Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents
A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1–C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibito...
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| creator | Wang, Hai-Hong Qiu, Ke-Ming Cui, Hong-En Yang, Yu-Shun Yin-Luo Xing, Man Qiu, Xiao-Yang Bai, Li-Fei Zhu, Hai-Liang |
| description | A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1–C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC50=0.18μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC50 value of 0.09 and 0.12μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.
A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1–C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC50=0.18μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC50 value of 0.09 and 0.12μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent. |
| doi_str_mv | 10.1016/j.bmc.2012.11.020 |
| format | Article |
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A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1–C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC50=0.18μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC50 value of 0.09 and 0.12μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2012.11.020</identifier><identifier>PMID: 23245802</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - toxicity ; Antitumor agents ; Benzodioxole ; Benzodioxoles - chemistry ; Binding Sites ; Cell Line, Tumor ; Cell Proliferation - drug effects ; chemistry ; HER-2 ; Humans ; inhibitory concentration 50 ; MCF-7 Cells ; Molecular Docking Simulation ; Protein Kinase Inhibitors - chemical synthesis ; Protein Kinase Inhibitors - chemistry ; Protein Kinase Inhibitors - toxicity ; Protein Structure, Tertiary ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - toxicity ; Pyrazoline ; Receptor, ErbB-2 - antagonists & inhibitors ; Receptor, ErbB-2 - metabolism ; Structure-Activity Relationship ; Thiazole ; Thiazoles - chemistry</subject><ispartof>Bioorganic & medicinal chemistry, 2013-01, Vol.21 (2), p.448-455</ispartof><rights>2012 Elsevier Ltd</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c476t-b77a9a6fd4a79b95a84a8d7d39073533bfeffb9a357dbd32345dd7d43f5bc7fd3</citedby><cites>FETCH-LOGICAL-c476t-b77a9a6fd4a79b95a84a8d7d39073533bfeffb9a357dbd32345dd7d43f5bc7fd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089612009042$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23245802$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Hai-Hong</creatorcontrib><creatorcontrib>Qiu, Ke-Ming</creatorcontrib><creatorcontrib>Cui, Hong-En</creatorcontrib><creatorcontrib>Yang, Yu-Shun</creatorcontrib><creatorcontrib>Yin-Luo</creatorcontrib><creatorcontrib>Xing, Man</creatorcontrib><creatorcontrib>Qiu, Xiao-Yang</creatorcontrib><creatorcontrib>Bai, Li-Fei</creatorcontrib><creatorcontrib>Zhu, Hai-Liang</creatorcontrib><title>Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1–C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC50=0.18μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC50 value of 0.09 and 0.12μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.
A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1–C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC50=0.18μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC50 value of 0.09 and 0.12μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.</description><subject>antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - toxicity</subject><subject>Antitumor agents</subject><subject>Benzodioxole</subject><subject>Benzodioxoles - chemistry</subject><subject>Binding Sites</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>chemistry</subject><subject>HER-2</subject><subject>Humans</subject><subject>inhibitory concentration 50</subject><subject>MCF-7 Cells</subject><subject>Molecular Docking Simulation</subject><subject>Protein Kinase Inhibitors - chemical synthesis</subject><subject>Protein Kinase Inhibitors - chemistry</subject><subject>Protein Kinase Inhibitors - toxicity</subject><subject>Protein Structure, Tertiary</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - toxicity</subject><subject>Pyrazoline</subject><subject>Receptor, ErbB-2 - antagonists & inhibitors</subject><subject>Receptor, ErbB-2 - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Thiazole</subject><subject>Thiazoles - chemistry</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1u1DAUhS0EosPAA7ABL1mQYMdJHItVVfEnVWJRurZu_DP1kNiD7YyYPgDPjaMpLGFly_7uuUfnIPSSkpoS2r_b1-Os6obQpqa0Jg15hDa07duKMUEfow0R_VCRQfQX6FlKe0JI0wr6FF00rGm7gTQb9Ovm5POdSS69xXOYjFomiFgH9d35HQavsTnCtEB2weNgcb5zcB-m01QdTnG9OW-wNtEdC3I0CavgMzi_To_G3wftws-iiyHhQ8jGZwdT0c1OgVcmYtiVt_QcPbEwJfPi4dyi248fvl19rq6_fvpydXldqZb3uRo5BwG91S1wMYoOhhYGzTUThLOOsdEaa0cBrON61KxhbafLd8tsNypuNduiN2fdQww_FpOynF1SZprAm7AkSTtCuGCE9_9HG854ybns3SJ6RlUMKUVj5SG6GeJJUiLXpuRelqbk2pSkVJamysyrB_llnI3-O_GnmgK8PgMWgoRddEne3hSF4pBSwtvV4fszYUpiR2eiTMqZkqp20agsdXD_MPAbwnyxFQ</recordid><startdate>20130115</startdate><enddate>20130115</enddate><creator>Wang, Hai-Hong</creator><creator>Qiu, Ke-Ming</creator><creator>Cui, Hong-En</creator><creator>Yang, Yu-Shun</creator><creator>Yin-Luo</creator><creator>Xing, Man</creator><creator>Qiu, Xiao-Yang</creator><creator>Bai, Li-Fei</creator><creator>Zhu, Hai-Liang</creator><general>Elsevier Ltd</general><scope>FBQ</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20130115</creationdate><title>Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents</title><author>Wang, Hai-Hong ; Qiu, Ke-Ming ; Cui, Hong-En ; Yang, Yu-Shun ; Yin-Luo ; Xing, Man ; Qiu, Xiao-Yang ; Bai, Li-Fei ; Zhu, Hai-Liang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c476t-b77a9a6fd4a79b95a84a8d7d39073533bfeffb9a357dbd32345dd7d43f5bc7fd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - toxicity</topic><topic>Antitumor agents</topic><topic>Benzodioxole</topic><topic>Benzodioxoles - chemistry</topic><topic>Binding Sites</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>chemistry</topic><topic>HER-2</topic><topic>Humans</topic><topic>inhibitory concentration 50</topic><topic>MCF-7 Cells</topic><topic>Molecular Docking Simulation</topic><topic>Protein Kinase Inhibitors - chemical synthesis</topic><topic>Protein Kinase Inhibitors - chemistry</topic><topic>Protein Kinase Inhibitors - toxicity</topic><topic>Protein Structure, Tertiary</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - toxicity</topic><topic>Pyrazoline</topic><topic>Receptor, ErbB-2 - antagonists & inhibitors</topic><topic>Receptor, ErbB-2 - metabolism</topic><topic>Structure-Activity Relationship</topic><topic>Thiazole</topic><topic>Thiazoles - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Hai-Hong</creatorcontrib><creatorcontrib>Qiu, Ke-Ming</creatorcontrib><creatorcontrib>Cui, Hong-En</creatorcontrib><creatorcontrib>Yang, Yu-Shun</creatorcontrib><creatorcontrib>Yin-Luo</creatorcontrib><creatorcontrib>Xing, Man</creatorcontrib><creatorcontrib>Qiu, Xiao-Yang</creatorcontrib><creatorcontrib>Bai, Li-Fei</creatorcontrib><creatorcontrib>Zhu, Hai-Liang</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Hai-Hong</au><au>Qiu, Ke-Ming</au><au>Cui, Hong-En</au><au>Yang, Yu-Shun</au><au>Yin-Luo</au><au>Xing, Man</au><au>Qiu, Xiao-Yang</au><au>Bai, Li-Fei</au><au>Zhu, Hai-Liang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2013-01-15</date><risdate>2013</risdate><volume>21</volume><issue>2</issue><spage>448</spage><epage>455</epage><pages>448-455</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1–C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC50=0.18μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC50 value of 0.09 and 0.12μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.
A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1–C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC50=0.18μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC50 value of 0.09 and 0.12μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>23245802</pmid><doi>10.1016/j.bmc.2012.11.020</doi><tpages>8</tpages></addata></record> |
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| subjects | antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - toxicity Antitumor agents Benzodioxole Benzodioxoles - chemistry Binding Sites Cell Line, Tumor Cell Proliferation - drug effects chemistry HER-2 Humans inhibitory concentration 50 MCF-7 Cells Molecular Docking Simulation Protein Kinase Inhibitors - chemical synthesis Protein Kinase Inhibitors - chemistry Protein Kinase Inhibitors - toxicity Protein Structure, Tertiary Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - toxicity Pyrazoline Receptor, ErbB-2 - antagonists & inhibitors Receptor, ErbB-2 - metabolism Structure-Activity Relationship Thiazole Thiazoles - chemistry |
| title | Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents |
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