Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities
We describe novel urea and carbamate derivatives of primaquine, and their cytostatic and antioxidant activities. 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]-urea ( 3c) shows extreme selectivity toward SW 620 colon cancer cells. The novel urea primaquine derivatives 3 were prepare...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2009-08, Vol.17 (15), p.5605-5613 |
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| creator | Šimunović, M. Perković, I. Zorc, B. Ester, K. Kralj, M. Hadjipavlou-Litina, D. Pontiki, E. |
| description | We describe novel urea and carbamate derivatives of primaquine, and their cytostatic and antioxidant activities. 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]-urea (
3c) shows extreme selectivity toward SW 620 colon cancer cells.
The novel urea primaquine derivatives
3 were prepared by aminolysis of primaquine benzotriazolide
2 with several hydroxyamines and ethylendiamine, while carbamates
4 were synthesized from the same precursor
2 and alcohols. All compounds are fully chemically characterized and evaluated for their cytostatic and antioxidant activities. The most prominent antiproliferative activity was obtained by compounds
3c,
3d,
3g, and
5b (IC
50
=
9–40
μM). 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]urea (
3c) showed extreme selectivity toward SW 620 colon cancer cells (IC
50
=
0.2
μM) and a bit less toward lung cancer cells H 460. Hydroxyurea
3h showed the highest interaction with DPPH. Primaquine twin drug
3g showed very significant inhibition on LOX soybean (IC
50
=
62
μM). Almost all the tested derivatives highly inhibited lipid peroxidation, significantly stronger than primaquine phosphate. |
| doi_str_mv | 10.1016/j.bmc.2009.06.030 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_20708041</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089609005847</els_id><sourcerecordid>20708041</sourcerecordid><originalsourceid>FETCH-LOGICAL-c412t-dd2dd802313454a69d9fc7d4e7d8c9c6cb92ee59553385a87e9135769e67f4103</originalsourceid><addsrcrecordid>eNp9kMtuFDEQRS0EIpPAB7BBvYFVuik_2m2TFYp4SZFYQLZYnnK18Gi6O7E9I-bvcTIj2LG6m3Ovqg5jrzh0HLh-t-nWE3YCwHagO5DwhK240qqV0vKnbAVWmxaM1WfsPOcNAAhl-XN2xm1vOFizYj9vE_nGz6FBn9Z-8oWaQCnufYl7ys0yNncpTv5-F2d633w_zOUX5ZgvGzyUJZeK4WPdzyUuv2Oo2Xis5Vgi5Rfs2ei3mV6e8oLdfvr44_pLe_Pt89frDzctKi5KG4IIwYCQXKpeeW2DHXEIioZg0KLGtRVEve17KU3vzUCWy37QlvQwKg7ygr097t6l5X5HubgpZqTt1s-07LITMIABxSvIjyCmJedEo3t8Lx0cB_cg1W1cleoepDrQrkqtnden8d16ovCvcbJYgTcnwGf02zH5GWP-ywk-WBDQV-7qyFFVsY-UXMZIM1KIibC4sMT_nPEHI-iVGg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>20708041</pqid></control><display><type>article</type><title>Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities</title><source>Elsevier ScienceDirect Journals Complete - AutoHoldings</source><source>MEDLINE</source><creator>Šimunović, M. ; Perković, I. ; Zorc, B. ; Ester, K. ; Kralj, M. ; Hadjipavlou-Litina, D. ; Pontiki, E.</creator><creatorcontrib>Šimunović, M. ; Perković, I. ; Zorc, B. ; Ester, K. ; Kralj, M. ; Hadjipavlou-Litina, D. ; Pontiki, E.</creatorcontrib><description>We describe novel urea and carbamate derivatives of primaquine, and their cytostatic and antioxidant activities. 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]-urea (
3c) shows extreme selectivity toward SW 620 colon cancer cells.
The novel urea primaquine derivatives
3 were prepared by aminolysis of primaquine benzotriazolide
2 with several hydroxyamines and ethylendiamine, while carbamates
4 were synthesized from the same precursor
2 and alcohols. All compounds are fully chemically characterized and evaluated for their cytostatic and antioxidant activities. The most prominent antiproliferative activity was obtained by compounds
3c,
3d,
3g, and
5b (IC
50
=
9–40
μM). 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]urea (
3c) showed extreme selectivity toward SW 620 colon cancer cells (IC
50
=
0.2
μM) and a bit less toward lung cancer cells H 460. Hydroxyurea
3h showed the highest interaction with DPPH. Primaquine twin drug
3g showed very significant inhibition on LOX soybean (IC
50
=
62
μM). Almost all the tested derivatives highly inhibited lipid peroxidation, significantly stronger than primaquine phosphate.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2009.06.030</identifier><identifier>PMID: 19581098</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antimalarials - chemical synthesis ; Antimalarials - chemistry ; Antimalarials - pharmacology ; Antineoplastic agents ; Antioxidants - chemical synthesis ; Antioxidants - chemistry ; Antioxidants - pharmacology ; Antiparasitic agents ; Biological and medical sciences ; Biphenyl Compounds - metabolism ; Carbamate ; Carbamates - chemical synthesis ; Carbamates - chemistry ; Carbamates - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cytostatic activity ; Cytostatic Agents - chemical synthesis ; Cytostatic Agents - chemistry ; Cytostatic Agents - pharmacology ; General aspects ; Glycine max - enzymology ; Humans ; Lipid peroxidation ; Lipid Peroxidation - drug effects ; Lipoxygenase - metabolism ; Medical sciences ; Molecular Structure ; Pharmacology. Drug treatments ; Picrates - metabolism ; Primaquine ; Primaquine - chemical synthesis ; Primaquine - chemistry ; Primaquine - pharmacology ; Soybean lipoxygenase ; Urea ; Urea - analogs & derivatives ; Urea - chemical synthesis ; Urea - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry, 2009-08, Vol.17 (15), p.5605-5613</ispartof><rights>2009 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c412t-dd2dd802313454a69d9fc7d4e7d8c9c6cb92ee59553385a87e9135769e67f4103</citedby><cites>FETCH-LOGICAL-c412t-dd2dd802313454a69d9fc7d4e7d8c9c6cb92ee59553385a87e9135769e67f4103</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2009.06.030$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27907,27908,45978</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21790205$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19581098$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Šimunović, M.</creatorcontrib><creatorcontrib>Perković, I.</creatorcontrib><creatorcontrib>Zorc, B.</creatorcontrib><creatorcontrib>Ester, K.</creatorcontrib><creatorcontrib>Kralj, M.</creatorcontrib><creatorcontrib>Hadjipavlou-Litina, D.</creatorcontrib><creatorcontrib>Pontiki, E.</creatorcontrib><title>Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>We describe novel urea and carbamate derivatives of primaquine, and their cytostatic and antioxidant activities. 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]-urea (
3c) shows extreme selectivity toward SW 620 colon cancer cells.
The novel urea primaquine derivatives
3 were prepared by aminolysis of primaquine benzotriazolide
2 with several hydroxyamines and ethylendiamine, while carbamates
4 were synthesized from the same precursor
2 and alcohols. All compounds are fully chemically characterized and evaluated for their cytostatic and antioxidant activities. The most prominent antiproliferative activity was obtained by compounds
3c,
3d,
3g, and
5b (IC
50
=
9–40
μM). 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]urea (
3c) showed extreme selectivity toward SW 620 colon cancer cells (IC
50
=
0.2
μM) and a bit less toward lung cancer cells H 460. Hydroxyurea
3h showed the highest interaction with DPPH. Primaquine twin drug
3g showed very significant inhibition on LOX soybean (IC
50
=
62
μM). Almost all the tested derivatives highly inhibited lipid peroxidation, significantly stronger than primaquine phosphate.</description><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antimalarials - chemical synthesis</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - pharmacology</subject><subject>Antineoplastic agents</subject><subject>Antioxidants - chemical synthesis</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - pharmacology</subject><subject>Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Biphenyl Compounds - metabolism</subject><subject>Carbamate</subject><subject>Carbamates - chemical synthesis</subject><subject>Carbamates - chemistry</subject><subject>Carbamates - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cytostatic activity</subject><subject>Cytostatic Agents - chemical synthesis</subject><subject>Cytostatic Agents - chemistry</subject><subject>Cytostatic Agents - pharmacology</subject><subject>General aspects</subject><subject>Glycine max - enzymology</subject><subject>Humans</subject><subject>Lipid peroxidation</subject><subject>Lipid Peroxidation - drug effects</subject><subject>Lipoxygenase - metabolism</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Picrates - metabolism</subject><subject>Primaquine</subject><subject>Primaquine - chemical synthesis</subject><subject>Primaquine - chemistry</subject><subject>Primaquine - pharmacology</subject><subject>Soybean lipoxygenase</subject><subject>Urea</subject><subject>Urea - analogs & derivatives</subject><subject>Urea - chemical synthesis</subject><subject>Urea - pharmacology</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMtuFDEQRS0EIpPAB7BBvYFVuik_2m2TFYp4SZFYQLZYnnK18Gi6O7E9I-bvcTIj2LG6m3Ovqg5jrzh0HLh-t-nWE3YCwHagO5DwhK240qqV0vKnbAVWmxaM1WfsPOcNAAhl-XN2xm1vOFizYj9vE_nGz6FBn9Z-8oWaQCnufYl7ys0yNncpTv5-F2d633w_zOUX5ZgvGzyUJZeK4WPdzyUuv2Oo2Xis5Vgi5Rfs2ei3mV6e8oLdfvr44_pLe_Pt89frDzctKi5KG4IIwYCQXKpeeW2DHXEIioZg0KLGtRVEve17KU3vzUCWy37QlvQwKg7ygr097t6l5X5HubgpZqTt1s-07LITMIABxSvIjyCmJedEo3t8Lx0cB_cg1W1cleoepDrQrkqtnden8d16ovCvcbJYgTcnwGf02zH5GWP-ywk-WBDQV-7qyFFVsY-UXMZIM1KIibC4sMT_nPEHI-iVGg</recordid><startdate>20090801</startdate><enddate>20090801</enddate><creator>Šimunović, M.</creator><creator>Perković, I.</creator><creator>Zorc, B.</creator><creator>Ester, K.</creator><creator>Kralj, M.</creator><creator>Hadjipavlou-Litina, D.</creator><creator>Pontiki, E.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20090801</creationdate><title>Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities</title><author>Šimunović, M. ; Perković, I. ; Zorc, B. ; Ester, K. ; Kralj, M. ; Hadjipavlou-Litina, D. ; Pontiki, E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c412t-dd2dd802313454a69d9fc7d4e7d8c9c6cb92ee59553385a87e9135769e67f4103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antimalarials - chemical synthesis</topic><topic>Antimalarials - chemistry</topic><topic>Antimalarials - pharmacology</topic><topic>Antineoplastic agents</topic><topic>Antioxidants - chemical synthesis</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - pharmacology</topic><topic>Antiparasitic agents</topic><topic>Biological and medical sciences</topic><topic>Biphenyl Compounds - metabolism</topic><topic>Carbamate</topic><topic>Carbamates - chemical synthesis</topic><topic>Carbamates - chemistry</topic><topic>Carbamates - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cytostatic activity</topic><topic>Cytostatic Agents - chemical synthesis</topic><topic>Cytostatic Agents - chemistry</topic><topic>Cytostatic Agents - pharmacology</topic><topic>General aspects</topic><topic>Glycine max - enzymology</topic><topic>Humans</topic><topic>Lipid peroxidation</topic><topic>Lipid Peroxidation - drug effects</topic><topic>Lipoxygenase - metabolism</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Picrates - metabolism</topic><topic>Primaquine</topic><topic>Primaquine - chemical synthesis</topic><topic>Primaquine - chemistry</topic><topic>Primaquine - pharmacology</topic><topic>Soybean lipoxygenase</topic><topic>Urea</topic><topic>Urea - analogs & derivatives</topic><topic>Urea - chemical synthesis</topic><topic>Urea - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Šimunović, M.</creatorcontrib><creatorcontrib>Perković, I.</creatorcontrib><creatorcontrib>Zorc, B.</creatorcontrib><creatorcontrib>Ester, K.</creatorcontrib><creatorcontrib>Kralj, M.</creatorcontrib><creatorcontrib>Hadjipavlou-Litina, D.</creatorcontrib><creatorcontrib>Pontiki, E.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Šimunović, M.</au><au>Perković, I.</au><au>Zorc, B.</au><au>Ester, K.</au><au>Kralj, M.</au><au>Hadjipavlou-Litina, D.</au><au>Pontiki, E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2009-08-01</date><risdate>2009</risdate><volume>17</volume><issue>15</issue><spage>5605</spage><epage>5613</epage><pages>5605-5613</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>We describe novel urea and carbamate derivatives of primaquine, and their cytostatic and antioxidant activities. 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]-urea (
3c) shows extreme selectivity toward SW 620 colon cancer cells.
The novel urea primaquine derivatives
3 were prepared by aminolysis of primaquine benzotriazolide
2 with several hydroxyamines and ethylendiamine, while carbamates
4 were synthesized from the same precursor
2 and alcohols. All compounds are fully chemically characterized and evaluated for their cytostatic and antioxidant activities. The most prominent antiproliferative activity was obtained by compounds
3c,
3d,
3g, and
5b (IC
50
=
9–40
μM). 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]urea (
3c) showed extreme selectivity toward SW 620 colon cancer cells (IC
50
=
0.2
μM) and a bit less toward lung cancer cells H 460. Hydroxyurea
3h showed the highest interaction with DPPH. Primaquine twin drug
3g showed very significant inhibition on LOX soybean (IC
50
=
62
μM). Almost all the tested derivatives highly inhibited lipid peroxidation, significantly stronger than primaquine phosphate.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19581098</pmid><doi>10.1016/j.bmc.2009.06.030</doi><tpages>9</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2009-08, Vol.17 (15), p.5605-5613 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings; MEDLINE |
| subjects | Antibiotics. Antiinfectious agents. Antiparasitic agents Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Antineoplastic agents Antioxidants - chemical synthesis Antioxidants - chemistry Antioxidants - pharmacology Antiparasitic agents Biological and medical sciences Biphenyl Compounds - metabolism Carbamate Carbamates - chemical synthesis Carbamates - chemistry Carbamates - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Cytostatic activity Cytostatic Agents - chemical synthesis Cytostatic Agents - chemistry Cytostatic Agents - pharmacology General aspects Glycine max - enzymology Humans Lipid peroxidation Lipid Peroxidation - drug effects Lipoxygenase - metabolism Medical sciences Molecular Structure Pharmacology. Drug treatments Picrates - metabolism Primaquine Primaquine - chemical synthesis Primaquine - chemistry Primaquine - pharmacology Soybean lipoxygenase Urea Urea - analogs & derivatives Urea - chemical synthesis Urea - pharmacology |
| title | Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities |
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