Design, synthesis and spectroscopic and crystallographic characterisation of novel functionalized pyrazole derivatives: biological evaluation for their cytotoxic, angiogenic and antioxidant activities
The current study presents the synthesis of functionalized pyrazoles ( 18–29 ) through 3 + 2 annulation reaction of ethyl 2-(arylidene)-3-oxobutanoates ( 8–13 ) with phenylhydrazine hydrochlorides ( 14–17 ) in acetic acid under reflux conditions. Structures of the synthesized new compounds were char...
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| Veröffentlicht in: | Research on chemical intermediates 2018-09, Vol.44 (9), p.5635-5652 |
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| creator | Dileep Kumar, Achutha Bharath, Srinivasan Dharmappa, Rekha N. Naveen, Shivalingegowda Lokanath, Neratur Krishnappagowda Ajay Kumar, Kariyappa |
| description | The current study presents the synthesis of functionalized pyrazoles (
18–29
) through 3 + 2 annulation reaction of ethyl 2-(arylidene)-3-oxobutanoates (
8–13
) with phenylhydrazine hydrochlorides (
14–17
) in acetic acid under reflux conditions. Structures of the synthesized new compounds were characterized by spectral and single-crystal X-ray diffraction studies. Preliminary assessment on their biological activities showed that compounds
19
,
23
and
28
have anticancer and antiangiogenic properties and compounds
20
,
24
and
26
have excellent diphenylpicrylhydrazyl (DPPH) radical scavenging activities. Detailed quantitative structure–activity relationship (QSAR) analysis provided insights into the molecular features that might have contributed towards increasing potency of inhibition. In summary, we present a study that has successfully demonstrated the synthesis of novel pyrazole analogues that display anticancer, antiangiogenic and DPPH free radical scavenging activities, making them lead molecules of choice for further development.
Graphical Abstract |
| doi_str_mv | 10.1007/s11164-018-3445-6 |
| format | Article |
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18–29
) through 3 + 2 annulation reaction of ethyl 2-(arylidene)-3-oxobutanoates (
8–13
) with phenylhydrazine hydrochlorides (
14–17
) in acetic acid under reflux conditions. Structures of the synthesized new compounds were characterized by spectral and single-crystal X-ray diffraction studies. Preliminary assessment on their biological activities showed that compounds
19
,
23
and
28
have anticancer and antiangiogenic properties and compounds
20
,
24
and
26
have excellent diphenylpicrylhydrazyl (DPPH) radical scavenging activities. Detailed quantitative structure–activity relationship (QSAR) analysis provided insights into the molecular features that might have contributed towards increasing potency of inhibition. In summary, we present a study that has successfully demonstrated the synthesis of novel pyrazole analogues that display anticancer, antiangiogenic and DPPH free radical scavenging activities, making them lead molecules of choice for further development.
Graphical Abstract</description><identifier>ISSN: 0922-6168</identifier><identifier>EISSN: 1568-5675</identifier><identifier>DOI: 10.1007/s11164-018-3445-6</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Acetic acid ; Antiangiogenics ; Anticancer properties ; Antioxidants ; Cancer ; Catalysis ; Chemical reactions ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Crystallography ; Free radicals ; Hydrochlorides ; Inorganic Chemistry ; Organic chemistry ; Physical Chemistry ; Pyrazole ; Scavenging ; Single crystals ; X-ray diffraction</subject><ispartof>Research on chemical intermediates, 2018-09, Vol.44 (9), p.5635-5652</ispartof><rights>Springer Science+Business Media B.V., part of Springer Nature 2018</rights><rights>Copyright Springer Science & Business Media 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c353t-86e7f5065bc35f64c668108945194f79bb71c1a23705ebb7bee759212a2ea3813</citedby><cites>FETCH-LOGICAL-c353t-86e7f5065bc35f64c668108945194f79bb71c1a23705ebb7bee759212a2ea3813</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11164-018-3445-6$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11164-018-3445-6$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,777,781,27905,27906,41469,42538,51300</link.rule.ids></links><search><creatorcontrib>Dileep Kumar, Achutha</creatorcontrib><creatorcontrib>Bharath, Srinivasan</creatorcontrib><creatorcontrib>Dharmappa, Rekha N.</creatorcontrib><creatorcontrib>Naveen, Shivalingegowda</creatorcontrib><creatorcontrib>Lokanath, Neratur Krishnappagowda</creatorcontrib><creatorcontrib>Ajay Kumar, Kariyappa</creatorcontrib><title>Design, synthesis and spectroscopic and crystallographic characterisation of novel functionalized pyrazole derivatives: biological evaluation for their cytotoxic, angiogenic and antioxidant activities</title><title>Research on chemical intermediates</title><addtitle>Res Chem Intermed</addtitle><description>The current study presents the synthesis of functionalized pyrazoles (
18–29
) through 3 + 2 annulation reaction of ethyl 2-(arylidene)-3-oxobutanoates (
8–13
) with phenylhydrazine hydrochlorides (
14–17
) in acetic acid under reflux conditions. Structures of the synthesized new compounds were characterized by spectral and single-crystal X-ray diffraction studies. Preliminary assessment on their biological activities showed that compounds
19
,
23
and
28
have anticancer and antiangiogenic properties and compounds
20
,
24
and
26
have excellent diphenylpicrylhydrazyl (DPPH) radical scavenging activities. Detailed quantitative structure–activity relationship (QSAR) analysis provided insights into the molecular features that might have contributed towards increasing potency of inhibition. In summary, we present a study that has successfully demonstrated the synthesis of novel pyrazole analogues that display anticancer, antiangiogenic and DPPH free radical scavenging activities, making them lead molecules of choice for further development.
Graphical Abstract</description><subject>Acetic acid</subject><subject>Antiangiogenics</subject><subject>Anticancer properties</subject><subject>Antioxidants</subject><subject>Cancer</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Crystallography</subject><subject>Free radicals</subject><subject>Hydrochlorides</subject><subject>Inorganic Chemistry</subject><subject>Organic chemistry</subject><subject>Physical Chemistry</subject><subject>Pyrazole</subject><subject>Scavenging</subject><subject>Single crystals</subject><subject>X-ray diffraction</subject><issn>0922-6168</issn><issn>1568-5675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1UcFu1DAUtBBILG0_gJslrg31S2LH4YZKoUiVuNBz5Hhfsq6CHWxv1PQL-1m8JZU4cXp-o5nx2MPYexAfQYjmKgGAqgsBuqjqWhbqFduBVLqQqpGv2U60ZVkoUPote5fSgxAgtRY79vwFkxv9JU-rzwc6J278nqcZbY4h2TA7-xexcU3ZTFMYo5kPBNqDicZmjC6Z7ILnYeA-LDjx4ejtCTGTe8I9n9donsKEfE_chbgLpk-8d4G8nDUTx8VMx81jCJFTDBe5XXPI4dHZS7p-dGFE_5LEeKI-uj1NTgHc4rLDdM7eDGZKePEyz9j915uf17fF3Y9v368_3xW2klUutMJmkELJnvZB1VYpDUK3tYS2Hpq27xuwYMqqERJp6REb2ZZQmhJNpaE6Yx823zmG30dMuXsIx0hvTV0ptK5qaNqaWLCxLH1iijh0c3S_TFw7EN2psG4rrKPCulNhnSJNuWkScf2I8Z_z_0V_ACion3Q</recordid><startdate>20180901</startdate><enddate>20180901</enddate><creator>Dileep Kumar, Achutha</creator><creator>Bharath, Srinivasan</creator><creator>Dharmappa, Rekha N.</creator><creator>Naveen, Shivalingegowda</creator><creator>Lokanath, Neratur Krishnappagowda</creator><creator>Ajay Kumar, Kariyappa</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20180901</creationdate><title>Design, synthesis and spectroscopic and crystallographic characterisation of novel functionalized pyrazole derivatives: biological evaluation for their cytotoxic, angiogenic and antioxidant activities</title><author>Dileep Kumar, Achutha ; Bharath, Srinivasan ; Dharmappa, Rekha N. ; Naveen, Shivalingegowda ; Lokanath, Neratur Krishnappagowda ; Ajay Kumar, Kariyappa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-86e7f5065bc35f64c668108945194f79bb71c1a23705ebb7bee759212a2ea3813</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acetic acid</topic><topic>Antiangiogenics</topic><topic>Anticancer properties</topic><topic>Antioxidants</topic><topic>Cancer</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Crystallography</topic><topic>Free radicals</topic><topic>Hydrochlorides</topic><topic>Inorganic Chemistry</topic><topic>Organic chemistry</topic><topic>Physical Chemistry</topic><topic>Pyrazole</topic><topic>Scavenging</topic><topic>Single crystals</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dileep Kumar, Achutha</creatorcontrib><creatorcontrib>Bharath, Srinivasan</creatorcontrib><creatorcontrib>Dharmappa, Rekha N.</creatorcontrib><creatorcontrib>Naveen, Shivalingegowda</creatorcontrib><creatorcontrib>Lokanath, Neratur Krishnappagowda</creatorcontrib><creatorcontrib>Ajay Kumar, Kariyappa</creatorcontrib><collection>CrossRef</collection><jtitle>Research on chemical intermediates</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dileep Kumar, Achutha</au><au>Bharath, Srinivasan</au><au>Dharmappa, Rekha N.</au><au>Naveen, Shivalingegowda</au><au>Lokanath, Neratur Krishnappagowda</au><au>Ajay Kumar, Kariyappa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis and spectroscopic and crystallographic characterisation of novel functionalized pyrazole derivatives: biological evaluation for their cytotoxic, angiogenic and antioxidant activities</atitle><jtitle>Research on chemical intermediates</jtitle><stitle>Res Chem Intermed</stitle><date>2018-09-01</date><risdate>2018</risdate><volume>44</volume><issue>9</issue><spage>5635</spage><epage>5652</epage><pages>5635-5652</pages><issn>0922-6168</issn><eissn>1568-5675</eissn><abstract>The current study presents the synthesis of functionalized pyrazoles (
18–29
) through 3 + 2 annulation reaction of ethyl 2-(arylidene)-3-oxobutanoates (
8–13
) with phenylhydrazine hydrochlorides (
14–17
) in acetic acid under reflux conditions. Structures of the synthesized new compounds were characterized by spectral and single-crystal X-ray diffraction studies. Preliminary assessment on their biological activities showed that compounds
19
,
23
and
28
have anticancer and antiangiogenic properties and compounds
20
,
24
and
26
have excellent diphenylpicrylhydrazyl (DPPH) radical scavenging activities. Detailed quantitative structure–activity relationship (QSAR) analysis provided insights into the molecular features that might have contributed towards increasing potency of inhibition. In summary, we present a study that has successfully demonstrated the synthesis of novel pyrazole analogues that display anticancer, antiangiogenic and DPPH free radical scavenging activities, making them lead molecules of choice for further development.
Graphical Abstract</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><doi>10.1007/s11164-018-3445-6</doi><tpages>18</tpages></addata></record> |
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| source | Springer Nature - Complete Springer Journals |
| subjects | Acetic acid Antiangiogenics Anticancer properties Antioxidants Cancer Catalysis Chemical reactions Chemical synthesis Chemistry Chemistry and Materials Science Crystallography Free radicals Hydrochlorides Inorganic Chemistry Organic chemistry Physical Chemistry Pyrazole Scavenging Single crystals X-ray diffraction |
| title | Design, synthesis and spectroscopic and crystallographic characterisation of novel functionalized pyrazole derivatives: biological evaluation for their cytotoxic, angiogenic and antioxidant activities |
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