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Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives
Six new 4-hydroxycoumarin derivatives have been synthesized. They were characterized by UV–vis, IR, 1H NMR, 13C NMR, mass spectral data, elemental analysis, TLC and melting point determination. The new 4-hydroxycoumarin derivatives are studied by computational methods – DFT (B3LYP) and force field m...
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| Published in: | European journal of medicinal chemistry 2008-04, Vol.43 (4), p.694-706 |
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| Main Authors: | , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c456t-a9a6e656a35e39fab21dcb795e33f2ced8790512665b472d7cc372c8b88c214e3 |
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| container_end_page | 706 |
| container_issue | 4 |
| container_start_page | 694 |
| container_title | European journal of medicinal chemistry |
| container_volume | 43 |
| creator | Stanchev, Stancho Momekov, Georgi Jensen, Frank Manolov, Ilia |
| description | Six new 4-hydroxycoumarin derivatives have been synthesized. They were characterized by UV–vis, IR,
1H NMR,
13C NMR, mass spectral data, elemental analysis, TLC and melting point determination. The new 4-hydroxycoumarin derivatives are studied by computational methods – DFT (B3LYP) and force field methods (MM2 and OPLS), in order to optimize their geometry and calculate quantum-chemical properties and conformational analysis. Five new 4-hydroxycoumarin derivatives were tested for cytotoxic activity in two tumor cell lines – HL-60 and EJ. The obtained results are compared with the utilized anticancer drug melphalan. Two of these compounds – ethyl 2-[(3,4-dihydroxyphenyl)(4-hydroxy-2-oxo-2
H-chromen-3-yl)methyl]-3-oxobutanoate (
SS-
16) and ethyl 2-[(4-hydroxy-2-oxo-2
H-chromen-3-yl)(3-nitrophenyl)methyl]-3-oxobutanoate (
SS-
21) show comparatively good cytotoxic properties. Their activity is weaker than melphalan.
SS-
16 seems to be more active than
SS-
21.
[Display omitted] Six new coumarin derivatives have been synthesized. They are studied by computational methods and for in vitro cytotoxic activity. The most active is ethyl 2-[(3,4-dihydroxyphenyl)(4-hydroxy-2-oxo-2
H-chromen-3-yl)methyl]-3-oxobutanoate (
SS-
16). |
| doi_str_mv | 10.1016/j.ejmech.2007.05.005 |
| format | article |
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1H NMR,
13C NMR, mass spectral data, elemental analysis, TLC and melting point determination. The new 4-hydroxycoumarin derivatives are studied by computational methods – DFT (B3LYP) and force field methods (MM2 and OPLS), in order to optimize their geometry and calculate quantum-chemical properties and conformational analysis. Five new 4-hydroxycoumarin derivatives were tested for cytotoxic activity in two tumor cell lines – HL-60 and EJ. The obtained results are compared with the utilized anticancer drug melphalan. Two of these compounds – ethyl 2-[(3,4-dihydroxyphenyl)(4-hydroxy-2-oxo-2
H-chromen-3-yl)methyl]-3-oxobutanoate (
SS-
16) and ethyl 2-[(4-hydroxy-2-oxo-2
H-chromen-3-yl)(3-nitrophenyl)methyl]-3-oxobutanoate (
SS-
21) show comparatively good cytotoxic properties. Their activity is weaker than melphalan.
SS-
16 seems to be more active than
SS-
21.
[Display omitted] Six new coumarin derivatives have been synthesized. They are studied by computational methods and for in vitro cytotoxic activity. The most active is ethyl 2-[(3,4-dihydroxyphenyl)(4-hydroxy-2-oxo-2
H-chromen-3-yl)methyl]-3-oxobutanoate (
SS-
16).</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2007.05.005</identifier><identifier>PMID: 17614164</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>4-Hydroxycoumarins ; 4-Hydroxycoumarins - chemical synthesis ; 4-Hydroxycoumarins - chemistry ; 4-Hydroxycoumarins - pharmacology ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; Cell Survival - drug effects ; Computational Biology ; Cytotoxic activity ; DFT calculations ; Drug Screening Assays, Antitumor ; General aspects ; HL-60 Cells - drug effects ; Humans ; Knoevenagel reaction ; Medical sciences ; Melphalan - pharmacology ; Michael reaction ; Models, Molecular ; Molecular Structure ; MTT ; Pharmacology. Drug treatments ; Spectrophotometry, Infrared</subject><ispartof>European journal of medicinal chemistry, 2008-04, Vol.43 (4), p.694-706</ispartof><rights>2007 Elsevier Masson SAS</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c456t-a9a6e656a35e39fab21dcb795e33f2ced8790512665b472d7cc372c8b88c214e3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20263366$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17614164$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Stanchev, Stancho</creatorcontrib><creatorcontrib>Momekov, Georgi</creatorcontrib><creatorcontrib>Jensen, Frank</creatorcontrib><creatorcontrib>Manolov, Ilia</creatorcontrib><title>Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Six new 4-hydroxycoumarin derivatives have been synthesized. They were characterized by UV–vis, IR,
1H NMR,
13C NMR, mass spectral data, elemental analysis, TLC and melting point determination. The new 4-hydroxycoumarin derivatives are studied by computational methods – DFT (B3LYP) and force field methods (MM2 and OPLS), in order to optimize their geometry and calculate quantum-chemical properties and conformational analysis. Five new 4-hydroxycoumarin derivatives were tested for cytotoxic activity in two tumor cell lines – HL-60 and EJ. The obtained results are compared with the utilized anticancer drug melphalan. Two of these compounds – ethyl 2-[(3,4-dihydroxyphenyl)(4-hydroxy-2-oxo-2
H-chromen-3-yl)methyl]-3-oxobutanoate (
SS-
16) and ethyl 2-[(4-hydroxy-2-oxo-2
H-chromen-3-yl)(3-nitrophenyl)methyl]-3-oxobutanoate (
SS-
21) show comparatively good cytotoxic properties. Their activity is weaker than melphalan.
SS-
16 seems to be more active than
SS-
21.
[Display omitted] Six new coumarin derivatives have been synthesized. They are studied by computational methods and for in vitro cytotoxic activity. The most active is ethyl 2-[(3,4-dihydroxyphenyl)(4-hydroxy-2-oxo-2
H-chromen-3-yl)methyl]-3-oxobutanoate (
SS-
16).</description><subject>4-Hydroxycoumarins</subject><subject>4-Hydroxycoumarins - chemical synthesis</subject><subject>4-Hydroxycoumarins - chemistry</subject><subject>4-Hydroxycoumarins - pharmacology</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>Computational Biology</subject><subject>Cytotoxic activity</subject><subject>DFT calculations</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>HL-60 Cells - drug effects</subject><subject>Humans</subject><subject>Knoevenagel reaction</subject><subject>Medical sciences</subject><subject>Melphalan - pharmacology</subject><subject>Michael reaction</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>MTT</subject><subject>Pharmacology. Drug treatments</subject><subject>Spectrophotometry, Infrared</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNp9kE2L1EAQhhtR3HH1H4j0RU8m9neSi7AsfsGCB_XipelUKkwPSXrs7oybf28vM-jNU1HwvC9VDyEvOas54-bdocbDjLCvBWNNzXTNmH5EdrwxbSWFVo_JjgkhKy2kuiLPUjqwQhjGnpKrAnHFjdqRn9-2Je8x-fSWQpiPa3bZh8VNNOV12KhbBgpbDjnce6AOsj_5vNEw0gV_U1XttyGG-w3COrvoFzpg9KdSccL0nDwZ3ZTwxWVekx8fP3y__Vzdff305fbmrgKlTa5c5wwabZzUKLvR9YIP0Ddd2eQoAIe26Zjmwhjdq0YMDYBsBLR924LgCuU1eXPuPcbwa8WU7ewT4DS5BcOabMNUx7jsCqjOIMSQUsTRHqMvZ2-WM_vg1B7s2al9cGqZtsVYib269K_9jMO_0EViAV5fAJfATWN0C_j0lxNMGCmNKdz7M4fFxsljtAk8LuVFHxGyHYL__yV_ALylmDo</recordid><startdate>20080401</startdate><enddate>20080401</enddate><creator>Stanchev, Stancho</creator><creator>Momekov, Georgi</creator><creator>Jensen, Frank</creator><creator>Manolov, Ilia</creator><general>Elsevier Masson SAS</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>7X8</scope></search><sort><creationdate>20080401</creationdate><title>Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives</title><author>Stanchev, Stancho ; Momekov, Georgi ; Jensen, Frank ; Manolov, Ilia</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c456t-a9a6e656a35e39fab21dcb795e33f2ced8790512665b472d7cc372c8b88c214e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>4-Hydroxycoumarins</topic><topic>4-Hydroxycoumarins - chemical synthesis</topic><topic>4-Hydroxycoumarins - chemistry</topic><topic>4-Hydroxycoumarins - pharmacology</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>Computational Biology</topic><topic>Cytotoxic activity</topic><topic>DFT calculations</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>HL-60 Cells - drug effects</topic><topic>Humans</topic><topic>Knoevenagel reaction</topic><topic>Medical sciences</topic><topic>Melphalan - pharmacology</topic><topic>Michael reaction</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>MTT</topic><topic>Pharmacology. Drug treatments</topic><topic>Spectrophotometry, Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Stanchev, Stancho</creatorcontrib><creatorcontrib>Momekov, Georgi</creatorcontrib><creatorcontrib>Jensen, Frank</creatorcontrib><creatorcontrib>Manolov, Ilia</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>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Stanchev, Stancho</au><au>Momekov, Georgi</au><au>Jensen, Frank</au><au>Manolov, Ilia</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2008-04-01</date><risdate>2008</risdate><volume>43</volume><issue>4</issue><spage>694</spage><epage>706</epage><pages>694-706</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>Six new 4-hydroxycoumarin derivatives have been synthesized. They were characterized by UV–vis, IR,
1H NMR,
13C NMR, mass spectral data, elemental analysis, TLC and melting point determination. The new 4-hydroxycoumarin derivatives are studied by computational methods – DFT (B3LYP) and force field methods (MM2 and OPLS), in order to optimize their geometry and calculate quantum-chemical properties and conformational analysis. Five new 4-hydroxycoumarin derivatives were tested for cytotoxic activity in two tumor cell lines – HL-60 and EJ. The obtained results are compared with the utilized anticancer drug melphalan. Two of these compounds – ethyl 2-[(3,4-dihydroxyphenyl)(4-hydroxy-2-oxo-2
H-chromen-3-yl)methyl]-3-oxobutanoate (
SS-
16) and ethyl 2-[(4-hydroxy-2-oxo-2
H-chromen-3-yl)(3-nitrophenyl)methyl]-3-oxobutanoate (
SS-
21) show comparatively good cytotoxic properties. Their activity is weaker than melphalan.
SS-
16 seems to be more active than
SS-
21.
[Display omitted] Six new coumarin derivatives have been synthesized. They are studied by computational methods and for in vitro cytotoxic activity. The most active is ethyl 2-[(3,4-dihydroxyphenyl)(4-hydroxy-2-oxo-2
H-chromen-3-yl)methyl]-3-oxobutanoate (
SS-
16).</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>17614164</pmid><doi>10.1016/j.ejmech.2007.05.005</doi><tpages>13</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2008-04, Vol.43 (4), p.694-706 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70490139 |
| source | ScienceDirect Journals |
| subjects | 4-Hydroxycoumarins 4-Hydroxycoumarins - chemical synthesis 4-Hydroxycoumarins - chemistry 4-Hydroxycoumarins - pharmacology Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor Cell Survival - drug effects Computational Biology Cytotoxic activity DFT calculations Drug Screening Assays, Antitumor General aspects HL-60 Cells - drug effects Humans Knoevenagel reaction Medical sciences Melphalan - pharmacology Michael reaction Models, Molecular Molecular Structure MTT Pharmacology. Drug treatments Spectrophotometry, Infrared |
| title | Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives |
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