Microwave-assisted and conventional synthesis of novel antimicrobial 1,2,4-triazole derivatives containing nalidixic acid skeleton
Carbothioamides , obtained from nalidixic acid, were converted to the corresponding 1,3-thiazolidine derivatives by cyclocondensation with 2-bromo-1-(4-chlorophenyl)ethanone. Treatment of with base afforded 1,2,4-triazoles . The synthesis of 1,3-oxazolidine was performed by the reaction of compound...
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| Veröffentlicht in: | Heterocyclic communications 2016-08, Vol.22 (4), p.229-237 |
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| container_title | Heterocyclic communications |
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| creator | Ceylan, Sule Bayrak, Hacer Basoglu Ozdemir, Serap Uygun, Yıldız Mermer, Arif Demirbas, Neslihan Ulker, Serdar |
| description | Carbothioamides
, obtained from nalidixic acid, were converted to the corresponding 1,3-thiazolidine derivatives
by cyclocondensation with 2-bromo-1-(4-chlorophenyl)ethanone. Treatment of
with base afforded 1,2,4-triazoles
. The synthesis of 1,3-oxazolidine
was performed by the reaction of compound
with ethyl bromoacetate. Treatment of
with acid produced 1,3,4-thiadiazole
. The reaction of compounds
and
with several heterocyclic amines in the presence of formaldehyde gave the corresponding Mannich bases
containing various pharmacophore groups. Conventional and microwave-assisted methods were used for the synthesis. The effect of an acid catalyst on Mannich reactions was investigated. The structures of the newly synthesized compounds were elucidated on the basis of
H NMR,
C NMR, FTIR, EIMS techniques, and elemental analysis. All compounds were screened for their antimicrobial activity. |
| doi_str_mv | 10.1515/hc-2016-0019 |
| format | Article |
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, obtained from nalidixic acid, were converted to the corresponding 1,3-thiazolidine derivatives
by cyclocondensation with 2-bromo-1-(4-chlorophenyl)ethanone. Treatment of
with base afforded 1,2,4-triazoles
. The synthesis of 1,3-oxazolidine
was performed by the reaction of compound
with ethyl bromoacetate. Treatment of
with acid produced 1,3,4-thiadiazole
. The reaction of compounds
and
with several heterocyclic amines in the presence of formaldehyde gave the corresponding Mannich bases
containing various pharmacophore groups. Conventional and microwave-assisted methods were used for the synthesis. The effect of an acid catalyst on Mannich reactions was investigated. The structures of the newly synthesized compounds were elucidated on the basis of
H NMR,
C NMR, FTIR, EIMS techniques, and elemental analysis. All compounds were screened for their antimicrobial activity.</description><identifier>ISSN: 0793-0283</identifier><identifier>EISSN: 2191-0197</identifier><identifier>DOI: 10.1515/hc-2016-0019</identifier><language>eng</language><publisher>Berlin: De Gruyter</publisher><subject>1,2,4-triazole ; Acids ; antimicrobial activity ; Antimicrobial agents ; Chemical synthesis ; Mannich base ; Microwaves ; nalidixic acid ; norfloxacin</subject><ispartof>Heterocyclic communications, 2016-08, Vol.22 (4), p.229-237</ispartof><rights>Copyright Walter de Gruyter GmbH Aug 2016</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c352t-9b19eae036cf754656402bc102cde347a36e6fdfe61a1f8ec8fb46c1c5b5bdbe3</citedby><cites>FETCH-LOGICAL-c352t-9b19eae036cf754656402bc102cde347a36e6fdfe61a1f8ec8fb46c1c5b5bdbe3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.degruyter.com/document/doi/10.1515/hc-2016-0019/pdf$$EPDF$$P50$$Gwalterdegruyter$$H</linktopdf><linktohtml>$$Uhttps://www.degruyter.com/document/doi/10.1515/hc-2016-0019/html$$EHTML$$P50$$Gwalterdegruyter$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,66901,68685</link.rule.ids></links><search><creatorcontrib>Ceylan, Sule</creatorcontrib><creatorcontrib>Bayrak, Hacer</creatorcontrib><creatorcontrib>Basoglu Ozdemir, Serap</creatorcontrib><creatorcontrib>Uygun, Yıldız</creatorcontrib><creatorcontrib>Mermer, Arif</creatorcontrib><creatorcontrib>Demirbas, Neslihan</creatorcontrib><creatorcontrib>Ulker, Serdar</creatorcontrib><title>Microwave-assisted and conventional synthesis of novel antimicrobial 1,2,4-triazole derivatives containing nalidixic acid skeleton</title><title>Heterocyclic communications</title><description>Carbothioamides
, obtained from nalidixic acid, were converted to the corresponding 1,3-thiazolidine derivatives
by cyclocondensation with 2-bromo-1-(4-chlorophenyl)ethanone. Treatment of
with base afforded 1,2,4-triazoles
. The synthesis of 1,3-oxazolidine
was performed by the reaction of compound
with ethyl bromoacetate. Treatment of
with acid produced 1,3,4-thiadiazole
. The reaction of compounds
and
with several heterocyclic amines in the presence of formaldehyde gave the corresponding Mannich bases
containing various pharmacophore groups. Conventional and microwave-assisted methods were used for the synthesis. The effect of an acid catalyst on Mannich reactions was investigated. The structures of the newly synthesized compounds were elucidated on the basis of
H NMR,
C NMR, FTIR, EIMS techniques, and elemental analysis. All compounds were screened for their antimicrobial activity.</description><subject>1,2,4-triazole</subject><subject>Acids</subject><subject>antimicrobial activity</subject><subject>Antimicrobial agents</subject><subject>Chemical synthesis</subject><subject>Mannich base</subject><subject>Microwaves</subject><subject>nalidixic acid</subject><subject>norfloxacin</subject><issn>0793-0283</issn><issn>2191-0197</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNptkDFv2zAQhYkiAWKk3vIDCGQ1Ux4lSma2IkjSAi66tLNAkaeYqUy6JK3UHfPLS8EZMvSWO-C-93D3CLkCfgMS5KetYYJDwzgH9YEsBChgZWzPyIK3qmJcrKsLskzpmZeqFciWL8jrN2dieNETMp2SSxkt1d5SE_yEPrvg9UjT0ectli0NA_VhwrEw2e1mae8KACuxqlmOTv8NI1KL0U06uwnTbJS1884_0WLlrPvjDNXGWZp-4Yg5-I_kfNBjwuVbvyQ_H-5_3H1hm--PX-8-b5ippMhM9aBQI68aM7SybmRTc9Eb4MJYrOpWVw02gx2wAQ3DGs166OvGgJG97G2P1SW5PvnuY_h9wJS753CI5ajUwZorgFYqVajViSq_pRRx6PbR7XQ8dsC7Oehua7o56G4OuuC3J_xFjxmjxad4OJbhnfd_ZELUQqjqHwlthsI</recordid><startdate>20160801</startdate><enddate>20160801</enddate><creator>Ceylan, Sule</creator><creator>Bayrak, Hacer</creator><creator>Basoglu Ozdemir, Serap</creator><creator>Uygun, Yıldız</creator><creator>Mermer, Arif</creator><creator>Demirbas, Neslihan</creator><creator>Ulker, Serdar</creator><general>De Gruyter</general><general>Walter de Gruyter GmbH</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20160801</creationdate><title>Microwave-assisted and conventional synthesis of novel antimicrobial 1,2,4-triazole derivatives containing nalidixic acid skeleton</title><author>Ceylan, Sule ; Bayrak, Hacer ; Basoglu Ozdemir, Serap ; Uygun, Yıldız ; Mermer, Arif ; Demirbas, Neslihan ; Ulker, Serdar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c352t-9b19eae036cf754656402bc102cde347a36e6fdfe61a1f8ec8fb46c1c5b5bdbe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>1,2,4-triazole</topic><topic>Acids</topic><topic>antimicrobial activity</topic><topic>Antimicrobial agents</topic><topic>Chemical synthesis</topic><topic>Mannich base</topic><topic>Microwaves</topic><topic>nalidixic acid</topic><topic>norfloxacin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ceylan, Sule</creatorcontrib><creatorcontrib>Bayrak, Hacer</creatorcontrib><creatorcontrib>Basoglu Ozdemir, Serap</creatorcontrib><creatorcontrib>Uygun, Yıldız</creatorcontrib><creatorcontrib>Mermer, Arif</creatorcontrib><creatorcontrib>Demirbas, Neslihan</creatorcontrib><creatorcontrib>Ulker, Serdar</creatorcontrib><collection>CrossRef</collection><jtitle>Heterocyclic communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ceylan, Sule</au><au>Bayrak, Hacer</au><au>Basoglu Ozdemir, Serap</au><au>Uygun, Yıldız</au><au>Mermer, Arif</au><au>Demirbas, Neslihan</au><au>Ulker, Serdar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-assisted and conventional synthesis of novel antimicrobial 1,2,4-triazole derivatives containing nalidixic acid skeleton</atitle><jtitle>Heterocyclic communications</jtitle><date>2016-08-01</date><risdate>2016</risdate><volume>22</volume><issue>4</issue><spage>229</spage><epage>237</epage><pages>229-237</pages><issn>0793-0283</issn><eissn>2191-0197</eissn><abstract>Carbothioamides
, obtained from nalidixic acid, were converted to the corresponding 1,3-thiazolidine derivatives
by cyclocondensation with 2-bromo-1-(4-chlorophenyl)ethanone. Treatment of
with base afforded 1,2,4-triazoles
. The synthesis of 1,3-oxazolidine
was performed by the reaction of compound
with ethyl bromoacetate. Treatment of
with acid produced 1,3,4-thiadiazole
. The reaction of compounds
and
with several heterocyclic amines in the presence of formaldehyde gave the corresponding Mannich bases
containing various pharmacophore groups. Conventional and microwave-assisted methods were used for the synthesis. The effect of an acid catalyst on Mannich reactions was investigated. The structures of the newly synthesized compounds were elucidated on the basis of
H NMR,
C NMR, FTIR, EIMS techniques, and elemental analysis. All compounds were screened for their antimicrobial activity.</abstract><cop>Berlin</cop><pub>De Gruyter</pub><doi>10.1515/hc-2016-0019</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Heterocyclic communications, 2016-08, Vol.22 (4), p.229-237 |
| issn | 0793-0283 2191-0197 |
| language | eng |
| recordid | cdi_proquest_journals_1809117599 |
| source | De Gruyter Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals |
| subjects | 1,2,4-triazole Acids antimicrobial activity Antimicrobial agents Chemical synthesis Mannich base Microwaves nalidixic acid norfloxacin |
| title | Microwave-assisted and conventional synthesis of novel antimicrobial 1,2,4-triazole derivatives containing nalidixic acid skeleton |
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