Synthesis and In-Vitro Antitumor Activities of Some Mannich Bases of 9-Alkyl-1,2,3,4-tetrahydrocarbazole-1-ones
A novel series of 2‐substituted aminomethyl‐9‐alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones 5a–q was synthesized via aminomethylation of 9‐alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones 4a–e with hydrochlorides of the respective amines 6a–m. The structures of these newly synthesized compounds were characterize...
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| Veröffentlicht in: | Archiv der Pharmazie (Weinheim) 2009-03, Vol.342 (3), p.165-172 |
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| container_title | Archiv der Pharmazie (Weinheim) |
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| creator | Chen, Jing Lou, Jianshu Liu, Tao Wu, Ru Dong, Xiaowu He, Qiaojun Yang, Bo Hu, Yongzhou |
| description | A novel series of 2‐substituted aminomethyl‐9‐alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones 5a–q was synthesized via aminomethylation of 9‐alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones 4a–e with hydrochlorides of the respective amines 6a–m. The structures of these newly synthesized compounds were characterized by 1H‐NMR, MS, and elemental analysis. All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines including human non‐small lung cancer cells (A549), human gastric adenocarcinoma (SGC), human colon cancer cell (HCT116), human myeoloid leukemia cells (K562), and one multi‐drug resistant subline (KB‐VCR). Most compounds showed moderate to potent cytotoxic activity against the tested cell lines. Preliminary mechanism research indicated that the most promising compound, 2‐diethylaminomethyl‐9‐methyl‐1,2,3,4‐tetrahydrocarbazole‐1‐one 5c, exhibited a potential inhibitory effect against microtubule. |
| doi_str_mv | 10.1002/ardp.200800179 |
| format | Article |
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The structures of these newly synthesized compounds were characterized by 1H‐NMR, MS, and elemental analysis. All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines including human non‐small lung cancer cells (A549), human gastric adenocarcinoma (SGC), human colon cancer cell (HCT116), human myeoloid leukemia cells (K562), and one multi‐drug resistant subline (KB‐VCR). Most compounds showed moderate to potent cytotoxic activity against the tested cell lines. Preliminary mechanism research indicated that the most promising compound, 2‐diethylaminomethyl‐9‐methyl‐1,2,3,4‐tetrahydrocarbazole‐1‐one 5c, exhibited a potential inhibitory effect against microtubule.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.200800179</identifier><identifier>PMID: 19212985</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>4-tetrahydrocarbazole-1-ones ; 9-Alkyl-1 ; 9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antitumor activity ; Carbazoles - chemical synthesis ; Carbazoles - pharmacology ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; Humans ; Mannich bases ; Mannich Bases - chemical synthesis ; Mannich Bases - pharmacology ; Microtubules ; Microtubules - drug effects ; Molecular Structure</subject><ispartof>Archiv der Pharmazie (Weinheim), 2009-03, Vol.342 (3), p.165-172</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3819-ddab11b9ede77a5d2cc2c82f6eaf80f621eb0783e32d70e81e52f378f7f34df23</citedby><cites>FETCH-LOGICAL-c3819-ddab11b9ede77a5d2cc2c82f6eaf80f621eb0783e32d70e81e52f378f7f34df23</cites></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.200800179$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fardp.200800179$$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/19212985$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Jing</creatorcontrib><creatorcontrib>Lou, Jianshu</creatorcontrib><creatorcontrib>Liu, Tao</creatorcontrib><creatorcontrib>Wu, Ru</creatorcontrib><creatorcontrib>Dong, Xiaowu</creatorcontrib><creatorcontrib>He, Qiaojun</creatorcontrib><creatorcontrib>Yang, Bo</creatorcontrib><creatorcontrib>Hu, Yongzhou</creatorcontrib><title>Synthesis and In-Vitro Antitumor Activities of Some Mannich Bases of 9-Alkyl-1,2,3,4-tetrahydrocarbazole-1-ones</title><title>Archiv der Pharmazie (Weinheim)</title><addtitle>Arch. Pharm. Pharm. Med. Chem</addtitle><description>A novel series of 2‐substituted aminomethyl‐9‐alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones 5a–q was synthesized via aminomethylation of 9‐alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones 4a–e with hydrochlorides of the respective amines 6a–m. The structures of these newly synthesized compounds were characterized by 1H‐NMR, MS, and elemental analysis. All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines including human non‐small lung cancer cells (A549), human gastric adenocarcinoma (SGC), human colon cancer cell (HCT116), human myeoloid leukemia cells (K562), and one multi‐drug resistant subline (KB‐VCR). Most compounds showed moderate to potent cytotoxic activity against the tested cell lines. Preliminary mechanism research indicated that the most promising compound, 2‐diethylaminomethyl‐9‐methyl‐1,2,3,4‐tetrahydrocarbazole‐1‐one 5c, exhibited a potential inhibitory effect against microtubule.</description><subject>4-tetrahydrocarbazole-1-ones</subject><subject>9-Alkyl-1</subject><subject>9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antitumor activity</subject><subject>Carbazoles - chemical synthesis</subject><subject>Carbazoles - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Mannich bases</subject><subject>Mannich Bases - chemical synthesis</subject><subject>Mannich Bases - pharmacology</subject><subject>Microtubules</subject><subject>Microtubules - drug effects</subject><subject>Molecular Structure</subject><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtv1DAURi0EokNhyxJlxWo8-DGJnWVaoK3UAmJ47SzHvtaYJvFge4D01zdVRi07VpauzndkHYReUrKihLA3OtrdihEiCaGifoQWtGQUr6lcP0YLwqsSV4zzI_QspZ-EEE5Y-RQd0ZpRVstygcJmHPIWkk-FHmxxMeBvPsdQNEP2ed-HWDQm-98-e0hFcMUm9FBc6WHwZluc6DRfa9x012OH6ZIt-XKNM-Sot6ONwejY6pvQAaY4DJCeoydOdwleHN5j9PX9uy-n5_jy49nFaXOJDZe0xtbqltK2BgtC6NIyY5iRzFWgnSSuYhRaIiQHzqwgICmUzHEhnXB8bR3jx-j17N3F8GsPKaveJwNdpwcI-6QqMbWQVE7gagZNDClFcGoXfa_jqChRd4nVXWJ1n3gavDqY920P9gE_NJ2Aegb--A7G_-hU8_ntp3_leN76lOHv_VbH6-nHXJTq-4czdbL5Ic-52KiK3wLGypd1</recordid><startdate>200903</startdate><enddate>200903</enddate><creator>Chen, Jing</creator><creator>Lou, Jianshu</creator><creator>Liu, Tao</creator><creator>Wu, Ru</creator><creator>Dong, Xiaowu</creator><creator>He, Qiaojun</creator><creator>Yang, Bo</creator><creator>Hu, Yongzhou</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</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></search><sort><creationdate>200903</creationdate><title>Synthesis and In-Vitro Antitumor Activities of Some Mannich Bases of 9-Alkyl-1,2,3,4-tetrahydrocarbazole-1-ones</title><author>Chen, Jing ; Lou, Jianshu ; Liu, Tao ; Wu, Ru ; Dong, Xiaowu ; He, Qiaojun ; Yang, Bo ; Hu, Yongzhou</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3819-ddab11b9ede77a5d2cc2c82f6eaf80f621eb0783e32d70e81e52f378f7f34df23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>4-tetrahydrocarbazole-1-ones</topic><topic>9-Alkyl-1</topic><topic>9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antitumor activity</topic><topic>Carbazoles - chemical synthesis</topic><topic>Carbazoles - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Mannich bases</topic><topic>Mannich Bases - chemical synthesis</topic><topic>Mannich Bases - pharmacology</topic><topic>Microtubules</topic><topic>Microtubules - drug effects</topic><topic>Molecular Structure</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Jing</creatorcontrib><creatorcontrib>Lou, Jianshu</creatorcontrib><creatorcontrib>Liu, Tao</creatorcontrib><creatorcontrib>Wu, Ru</creatorcontrib><creatorcontrib>Dong, Xiaowu</creatorcontrib><creatorcontrib>He, Qiaojun</creatorcontrib><creatorcontrib>Yang, Bo</creatorcontrib><creatorcontrib>Hu, Yongzhou</creatorcontrib><collection>Istex</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><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Jing</au><au>Lou, Jianshu</au><au>Liu, Tao</au><au>Wu, Ru</au><au>Dong, Xiaowu</au><au>He, Qiaojun</au><au>Yang, Bo</au><au>Hu, Yongzhou</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and In-Vitro Antitumor Activities of Some Mannich Bases of 9-Alkyl-1,2,3,4-tetrahydrocarbazole-1-ones</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><addtitle>Arch. Pharm. Pharm. Med. Chem</addtitle><date>2009-03</date><risdate>2009</risdate><volume>342</volume><issue>3</issue><spage>165</spage><epage>172</epage><pages>165-172</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><abstract>A novel series of 2‐substituted aminomethyl‐9‐alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones 5a–q was synthesized via aminomethylation of 9‐alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones 4a–e with hydrochlorides of the respective amines 6a–m. The structures of these newly synthesized compounds were characterized by 1H‐NMR, MS, and elemental analysis. All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines including human non‐small lung cancer cells (A549), human gastric adenocarcinoma (SGC), human colon cancer cell (HCT116), human myeoloid leukemia cells (K562), and one multi‐drug resistant subline (KB‐VCR). Most compounds showed moderate to potent cytotoxic activity against the tested cell lines. Preliminary mechanism research indicated that the most promising compound, 2‐diethylaminomethyl‐9‐methyl‐1,2,3,4‐tetrahydrocarbazole‐1‐one 5c, exhibited a potential inhibitory effect against microtubule.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>19212985</pmid><doi>10.1002/ardp.200800179</doi><tpages>8</tpages></addata></record> |
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| subjects | 4-tetrahydrocarbazole-1-ones 9-Alkyl-1 9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antitumor activity Carbazoles - chemical synthesis Carbazoles - pharmacology Cell Line, Tumor Drug Screening Assays, Antitumor Humans Mannich bases Mannich Bases - chemical synthesis Mannich Bases - pharmacology Microtubules Microtubules - drug effects Molecular Structure |
| title | Synthesis and In-Vitro Antitumor Activities of Some Mannich Bases of 9-Alkyl-1,2,3,4-tetrahydrocarbazole-1-ones |
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