Synthesis of New 4‑Thiazolidinone‑, Pyrazoline‑, and Isatin-Based Conjugates with Promising Antitumor Activity
The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1–23 and 3-(3,5-diarylpyrazol-1-yl)-2,3-dihydro-1H-indol-2-ones 24–39 are performed. In vitro anticancer activity of the synthesized...
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| Veröffentlicht in: | Journal of medicinal chemistry 2012-10, Vol.55 (20), p.8630-8641 |
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| creator | Havrylyuk, Dmytro Zimenkovsky, Borys Vasylenko, Olexandr Gzella, Andrzej Lesyk, Roman |
| description | The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1–23 and 3-(3,5-diarylpyrazol-1-yl)-2,3-dihydro-1H-indol-2-ones 24–39 are performed. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute. Most of them displayed anticancer activity on leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers cell lines. The structure–activity relationship is discussed. The most effective anticancer compound 10 was found to be active with mean GI50 and TGI values of 0.071 μM and 0.76 μM, respectively. It demonstrated the highest antiproliferative influence on the non-small-cell lung cancer cell line HOP-92 (GI50 < 0.01 μM), colon cancer line HCT-116 (GI50 = 0.018 μM), CNS cancer cell line SNB-75 (GI50 = 0.0159 μM), ovarian cancer cell line NCI/ADR-RES (GI50 = 0.0169 μM), and renal cancer cell line RXF 393 (GI50 = 0.0197 μM). |
| doi_str_mv | 10.1021/jm300789g |
| format | Article |
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In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute. Most of them displayed anticancer activity on leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers cell lines. The structure–activity relationship is discussed. The most effective anticancer compound 10 was found to be active with mean GI50 and TGI values of 0.071 μM and 0.76 μM, respectively. It demonstrated the highest antiproliferative influence on the non-small-cell lung cancer cell line HOP-92 (GI50 < 0.01 μM), colon cancer line HCT-116 (GI50 = 0.018 μM), CNS cancer cell line SNB-75 (GI50 = 0.0159 μM), ovarian cancer cell line NCI/ADR-RES (GI50 = 0.0169 μM), and renal cancer cell line RXF 393 (GI50 = 0.0197 μM).</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm300789g</identifier><identifier>PMID: 22992049</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; Humans ; Isatin - analogs & derivatives ; Isatin - chemical synthesis ; Isatin - chemistry ; Isatin - pharmacology ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Structure-Activity Relationship ; Thiazolidines - chemical synthesis ; Thiazolidines - chemistry ; Thiazolidines - pharmacology</subject><ispartof>Journal of medicinal chemistry, 2012-10, Vol.55 (20), p.8630-8641</ispartof><rights>Copyright © 2012 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-7e19e07d7a6e76606627cecdffec091508bdd103a00b1f3b59eb971a9035f7a93</citedby><cites>FETCH-LOGICAL-a315t-7e19e07d7a6e76606627cecdffec091508bdd103a00b1f3b59eb971a9035f7a93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm300789g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm300789g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22992049$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Havrylyuk, Dmytro</creatorcontrib><creatorcontrib>Zimenkovsky, Borys</creatorcontrib><creatorcontrib>Vasylenko, Olexandr</creatorcontrib><creatorcontrib>Gzella, Andrzej</creatorcontrib><creatorcontrib>Lesyk, Roman</creatorcontrib><title>Synthesis of New 4‑Thiazolidinone‑, Pyrazoline‑, and Isatin-Based Conjugates with Promising Antitumor Activity</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1–23 and 3-(3,5-diarylpyrazol-1-yl)-2,3-dihydro-1H-indol-2-ones 24–39 are performed. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute. Most of them displayed anticancer activity on leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers cell lines. The structure–activity relationship is discussed. The most effective anticancer compound 10 was found to be active with mean GI50 and TGI values of 0.071 μM and 0.76 μM, respectively. It demonstrated the highest antiproliferative influence on the non-small-cell lung cancer cell line HOP-92 (GI50 < 0.01 μM), colon cancer line HCT-116 (GI50 = 0.018 μM), CNS cancer cell line SNB-75 (GI50 = 0.0159 μM), ovarian cancer cell line NCI/ADR-RES (GI50 = 0.0169 μM), and renal cancer cell line RXF 393 (GI50 = 0.0197 μM).</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Isatin - analogs & derivatives</subject><subject>Isatin - chemical synthesis</subject><subject>Isatin - chemistry</subject><subject>Isatin - pharmacology</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Thiazolidines - chemical synthesis</subject><subject>Thiazolidines - chemistry</subject><subject>Thiazolidines - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAQRS0EgvJY8APIGySQCIztJq6XpeIlIUAC1pGTTFpXjQ22AyorfoFf5EsItLBiNZqro6uZQ8gug2MGnJ1MGwEgB2q8Qnos5ZD0B9BfJT0AzhOecbFBNkOYAoBgXKyTDc6V4tBXPRLv5zZOMJhAXU1v8JX2P98_HiZGv7mZqYx1FrvgiN7N_U-0XLWt6FXQ0djkVAes6MjZaTvWEQN9NXFC77xrTDB2TIc2mtg2ztNhGc2LifNtslbrWcCd5dwij-dnD6PL5Pr24mo0vE60YGlMJDKFICupM5RZBlnGZYllVddYgmIpDIqqYiA0QMFqUaQKCyWZViDSWmoltsjBovfJu-cWQ8y7k0qczbRF14acMZamXEqedujhAi29C8FjnT9502g_zxnk35LzP8kdu7esbYsGqz_y12oH7C8AXYZ86lpvuy__KfoC0iiG9A</recordid><startdate>20121025</startdate><enddate>20121025</enddate><creator>Havrylyuk, Dmytro</creator><creator>Zimenkovsky, Borys</creator><creator>Vasylenko, Olexandr</creator><creator>Gzella, Andrzej</creator><creator>Lesyk, Roman</creator><general>American Chemical Society</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>20121025</creationdate><title>Synthesis of New 4‑Thiazolidinone‑, Pyrazoline‑, and Isatin-Based Conjugates with Promising Antitumor Activity</title><author>Havrylyuk, Dmytro ; Zimenkovsky, Borys ; Vasylenko, Olexandr ; Gzella, Andrzej ; Lesyk, Roman</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-7e19e07d7a6e76606627cecdffec091508bdd103a00b1f3b59eb971a9035f7a93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Isatin - analogs & derivatives</topic><topic>Isatin - chemical synthesis</topic><topic>Isatin - chemistry</topic><topic>Isatin - pharmacology</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Thiazolidines - chemical synthesis</topic><topic>Thiazolidines - chemistry</topic><topic>Thiazolidines - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Havrylyuk, Dmytro</creatorcontrib><creatorcontrib>Zimenkovsky, Borys</creatorcontrib><creatorcontrib>Vasylenko, Olexandr</creatorcontrib><creatorcontrib>Gzella, Andrzej</creatorcontrib><creatorcontrib>Lesyk, Roman</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>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Havrylyuk, Dmytro</au><au>Zimenkovsky, Borys</au><au>Vasylenko, Olexandr</au><au>Gzella, Andrzej</au><au>Lesyk, Roman</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of New 4‑Thiazolidinone‑, Pyrazoline‑, and Isatin-Based Conjugates with Promising Antitumor Activity</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2012-10-25</date><risdate>2012</risdate><volume>55</volume><issue>20</issue><spage>8630</spage><epage>8641</epage><pages>8630-8641</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1–23 and 3-(3,5-diarylpyrazol-1-yl)-2,3-dihydro-1H-indol-2-ones 24–39 are performed. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute. Most of them displayed anticancer activity on leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers cell lines. The structure–activity relationship is discussed. The most effective anticancer compound 10 was found to be active with mean GI50 and TGI values of 0.071 μM and 0.76 μM, respectively. It demonstrated the highest antiproliferative influence on the non-small-cell lung cancer cell line HOP-92 (GI50 < 0.01 μM), colon cancer line HCT-116 (GI50 = 0.018 μM), CNS cancer cell line SNB-75 (GI50 = 0.0159 μM), ovarian cancer cell line NCI/ADR-RES (GI50 = 0.0169 μM), and renal cancer cell line RXF 393 (GI50 = 0.0197 μM).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>22992049</pmid><doi>10.1021/jm300789g</doi><tpages>12</tpages></addata></record> |
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| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor Drug Screening Assays, Antitumor Humans Isatin - analogs & derivatives Isatin - chemical synthesis Isatin - chemistry Isatin - pharmacology Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Structure-Activity Relationship Thiazolidines - chemical synthesis Thiazolidines - chemistry Thiazolidines - pharmacology |
| title | Synthesis of New 4‑Thiazolidinone‑, Pyrazoline‑, and Isatin-Based Conjugates with Promising Antitumor Activity |
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