Coumarin-carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking
A series of novel pyrazoline scaffolds from coumarin-carbazole chalcones were synthesized. We explored various acetyl, amide, and phenyl substituents at the N -1 position of the pyrazoline core. The synthesized compounds were characterized by FTIR, 1 H-NMR, 13 C-NMR, DEPT, and mass spectroscopic tec...
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| Veröffentlicht in: | RSC advances 2021-08, Vol.11 (44), p.27627-27644 |
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| creator | Patel, Mrugesh Pandey, Nilesh Timaniya, Jignesh Parikh, Paranjay Chauhan, Alex Jain, Neeraj Patel, Kaushal |
| description | A series of novel pyrazoline scaffolds from coumarin-carbazole chalcones were synthesized. We explored various acetyl, amide, and phenyl substituents at the
N
-1 position of the pyrazoline core. The synthesized compounds were characterized by FTIR,
1
H-NMR,
13
C-NMR, DEPT, and mass spectroscopic techniques. The
in vitro
cytotoxicity study of all the synthesized compounds was evaluated against HeLa, NCI-H520 and NRK-52E cell lines. Compounds
4a
and
7b
became the most active compounds and exhibited their potential to arrest the cell cycle progression and induce apoptosis in both the cell lines. In addition, molecular docking studies revealed a higher binding affinity of both the molecules with CDK2 protein. Based on the obtained results, a comprehensive analysis is warranted to establish the role of compounds
4a
and
7b
as promising cancer therapeutic agents.
Coumarin-carbazole based functionalised pyrazolines: synthesis, anticancer activity and molecular docking. |
| doi_str_mv | 10.1039/d1ra03970a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_journals_2562161669</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2562161669</sourcerecordid><originalsourceid>FETCH-LOGICAL-c358t-e2701acc38b7629152f4e57fa5838bf2861aa85ed709a54b8cb6db67272d86993</originalsourceid><addsrcrecordid>eNpdks9LHDEUx4NYVNSLd2XAi4hjk8zkx_RQWLbVCoJQ2nN4k8nsRmeTNZkRdk_905t1df2RHF6S74dv3ssLQkcEXxJcVF8bEiBFgWEL7VFc8pxiXm2_W--iwxjvcRqcEcrJDtotWCkxl3gP_Rv7YQbBulxDqGHpO5PVEE2TtYPTvfUOOrtM2_kirFTrTPyWxYXrpybaeJHpKQTQvQl2CSv8IgPXWw1Om5BZ92RibyfPShKabJYu0EMHIWu8frBucoC-tNBFc_gS99Hfq59_xr_y27vrm_HoNtcFk31uqMAEtC5kLTitCKNtaZhogcl01FLJCYBkphG4AlbWUte8qbmggjaSV1Wxj76vfedDPTONNq4P0Kl5sKn8hfJg1UfF2ama-CdV4UJILJPB2YtB8I9DKkvNbNSm68AZP0RFOeOiTJMm9PQTeu-HkF4yUYxTwgnnq4zO15QOPsZg2k0yBKtVb9UP8nv03NtRgk_ep79BXzuZgOM1EKLeqG-fo_gP582sdA</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2562161669</pqid></control><display><type>article</type><title>Coumarin-carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking</title><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>PubMed Central</source><source>PubMed Central Open Access</source><creator>Patel, Mrugesh ; Pandey, Nilesh ; Timaniya, Jignesh ; Parikh, Paranjay ; Chauhan, Alex ; Jain, Neeraj ; Patel, Kaushal</creator><creatorcontrib>Patel, Mrugesh ; Pandey, Nilesh ; Timaniya, Jignesh ; Parikh, Paranjay ; Chauhan, Alex ; Jain, Neeraj ; Patel, Kaushal</creatorcontrib><description>A series of novel pyrazoline scaffolds from coumarin-carbazole chalcones were synthesized. We explored various acetyl, amide, and phenyl substituents at the
N
-1 position of the pyrazoline core. The synthesized compounds were characterized by FTIR,
1
H-NMR,
13
C-NMR, DEPT, and mass spectroscopic techniques. The
in vitro
cytotoxicity study of all the synthesized compounds was evaluated against HeLa, NCI-H520 and NRK-52E cell lines. Compounds
4a
and
7b
became the most active compounds and exhibited their potential to arrest the cell cycle progression and induce apoptosis in both the cell lines. In addition, molecular docking studies revealed a higher binding affinity of both the molecules with CDK2 protein. Based on the obtained results, a comprehensive analysis is warranted to establish the role of compounds
4a
and
7b
as promising cancer therapeutic agents.
Coumarin-carbazole based functionalised pyrazolines: synthesis, anticancer activity and molecular docking.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d1ra03970a</identifier><identifier>PMID: 35480680</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Apoptosis ; Carbazoles ; Cell cycle ; Chemical compounds ; Chemical synthesis ; Chemistry ; Coumarin ; Molecular docking ; NMR ; Nuclear magnetic resonance ; Pharmacology ; Toxicity</subject><ispartof>RSC advances, 2021-08, Vol.11 (44), p.27627-27644</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2021</rights><rights>This journal is © The Royal Society of Chemistry 2021 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c358t-e2701acc38b7629152f4e57fa5838bf2861aa85ed709a54b8cb6db67272d86993</citedby><cites>FETCH-LOGICAL-c358t-e2701acc38b7629152f4e57fa5838bf2861aa85ed709a54b8cb6db67272d86993</cites><orcidid>0000-0002-1415-3652 ; 0000-0002-8404-3504</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9037808/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9037808/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35480680$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Patel, Mrugesh</creatorcontrib><creatorcontrib>Pandey, Nilesh</creatorcontrib><creatorcontrib>Timaniya, Jignesh</creatorcontrib><creatorcontrib>Parikh, Paranjay</creatorcontrib><creatorcontrib>Chauhan, Alex</creatorcontrib><creatorcontrib>Jain, Neeraj</creatorcontrib><creatorcontrib>Patel, Kaushal</creatorcontrib><title>Coumarin-carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>A series of novel pyrazoline scaffolds from coumarin-carbazole chalcones were synthesized. We explored various acetyl, amide, and phenyl substituents at the
N
-1 position of the pyrazoline core. The synthesized compounds were characterized by FTIR,
1
H-NMR,
13
C-NMR, DEPT, and mass spectroscopic techniques. The
in vitro
cytotoxicity study of all the synthesized compounds was evaluated against HeLa, NCI-H520 and NRK-52E cell lines. Compounds
4a
and
7b
became the most active compounds and exhibited their potential to arrest the cell cycle progression and induce apoptosis in both the cell lines. In addition, molecular docking studies revealed a higher binding affinity of both the molecules with CDK2 protein. Based on the obtained results, a comprehensive analysis is warranted to establish the role of compounds
4a
and
7b
as promising cancer therapeutic agents.
Coumarin-carbazole based functionalised pyrazolines: synthesis, anticancer activity and molecular docking.</description><subject>Apoptosis</subject><subject>Carbazoles</subject><subject>Cell cycle</subject><subject>Chemical compounds</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Coumarin</subject><subject>Molecular docking</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Pharmacology</subject><subject>Toxicity</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdks9LHDEUx4NYVNSLd2XAi4hjk8zkx_RQWLbVCoJQ2nN4k8nsRmeTNZkRdk_905t1df2RHF6S74dv3ssLQkcEXxJcVF8bEiBFgWEL7VFc8pxiXm2_W--iwxjvcRqcEcrJDtotWCkxl3gP_Rv7YQbBulxDqGHpO5PVEE2TtYPTvfUOOrtM2_kirFTrTPyWxYXrpybaeJHpKQTQvQl2CSv8IgPXWw1Om5BZ92RibyfPShKabJYu0EMHIWu8frBucoC-tNBFc_gS99Hfq59_xr_y27vrm_HoNtcFk31uqMAEtC5kLTitCKNtaZhogcl01FLJCYBkphG4AlbWUte8qbmggjaSV1Wxj76vfedDPTONNq4P0Kl5sKn8hfJg1UfF2ama-CdV4UJILJPB2YtB8I9DKkvNbNSm68AZP0RFOeOiTJMm9PQTeu-HkF4yUYxTwgnnq4zO15QOPsZg2k0yBKtVb9UP8nv03NtRgk_ep79BXzuZgOM1EKLeqG-fo_gP582sdA</recordid><startdate>20210809</startdate><enddate>20210809</enddate><creator>Patel, Mrugesh</creator><creator>Pandey, Nilesh</creator><creator>Timaniya, Jignesh</creator><creator>Parikh, Paranjay</creator><creator>Chauhan, Alex</creator><creator>Jain, Neeraj</creator><creator>Patel, Kaushal</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-1415-3652</orcidid><orcidid>https://orcid.org/0000-0002-8404-3504</orcidid></search><sort><creationdate>20210809</creationdate><title>Coumarin-carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking</title><author>Patel, Mrugesh ; Pandey, Nilesh ; Timaniya, Jignesh ; Parikh, Paranjay ; Chauhan, Alex ; Jain, Neeraj ; Patel, Kaushal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c358t-e2701acc38b7629152f4e57fa5838bf2861aa85ed709a54b8cb6db67272d86993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Apoptosis</topic><topic>Carbazoles</topic><topic>Cell cycle</topic><topic>Chemical compounds</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Coumarin</topic><topic>Molecular docking</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Pharmacology</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Patel, Mrugesh</creatorcontrib><creatorcontrib>Pandey, Nilesh</creatorcontrib><creatorcontrib>Timaniya, Jignesh</creatorcontrib><creatorcontrib>Parikh, Paranjay</creatorcontrib><creatorcontrib>Chauhan, Alex</creatorcontrib><creatorcontrib>Jain, Neeraj</creatorcontrib><creatorcontrib>Patel, Kaushal</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Patel, Mrugesh</au><au>Pandey, Nilesh</au><au>Timaniya, Jignesh</au><au>Parikh, Paranjay</au><au>Chauhan, Alex</au><au>Jain, Neeraj</au><au>Patel, Kaushal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Coumarin-carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2021-08-09</date><risdate>2021</risdate><volume>11</volume><issue>44</issue><spage>27627</spage><epage>27644</epage><pages>27627-27644</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>A series of novel pyrazoline scaffolds from coumarin-carbazole chalcones were synthesized. We explored various acetyl, amide, and phenyl substituents at the
N
-1 position of the pyrazoline core. The synthesized compounds were characterized by FTIR,
1
H-NMR,
13
C-NMR, DEPT, and mass spectroscopic techniques. The
in vitro
cytotoxicity study of all the synthesized compounds was evaluated against HeLa, NCI-H520 and NRK-52E cell lines. Compounds
4a
and
7b
became the most active compounds and exhibited their potential to arrest the cell cycle progression and induce apoptosis in both the cell lines. In addition, molecular docking studies revealed a higher binding affinity of both the molecules with CDK2 protein. Based on the obtained results, a comprehensive analysis is warranted to establish the role of compounds
4a
and
7b
as promising cancer therapeutic agents.
Coumarin-carbazole based functionalised pyrazolines: synthesis, anticancer activity and molecular docking.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35480680</pmid><doi>10.1039/d1ra03970a</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0002-1415-3652</orcidid><orcidid>https://orcid.org/0000-0002-8404-3504</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Apoptosis Carbazoles Cell cycle Chemical compounds Chemical synthesis Chemistry Coumarin Molecular docking NMR Nuclear magnetic resonance Pharmacology Toxicity |
| title | Coumarin-carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking |
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