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Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives
Background Coumarin and its derivatives are biologically very active. It was found that the enhanced activities are dependent on the coumarin nucleus. Biological significance of these compounds include anti-bacterial, anti-thrombotic and vasodilatory, anti-mutagenic, lipoxygenase and cyclooxygenase...
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| Published in: | BMC chemistry 2013-04, Vol.7 (1), p.68-68, Article 68 |
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| creator | Rehman, Sadia Ikram, Muhammad Baker, Robert J Zubair, Muhammad Azad, Effat Min, Soyoung Riaz, Kashif Mok, KH Rehman, Saeed-Ur |
| description | Background
Coumarin and its derivatives are biologically very active. It was found that the enhanced activities are dependent on the coumarin nucleus. Biological significance of these compounds include anti-bacterial, anti-thrombotic and vasodilatory, anti-mutagenic, lipoxygenase and cyclooxygenase inhibition, scavenging of reactive oxygen species, and anti-tumourigenic. Our interest in medicinal chemistry of dicoumarol compounds have been developed by keeping in view the importance of coumarins along with its derivatives in medicinal chemistry. All the synthesized compounds were fully characterized by spectroscopic and analytical techniques and were screened for antimicrobial and U2OS bone cancer activities.
Results
4-hydroxycoumarin was derivatized by condensing with different aldehydes yielding the dicoumarol and translactonized products. Elemental analyses, ESI(+,−) MS,
1
H and
13
C{
1
H}-NMR, infrared spectroscopy and conductance studies were used to characterize the synthesized compounds which revealed the dicoumarol and dichromone structures for the compounds. The compounds were screened against U2OS cancerous cells and pathogenic micro organisms. The compounds with intermolecular H-bonding were found more active revealing a possible relationship among hydrogen bonding, cytotoxicity and antimicrobial activities.
Conclusion
Coumarin based drugs can be designed for the possible treatment of U2OS leukemia. |
| doi_str_mv | 10.1186/1752-153X-7-68 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3668295</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1709717240</sourcerecordid><originalsourceid>FETCH-LOGICAL-b582t-8f9f1446dedff4c18f04be895a6d29a5e294b1b9854a4378115688702bbe266d3</originalsourceid><addsrcrecordid>eNqFkktr3DAURkVpaYY02y6LoJsuxokk67kphNAXBLJIA9kJ2ZYyCraVSrYh-fW9w6RD0gddCXGPjj4-CaG3lBxTquUJVYJVVNTXlaqkfoFWTEpaaUKvX6LVfniAjkq5JYQwKoiq-Wt0wGqhVS3rFVou78dp40ssa9xuXHbt5HN8cFNM4xrHES9xygm7cYpDbHNqouvXsO3wFbu4xNM8pBzb2Lkew9EIdPQFp4C7GILPfpxwm-bBZVB1YF7AvPjyBr0Kri_-6HE9RFefP30_-1qdX3z5dnZ6XjVCs6nSwQTKuex8FwJvqQ6EN14b4WTHjBOeGd7QxmjBHa-VplRIrRVhTeOhi64-RB933ru5GXzXQp7senuXI0S6t8lF-3wyxo29SYutpdTMCBCc7gRNTP8QPJ-0abDb6u22equs1OD48Bgipx-zL5MdYml937vRp7kAToyiinHyf7Q2xhDDCAX0_W_obZrzCG0CJbnWWlIF1PGOgrcrJfuwj06J3X6iP8O-e9rYHv_1ZQA42QEFRuONz0_u_bvyJ-mH08k</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1364888617</pqid></control><display><type>article</type><title>Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives</title><source>Full-Text Journals in Chemistry (Open access)</source><source>Springer Nature - SpringerLink Journals - Fully Open Access </source><source>Publicly Available Content (ProQuest)</source><source>PubMed Central</source><creator>Rehman, Sadia ; Ikram, Muhammad ; Baker, Robert J ; Zubair, Muhammad ; Azad, Effat ; Min, Soyoung ; Riaz, Kashif ; Mok, KH ; Rehman, Saeed-Ur</creator><creatorcontrib>Rehman, Sadia ; Ikram, Muhammad ; Baker, Robert J ; Zubair, Muhammad ; Azad, Effat ; Min, Soyoung ; Riaz, Kashif ; Mok, KH ; Rehman, Saeed-Ur</creatorcontrib><description>Background
Coumarin and its derivatives are biologically very active. It was found that the enhanced activities are dependent on the coumarin nucleus. Biological significance of these compounds include anti-bacterial, anti-thrombotic and vasodilatory, anti-mutagenic, lipoxygenase and cyclooxygenase inhibition, scavenging of reactive oxygen species, and anti-tumourigenic. Our interest in medicinal chemistry of dicoumarol compounds have been developed by keeping in view the importance of coumarins along with its derivatives in medicinal chemistry. All the synthesized compounds were fully characterized by spectroscopic and analytical techniques and were screened for antimicrobial and U2OS bone cancer activities.
Results
4-hydroxycoumarin was derivatized by condensing with different aldehydes yielding the dicoumarol and translactonized products. Elemental analyses, ESI(+,−) MS,
1
H and
13
C{
1
H}-NMR, infrared spectroscopy and conductance studies were used to characterize the synthesized compounds which revealed the dicoumarol and dichromone structures for the compounds. The compounds were screened against U2OS cancerous cells and pathogenic micro organisms. The compounds with intermolecular H-bonding were found more active revealing a possible relationship among hydrogen bonding, cytotoxicity and antimicrobial activities.
Conclusion
Coumarin based drugs can be designed for the possible treatment of U2OS leukemia.</description><identifier>ISSN: 1752-153X</identifier><identifier>ISSN: 2661-801X</identifier><identifier>EISSN: 2661-801X</identifier><identifier>EISSN: 1752-153X</identifier><identifier>DOI: 10.1186/1752-153X-7-68</identifier><identifier>PMID: 23587363</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Aldehydes ; Antiinfectives and antibacterials ; Antimicrobial agents ; Biological Chemistry ; Bones ; Cancer therapies ; Chemistry ; Chemistry/Food Science ; Coumarin ; Derivatives ; Leukemia ; Leukemias ; Lipoxygenase ; Melanoma ; Nuclei ; Research Article ; Skin cancer</subject><ispartof>BMC chemistry, 2013-04, Vol.7 (1), p.68-68, Article 68</ispartof><rights>Rehman et al.; licensee Chemistry Central Ltd. 2013. This article is published under license to BioMed Central Ltd. This is an Open Access article distributed under the terms of the Creative Commons Attribution License ( ), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.</rights><rights>2013 Rehman et al.; licensee Chemistry Central Ltd. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.</rights><rights>Copyright © 2013 Rehman et al.; licensee Chemistry Central Ltd. 2013 Rehman et al.; licensee Chemistry Central Ltd.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-b582t-8f9f1446dedff4c18f04be895a6d29a5e294b1b9854a4378115688702bbe266d3</citedby><cites>FETCH-LOGICAL-b582t-8f9f1446dedff4c18f04be895a6d29a5e294b1b9854a4378115688702bbe266d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1364888617/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1364888617?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25752,27923,27924,37011,44589,53790,53792,74897</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23587363$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rehman, Sadia</creatorcontrib><creatorcontrib>Ikram, Muhammad</creatorcontrib><creatorcontrib>Baker, Robert J</creatorcontrib><creatorcontrib>Zubair, Muhammad</creatorcontrib><creatorcontrib>Azad, Effat</creatorcontrib><creatorcontrib>Min, Soyoung</creatorcontrib><creatorcontrib>Riaz, Kashif</creatorcontrib><creatorcontrib>Mok, KH</creatorcontrib><creatorcontrib>Rehman, Saeed-Ur</creatorcontrib><title>Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives</title><title>BMC chemistry</title><addtitle>Chemistry Central Journal</addtitle><addtitle>Chem Cent J</addtitle><description>Background
Coumarin and its derivatives are biologically very active. It was found that the enhanced activities are dependent on the coumarin nucleus. Biological significance of these compounds include anti-bacterial, anti-thrombotic and vasodilatory, anti-mutagenic, lipoxygenase and cyclooxygenase inhibition, scavenging of reactive oxygen species, and anti-tumourigenic. Our interest in medicinal chemistry of dicoumarol compounds have been developed by keeping in view the importance of coumarins along with its derivatives in medicinal chemistry. All the synthesized compounds were fully characterized by spectroscopic and analytical techniques and were screened for antimicrobial and U2OS bone cancer activities.
Results
4-hydroxycoumarin was derivatized by condensing with different aldehydes yielding the dicoumarol and translactonized products. Elemental analyses, ESI(+,−) MS,
1
H and
13
C{
1
H}-NMR, infrared spectroscopy and conductance studies were used to characterize the synthesized compounds which revealed the dicoumarol and dichromone structures for the compounds. The compounds were screened against U2OS cancerous cells and pathogenic micro organisms. The compounds with intermolecular H-bonding were found more active revealing a possible relationship among hydrogen bonding, cytotoxicity and antimicrobial activities.
Conclusion
Coumarin based drugs can be designed for the possible treatment of U2OS leukemia.</description><subject>Aldehydes</subject><subject>Antiinfectives and antibacterials</subject><subject>Antimicrobial agents</subject><subject>Biological Chemistry</subject><subject>Bones</subject><subject>Cancer therapies</subject><subject>Chemistry</subject><subject>Chemistry/Food Science</subject><subject>Coumarin</subject><subject>Derivatives</subject><subject>Leukemia</subject><subject>Leukemias</subject><subject>Lipoxygenase</subject><subject>Melanoma</subject><subject>Nuclei</subject><subject>Research Article</subject><subject>Skin cancer</subject><issn>1752-153X</issn><issn>2661-801X</issn><issn>2661-801X</issn><issn>1752-153X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><recordid>eNqFkktr3DAURkVpaYY02y6LoJsuxokk67kphNAXBLJIA9kJ2ZYyCraVSrYh-fW9w6RD0gddCXGPjj4-CaG3lBxTquUJVYJVVNTXlaqkfoFWTEpaaUKvX6LVfniAjkq5JYQwKoiq-Wt0wGqhVS3rFVou78dp40ssa9xuXHbt5HN8cFNM4xrHES9xygm7cYpDbHNqouvXsO3wFbu4xNM8pBzb2Lkew9EIdPQFp4C7GILPfpxwm-bBZVB1YF7AvPjyBr0Kri_-6HE9RFefP30_-1qdX3z5dnZ6XjVCs6nSwQTKuex8FwJvqQ6EN14b4WTHjBOeGd7QxmjBHa-VplRIrRVhTeOhi64-RB933ru5GXzXQp7senuXI0S6t8lF-3wyxo29SYutpdTMCBCc7gRNTP8QPJ-0abDb6u22equs1OD48Bgipx-zL5MdYml937vRp7kAToyiinHyf7Q2xhDDCAX0_W_obZrzCG0CJbnWWlIF1PGOgrcrJfuwj06J3X6iP8O-e9rYHv_1ZQA42QEFRuONz0_u_bvyJ-mH08k</recordid><startdate>20130415</startdate><enddate>20130415</enddate><creator>Rehman, Sadia</creator><creator>Ikram, Muhammad</creator><creator>Baker, Robert J</creator><creator>Zubair, Muhammad</creator><creator>Azad, Effat</creator><creator>Min, Soyoung</creator><creator>Riaz, Kashif</creator><creator>Mok, KH</creator><creator>Rehman, Saeed-Ur</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><general>BioMed Central Ltd</general><general>BioMed Central</general><scope>C6C</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7SR</scope><scope>7X7</scope><scope>7XB</scope><scope>8AO</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>K9.</scope><scope>KB.</scope><scope>M0S</scope><scope>M2O</scope><scope>MBDVC</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7QL</scope><scope>7T7</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>5PM</scope></search><sort><creationdate>20130415</creationdate><title>Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives</title><author>Rehman, Sadia ; Ikram, Muhammad ; Baker, Robert J ; Zubair, Muhammad ; Azad, Effat ; Min, Soyoung ; Riaz, Kashif ; Mok, KH ; Rehman, Saeed-Ur</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-b582t-8f9f1446dedff4c18f04be895a6d29a5e294b1b9854a4378115688702bbe266d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Aldehydes</topic><topic>Antiinfectives and antibacterials</topic><topic>Antimicrobial agents</topic><topic>Biological Chemistry</topic><topic>Bones</topic><topic>Cancer therapies</topic><topic>Chemistry</topic><topic>Chemistry/Food Science</topic><topic>Coumarin</topic><topic>Derivatives</topic><topic>Leukemia</topic><topic>Leukemias</topic><topic>Lipoxygenase</topic><topic>Melanoma</topic><topic>Nuclei</topic><topic>Research Article</topic><topic>Skin cancer</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rehman, Sadia</creatorcontrib><creatorcontrib>Ikram, Muhammad</creatorcontrib><creatorcontrib>Baker, Robert J</creatorcontrib><creatorcontrib>Zubair, Muhammad</creatorcontrib><creatorcontrib>Azad, Effat</creatorcontrib><creatorcontrib>Min, Soyoung</creatorcontrib><creatorcontrib>Riaz, Kashif</creatorcontrib><creatorcontrib>Mok, KH</creatorcontrib><creatorcontrib>Rehman, Saeed-Ur</creatorcontrib><collection>SpringerOpen</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Engineered Materials Abstracts</collection><collection>ProQuest Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>ProQuest Pharma Collection</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>ProQuest research library</collection><collection>Research Library (Corporate)</collection><collection>Materials Science Collection</collection><collection>Publicly Available Content (ProQuest)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>BMC chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rehman, Sadia</au><au>Ikram, Muhammad</au><au>Baker, Robert J</au><au>Zubair, Muhammad</au><au>Azad, Effat</au><au>Min, Soyoung</au><au>Riaz, Kashif</au><au>Mok, KH</au><au>Rehman, Saeed-Ur</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives</atitle><jtitle>BMC chemistry</jtitle><stitle>Chemistry Central Journal</stitle><addtitle>Chem Cent J</addtitle><date>2013-04-15</date><risdate>2013</risdate><volume>7</volume><issue>1</issue><spage>68</spage><epage>68</epage><pages>68-68</pages><artnum>68</artnum><issn>1752-153X</issn><issn>2661-801X</issn><eissn>2661-801X</eissn><eissn>1752-153X</eissn><abstract>Background
Coumarin and its derivatives are biologically very active. It was found that the enhanced activities are dependent on the coumarin nucleus. Biological significance of these compounds include anti-bacterial, anti-thrombotic and vasodilatory, anti-mutagenic, lipoxygenase and cyclooxygenase inhibition, scavenging of reactive oxygen species, and anti-tumourigenic. Our interest in medicinal chemistry of dicoumarol compounds have been developed by keeping in view the importance of coumarins along with its derivatives in medicinal chemistry. All the synthesized compounds were fully characterized by spectroscopic and analytical techniques and were screened for antimicrobial and U2OS bone cancer activities.
Results
4-hydroxycoumarin was derivatized by condensing with different aldehydes yielding the dicoumarol and translactonized products. Elemental analyses, ESI(+,−) MS,
1
H and
13
C{
1
H}-NMR, infrared spectroscopy and conductance studies were used to characterize the synthesized compounds which revealed the dicoumarol and dichromone structures for the compounds. The compounds were screened against U2OS cancerous cells and pathogenic micro organisms. The compounds with intermolecular H-bonding were found more active revealing a possible relationship among hydrogen bonding, cytotoxicity and antimicrobial activities.
Conclusion
Coumarin based drugs can be designed for the possible treatment of U2OS leukemia.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>23587363</pmid><doi>10.1186/1752-153X-7-68</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1752-153X |
| ispartof | BMC chemistry, 2013-04, Vol.7 (1), p.68-68, Article 68 |
| issn | 1752-153X 2661-801X 2661-801X 1752-153X |
| language | eng |
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| source | Full-Text Journals in Chemistry (Open access); Springer Nature - SpringerLink Journals - Fully Open Access ; Publicly Available Content (ProQuest); PubMed Central |
| subjects | Aldehydes Antiinfectives and antibacterials Antimicrobial agents Biological Chemistry Bones Cancer therapies Chemistry Chemistry/Food Science Coumarin Derivatives Leukemia Leukemias Lipoxygenase Melanoma Nuclei Research Article Skin cancer |
| title | Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives |
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