Thiazolyl-pyrazole-biscoumarin synthesis and evaluation of their antibacterial and antioxidant activities
A series of novel 3-(2-oxo-2 H -chromen-3-yl)-1-(4-(2-oxo-2 H -chromen-3-yl)thiazol-2-yl)-5-aryl-1 H -pyrazol-1-ium bromides have been prepared through a one-pot three-component cyclocondensation of various coumarin chalcones, thiosemicarbazide and 2-bromocoumarin. The key features of this reaction...
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| Veröffentlicht in: | Research on chemical intermediates 2017-02, Vol.43 (2), p.661-678 |
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| creator | Mahmoodi, Nosrat O. Ghodsi, Shahryar |
| description | A series of novel 3-(2-oxo-2
H
-chromen-3-yl)-1-(4-(2-oxo-2
H
-chromen-3-yl)thiazol-2-yl)-5-aryl-1
H
-pyrazol-1-ium bromides have been prepared through a one-pot three-component cyclocondensation of various coumarin chalcones, thiosemicarbazide and 2-bromocoumarin. The key features of this reaction are the incorporation of four heterocyclic rings in the structure of target products, using commonly available and inexpensive catalysts, high yields, and simple reaction conditions. Final salt products were obtained by self-capturing of a proton by the nitrogen of the pyrazole moiety. The easy work-up and mild reaction conditions are notable features of this protocol. The antioxidant, antibacterial, and anti-fungal activities of the synthetic products were examined. Most of the compounds showed good biological capacity in comparison to references.
Graphical Abstract |
| doi_str_mv | 10.1007/s11164-016-2644-2 |
| format | Article |
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H
-chromen-3-yl)-1-(4-(2-oxo-2
H
-chromen-3-yl)thiazol-2-yl)-5-aryl-1
H
-pyrazol-1-ium bromides have been prepared through a one-pot three-component cyclocondensation of various coumarin chalcones, thiosemicarbazide and 2-bromocoumarin. The key features of this reaction are the incorporation of four heterocyclic rings in the structure of target products, using commonly available and inexpensive catalysts, high yields, and simple reaction conditions. Final salt products were obtained by self-capturing of a proton by the nitrogen of the pyrazole moiety. The easy work-up and mild reaction conditions are notable features of this protocol. The antioxidant, antibacterial, and anti-fungal activities of the synthetic products were examined. Most of the compounds showed good biological capacity in comparison to references.
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H
-chromen-3-yl)-1-(4-(2-oxo-2
H
-chromen-3-yl)thiazol-2-yl)-5-aryl-1
H
-pyrazol-1-ium bromides have been prepared through a one-pot three-component cyclocondensation of various coumarin chalcones, thiosemicarbazide and 2-bromocoumarin. The key features of this reaction are the incorporation of four heterocyclic rings in the structure of target products, using commonly available and inexpensive catalysts, high yields, and simple reaction conditions. Final salt products were obtained by self-capturing of a proton by the nitrogen of the pyrazole moiety. The easy work-up and mild reaction conditions are notable features of this protocol. The antioxidant, antibacterial, and anti-fungal activities of the synthetic products were examined. Most of the compounds showed good biological capacity in comparison to references.
Graphical Abstract</description><subject>Antiinfectives and antibacterials</subject><subject>Antioxidants</subject><subject>Bromides</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Coumarin</subject><subject>Fungicides</subject><subject>Inorganic Chemistry</subject><subject>Physical Chemistry</subject><subject>Pyrazole</subject><issn>0922-6168</issn><issn>1568-5675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1UDtPwzAQthBIlMIPYIvEbPBdYicZUcVLqsTS3XJsh7oKcbGTivDrcQkDC9OdvtfpPkKugd0CY-VdBABRUAaCoigKiidkAVxUlIuSn5IFqxGpAFGdk4sYd4wBryq2IG6zderLd1NH91M4bpY2Lmo_vqvg-ixO_bC10cVM9SazB9WNanC-z3ybJcKFhA-uUXqwwanuR3VE_KczaWaJcAc3OBsvyVmrumivfueSbB4fNqtnun59elndr6nOQQy0MnVbCtGKwkCtGDY2t7lpUTNrcq2xsGjQNHWubcl5gZprzHXJqrrmCCJfkps5dh_8x2jjIHd-DH26KCF9XFZYMpZUMKt08DEG28p9cOnjSQKTx0LlXKhMhcpjoRKTB2dPTNr-zYY_yf-avgFFn3sv</recordid><startdate>20170201</startdate><enddate>20170201</enddate><creator>Mahmoodi, Nosrat O.</creator><creator>Ghodsi, Shahryar</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20170201</creationdate><title>Thiazolyl-pyrazole-biscoumarin synthesis and evaluation of their antibacterial and antioxidant activities</title><author>Mahmoodi, Nosrat O. ; Ghodsi, Shahryar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-8d9f766f64d19a02be3e3df2c0ed3cc24e2d2db93ce75542c5c23c7089952163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Antiinfectives and antibacterials</topic><topic>Antioxidants</topic><topic>Bromides</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Coumarin</topic><topic>Fungicides</topic><topic>Inorganic Chemistry</topic><topic>Physical Chemistry</topic><topic>Pyrazole</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mahmoodi, Nosrat O.</creatorcontrib><creatorcontrib>Ghodsi, Shahryar</creatorcontrib><collection>CrossRef</collection><jtitle>Research on chemical intermediates</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mahmoodi, Nosrat O.</au><au>Ghodsi, Shahryar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiazolyl-pyrazole-biscoumarin synthesis and evaluation of their antibacterial and antioxidant activities</atitle><jtitle>Research on chemical intermediates</jtitle><stitle>Res Chem Intermed</stitle><date>2017-02-01</date><risdate>2017</risdate><volume>43</volume><issue>2</issue><spage>661</spage><epage>678</epage><pages>661-678</pages><issn>0922-6168</issn><eissn>1568-5675</eissn><abstract>A series of novel 3-(2-oxo-2
H
-chromen-3-yl)-1-(4-(2-oxo-2
H
-chromen-3-yl)thiazol-2-yl)-5-aryl-1
H
-pyrazol-1-ium bromides have been prepared through a one-pot three-component cyclocondensation of various coumarin chalcones, thiosemicarbazide and 2-bromocoumarin. The key features of this reaction are the incorporation of four heterocyclic rings in the structure of target products, using commonly available and inexpensive catalysts, high yields, and simple reaction conditions. Final salt products were obtained by self-capturing of a proton by the nitrogen of the pyrazole moiety. The easy work-up and mild reaction conditions are notable features of this protocol. The antioxidant, antibacterial, and anti-fungal activities of the synthetic products were examined. Most of the compounds showed good biological capacity in comparison to references.
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| ispartof | Research on chemical intermediates, 2017-02, Vol.43 (2), p.661-678 |
| issn | 0922-6168 1568-5675 |
| language | eng |
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| subjects | Antiinfectives and antibacterials Antioxidants Bromides Catalysis Chemistry Chemistry and Materials Science Coumarin Fungicides Inorganic Chemistry Physical Chemistry Pyrazole |
| title | Thiazolyl-pyrazole-biscoumarin synthesis and evaluation of their antibacterial and antioxidant activities |
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