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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Sociedade Brasileira de Química
2003-01-01
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| Series: | Journal of the Brazilian Chemical Society |
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| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000500014 |
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doaj-24ba3939f57f4e21b827606ef677d0342020-11-25T00:50:46ZengSociedade 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 |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Al-Soud Yaseen A. Al-Masoudi Najim A. |
| 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 |
| author_facet |
Al-Soud Yaseen A. Al-Masoudi Najim A. |
| author_sort |
Al-Soud Yaseen A. |
| 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_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_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_sort |
new class of dihaloquinolones bearing n'-aldehydoglycosylhydrazides, mercapto-1,2,4-triazole, oxadiazoline and a-amino ester precursors: synthesis and antimicrobial activity |
| publisher |
Sociedade Brasileira de Química |
| series |
Journal of the Brazilian Chemical Society |
| issn |
0103-5053 |
| publishDate |
2003-01-01 |
| 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. |
| topic |
antimicrobial activity hydrazides quinolones |
| url |
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000500014 |
| work_keys_str_mv |
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