Benzylidene 2-Aminoimidazolones Derivatives: Synthesis and in Vitro Evaluation of Anti-tumor Carcinoma Activity
A series of benzylidene 2-aminoimidazolones derivatives were synthesized. Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay ag...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2013/10/01, Vol.61(10), pp.1081-1084 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | Ling, Yong Wang, Zhi-Qiang Xiao, You-An Zhu, Chenyu Shen, Liucen Wang, Xue-Min Hui, Yi Wang, Xin-Yang |
| description | A series of benzylidene 2-aminoimidazolones derivatives were synthesized. Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against five human cancer cell lines in vitro. Compound 2b exhibited the strongest antitumor activities with IC50 values ranging from 12.87–17.10 µ M which were nearly 1–3.5 fold less than that of 5-FU (IC50=18.39–56.12 µ M ) in vitro. Furthermore, compound 2b could induce SMMC-7721 cell apoptosis in a dose-dependent manner. Therefore, our novel findings may provide a new framework for the design of new benzylidene 2-aminoimidazolones derivatives for the treatment of cancer. |
| doi_str_mv | 10.1248/cpb.c13-00340 |
| format | Article |
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Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against five human cancer cell lines in vitro. Compound 2b exhibited the strongest antitumor activities with IC50 values ranging from 12.87–17.10 µ M which were nearly 1–3.5 fold less than that of 5-FU (IC50=18.39–56.12 µ M ) in vitro. Furthermore, compound 2b could induce SMMC-7721 cell apoptosis in a dose-dependent manner. Therefore, our novel findings may provide a new framework for the design of new benzylidene 2-aminoimidazolones derivatives for the treatment of cancer.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c13-00340</identifier><identifier>PMID: 24088700</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>2-aminoimidazolone derivative ; anti-tumor agent ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - toxicity ; Apoptosis - drug effects ; Benzylidene Compounds - chemistry ; cell apoptosis ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Drug Screening Assays, Antitumor ; Hep G2 Cells ; Humans ; Imidazoles - chemical synthesis ; Imidazoles - chemistry ; Imidazoles - toxicity ; inhibitory activity ; Structure-Activity Relationship ; synthesis</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2013/10/01, Vol.61(10), pp.1081-1084</ispartof><rights>2013 The Pharmaceutical Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c540t-9196b910fc5edd2358f96558d470ba048742f62cf1ab4f6af70aab67a2d97b973</citedby><cites>FETCH-LOGICAL-c540t-9196b910fc5edd2358f96558d470ba048742f62cf1ab4f6af70aab67a2d97b973</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24088700$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ling, Yong</creatorcontrib><creatorcontrib>Wang, Zhi-Qiang</creatorcontrib><creatorcontrib>Xiao, You-An</creatorcontrib><creatorcontrib>Zhu, Chenyu</creatorcontrib><creatorcontrib>Shen, Liucen</creatorcontrib><creatorcontrib>Wang, Xue-Min</creatorcontrib><creatorcontrib>Hui, Yi</creatorcontrib><creatorcontrib>Wang, Xin-Yang</creatorcontrib><title>Benzylidene 2-Aminoimidazolones Derivatives: Synthesis and in Vitro Evaluation of Anti-tumor Carcinoma Activity</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A series of benzylidene 2-aminoimidazolones derivatives were synthesized. Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against five human cancer cell lines in vitro. Compound 2b exhibited the strongest antitumor activities with IC50 values ranging from 12.87–17.10 µ M which were nearly 1–3.5 fold less than that of 5-FU (IC50=18.39–56.12 µ M ) in vitro. Furthermore, compound 2b could induce SMMC-7721 cell apoptosis in a dose-dependent manner. Therefore, our novel findings may provide a new framework for the design of new benzylidene 2-aminoimidazolones derivatives for the treatment of cancer.</description><subject>2-aminoimidazolone derivative</subject><subject>anti-tumor agent</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - toxicity</subject><subject>Apoptosis - drug effects</subject><subject>Benzylidene Compounds - chemistry</subject><subject>cell apoptosis</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Hep G2 Cells</subject><subject>Humans</subject><subject>Imidazoles - chemical synthesis</subject><subject>Imidazoles - chemistry</subject><subject>Imidazoles - toxicity</subject><subject>inhibitory activity</subject><subject>Structure-Activity Relationship</subject><subject>synthesis</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkDtvFDEURi1ERJZASYtc0jhcP8YzQ7dsAkSKlCJAa3k8NnE0Yy-2Z6XNr4-TDUtzv-IeneIg9IHCOWWi-2y2w7mhnABwAa_QinLRkoYx_hqtAKAnjEt-it7mfA_AGmj5G3TKBHRdC7BC8asND_vJjzZYzMh69iH62Y_6IU4x2IwvbPI7XfzO5i_4dh_Knc0-Yx1G7AP-7UuK-HKnp6UyMeDo8DoUT8oyx4Q3OpkqnDVem6rwZf8OnTg9Zfv-Zc_Qr2-XPzc_yPXN96vN-pqYRkAhPe3l0FNwprHjyHjTuV42TTeKFgYNomsFc5IZR_UgnNSuBa0H2Wo29u3Qt_wMfTp4tyn-XWwuavbZ2GnSwcYlKypE7SUlkxUlB9SkmHOyTm2Tn3XaKwrqqbGqjVVtrJ4bV_7ji3oZZjse6X9RK3BxAO5z0X_sEdCpeDPZZ52kT_Z6j97_7zudlA38EXmwkS4</recordid><startdate>2013</startdate><enddate>2013</enddate><creator>Ling, Yong</creator><creator>Wang, Zhi-Qiang</creator><creator>Xiao, You-An</creator><creator>Zhu, Chenyu</creator><creator>Shen, Liucen</creator><creator>Wang, Xue-Min</creator><creator>Hui, Yi</creator><creator>Wang, Xin-Yang</creator><general>The Pharmaceutical Society of Japan</general><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></search><sort><creationdate>2013</creationdate><title>Benzylidene 2-Aminoimidazolones Derivatives: Synthesis and in Vitro Evaluation of Anti-tumor Carcinoma Activity</title><author>Ling, Yong ; Wang, Zhi-Qiang ; Xiao, You-An ; Zhu, Chenyu ; Shen, Liucen ; Wang, Xue-Min ; Hui, Yi ; Wang, Xin-Yang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c540t-9196b910fc5edd2358f96558d470ba048742f62cf1ab4f6af70aab67a2d97b973</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>2-aminoimidazolone derivative</topic><topic>anti-tumor agent</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - toxicity</topic><topic>Apoptosis - drug effects</topic><topic>Benzylidene Compounds - chemistry</topic><topic>cell apoptosis</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Hep G2 Cells</topic><topic>Humans</topic><topic>Imidazoles - chemical synthesis</topic><topic>Imidazoles - chemistry</topic><topic>Imidazoles - toxicity</topic><topic>inhibitory activity</topic><topic>Structure-Activity Relationship</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ling, Yong</creatorcontrib><creatorcontrib>Wang, Zhi-Qiang</creatorcontrib><creatorcontrib>Xiao, You-An</creatorcontrib><creatorcontrib>Zhu, Chenyu</creatorcontrib><creatorcontrib>Shen, Liucen</creatorcontrib><creatorcontrib>Wang, Xue-Min</creatorcontrib><creatorcontrib>Hui, Yi</creatorcontrib><creatorcontrib>Wang, Xin-Yang</creatorcontrib><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><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ling, Yong</au><au>Wang, Zhi-Qiang</au><au>Xiao, You-An</au><au>Zhu, Chenyu</au><au>Shen, Liucen</au><au>Wang, Xue-Min</au><au>Hui, Yi</au><au>Wang, Xin-Yang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Benzylidene 2-Aminoimidazolones Derivatives: Synthesis and in Vitro Evaluation of Anti-tumor Carcinoma Activity</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2013</date><risdate>2013</risdate><volume>61</volume><issue>10</issue><spage>1081</spage><epage>1084</epage><pages>1081-1084</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A series of benzylidene 2-aminoimidazolones derivatives were synthesized. Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against five human cancer cell lines in vitro. Compound 2b exhibited the strongest antitumor activities with IC50 values ranging from 12.87–17.10 µ M which were nearly 1–3.5 fold less than that of 5-FU (IC50=18.39–56.12 µ M ) in vitro. Furthermore, compound 2b could induce SMMC-7721 cell apoptosis in a dose-dependent manner. 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| subjects | 2-aminoimidazolone derivative anti-tumor agent Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - toxicity Apoptosis - drug effects Benzylidene Compounds - chemistry cell apoptosis Cell Line, Tumor Cell Proliferation - drug effects Drug Screening Assays, Antitumor Hep G2 Cells Humans Imidazoles - chemical synthesis Imidazoles - chemistry Imidazoles - toxicity inhibitory activity Structure-Activity Relationship synthesis |
| title | Benzylidene 2-Aminoimidazolones Derivatives: Synthesis and in Vitro Evaluation of Anti-tumor Carcinoma Activity |
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