Synthesis of 1H-Pyrazole-1-carboxamide Derivatives and Their Antiproliferative Activity against Melanoma Cell Line
Synthesis of a new series of 1H‐pyrazole‐1‐carboxamide derivatives is described. Their antiproliferative activity against A375 human melanoma cell line was tested and the effect of substituents on the diarylpyrazole scaffold was investigated. The pharmacological results indicated that most of the ne...
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| Veröffentlicht in: | Archiv der Pharmazie (Weinheim) 2011-03, Vol.344 (3), p.197-204 |
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| container_title | Archiv der Pharmazie (Weinheim) |
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| creator | El-Gamal, Mohammed I. Sim, Tae Bo Hong, Jun Hee Cho, Jung-Hyuck Yoo, Kyung Ho Oh, Chang-Hyun |
| description | Synthesis of a new series of 1H‐pyrazole‐1‐carboxamide derivatives is described. Their antiproliferative activity against A375 human melanoma cell line was tested and the effect of substituents on the diarylpyrazole scaffold was investigated. The pharmacological results indicated that most of the newly synthesized compounds showed moderate activity against A375, compared with sorafenib. Among all of these derivatives, compound IIe which has N‐methylpiperazinyl and phenolic moieties showed the most potent antiproliferative activity against A375 human melanoma cell line.
A new series of 3,4‐diaryl‐1H‐pyrazole‐1‐carboxamide derivatives was synthesized. Compound IIe having m‐hydroxyphenyl substituted N‐methylpiperazinyl moieties showed the most potent antiproliferative activity against A375 human melanoma cell line. |
| doi_str_mv | 10.1002/ardp.201000057 |
| format | Article |
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A new series of 3,4‐diaryl‐1H‐pyrazole‐1‐carboxamide derivatives was synthesized. Compound IIe having m‐hydroxyphenyl substituted N‐methylpiperazinyl moieties showed the most potent antiproliferative activity against A375 human melanoma cell line.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.201000057</identifier><identifier>PMID: 21384419</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>1H-Pyrazole-1-carboxamide ; 3,4‐Diarylpyrazole ; 4-Diarylpyrazole ; A375 ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antiproliferative activity ; Berries ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Derivatives ; Drug Screening Assays, Antitumor ; Humans ; Melanoma ; Melanoma - drug therapy ; Melanoma - pathology ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Structure-Activity Relationship</subject><ispartof>Archiv der Pharmazie (Weinheim), 2011-03, Vol.344 (3), p.197-204</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fardp.201000057$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fardp.201000057$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21384419$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>El-Gamal, Mohammed I.</creatorcontrib><creatorcontrib>Sim, Tae Bo</creatorcontrib><creatorcontrib>Hong, Jun Hee</creatorcontrib><creatorcontrib>Cho, Jung-Hyuck</creatorcontrib><creatorcontrib>Yoo, Kyung Ho</creatorcontrib><creatorcontrib>Oh, Chang-Hyun</creatorcontrib><title>Synthesis of 1H-Pyrazole-1-carboxamide Derivatives and Their Antiproliferative Activity against Melanoma Cell Line</title><title>Archiv der Pharmazie (Weinheim)</title><addtitle>Arch. Pharm. Pharm. Med. Chem</addtitle><description>Synthesis of a new series of 1H‐pyrazole‐1‐carboxamide derivatives is described. Their antiproliferative activity against A375 human melanoma cell line was tested and the effect of substituents on the diarylpyrazole scaffold was investigated. The pharmacological results indicated that most of the newly synthesized compounds showed moderate activity against A375, compared with sorafenib. Among all of these derivatives, compound IIe which has N‐methylpiperazinyl and phenolic moieties showed the most potent antiproliferative activity against A375 human melanoma cell line.
A new series of 3,4‐diaryl‐1H‐pyrazole‐1‐carboxamide derivatives was synthesized. Compound IIe having m‐hydroxyphenyl substituted N‐methylpiperazinyl moieties showed the most potent antiproliferative activity against A375 human melanoma cell line.</description><subject>1H-Pyrazole-1-carboxamide</subject><subject>3,4‐Diarylpyrazole</subject><subject>4-Diarylpyrazole</subject><subject>A375</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiproliferative activity</subject><subject>Berries</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Derivatives</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Melanoma</subject><subject>Melanoma - drug therapy</subject><subject>Melanoma - pathology</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkc1vEzEQxS1ERUPhyhFZ4sDJrb221_YxSqCpFEoF5eNmedez1GU_UnvTdvnrcUmbA6eZ0fze6GkeQm8YPWaUFicu-s1xQXNPqVTP0IzJghHBtHiOZpSXkpQF54foZUrXGeG0kC_QYcG4FoKZGYpfp368ghQSHhrMVuRiiu7P0AJhpHaxGu5dFzzgJcRw68ZwCwm73uPLKwgRz_sxbOLQhgbivyWe17mEccLulwt9GvEnaF0_dA4voG3xOvTwCh00rk3w-rEeoW8fP1wuVmT9-fRsMV-TwItSEe-FMVo42YDxzjdCiEoCo4aDNII64anQVQmV8mBqwzSX0pROFXVN61oafoTe7-5mhzdbSKPtQqqzC9fDsE1Wy5IppoTO5Lv_yOthG_tszjIphFaaK5Wpt4_UturA200MnYuTfXpmBswOuAstTPs9o_YhKvsQld1HZedflhf7KWvJThvSCPd7rYu_bam4kvbH-ally-XqZ_m9tAv-F7WMlqw</recordid><startdate>201103</startdate><enddate>201103</enddate><creator>El-Gamal, Mohammed I.</creator><creator>Sim, Tae Bo</creator><creator>Hong, Jun Hee</creator><creator>Cho, Jung-Hyuck</creator><creator>Yoo, Kyung Ho</creator><creator>Oh, Chang-Hyun</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>201103</creationdate><title>Synthesis of 1H-Pyrazole-1-carboxamide Derivatives and Their Antiproliferative Activity against Melanoma Cell Line</title><author>El-Gamal, Mohammed I. ; Sim, Tae Bo ; Hong, Jun Hee ; Cho, Jung-Hyuck ; Yoo, Kyung Ho ; Oh, Chang-Hyun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i3267-dd49984a5fe9dadf444b5e1093e5940a4d048b6eb7de9c91835596a72cc0cc593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>1H-Pyrazole-1-carboxamide</topic><topic>3,4‐Diarylpyrazole</topic><topic>4-Diarylpyrazole</topic><topic>A375</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antiproliferative activity</topic><topic>Berries</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Derivatives</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Melanoma</topic><topic>Melanoma - drug therapy</topic><topic>Melanoma - pathology</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>El-Gamal, Mohammed I.</creatorcontrib><creatorcontrib>Sim, Tae Bo</creatorcontrib><creatorcontrib>Hong, Jun Hee</creatorcontrib><creatorcontrib>Cho, Jung-Hyuck</creatorcontrib><creatorcontrib>Yoo, Kyung Ho</creatorcontrib><creatorcontrib>Oh, Chang-Hyun</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>El-Gamal, Mohammed I.</au><au>Sim, Tae Bo</au><au>Hong, Jun Hee</au><au>Cho, Jung-Hyuck</au><au>Yoo, Kyung Ho</au><au>Oh, Chang-Hyun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 1H-Pyrazole-1-carboxamide Derivatives and Their Antiproliferative Activity against Melanoma Cell Line</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><addtitle>Arch. Pharm. Pharm. Med. Chem</addtitle><date>2011-03</date><risdate>2011</risdate><volume>344</volume><issue>3</issue><spage>197</spage><epage>204</epage><pages>197-204</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><abstract>Synthesis of a new series of 1H‐pyrazole‐1‐carboxamide derivatives is described. Their antiproliferative activity against A375 human melanoma cell line was tested and the effect of substituents on the diarylpyrazole scaffold was investigated. The pharmacological results indicated that most of the newly synthesized compounds showed moderate activity against A375, compared with sorafenib. Among all of these derivatives, compound IIe which has N‐methylpiperazinyl and phenolic moieties showed the most potent antiproliferative activity against A375 human melanoma cell line.
A new series of 3,4‐diaryl‐1H‐pyrazole‐1‐carboxamide derivatives was synthesized. Compound IIe having m‐hydroxyphenyl substituted N‐methylpiperazinyl moieties showed the most potent antiproliferative activity against A375 human melanoma cell line.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>21384419</pmid><doi>10.1002/ardp.201000057</doi><tpages>8</tpages></addata></record> |
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| subjects | 1H-Pyrazole-1-carboxamide 3,4‐Diarylpyrazole 4-Diarylpyrazole A375 Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antiproliferative activity Berries Cell Line, Tumor Cell Proliferation - drug effects Derivatives Drug Screening Assays, Antitumor Humans Melanoma Melanoma - drug therapy Melanoma - pathology Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Structure-Activity Relationship |
| title | Synthesis of 1H-Pyrazole-1-carboxamide Derivatives and Their Antiproliferative Activity against Melanoma Cell Line |
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