Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents
A series of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a–j were obtained via multistep synthesis from hydroxybenzophenones 4a–e. The cytotoxicity of compounds 9a–j was evaluated against human leukemia cell lines (K562 and CEM). The compounds exhibited moderate to good anti-cancer activity wit...
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| Veröffentlicht in: | European journal of medicinal chemistry 2013-05, Vol.63, p.536-543 |
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| container_title | European journal of medicinal chemistry |
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| creator | Gurupadaswamy, H.D. Girish, V. Kavitha, C.V. Raghavan, Sathees C. Khanum, Shaukath Ara |
| description | A series of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a–j were obtained via multistep synthesis from hydroxybenzophenones 4a–e. The cytotoxicity of compounds 9a–j was evaluated against human leukemia cell lines (K562 and CEM). The compounds exhibited moderate to good anti-cancer activity with compounds 9b and 9i having a chloro group exhibiting the best activity (IC50 = 10 μM). Compound 9i exhibited activity against both the cell lines and 9b only exhibited activity against CEM. Further, a lactate dehydrogenase (LDH) assay and DNA fragmentation studies of the compounds 9a–j were also performed.
[Display omitted] 2,5-Di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a–j were synthesized and examined for cytotoxicity on human leukemia cell lines. Further, a lactate dehydrogenase assay and DNA fragmentation studies were also performed.
► Synthesis of biologically active analogs of 1,3,4-oxadiazoles was carried out. ► Cytotoxicity of the synthesized compounds was evaluated against human leukemia cell lines. ► Compounds exhibited moderate to good anti-cancer activity. ► Lactate dehydrogenase assay and DNA fragmentation studies were also performed. |
| doi_str_mv | 10.1016/j.ejmech.2013.02.040 |
| format | Article |
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[Display omitted] 2,5-Di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a–j were synthesized and examined for cytotoxicity on human leukemia cell lines. Further, a lactate dehydrogenase assay and DNA fragmentation studies were also performed.
► Synthesis of biologically active analogs of 1,3,4-oxadiazoles was carried out. ► Cytotoxicity of the synthesized compounds was evaluated against human leukemia cell lines. ► Compounds exhibited moderate to good anti-cancer activity. ► Lactate dehydrogenase assay and DNA fragmentation studies were also performed.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2013.02.040</identifier><identifier>PMID: 23535322</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>1,3,4-Oxadiazoles ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Apoptosis ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cell Survival - drug effects ; Cytotoxicity ; DNA Fragmentation - drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Humans ; Inhibitory Concentration 50 ; Intracellular Space - drug effects ; Intracellular Space - enzymology ; K562 Cells ; L-Lactate Dehydrogenase - metabolism ; L-Lactate Dehydrogenase - secretion ; Models, Chemical ; Molecular Structure ; Oxadiazoles - chemical synthesis ; Oxadiazoles - chemistry ; Oxadiazoles - pharmacology ; Time Factors</subject><ispartof>European journal of medicinal chemistry, 2013-05, Vol.63, p.536-543</ispartof><rights>2013 Elsevier Masson SAS</rights><rights>Copyright © 2013 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-d52d37b1167c6cf4a8f965681a242a21aa4c3082438b8909dc4d9e6603609b5f3</citedby><cites>FETCH-LOGICAL-c362t-d52d37b1167c6cf4a8f965681a242a21aa4c3082438b8909dc4d9e6603609b5f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2013.02.040$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23535322$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gurupadaswamy, H.D.</creatorcontrib><creatorcontrib>Girish, V.</creatorcontrib><creatorcontrib>Kavitha, C.V.</creatorcontrib><creatorcontrib>Raghavan, Sathees C.</creatorcontrib><creatorcontrib>Khanum, Shaukath Ara</creatorcontrib><title>Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A series of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a–j were obtained via multistep synthesis from hydroxybenzophenones 4a–e. The cytotoxicity of compounds 9a–j was evaluated against human leukemia cell lines (K562 and CEM). The compounds exhibited moderate to good anti-cancer activity with compounds 9b and 9i having a chloro group exhibiting the best activity (IC50 = 10 μM). Compound 9i exhibited activity against both the cell lines and 9b only exhibited activity against CEM. Further, a lactate dehydrogenase (LDH) assay and DNA fragmentation studies of the compounds 9a–j were also performed.
[Display omitted] 2,5-Di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a–j were synthesized and examined for cytotoxicity on human leukemia cell lines. Further, a lactate dehydrogenase assay and DNA fragmentation studies were also performed.
► Synthesis of biologically active analogs of 1,3,4-oxadiazoles was carried out. ► Cytotoxicity of the synthesized compounds was evaluated against human leukemia cell lines. ► Compounds exhibited moderate to good anti-cancer activity. ► Lactate dehydrogenase assay and DNA fragmentation studies were also performed.</description><subject>1,3,4-Oxadiazoles</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cell Survival - drug effects</subject><subject>Cytotoxicity</subject><subject>DNA Fragmentation - drug effects</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Intracellular Space - drug effects</subject><subject>Intracellular Space - enzymology</subject><subject>K562 Cells</subject><subject>L-Lactate Dehydrogenase - metabolism</subject><subject>L-Lactate Dehydrogenase - secretion</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Oxadiazoles - chemical synthesis</subject><subject>Oxadiazoles - chemistry</subject><subject>Oxadiazoles - pharmacology</subject><subject>Time Factors</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMtu1DAUhi0EokPhDRDKskjjcHx8mWSDhCpuUiUWwNpy7BPGoyQucaZqeHo8TGGJzuLf_Bedj7GXAmoBwrw51HQYye9rBCFrwBoUPGIbsTMNl6jVY7YBRMk1SnXBnuV8AABtAJ6yC5S6HOKGdV_XadlTjrlyU6jozg1Ht8Q0VamvcKt5iFeKu3kd0jr8kft1pGW_Dq-52Mqt4uneheh-pYFKxallidy7ydNcuR80Lfk5e9K7IdOLB71k3z-8_3b9id98-fj5-t0N99LgwoPGIHedEGbnje-Va_rWaNMIhwodCueUl9Cgkk3XtNAGr0JLxoA00Ha6l5fs6tx7O6efR8qLHWP2NAxuonTMVkijQYvWNMWqzlY_p5xn6u3tHMfynhVgT3TtwZ7p2hNdC2gL3RJ79bBw7EYK_0J_cRbD27OByp93kWabfaTCIsSZ_GJDiv9f-A3dUouH</recordid><startdate>20130501</startdate><enddate>20130501</enddate><creator>Gurupadaswamy, H.D.</creator><creator>Girish, V.</creator><creator>Kavitha, C.V.</creator><creator>Raghavan, Sathees C.</creator><creator>Khanum, Shaukath Ara</creator><general>Elsevier Masson SAS</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>20130501</creationdate><title>Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents</title><author>Gurupadaswamy, H.D. ; Girish, V. ; Kavitha, C.V. ; Raghavan, Sathees C. ; Khanum, Shaukath Ara</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-d52d37b1167c6cf4a8f965681a242a21aa4c3082438b8909dc4d9e6603609b5f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>1,3,4-Oxadiazoles</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Apoptosis</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cell Survival - drug effects</topic><topic>Cytotoxicity</topic><topic>DNA Fragmentation - drug effects</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Intracellular Space - drug effects</topic><topic>Intracellular Space - enzymology</topic><topic>K562 Cells</topic><topic>L-Lactate Dehydrogenase - metabolism</topic><topic>L-Lactate Dehydrogenase - secretion</topic><topic>Models, Chemical</topic><topic>Molecular Structure</topic><topic>Oxadiazoles - chemical synthesis</topic><topic>Oxadiazoles - chemistry</topic><topic>Oxadiazoles - pharmacology</topic><topic>Time Factors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gurupadaswamy, H.D.</creatorcontrib><creatorcontrib>Girish, V.</creatorcontrib><creatorcontrib>Kavitha, C.V.</creatorcontrib><creatorcontrib>Raghavan, Sathees C.</creatorcontrib><creatorcontrib>Khanum, Shaukath Ara</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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gurupadaswamy, H.D.</au><au>Girish, V.</au><au>Kavitha, C.V.</au><au>Raghavan, Sathees C.</au><au>Khanum, Shaukath Ara</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2013-05-01</date><risdate>2013</risdate><volume>63</volume><spage>536</spage><epage>543</epage><pages>536-543</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>A series of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a–j were obtained via multistep synthesis from hydroxybenzophenones 4a–e. The cytotoxicity of compounds 9a–j was evaluated against human leukemia cell lines (K562 and CEM). The compounds exhibited moderate to good anti-cancer activity with compounds 9b and 9i having a chloro group exhibiting the best activity (IC50 = 10 μM). Compound 9i exhibited activity against both the cell lines and 9b only exhibited activity against CEM. Further, a lactate dehydrogenase (LDH) assay and DNA fragmentation studies of the compounds 9a–j were also performed.
[Display omitted] 2,5-Di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a–j were synthesized and examined for cytotoxicity on human leukemia cell lines. Further, a lactate dehydrogenase assay and DNA fragmentation studies were also performed.
► Synthesis of biologically active analogs of 1,3,4-oxadiazoles was carried out. ► Cytotoxicity of the synthesized compounds was evaluated against human leukemia cell lines. ► Compounds exhibited moderate to good anti-cancer activity. ► Lactate dehydrogenase assay and DNA fragmentation studies were also performed.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>23535322</pmid><doi>10.1016/j.ejmech.2013.02.040</doi><tpages>8</tpages></addata></record> |
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| subjects | 1,3,4-Oxadiazoles Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Apoptosis Cell Line, Tumor Cell Proliferation - drug effects Cell Survival - drug effects Cytotoxicity DNA Fragmentation - drug effects Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Humans Inhibitory Concentration 50 Intracellular Space - drug effects Intracellular Space - enzymology K562 Cells L-Lactate Dehydrogenase - metabolism L-Lactate Dehydrogenase - secretion Models, Chemical Molecular Structure Oxadiazoles - chemical synthesis Oxadiazoles - chemistry Oxadiazoles - pharmacology Time Factors |
| title | Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents |
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