ef677d0342022-12-22T00:41:21ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50532003-01-01145790796A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activityAl-Soud Yaseen A.Al-Masoudi Najim A.Reaction of the quinolones 6-8 with hydrazine afforded the hydrazide 9-11 in moderate yields. Condensation of 9 and 11 with CS2 /KOH furnished the potassium salts 13 and 14, respectively, which spontaneously afforded the 3-(1,2,4-triazolyl)-quinolones 15 and 16, respectively, on treatment with hydrazine. Reaction of 9 in refluxing CS2 /KOH gave the 3-(1,2,4-oxadiazolyl)-quinolone 17. Alternatively, 15 was prepared from 17. The azide derivative 12, obtained from 10, furnished the a-amino ester derivative 18, on reaction with the glycine ethyl ester. Coupling of 10 with various sugars gave the N'-aldehydoglycosyl-quinolone-3-yl)carbohydrazides 19a-e. The newly synthesized compounds were screened for their antibacterial activity.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000500014antimicrobial activityhydrazidesquinolones |
| spellingShingle | Al-Soud Yaseen A. Al-Masoudi Najim A. A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity Journal of the Brazilian Chemical Society antimicrobial activity hydrazides quinolones |
| title | A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity |
| title_full | A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity |
| title_fullStr | A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity |
| title_full_unstemmed | A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity |
| title_short | A new class of dihaloquinolones bearing N'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity |
| title_sort | new class of dihaloquinolones bearing n aldehydoglycosylhydrazides mercapto 1 2 4 triazole oxadiazoline and a amino ester precursors synthesis and antimicrobial activity |
| topic | antimicrobial activity hydrazides quinolones |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000500014 |
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