<?xml version="1.0" encoding="ISO-8859-1"?><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
<front>
<journal-meta>
<journal-id>0120-2804</journal-id>
<journal-title><![CDATA[Revista Colombiana de Química]]></journal-title>
<abbrev-journal-title><![CDATA[Rev.Colomb.Quim.]]></abbrev-journal-title>
<issn>0120-2804</issn>
<publisher>
<publisher-name><![CDATA[Departamento de Química,  Universidad Nacional de Colombia.]]></publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id>S0120-28042020000300013</article-id>
<article-id pub-id-type="doi">10.15446/rcq.v49n3.871519</article-id>
<title-group>
<article-title xml:lang="en"><![CDATA[Synthesis and cytotoxic evaluation of protoanemonin and three brominated derivatives]]></article-title>
<article-title xml:lang="es"><![CDATA[Síntesis y evaluación citotóxica de la protoanemonina y tres derivados bromados]]></article-title>
<article-title xml:lang="pt"><![CDATA[Síntese e avaliação citotóxica de protoanemonina e três derivados bromados]]></article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Villegas Pañeda]]></surname>
<given-names><![CDATA[Alejandra Guadalupe]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Ramírez Apan]]></surname>
<given-names><![CDATA[María Teresa]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
</contrib-group>
<aff id="Af1">
<institution><![CDATA[,Universidad Nacional Autónoma de México  ]]></institution>
<addr-line><![CDATA[ Estado de México]]></addr-line>
<country>Mexico</country>
</aff>
<aff id="Af2">
<institution><![CDATA[,Universidad Nacional Autónoma de México  ]]></institution>
<addr-line><![CDATA[ Ciudad de México]]></addr-line>
<country>Mexico</country>
</aff>
<pub-date pub-type="pub">
<day>00</day>
<month>12</month>
<year>2020</year>
</pub-date>
<pub-date pub-type="epub">
<day>00</day>
<month>12</month>
<year>2020</year>
</pub-date>
<volume>49</volume>
<numero>3</numero>
<fpage>13</fpage>
<lpage>18</lpage>
<copyright-statement/>
<copyright-year/>
<self-uri xlink:href="http://www.scielo.org.co/scielo.php?script=sci_arttext&amp;pid=S0120-28042020000300013&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.co/scielo.php?script=sci_abstract&amp;pid=S0120-28042020000300013&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.co/scielo.php?script=sci_pdf&amp;pid=S0120-28042020000300013&amp;lng=en&amp;nrm=iso"></self-uri><abstract abstract-type="short" xml:lang="en"><p><![CDATA[Abstract The protoanemonin, a natural furanone, was synthesized from (Z)-4-bromo-5-(bromomethylene)-furan-2(5H)-one by a reductive dehalogenation reaction with zinc. The 5-(dibromomethylene)-2(5H)-furanone and (E)-5-(bromomethylene)-2(5H)-furanone were also synthetized from levulinic acid bromination and acid promoted cyclization. The antiproliferative activity of all synthesized compounds against the human cancer cell lines PC-3 (prostate) and U-251 (glioblastoma) was investigated. The results showed that all the obtained furanones are more active than the reference drug cisplatin, with iC50 values in the range of 0.31 ± 0.02 to 7.30 ± 0.08 µM. However, (E)-5-(bromomethylene)-2(5H)-furanone, with a bromine atom in the double bond, was the most active, and demonstrated to be about 25-fold more active than the reference drug cisplatin.]]></p></abstract>
<abstract abstract-type="short" xml:lang="es"><p><![CDATA[Resumen La protoanemonina, una furanona de origen natural, fue sintetizada a partir de la (Z)-4-bromo-5-(bromometilen)-furan-2(5H)-ona mediante una deshalogenación reductiva con zinc. La 5-(dibromometilen)-2(5H)-furanona y la (E)-5-(bromometilen)-2(5H)-furanona también fueron sintetizadas a partir del ácido levulínico mediante bromación y posterior ciclación promovida por ácido. Se investigó la actividad antiproliferativa de todos los compuestos sintetizados en las líneas celulares de cáncer humano PC-3 (próstata) y U-251 (glioblastoma). Los resultados demostraron que todas las furanonas obtenidas son más activas que el fármaco de referencia cisplatino, con un intervalo de Ci50 de 0,31 ± 0,02 hasta 7,30 ± 0,08 µM. Sin embargo, la (E)-5-(bromometilen)-2(5H)-furanona, con un átomo de bromo en el doble enlace, demostró ser 25 veces más activa que el fármaco de referencia cisplatino.]]></p></abstract>
<abstract abstract-type="short" xml:lang="pt"><p><![CDATA[Resumo Protoanemonina, uma furanona natural, foi sintetizada de (Z)-4-bromo-5-(bromometileno)-furan-2(5H)-ona por desalógenação redutora do zinco. Também foram sintetizados 5-(Dibromometileno)-2(5H)-furanona e (E)-5-(Bromometileno)-2(5H)-furanona a partir da brominação com ácido levulínico e ciclização promovida por ácido. Foi investigada a atividade antiproliferativa de todos os compostos sintetizados nas linhas celulares humanas de câncer PC-3 (próstata) e U-251 (glioblastoma). Os resultados mostram que todos os furanonas obtidos são mais ativos que a cisplatina do medicamento de referência, com intervalo Ci50 de 0,31 ± 0,02 até 7,30 ± 0,08 µM. Entretanto, a mais ativa foi a (E)-5-(Bromometileno)-2(5H)-furanona, que com um átomo de bromo na dupla ligação exocíclica, provou ser 25 vezes mais ativa que a medicamento de referência cisplatina.]]></p></abstract>
<kwd-group>
<kwd lng="en"><![CDATA[Cytotoxic]]></kwd>
<kwd lng="en"><![CDATA[furanone]]></kwd>
<kwd lng="en"><![CDATA[protoanemonin]]></kwd>
<kwd lng="en"><![CDATA[synthesis]]></kwd>
<kwd lng="es"><![CDATA[citotóxico]]></kwd>
<kwd lng="es"><![CDATA[furanona]]></kwd>
<kwd lng="es"><![CDATA[protoanemonina]]></kwd>
<kwd lng="es"><![CDATA[síntesis]]></kwd>
<kwd lng="pt"><![CDATA[citotóxico]]></kwd>
<kwd lng="pt"><![CDATA[furanona]]></kwd>
<kwd lng="pt"><![CDATA[protoanemonina]]></kwd>
<kwd lng="pt"><![CDATA[síntese]]></kwd>
</kwd-group>
</article-meta>
</front><back>
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