Base de dados : MEDLINE
Pesquisa : D02.455.426.392 [Categoria DeCS]
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[PMID]:28010882
[Au] Autor:Shirneshan G; Bakhtiari AR; Memariani M
[Ad] Endereço:Department of Environmental Sciences, Faculty of Natural Resources and Marine Science, Tarbiat Modares University, P.O. Box 46414-356, Noor, Mazandaran, Iran.
[Ti] Título:Identifying the source of petroleum pollution in sediment cores of southwest of the Caspian Sea using chemical fingerprinting of aliphatic and alicyclic hydrocarbons.
[So] Source:Mar Pollut Bull;115(1-2):383-390, 2017 Feb 15.
[Is] ISSN:1879-3363
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:In this study, the concentration and sources of aliphatic and petroleum markers were investigated in 105 samples of Anzali, Rezvanshahr and Astara cores from the southwest of Caspian Sea. Petroleum importation was diagnosed as a main source in most depths of cores by the results of unresolved complex mixture, carbon preference index and hopanes and steranes. From the chemical diagnostic parameters, petroleum inputs in sediment of cores were determined to be different during years and the sources of hydrocarbons in some sections differed than Anzali and Turkmenistan and Azerbaijan oils. Diagenic ratios in most sediments of upper and middle sections in Astara core were determined to be highly similar to those of Azerbaijan oil, while the presence of Turkmenistan and Anzali oils were detected in a few sections of Anzali and Rezvanshahr cores and only five layers of downer section in Anzali core, respectively.
[Mh] Termos MeSH primário: Sedimentos Geológicos/química
Hidrocarbonetos/análise
Poluição por Petróleo/análise
Poluentes Químicos da Água/análise
[Mh] Termos MeSH secundário: Monitoramento Ambiental
Hidrocarbonetos Alicíclicos/análise
Oceanos e Mares
Petróleo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Hydrocarbons); 0 (Hydrocarbons, Alicyclic); 0 (Petroleum); 0 (Water Pollutants, Chemical)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:171106
[Lr] Data última revisão:
171106
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161225
[St] Status:MEDLINE


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[PMID]:27121188
[Au] Autor:Li W; Li X; Zhang B; Gao C; Chen Y; Jiang Y
[Ti] Título:Current Progresses and Trends in the Development of Progesterone Receptor Modulators.
[So] Source:Curr Med Chem;23(23):2507-54, 2016.
[Is] ISSN:1875-533X
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:The progesterone receptor (PR) is a ligand-activated steroid receptor in the nuclear receptor (NR) superfamily of transcription factor. Besides gynecological and obstetrical indications, the involvement/mechanism of PR in many other diseases, such as oncology, neurology, immunology, etc. has been revealed and studied in recent decades. Therapeutic agents that selectively activate or inhibit PR have been developed. PR agonists have generally been used in oral contraception and postmenopausal hormone replacement therapy (HRT), typically in combination with estrogens. PR antagonists and selective PR modulators (SPRMs) can be useful therapies for hormone dependent breast and prostate cancers, nonmalignant chronic conditions such as fibroids, and endometriosis. This review provides an overview and detailed discussions about the recent development of chemical structures of the PR ligands, their structural characteristics (particularly those contributing to their activity and selectivity), in vitro/in vivo studies and clinical trial outcomes, and the synthetic methodologies.
[Mh] Termos MeSH primário: Ligantes
Receptores de Progesterona/metabolismo
[Mh] Termos MeSH secundário: Boranos/síntese química
Boranos/química
Boranos/metabolismo
Cumarínicos/síntese química
Cumarínicos/química
Cumarínicos/metabolismo
Compostos Heterocíclicos de Anéis Fundidos/síntese química
Compostos Heterocíclicos de Anéis Fundidos/química
Compostos Heterocíclicos de Anéis Fundidos/metabolismo
Terapia de Reposição Hormonal
Seres Humanos
Hidrocarbonetos Alicíclicos/síntese química
Hidrocarbonetos Alicíclicos/química
Hidrocarbonetos Alicíclicos/metabolismo
Indóis/síntese química
Indóis/química
Indóis/metabolismo
Ligação Proteica
Receptores de Progesterona/agonistas
Receptores de Progesterona/antagonistas & inibidores
Esteroides/síntese química
Esteroides/química
Esteroides/metabolismo
Vitamina D/análogos & derivados
Vitamina D/síntese química
Vitamina D/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (Boranes); 0 (Coumarins); 0 (Heterocyclic Compounds, Fused-Ring); 0 (Hydrocarbons, Alicyclic); 0 (Indoles); 0 (Ligands); 0 (Receptors, Progesterone); 0 (Steroids); 1406-16-2 (Vitamin D); A4VZ22K1WT (coumarin)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:170206
[Lr] Data última revisão:
170206
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160429
[St] Status:MEDLINE


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[PMID]:26892182
[Au] Autor:Young LM; Geldenhuys WJ; Domingo OC; Malan SF; Van der Schyf CJ
[Ad] Endereço:Department of Pharmaceutical Sciences, Northeast Ohio Medical University, Rootstown, OH, USA.
[Ti] Título:Synthesis and Biological Evaluation of Pentacycloundecylamines and Triquinylamines as Voltage-Gated Calcium Channel Blockers.
[So] Source:Arch Pharm (Weinheim);349(4):252-67, 2016 Apr.
[Is] ISSN:1521-4184
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:Preclinical studies for neurodegenerative diseases have shown a multi-targeted approach to be successful in the treatment of these complex disorders with several pathoetiological pathways. Polycyclic compounds, such as NGP1-01 (7a), have demonstrated the ability to target multiple mechanisms of the complex etiology and are referred to as multifunctional compounds. These compounds have served as scaffolds with the ability to attenuate Ca(2+) overload and excitotoxicity through several pathways. In this study, our focus was on mitigating Ca(2+) overload through the L-type calcium channels (LTCC). Here, we report the synthesis and biological evaluation of several novel polycyclic compounds. We determined the IC50 values for both the pentacycloundecylamines and the triquinylamines by means of a high-throughput fluorescence calcium flux assay utilizing Fura-2/AM. The potential of these compounds to offer protection against hydrogen peroxide-induced cell death was also evaluated. Overall, 8-benzylamino-8,11-oxapentacyclo[5.4.0.0(2,6) .0(3,10) .0(5,9) ]undecane (NGP1-01, 7a) had the most favorable pharmacological profile with an IC50 value of 86 µM for LTCC inhibition and significant reduction of hydrogen peroxide-induced cell death. In general, the triquinylamines were more active as LTCC blockers than the oxa-pentacycloundecylamines. The aza-pentacycloundecylamines were potent LTCC inhibitors, with 8-hydroxy-N-phenylethyl-8,11-azapentacyclo[5.4.0.0(2,6) .0(3,10) .0(5,9) ]undecane (8b) also able to offer significant protection in the cell viability assays.
[Mh] Termos MeSH primário: Aminas/química
Bloqueadores dos Canais de Cálcio/química
Canais de Cálcio Tipo L/metabolismo
Cálcio/metabolismo
Hidrocarbonetos Alicíclicos/química
Quinonas/química
[Mh] Termos MeSH secundário: Aminas/síntese química
Aminas/farmacologia
Animais
Apoptose/efeitos dos fármacos
Bloqueadores dos Canais de Cálcio/síntese química
Bloqueadores dos Canais de Cálcio/farmacologia
Sobrevivência Celular/efeitos dos fármacos
Hidrocarbonetos Alicíclicos/síntese química
Hidrocarbonetos Alicíclicos/farmacologia
Peróxido de Hidrogênio/farmacologia
L-Lactato Desidrogenase/metabolismo
Células PC12
Quinonas/síntese química
Quinonas/farmacologia
Ratos
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Amines); 0 (Calcium Channel Blockers); 0 (Calcium Channels, L-Type); 0 (Hydrocarbons, Alicyclic); 0 (Quinones); BBX060AN9V (Hydrogen Peroxide); EC 1.1.1.27 (L-Lactate Dehydrogenase); SY7Q814VUP (Calcium)
[Em] Mês de entrada:1701
[Cu] Atualização por classe:170714
[Lr] Data última revisão:
170714
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160220
[St] Status:MEDLINE
[do] DOI:10.1002/ardp.201500293


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[PMID]:26854865
[Au] Autor:Candeias NR; Paterna R; Gois PM
[Ad] Endereço:Department of Chemistry and Bioengineering, Tampere University of Technology , Korkeakoulunkatu 8, Tampere, FI-33101 Finland.
[Ti] Título:Homologation Reaction of Ketones with Diazo Compounds.
[So] Source:Chem Rev;116(5):2937-81, 2016 Mar 09.
[Is] ISSN:1520-6890
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:This review covers the addition of diazo compounds to ketones to afford homologated ketones, either in the presence or in the absence of promoters or catalysts. Reactions with diazoalkanes, aryldiazomethanes, trimethylsilyldiazomethane, α-diazo esters, and disubstituted diazo compounds are covered, commenting on the complex regiochemistry of the reaction and the nature of the catalysts and promoters. The recent reports on the enantioselective version of ketone homologation reactions are gathered in one section, followed by reports on the use of cyclic ketones ring expansion in total synthesis. Although the first reports of this reaction appeared in the literature almost one century ago, the recent achievements, in particular, for the asymmetric version, forecast the development of new breakthroughs in the synthetically valuable field of diazo chemistry.
[Mh] Termos MeSH primário: Compostos de Diazônio/química
Cetonas/química
[Mh] Termos MeSH secundário: Técnicas de Química Sintética
Compostos Heterocíclicos/síntese química
Hidrocarbonetos Alicíclicos/síntese química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T; REVIEW
[Nm] Nome de substância:
0 (Diazonium Compounds); 0 (Heterocyclic Compounds); 0 (Hydrocarbons, Alicyclic); 0 (Ketones)
[Em] Mês de entrada:1612
[Cu] Atualização por classe:161230
[Lr] Data última revisão:
161230
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160209
[St] Status:MEDLINE
[do] DOI:10.1021/acs.chemrev.5b00381


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[PMID]:26644508
[Au] Autor:Jetter R; Riederer M
[Ad] Endereço:Department of Botany, University of British Columbia, Vancouver, British Columbia, Canada V6T 1Z4 (R.J.);Department of Chemistry, University of British Columbia, Vancouver, British Columbia, Canada V6T 1Z1 (R.J.); andUniversität Würzburg, Julius-von-Sachs-Institut für Biowissenschaften, D-97082 Wuerzburg, Germany (M.R.) reinhard.jetter@botany.ubc.ca.
[Ti] Título:Localization of the Transpiration Barrier in the Epi- and Intracuticular Waxes of Eight Plant Species: Water Transport Resistances Are Associated with Fatty Acyl Rather Than Alicyclic Components.
[So] Source:Plant Physiol;170(2):921-34, 2016 Feb.
[Is] ISSN:1532-2548
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Plant cuticular waxes play a crucial role in limiting nonstomatal water loss. The goal of this study was to localize the transpiration barrier within the layered structure of cuticles of eight selected plant species and to put its physiological function into context with the chemical composition of the intracuticular and epicuticular wax layers. Four plant species (Tetrastigma voinierianum, Oreopanax guatemalensis, Monstera deliciosa, and Schefflera elegantissima) contained only very-long-chain fatty acid (VLCFA) derivatives such as alcohols, alkyl esters, aldehydes, and alkanes in their waxes. Even though the epicuticular and intracuticular waxes of these species had very similar compositions, only the intracuticular wax was important for the transpiration barrier. In contrast, four other species (Citrus aurantium, Euonymus japonica, Clusia flava, and Garcinia spicata) had waxes containing VLCFA derivatives, together with high percentages of alicyclic compounds (triterpenoids, steroids, or tocopherols) largely restricted to the intracuticular wax layer. In these species, both the epicuticular and intracuticular waxes contributed equally to the cuticular transpiration barrier. We conclude that the cuticular transpiration barrier is primarily formed by the intracuticular wax but that the epicuticular wax layer may also contribute to it, depending on species-specific cuticle composition. The barrier is associated mainly with VLCFA derivatives and less (if at all) with alicyclic wax constituents. The sealing properties of the epicuticular and intracuticular layers were not correlated with other characteristics, such as the absolute wax amounts and thicknesses of these layers.
[Mh] Termos MeSH primário: Ácidos Graxos/metabolismo
Hidrocarbonetos Alicíclicos/metabolismo
Epiderme Vegetal/fisiologia
Transpiração Vegetal/fisiologia
Água/metabolismo
Ceras/metabolismo
[Mh] Termos MeSH secundário: Transporte Biológico
Cromatografia Gasosa
Epiderme Vegetal/ultraestrutura
Polímeros/metabolismo
Especificidade da Espécie
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Fatty Acids); 0 (Hydrocarbons, Alicyclic); 0 (Polymers); 0 (Waxes); 059QF0KO0R (Water)
[Em] Mês de entrada:1610
[Cu] Atualização por classe:170220
[Lr] Data última revisão:
170220
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:151209
[St] Status:MEDLINE
[do] DOI:10.1104/pp.15.01699


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[PMID]:26275226
[Au] Autor:Hertkorn N; Harir M; Schmitt-Kopplin P
[Ad] Endereço:Helmholtz Zentrum Muenchen, German Research Center for Environmental Health, Research Unit Analytical Biogeochemistry (BGC), Ingolstaedter Landstrasse 1, Neuherberg, Germany.
[Ti] Título:Nontarget analysis of Murchison soluble organic matter by high-field NMR spectroscopy and FTICR mass spectrometry.
[So] Source:Magn Reson Chem;53(9):754-68, 2015 Sep.
[Is] ISSN:1097-458X
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:High-field NMR spectra of Murchison meteorite methanolic extracts revealed primarily aliphatic extraterrestrial organic matter (EOM) with near statistical branching of commonly C(3-5) units separated by heteroatoms and aromatic units. The ratios of CCH, OCH and C(sp2)H units were 89 : 8 : 3, whereas carbon-based aliphatic chain termination was in the order methyl > -COOH > -CH(CH3)COOH. Aliphatic methine carbon was abundant, but its weak NMR signatures were primarily deduced from JRES (J-resolved) NMR spectra. Carbon NMR spectra were dominated by methylene and methyl carbon; strong apodization revealed methine carbon, of which about 20% was aromatic. Extrapolation provided 5-7% aromatic carbon present in Murchison soluble EOM. Compositional heterogeneity in Murchison methanolic extracts was visible in NMR and Fourier transform ion cyclotron (FTICR) mass spectra obtained from a few cubic millimeters of solid Murchison meteorite; increasing sample size enhanced uniformity of NMR spectra. Intrinsic chemical diversity and pH-dependent chemical shift variance contributed to the disparity of NMR spectra. FTICR mass spectra provided distinct clustering of CHO/CHOS and CHNO/CHNOS molecular series and confirmed the prevalence of aliphatic/alicyclic (73%) over single aromatic (21%) and polyaromatic (6%) molecular compositions, suggesting extensive aliphatic substitution of aromatic units as proposed by NMR. Murchison soluble EOM molecules feature a center with enhanced aromatic and heteroatom content, which provides rather diffuse and weak NMR signatures resulting from a huge overall chemical diversity. The periphery of Murchison EOM molecules comprises flexible branched aliphatic chains and aliphatic carboxylic acids. These project on narrow ranges of chemical shift, facilitating observation in one-dimensional and two-dimensional NMR spectra. The conformational entropy provided by these flexible surface moieties facilitates the solubility of EOM.
[Mh] Termos MeSH primário: Carbono/análise
Ácidos Carboxílicos/isolamento & purificação
Meio Ambiente Extraterreno/química
Hidrocarbonetos Alicíclicos/isolamento & purificação
Hidrocarbonetos Aromáticos/isolamento & purificação
Meteoroides
[Mh] Termos MeSH secundário: Ciclotrons
Entropia
Análise de Fourier
Concentração de Íons de Hidrogênio
Espectroscopia de Ressonância Magnética/métodos
Metanol/química
Solventes/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Carboxylic Acids); 0 (Hydrocarbons, Alicyclic); 0 (Hydrocarbons, Aromatic); 0 (Solvents); 7440-44-0 (Carbon); Y4S76JWI15 (Methanol)
[Em] Mês de entrada:1605
[Cu] Atualização por classe:150815
[Lr] Data última revisão:
150815
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150815
[St] Status:MEDLINE
[do] DOI:10.1002/mrc.4249


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[PMID]:25721263
[Au] Autor:Ma L; Dong JY
[Ad] Endereço:CAS Key Laboratory of Engineering Plastics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China; University of Chinese Academy of Sciences, Beijing, 100049, China.
[Ti] Título:Comonomer-induced stereo-selectivity enhancement in a c2 -symmetric metallocene-catalyzed propylene polymerization.
[So] Source:Macromol Rapid Commun;36(8):733-8, 2015 Apr.
[Is] ISSN:1521-3927
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:Propylene polymerization is carried out with a C 2 -symmetric metallocene catalyst of rac-Et(Ind)2 ZrCl2 /MAO at 40 °C in the presence of a cyclo-triene of trans,trans,cis-1,5,9-cyclododecatriene ((E,E,Z)-CDT). Comonomer incorporations are rather low (<0.10 mol%). However, it is shown for the first time that the comonomer causes a noticeable increase in poly-propylene -isotacticity (>7% in [mmmm]). (E,E,Z)-CDT is speculated to coordinate to the metal center forming comonomer-complexed active sites in charge of the entire polymerization reaction with decreased activity however increased propylene -enantiomorphic selectivity.
[Mh] Termos MeSH primário: Compostos Organometálicos/química
Polimerização
Polipropilenos/síntese química
[Mh] Termos MeSH secundário: Alcenos/síntese química
Alcenos/química
Catálise
Hidrocarbonetos Alicíclicos/química
Estrutura Molecular
Compostos Organometálicos/síntese química
Polipropilenos/química
Estereoisomerismo
Zircônio/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alkenes); 0 (Hydrocarbons, Alicyclic); 0 (Organometallic Compounds); 0 (Polypropylenes); 0 (metallocene); 4904-61-4 (1,5,9-cyclododecatriene); AUG1H506LY (propylene); C6V6S92N3C (Zirconium)
[Em] Mês de entrada:1604
[Cu] Atualização por classe:150417
[Lr] Data última revisão:
150417
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150228
[St] Status:MEDLINE
[do] DOI:10.1002/marc.201400736


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[PMID]:25281108
[Au] Autor:Pindado Jiménez O; Pérez Pastor RM; Escolano Segovia O; del Reino Querencia S
[Ad] Endereço:Division of Chemistry, Technology Department, CIEMAT. Av. Complutense 40, 28040 Madrid, Spain. Electronic address: oscar.pindado@ciemat.es.
[Ti] Título:Exploring petroleum hydrocarbons in groundwater by double solid phase extraction coupled to gas chromatography-flame ionization detector.
[So] Source:Talanta;131:315-24, 2015 Jan.
[Is] ISSN:1873-3573
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:This work proposes an analytical procedure for measuring aliphatic and aromatic hydrocarbons fractions present in groundwater. In this method, hydrocarbons are solid phase extracted (SPE) twice from the groundwater and the resulting fractions are analyzed by gas chromatography with flame ionization detection. The first SPE disposes the hydrocarbons present in groundwater in organic solvents and the second SPE divides them into aliphatic and aromatic hydrocarbons. The validation study is carried out and its uncertainties are discussed. Identifying the main sources of uncertainty is evaluated through applying the bottom-up approach. Limits of detection for hydrocarbons ranges are below 5 µg L(-1), precision is not above of 30%, and acceptable recoveries are reached for aliphatic and aromatic fractions studied. The uncertainty due to volume of the sample, factor of calibration and recovery are the highest contributions. The expanded uncertainty range from 13% to 26% for the aliphatic hydrocarbons ranges and from 14% to 23% for the aromatic hydrocarbons ranges. As application, the proposed method is satisfactorily applied to a set of groundwater samples collected in a polluted area where there is evidence to present a high degree of hydrocarbons. The results have shown the range of aliphatic hydrocarbons >C21-C35 is the most abundant, with values ranging from 215 µg L(-1) to 354 µg L(-1), which it is associated to a contamination due to diesel.
[Mh] Termos MeSH primário: Cromatografia Gasosa/métodos
Água Subterrânea/análise
Hidrocarbonetos Alicíclicos/análise
Hidrocarbonetos Aromáticos/análise
Petróleo/análise
Extração em Fase Sólida/métodos
Poluentes Químicos da Água/análise
[Mh] Termos MeSH secundário: Ionização de Chama/métodos
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Hydrocarbons, Alicyclic); 0 (Hydrocarbons, Aromatic); 0 (Petroleum); 0 (Water Pollutants, Chemical)
[Em] Mês de entrada:1506
[Cu] Atualização por classe:141004
[Lr] Data última revisão:
141004
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:141005
[St] Status:MEDLINE


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[PMID]:25329785
[Au] Autor:Kraft P; Di Cristofaro V; Jordi S
[Ad] Endereço:Givaudan Schweiz AG, Fragrance Research, Überlandstrasse 138, CH-8600 Dübendorf, (phone: +41-44-8242520; fax: +41-44-8242926). philip.kraft@givaudan.com.
[Ti] Título:From Cassyrane to cashmeran - the molecular parameters of odorants.
[So] Source:Chem Biodivers;11(10):1567-96, 2014 Oct.
[Is] ISSN:1612-1880
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:This review, including some new experimental results, is the summary of a talk at the 'flavors & fragrances 2013' conference in Leipzig, organized jointly by the GDCh, the Liebig-Vereinigung, and the EuCheMS. After times of searching for natural odor principles and serendipitous discoveries by chemical inspiration, directed odorant design today offers the highest hit rates for the discovery of new odorants, although serendipity still plays a role. Keeping intact the electronic shape required for a certain olfactophore-binding geometry, one can add or subtract structural elements, rigidify molecular structures, or introduce more structural flexibility. To find out which structural features are critical, the 'seco-approach', in which different fragments are removed by cutting strategic bonds, is the most analytical. Following this approach, such ingredients as Serenolide, Sylkolide, and Pomarose were designed. Transferring this design principle from the family of damascones to that of the theaspiranes led to the discovery of Cassyrane, though completely different structural features turned out to be relevant. Application of the seco-concept to a 3,7a-substituted 2,6,7,7a-tetrahydro-1H-inden-5-yl musk lead structure derived from carotol resulted in the discovery of a new family of dienone musks with novel structure-odor correlations. However, cutting the C(2)-O bond of Cassyrane and oxidizing the resulting seco-structure to the 1,2,5,1″-tetradehydro derivative links the family of dienone musks with that of blackcurrant odorants, but the resulting target structures turned out to be potent orris odorants. (3E,5E)-5-(tert-Butyl)octadeca-3,5-dien-2-one even possesses the lowest odor threshold in the whole ionone family (0.036 ng/l air), which could be rationalized by a superposition analysis on (-)-cis-γ-irone. In the course of the synthesis of these high-impact orris odorants, we discovered that, depending on the reaction conditions, the dehydration step of the intermediate 5-hydroxyalk-3-yn-2-ones was accompanied by a carbenium-ion rearrangement. Depending on the substitution pattern, these rearrangement products and their derivatives possessed interesting musky-woody olfactory properties reminiscent of Cashmeran, demonstrating that the same structural elements can code for completely different odors, i.e., cassis, musk, orris, violet, and Cashmeran-type, depending only on their spatial arrangement.
[Mh] Termos MeSH primário: Furanos/química
Hidrocarbonetos Alicíclicos/química
Indanos/química
Odorantes/análise
[Mh] Termos MeSH secundário: Estrutura Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Furans); 0 (Hydrocarbons, Alicyclic); 0 (Indans); 0 (cassyrane); BZR4438MY4 (6,7-dihydro-1,1,2,3,3-pentamethyl-4-(5H)indanone)
[Em] Mês de entrada:1506
[Cu] Atualização por classe:161125
[Lr] Data última revisão:
161125
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:141021
[St] Status:MEDLINE
[do] DOI:10.1002/cbdv.201400071


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[PMID]:25260123
[Au] Autor:Ramsaywack S; Karaca S; Gholami M; Murray AH; Hampel F; McDonald R; Elmaci N; Lüthi HP; Tykwinski RR
[Ad] Endereço:Department of Chemistry, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
[Ti] Título:Donor- and/or acceptor-substituted expanded radialenes: theory, synthesis, and properties.
[So] Source:J Org Chem;79(21):10013-29, 2014 Nov 07.
[Is] ISSN:1520-6904
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The synthesis of donor- (D) and/or acceptor (A)-expanded [4]radialenes has been developed on the basis of readily available dibromoolefin (7), tetraethynylethene (10 and 20), and vinyl triflate (12) building blocks. The successful formation of D/A radialenes relies especially on (1) effective use of a series alkynyl protecting groups, (2) Sonogashira cross-coupling reactions, and (3) the development of ring closing reactions to form the desired macrocyclic products. The expanded [4]radialene products have been investigated by spectroscopic (UV-vis absorption and emission) and quantum chemical computational methods (density functional theory and time dependent DFT). The combined use of theory and experiment provides a basis to evaluate the extent of D/A interactions via the cross-conjugated radialene framework as well as an interpretation of the origin of D/A interactions at an orbital level.
[Mh] Termos MeSH primário: Alquinos/química
Hidrocarbonetos Alicíclicos/química
Hidrocarbonetos Alicíclicos/síntese química
Hidrocarbonetos Bromados/química
Compostos Macrocíclicos/síntese química
[Mh] Termos MeSH secundário: Compostos Macrocíclicos/química
Estrutura Molecular
Teoria Quântica
Espectrofotometria Ultravioleta
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alkynes); 0 (Hydrocarbons, Alicyclic); 0 (Hydrocarbons, Brominated); 0 (Macrocyclic Compounds)
[Em] Mês de entrada:1509
[Cu] Atualização por classe:150105
[Lr] Data última revisão:
150105
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:140927
[St] Status:MEDLINE
[do] DOI:10.1021/jo5016085



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