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Robust approach leading to novel densely functionalized four-cyclic benzo[e]pyrazolo[5′,1′:2,3]pyrimido[4,5-b][1,4]diazepines with antibacterial activity toward resistant strains
A straightforward approach for the regioselective synthesis of various derivatives of benzo[ e ]pyrazolo[5′,1′:2,3]pyrimido[4,5- b ] [1, 4] diazepine as a novel heterocyclic system from the annulation of 6-bromo-7-chloro-3-cyano-2-(ethylthio)-5-methylpyrazolo[1,5- a ]pyrimidine with several 2-amino-...
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| Published in: | Journal of the Iranian Chemical Society 2020-07, Vol.17 (7), p.1555-1566 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c356t-d8719b6f18e81af8870b141abb51164d988493a8891a1d32048b36d0c87d63a3 |
| container_end_page | 1566 |
| container_issue | 7 |
| container_start_page | 1555 |
| container_title | Journal of the Iranian Chemical Society |
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| creator | Sheikhi-Mohammareh, Seddigheh Mashreghi, Mansour Shiri, Ali |
| description | A straightforward approach for the regioselective synthesis of various derivatives of benzo[
e
]pyrazolo[5′,1′:2,3]pyrimido[4,5-
b
] [1, 4] diazepine as a novel heterocyclic system from the annulation of 6-bromo-7-chloro-3-cyano-2-(ethylthio)-5-methylpyrazolo[1,5-
a
]pyrimidine with several 2-amino-
N
-substituted benzamides as bident nucleophiles in the presence of K
2
CO
3
and DMF has been disclosed. The right regioisomer was elucidated by
2
D-NOESY NMR spectroscopy, as well. Most of the novel synthetic compounds exhibited antimicrobial activity though relatively at high concentrations against multi-drug-resistant
Klebsiella pneumoniae
and
Escherichia coli
clinical isolates possessed of strong biofilm formation ability.
N
-Cyclohexyl-substituted pyrazolopyrimidobenzodiazepine (
3
h
) as the most potent compound represented 100% growth inhibitory on both types of bacterial strains, which brings promises for further changes to develop potential antimicrobial drugs.
Graphical abstract |
| doi_str_mv | 10.1007/s13738-020-01875-5 |
| format | article |
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e
]pyrazolo[5′,1′:2,3]pyrimido[4,5-
b
] [1, 4] diazepine as a novel heterocyclic system from the annulation of 6-bromo-7-chloro-3-cyano-2-(ethylthio)-5-methylpyrazolo[1,5-
a
]pyrimidine with several 2-amino-
N
-substituted benzamides as bident nucleophiles in the presence of K
2
CO
3
and DMF has been disclosed. The right regioisomer was elucidated by
2
D-NOESY NMR spectroscopy, as well. Most of the novel synthetic compounds exhibited antimicrobial activity though relatively at high concentrations against multi-drug-resistant
Klebsiella pneumoniae
and
Escherichia coli
clinical isolates possessed of strong biofilm formation ability.
N
-Cyclohexyl-substituted pyrazolopyrimidobenzodiazepine (
3
h
) as the most potent compound represented 100% growth inhibitory on both types of bacterial strains, which brings promises for further changes to develop potential antimicrobial drugs.
Graphical abstract</description><identifier>ISSN: 1735-207X</identifier><identifier>EISSN: 1735-2428</identifier><identifier>DOI: 10.1007/s13738-020-01875-5</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Analytical Chemistry ; Antimicrobial agents ; Biochemistry ; Chemical reactions ; Chemistry ; Chemistry and Materials Science ; Drug resistance ; E coli ; Inorganic Chemistry ; Klebsiella ; NMR spectroscopy ; Nucleophiles ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Potassium carbonate ; Substitutes</subject><ispartof>Journal of the Iranian Chemical Society, 2020-07, Vol.17 (7), p.1555-1566</ispartof><rights>Iranian Chemical Society 2020</rights><rights>Iranian Chemical Society 2020.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-d8719b6f18e81af8870b141abb51164d988493a8891a1d32048b36d0c87d63a3</citedby><cites>FETCH-LOGICAL-c356t-d8719b6f18e81af8870b141abb51164d988493a8891a1d32048b36d0c87d63a3</cites><orcidid>0000-0002-5736-6287</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Sheikhi-Mohammareh, Seddigheh</creatorcontrib><creatorcontrib>Mashreghi, Mansour</creatorcontrib><creatorcontrib>Shiri, Ali</creatorcontrib><title>Robust approach leading to novel densely functionalized four-cyclic benzo[e]pyrazolo[5′,1′:2,3]pyrimido[4,5-b][1,4]diazepines with antibacterial activity toward resistant strains</title><title>Journal of the Iranian Chemical Society</title><addtitle>J IRAN CHEM SOC</addtitle><description>A straightforward approach for the regioselective synthesis of various derivatives of benzo[
e
]pyrazolo[5′,1′:2,3]pyrimido[4,5-
b
] [1, 4] diazepine as a novel heterocyclic system from the annulation of 6-bromo-7-chloro-3-cyano-2-(ethylthio)-5-methylpyrazolo[1,5-
a
]pyrimidine with several 2-amino-
N
-substituted benzamides as bident nucleophiles in the presence of K
2
CO
3
and DMF has been disclosed. The right regioisomer was elucidated by
2
D-NOESY NMR spectroscopy, as well. Most of the novel synthetic compounds exhibited antimicrobial activity though relatively at high concentrations against multi-drug-resistant
Klebsiella pneumoniae
and
Escherichia coli
clinical isolates possessed of strong biofilm formation ability.
N
-Cyclohexyl-substituted pyrazolopyrimidobenzodiazepine (
3
h
) as the most potent compound represented 100% growth inhibitory on both types of bacterial strains, which brings promises for further changes to develop potential antimicrobial drugs.
Graphical abstract</description><subject>Analytical Chemistry</subject><subject>Antimicrobial agents</subject><subject>Biochemistry</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Drug resistance</subject><subject>E coli</subject><subject>Inorganic Chemistry</subject><subject>Klebsiella</subject><subject>NMR spectroscopy</subject><subject>Nucleophiles</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Potassium carbonate</subject><subject>Substitutes</subject><issn>1735-207X</issn><issn>1735-2428</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9UU1rFTEUHUTB2voHXAXcvmjuJJnkuZNiVSgIpQvh8Qj5mjZlTMYkr2Xeyt_kwh_kLzH1Wbpzc-_hcs7h3nu67hWQN0CIeFuACiox6QkmIAXH_El3BIJy3LNePn3ARHx93r0o5YYQLghnR92vi2R2pSI9zzlpe40mr12IV6gmFNOtn5DzsfhpQeMu2hpS1FPYe4fGtMvYLnYKFhkf92njt_OS9T5NacN___i5glbe9St6Pw7fgksbtuLYbDewYlsX9N7PIfqC7kK9RjrWYLStPgc9oQbCbahL2-JOZ4eyL6HUxkGlZh1iOemejXoq_uW_ftxdnn24PP2Ez798_Hz6_hxbyoeKnRSwNsMI0kvQo5SCGGCgjeEAA3NrKdmaainXoMHRnjBp6OCIlcINVNPj7vXBtj3n-86Xqm7a2e0FRfUMAHpGKGms_sCyOZWS_ajmdrDOiwKi7uNRh3hUi0f9jUfxJqIHUWnkeOXzo_V_VH8AL0CYlg</recordid><startdate>20200701</startdate><enddate>20200701</enddate><creator>Sheikhi-Mohammareh, Seddigheh</creator><creator>Mashreghi, Mansour</creator><creator>Shiri, Ali</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-5736-6287</orcidid></search><sort><creationdate>20200701</creationdate><title>Robust approach leading to novel densely functionalized four-cyclic benzo[e]pyrazolo[5′,1′:2,3]pyrimido[4,5-b][1,4]diazepines with antibacterial activity toward resistant strains</title><author>Sheikhi-Mohammareh, Seddigheh ; Mashreghi, Mansour ; Shiri, Ali</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-d8719b6f18e81af8870b141abb51164d988493a8891a1d32048b36d0c87d63a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Analytical Chemistry</topic><topic>Antimicrobial agents</topic><topic>Biochemistry</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Drug resistance</topic><topic>E coli</topic><topic>Inorganic Chemistry</topic><topic>Klebsiella</topic><topic>NMR spectroscopy</topic><topic>Nucleophiles</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Potassium carbonate</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sheikhi-Mohammareh, Seddigheh</creatorcontrib><creatorcontrib>Mashreghi, Mansour</creatorcontrib><creatorcontrib>Shiri, Ali</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of the Iranian Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sheikhi-Mohammareh, Seddigheh</au><au>Mashreghi, Mansour</au><au>Shiri, Ali</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Robust approach leading to novel densely functionalized four-cyclic benzo[e]pyrazolo[5′,1′:2,3]pyrimido[4,5-b][1,4]diazepines with antibacterial activity toward resistant strains</atitle><jtitle>Journal of the Iranian Chemical Society</jtitle><stitle>J IRAN CHEM SOC</stitle><date>2020-07-01</date><risdate>2020</risdate><volume>17</volume><issue>7</issue><spage>1555</spage><epage>1566</epage><pages>1555-1566</pages><issn>1735-207X</issn><eissn>1735-2428</eissn><abstract>A straightforward approach for the regioselective synthesis of various derivatives of benzo[
e
]pyrazolo[5′,1′:2,3]pyrimido[4,5-
b
] [1, 4] diazepine as a novel heterocyclic system from the annulation of 6-bromo-7-chloro-3-cyano-2-(ethylthio)-5-methylpyrazolo[1,5-
a
]pyrimidine with several 2-amino-
N
-substituted benzamides as bident nucleophiles in the presence of K
2
CO
3
and DMF has been disclosed. The right regioisomer was elucidated by
2
D-NOESY NMR spectroscopy, as well. Most of the novel synthetic compounds exhibited antimicrobial activity though relatively at high concentrations against multi-drug-resistant
Klebsiella pneumoniae
and
Escherichia coli
clinical isolates possessed of strong biofilm formation ability.
N
-Cyclohexyl-substituted pyrazolopyrimidobenzodiazepine (
3
h
) as the most potent compound represented 100% growth inhibitory on both types of bacterial strains, which brings promises for further changes to develop potential antimicrobial drugs.
Graphical abstract</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s13738-020-01875-5</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-5736-6287</orcidid></addata></record> |
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| source | Springer Link |
| subjects | Analytical Chemistry Antimicrobial agents Biochemistry Chemical reactions Chemistry Chemistry and Materials Science Drug resistance E coli Inorganic Chemistry Klebsiella NMR spectroscopy Nucleophiles Organic Chemistry Original Paper Physical Chemistry Potassium carbonate Substitutes |
| title | Robust approach leading to novel densely functionalized four-cyclic benzo[e]pyrazolo[5′,1′:2,3]pyrimido[4,5-b][1,4]diazepines with antibacterial activity toward resistant strains |
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