Lactones

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David W. Lupton - One of the best experts on this subject based on the ideXlab platform.

Santos, Wagner Wendell Cruz Dos - One of the best experts on this subject based on the ideXlab platform.

  • Síntese e avaliação farmacológica de lactonas de 14 - membros planejadas a partir dos lipídeos fenólicos não - isoprenóides de anacardium occidentale
    2010
    Co-Authors: Santos, Wagner Wendell Cruz Dos
    Abstract:

    O liquido da casca da castanha (LCC) é uma importante fonte de lipídios fenólicos não isoprenóides, por exemplo, os ácidos anacárdicos, cardóis, cardanóis e metil cardóis. Devido apresentarem caráter aromático e acíclico associado à existência de grupos funcionais ligados ao anel aromático e a presença de múltiplas insaturações na cadeia alifática, esses lipídios do LCC se configuram como matéria prima versátil para diversas transformações químicas. O presente trabalho descreve a síntese de lactonas de 14-membros fundidas ao anel aromático, consideradas como análogos da zearalenona, a partir dos ácidos anacárdicos. Adicionalmente, neste trabalho é apresentada a elucidação estrutural de todas as novas entidades químicas, os resultados dos estudos teóricos de conformação e mínimos globais de energia de um grupo de lactonas e a avaliação da atividade biológica frente a larvas de Artemia salina e citoxicidade em três linhagens de células tumorais (HCT-8, HL60 e SF295) das lactonas preparadas. ______________________________________________________________________________________ ABSTRACTThe cashew nut shell liquid (CNSL) is an important source of non-isoprenoid phenolic lipids, such as anacardic acid, cardol, cardanol and methylcardol. Due to its structure – an aromatic ring with several functional groups and double bonds on the aliphatic side chain –, these phenolic lipids are versatile raw materials for several chemical transformations. The present study describes the preparation of novel Lactones which feature an aromatic ring fused with a core 14-membered lactone ring, characterized as analogues of the zearalenone, starting from anacardic acids. Also presented are the structural elucidations of all new chemical entities, the results of the teorical study of the conformation and minimum global energy of some Lactones and the evaluation of biological activity such as toxicity against larvae of Artemia salina, cytotoxic in three lines of tumor cells (HCT-8, HL60 e SF295) by the synthetized Lactones

  • Síntese e avaliação farmacológica de lactonas de 14 - membros planejadas a partir dos lipídeos fenólicos não - isoprenóides de anacardium occidentale
    2008
    Co-Authors: Santos, Wagner Wendell Cruz Dos
    Abstract:

    Dissertação (mestrado)—Universidade de Brasília, Instituto de Química, 2008.O liquido da casca da castanha (LCC) é uma importante fonte de lipídios fenólicos não isoprenóides, por exemplo, os ácidos anacárdicos, cardóis, cardanóis e metil cardóis. Devido apresentarem caráter aromático e acíclico associado à existência de grupos funcionais ligados ao anel aromático e a presença de múltiplas insaturações na cadeia alifática, esses lipídios do LCC se configuram como matéria prima versátil para diversas transformações químicas. O presente trabalho descreve a síntese de lactonas de 14-membros fundidas ao anel aromático, consideradas como análogos da zearalenona, a partir dos ácidos anacárdicos. Adicionalmente, neste trabalho é apresentada a elucidação estrutural de todas as novas entidades químicas, os resultados dos estudos teóricos de conformação e mínimos globais de energia de um grupo de lactonas e a avaliação da atividade biológica frente a larvas de Artemia salina e citoxicidade em três linhagens de células tumorais (HCT-8, HL60 e SF295) das lactonas preparadas. ______________________________________________________________________________________ ABSTRACTThe cashew nut shell liquid (CNSL) is an important source of non-isoprenoid phenolic lipids, such as anacardic acid, cardol, cardanol and methylcardol. Due to its structure – an aromatic ring with several functional groups and double bonds on the aliphatic side chain –, these phenolic lipids are versatile raw materials for several chemical transformations. The present study describes the preparation of novel Lactones which feature an aromatic ring fused with a core 14-membered lactone ring, characterized as analogues of the zearalenone, starting from anacardic acids. Also presented are the structural elucidations of all new chemical entities, the results of the teorical study of the conformation and minimum global energy of some Lactones and the evaluation of biological activity such as toxicity against larvae of Artemia salina, cytotoxic in three lines of tumor cells (HCT-8, HL60 e SF295) by the synthetized Lactones

Lisa Candish - One of the best experts on this subject based on the ideXlab platform.

Carlos Kleber Zago De Andrade - One of the best experts on this subject based on the ideXlab platform.

  • Preparação de lactonas via formação de ligação carbono-carbono : sinteses formais de (-)-serriconina, (+)-lactona de Prelog-Djerassi e estudos visando a sintese do (+)-10-desoximetinolideo
    2017
    Co-Authors: Carlos Kleber Zago De Andrade
    Abstract:

    Resumo: Uma metodologia de obtenção de d-lactonas foi desenvolvida em que substratos, cujos centros assimétricos são controlados por reações de condensação aldólica estereosseletiva, sofrem alquilação intramolecular e o anel lactônico é formado via ligação C-C. Nos estudos iniciais de desenvolvimento da metodologia (capítulo I), lactonas modelos foram obtidas dos substratos 19, 20, 22 e 23. A rota sintética envolveu 5 etapas, com rendimento total na faixa de 38-49%. As melhores condições para a reação de formação das d-lactonas envolveram o uso de enolatos de potássio e o rendimento da ciclização atingiu 78%. A metodologia desenvolvida foi aplicada na síntese de d-lactonas com interesse sintético relevado. Assim, a d-lactona 64, precursora do feromônio serricornina, foi sintetizada em 6 etapas e 26% de rendimento total, empregando-se condensação aldólica com enolatos de boro para o controle dos centros assimétricos (capítulo II). A lactona 166, um equivalente sintético da lactona de Prelog-Djerassi, foi obtida tanto em sua forma racêmica (capítulo lII) quanto quiral (capítulo IV), empregando-se condensação aldólica com sililcetenotioacetais no primeiro caso e enolato de boro no segundo. A lactona 166 racêmica foi obtida em 7 etapas e 25% de rendimento total e a quiral, em 8 etapas e 22% de rendimento total. A lactona 166 quiral obtida na síntese anterior foi usada como intermediário nos estudos realizados de preparação de um dos fragmentos do (+)-10-desoximetinolídeo, aglicona do antibiótico macrolídico (+)-10-desoximetimicina (capítulo V). O outro fragmento, o iodeto vinílico 300, foi obtido em 5 etapas e 26% de rendimento total. Tentativas de acoplamento dos 2 fragmentos foram impossibilitadas pela não obtenção do cetofosfonato 279, necessário para a reação de fechamento do anel macrocíclico (reação de Wittig-Horner). A macrolactona modelo de 12 membros 318 foi obtida por reação intramolecular entre um aldeído e um iodeto vinílico, mediada por Cr/Ni, em 63% de rendimento (capítulo VI). O sucesso desta ciclização possibilita sua utilização na síntese de antibióticos macrolídicos como método alternativo aos métodos até então utilizados.Abstract: A methodology for the preparation of d-Lactones was developed where substrates with asymmetric centers controlled by aldol condensation reactions suffer intramolecular alkylation resulting formation of the lactonic ring via a C-C bonding formation process. ln the initial studies concerning the development of the methodology (chapter I), model Lactones were obtained from substrates 19, 20, 22 and 23. The synthetic route involved 5 steps, with overall yield ranging between 38-49%. The best reaction conditions were achieved with potassium enolates and the cyclization yield was 78%. The developed methodology was applied to the synthesis of relevant d-Lactones. Lactone 64, precursor of the sex pheromone serricornine 36, was prepared in 6 steps and 26% overall yield, employing aldol condensation with boron enolates to assure the correct stereochemistry of the asymmetric centers (chapter lI). Lactone 166, a synthetic equivalent of the Prelog-Djerassi lactonic acid, was obtained either in the racemic (chapter IlI) or chiral form (chapter IV), employing aldol condensation with silyl ketene acetals in the first case and boron enolate in the second case. Racemic 166 was prepared in 7 steps and 25% overall yield and chiral 166 in 8 steps and 22% overall yield. Chiral 166 was explored as a synthetic intermediate in the preparation of the C(1)-C(8) fragment of (+)-10-desoxymethynolide, aglicon of the macrolide antibiotic (+)-10-desoxymethymicyn (chapter V). Vinyl iodide 300, the C(9)-C(13) fragment, was obtained in 5 steps and 26% overall yield. Coupling of these 2 fragments was not possible due to the difficulties in the preparation of ketophosphonate 279, the ultimate precursor for the postulated macrocyclization via a Wittig-Horner reaction. The 12-membered model macrolactone 318 was obtained via intramolecular reaction between an aldehyde and a vinyl iodide, mediated by Cr/Ni, in 63% yield (chapter V). The success of this cyclization allows one to consider it as an alternative method for the construction of these macrolide antibiotics

  • Preparação de lactonas via formação de ligação carbono-carbono : sinteses formais de (-)-serriconina, (+)-lactona de Prelog-Djerassi e estudos visando a sintese do (+)-10-desoximetinolideo
    Universidade Estadual de Campinas . Instituto de Quimica, 1996
    Co-Authors: Carlos Kleber Zago De Andrade
    Abstract:

    Uma metodologia de obtenção de d-lactonas foi desenvolvida em que substratos, cujos centros assimétricos são controlados por reações de condensação aldólica estereosseletiva, sofrem alquilação intramolecular e o anel lactônico é formado via ligação C-C. Nos estudos iniciais de desenvolvimento da metodologia (capítulo I), lactonas modelos foram obtidas dos substratos 19, 20, 22 e 23. A rota sintética envolveu 5 etapas, com rendimento total na faixa de 38-49%. As melhores condições para a reação de formação das d-lactonas envolveram o uso de enolatos de potássio e o rendimento da ciclização atingiu 78%. A metodologia desenvolvida foi aplicada na síntese de d-lactonas com interesse sintético relevado. Assim, a d-lactona 64, precursora do feromônio serricornina, foi sintetizada em 6 etapas e 26% de rendimento total, empregando-se condensação aldólica com enolatos de boro para o controle dos centros assimétricos (capítulo II). A lactona 166, um equivalente sintético da lactona de Prelog-Djerassi, foi obtida tanto em sua forma racêmica (capítulo lII) quanto quiral (capítulo IV), empregando-se condensação aldólica com sililcetenotioacetais no primeiro caso e enolato de boro no segundo. A lactona 166 racêmica foi obtida em 7 etapas e 25% de rendimento total e a quiral, em 8 etapas e 22% de rendimento total. A lactona 166 quiral obtida na síntese anterior foi usada como intermediário nos estudos realizados de preparação de um dos fragmentos do (+)-10-desoximetinolídeo, aglicona do antibiótico macrolídico (+)-10-desoximetimicina (capítulo V). O outro fragmento, o iodeto vinílico 300, foi obtido em 5 etapas e 26% de rendimento total. Tentativas de acoplamento dos 2 fragmentos foram impossibilitadas pela não obtenção do cetofosfonato 279, necessário para a reação de fechamento do anel macrocíclico (reação de Wittig-Horner). A macrolactona modelo de 12 membros 318 foi obtida por reação intramolecular entre um aldeído e um iodeto vinílico, mediada por Cr/Ni, em 63% de rendimento (capítulo VI). O sucesso desta ciclização possibilita sua utilização na síntese de antibióticos macrolídicos como método alternativo aos métodos até então utilizados.A methodology for the preparation of d-Lactones was developed where substrates with asymmetric centers controlled by aldol condensation reactions suffer intramolecular alkylation resulting formation of the lactonic ring via a C-C bonding formation process. ln the initial studies concerning the development of the methodology (chapter I), model Lactones were obtained from substrates 19, 20, 22 and 23. The synthetic route involved 5 steps, with overall yield ranging between 38-49%. The best reaction conditions were achieved with potassium enolates and the cyclization yield was 78%. The developed methodology was applied to the synthesis of relevant d-Lactones. Lactone 64, precursor of the sex pheromone serricornine 36, was prepared in 6 steps and 26% overall yield, employing aldol condensation with boron enolates to assure the correct stereochemistry of the asymmetric centers (chapter lI). Lactone 166, a synthetic equivalent of the Prelog-Djerassi lactonic acid, was obtained either in the racemic (chapter IlI) or chiral form (chapter IV), employing aldol condensation with silyl ketene acetals in the first case and boron enolate in the second case. Racemic 166 was prepared in 7 steps and 25% overall yield and chiral 166 in 8 steps and 22% overall yield. Chiral 166 was explored as a synthetic intermediate in the preparation of the C(1)-C(8) fragment of (+)-10-desoxymethynolide, aglicon of the macrolide antibiotic (+)-10-desoxymethymicyn (chapter V). Vinyl iodide 300, the C(9)-C(13) fragment, was obtained in 5 steps and 26% overall yield. Coupling of these 2 fragments was not possible due to the difficulties in the preparation of ketophosphonate 279, the ultimate precursor for the postulated macrocyclization via a Wittig-Horner reaction. The 12-membered model macrolactone 318 was obtained via intramolecular reaction between an aldehyde and a vinyl iodide, mediated by Cr/Ni, in 63% yield (chapter V). The success of this cyclization allows one to consider it as an alternative method for the construction of these macrolide antibiotics

Daise Lopes - One of the best experts on this subject based on the ideXlab platform.

  • 14 methylpentadecano 15 lactone muscolide a new macrocyclic lactone from the oil of angelica archangelica l
    Chemistry & Biodiversity, 2004
    Co-Authors: Daise Lopes, Herbert Strobl, P Kolodziejczyk
    Abstract:

    The chemical composition of seed and root oils from Angelica archangelica L. was investigated. Analyses were performed by GC/MS and GC using two columns of different polarities (polyethylene glycol (DB-Wax) and 5% phenyl/95% polydimethylsiloxane (HP-5)), for the separation of several co-eluting components. A total of 58 compounds were identified, accounting for 96.3% (seed) and 93.5% (root) of the oils, respectively. A high content of beta-phellandrene (74.7%) was found in Angelica seed oil. Root oil contained a larger amount of macrocyclic Lactones (1.3%) in comparison to the seed oil (0.4%). Different harvest dates produced only slight changes in the root-oil composition. In root oil harvested in summer, the beta-phellandrene content increased by ca. 36%, but no significant changes in the relative compositions of other components were observed. Fresh root oils were collected in five fractions (constant time intervals) during steam distillation (see Table). The highest-boiling fraction contained 9.3% of macrocyclic Lactones such as tridecano-13-lactone (5.0%), 12-methyltridecano-13-lactone (0.4%), tetradecano-14-lactone (0.1%), pentadecano-15-lactone (3.5%), 14-methylpentadecano-15-lactone (1; trace), hexadecano-16-lactone (trace), and heptadecano-17-lactone (0.2%). This is the first report of the occurrence of 14-methylpentadecano-15-lactone (muscolide; 1) in a natural product.

  • 14 methylpentadecano 15 lactone muscolide a new macrocyclic lactone from the oil of angelica archangelica l
    Chemistry & Biodiversity, 2004
    Co-Authors: Daise Lopes, Herbert Strobl, P Kolodziejczyk
    Abstract:

    The chemical composition of seed and root oils from Angelica archangelicaL. was investigated. Analyses were performed by GC/MS and GC using two columns of different polarities (polyethylene glycol (DB-Wax) and 5% phenyl/95% polydimethylsiloxane (HP-5)), for the separation of several co-eluting components. A total of 58 compounds were identified, accounting for 96.3% (seed) and 93.5% (root) of the oils, respectively. A high content of β-phellandrene (74.7%) was found in Angelica seed oil. Root oil contained a larger amount of macrocyclic Lactones (1.3%) in comparison to the seed oil (0.4%). Different harvest dates produced only slight changes in the root-oil composition. In root oil harvested in summer, the β-phellandrene content increased by ca. 36%, but no significant changes in the relative compositions of other components were observed. Fresh root oils were collected in five fractions (constant time intervals) during steam distillation (see Table). The highest-boiling fraction contained 9.3% of macrocyclic Lactones such as tridecano-13-lactone (5.0%), 12-methyltridecano-13-lactone (0.4%), tetradecano-14-lactone (0.1%), pentadecano-15-lactone (3.5%), 14-methylpentadecano-15-lactone (1; trace), hexadecano-16-lactone (trace), and heptadecano-17-lactone (0.2%). This is the first report of the occurrence of 14-methylpentadecano-15-lactone (muscolide; 1) in a natural product.

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