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[PMID]:28460114
[Au] Autor:Reynolds HT; Slot JC; Divon HH; Lysøe E; Proctor RH; Brown DW
[Ad] Endereço:Department of Plant Pathology, The Ohio State University, Columbus, OH.
[Ti] Título:Differential Retention of Gene Functions in a Secondary Metabolite Cluster.
[So] Source:Mol Biol Evol;34(8):2002-2015, 2017 Aug 01.
[Is] ISSN:1537-1719
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:In fungi, distribution of secondary metabolite (SM) gene clusters is often associated with host- or environment-specific benefits provided by SMs. In the plant pathogen Alternaria brassicicola (Dothideomycetes), the DEP cluster confers an ability to synthesize the SM depudecin, a histone deacetylase inhibitor that contributes weakly to virulence. The DEP cluster includes genes encoding enzymes, a transporter, and a transcription regulator. We investigated the distribution and evolution of the DEP cluster in 585 fungal genomes and found a wide but sporadic distribution among Dothideomycetes, Sordariomycetes, and Eurotiomycetes. We confirmed DEP gene expression and depudecin production in one fungus, Fusarium langsethiae. Phylogenetic analyses suggested 6-10 horizontal gene transfers (HGTs) of the cluster, including a transfer that led to the presence of closely related cluster homologs in Alternaria and Fusarium. The analyses also indicated that HGTs were frequently followed by loss/pseudogenization of one or more DEP genes. Independent cluster inactivation was inferred in at least four fungal classes. Analyses of transitions among functional, pseudogenized, and absent states of DEP genes among Fusarium species suggest enzyme-encoding genes are lost at higher rates than the transporter (DEP3) and regulatory (DEP6) genes. The phenotype of an experimentally-induced DEP3 mutant of Fusarium did not support the hypothesis that selective retention of DEP3 and DEP6 protects fungi from exogenous depudecin. Together, the results suggest that HGT and gene loss have contributed significantly to DEP cluster distribution, and that some DEP genes provide a greater fitness benefit possibly due to a differential tendency to form network connections.
[Mh] Termos MeSH primário: Alcadienos/metabolismo
Compostos de Epóxi/metabolismo
Álcoois Graxos/metabolismo
Genoma Fúngico/genética
Família Multigênica/genética
[Mh] Termos MeSH secundário: Ascomicetos/genética
Bases de Dados de Ácidos Nucleicos
Evolução Molecular
Proteínas Fúngicas/genética
Fusarium/genética
Perfilação da Expressão Gênica/métodos
Regulação Fúngica da Expressão Gênica/genética
Transferência Genética Horizontal/genética
Filogenia
Metabolismo Secundário/genética
Virulência/genética
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkadienes); 0 (Epoxy Compounds); 0 (Fatty Alcohols); 0 (Fungal Proteins); 139508-73-9 (depudecin)
[Em] Mês de entrada:1802
[Cu] Atualização por classe:180201
[Lr] Data última revisão:
180201
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170502
[St] Status:MEDLINE
[do] DOI:10.1093/molbev/msx145


  2 / 1109 MEDLINE  
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[PMID]:28601720
[Au] Autor:Zhang X; Guo S; Chen C; Perez GR; Zhang C; Patanapongpibul M; Subrahmanyam N; Wang R; Keith J; Chen G; Dong Y; Zhang Q; Zhong Q; Zheng S; Wang G; Chen QH
[Ad] Endereço:Department of Chemistry, California State University, Fresno, 2555 E. San Ramon Avenue, M/S SB70, Fresno, CA 93740, USA.
[Ti] Título:Asymmetric 1,5-diarylpenta-1,4-dien-3-ones: Antiproliferative activity in prostate epithelial cell models and pharmacokinetic studies.
[So] Source:Eur J Med Chem;137:263-279, 2017 Sep 08.
[Is] ISSN:1768-3254
[Cp] País de publicação:France
[La] Idioma:eng
[Ab] Resumo:To further engineer dienones with optimal combinations of potency and bioavailability, thirty-four asymmetric 1,5-diarylpenta-1,4-dien-3-ones (25-58) have been designed and synthesized for the evaluation of their in vitro anti-proliferative activity in three human prostate cancer cell lines and one non-neoplastic prostate epithelial cell line. All these asymmetric dienones are sufficiently more potent than curcumin and their corresponding symmetric counterparts. The optimal dienone 58, with IC values in the range of 0.03-0.12 µM, is 636-, 219-, and 454-fold more potent than curcumin in three prostate cancer cell models. Dienones 28 and 49 emerged as the most promising asymmetric dienones that warrant further preclinical studies. The two lead compounds demonstrated substantially improved potency in cell models and superior bioavailability in rats, while exhibiting no acute toxicity in the animals at the dose of 10 mg/kg. Dienones 28 and 46 can induce PC-3 cell cycle regulation at the G /G phase. However, dienone 28 induces PC-3 cell death in a different way from 46 even though they share the same scaffold, indicating that terminal heteroaromatic rings are critical to the action of mechanism for each specific dienone.
[Mh] Termos MeSH primário: Alcadienos/farmacologia
Antineoplásicos/farmacologia
Células Epiteliais/efeitos dos fármacos
Neoplasias da Próstata/tratamento farmacológico
[Mh] Termos MeSH secundário: Alcadienos/síntese química
Alcadienos/química
Animais
Antineoplásicos/síntese química
Antineoplásicos/química
Apoptose/efeitos dos fármacos
Ciclo Celular/efeitos dos fármacos
Linhagem Celular Tumoral
Proliferação Celular/efeitos dos fármacos
Relação Dose-Resposta a Droga
Ensaios de Seleção de Medicamentos Antitumorais
Células Epiteliais/patologia
Seres Humanos
Masculino
Microssomos Hepáticos/efeitos dos fármacos
Estrutura Molecular
Neoplasias da Próstata/patologia
Ratos
Ratos Sprague-Dawley
Relação Estrutura-Atividade
Células Tumorais Cultivadas
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkadienes); 0 (Antineoplastic Agents)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170920
[Lr] Data última revisão:
170920
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170612
[St] Status:MEDLINE


  3 / 1109 MEDLINE  
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[PMID]:28284806
[Au] Autor:Wang ZS; Chen LZ; Zhou HP; Liu XH; Chen FH
[Ad] Endereço:School of Pharmacy, Anhui Medical University, Hefei 230032, PR China.
[Ti] Título:Diarylpentadienone derivatives (curcumin analogues): Synthesis and anti-inflammatory activity.
[So] Source:Bioorg Med Chem Lett;27(8):1803-1807, 2017 04 15.
[Is] ISSN:1464-3405
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:A series of new (2E,4E)-1-(substitutedphenyl)-5-(substitutedphenyl)penta-2,4-dien-1-one derivatives were designed and synthesized. Compounds 3i, 3k were determined by X-ray. All of the compounds have been screened for their anti-inflammatory activity characterized by evaluating their inhibition against LPS-induced IL-6 and TNF-α release in cell RAW 264.7 stimulated with LPS. Compound 3i showed the highest anti-inflammatory activity on decreasing IL-6 and TNF-α. The further study showed that title compound 3i inhibited expression of proteins p-p65, iNOS, COX-2 LPS-induced. Immunofluorescence also revealed compound 3i could lightly reduce activation p65 in nuclei. These results indicate that compound 3i anti-inflammatory role may partly due to its inhibitory effect on the NF-κB signaling pathway.
[Mh] Termos MeSH primário: Alcadienos/química
Alcadienos/farmacologia
Anti-Inflamatórios/química
Anti-Inflamatórios/farmacologia
Curcumina/análogos & derivados
Curcumina/farmacologia
[Mh] Termos MeSH secundário: Animais
Interleucina-6/imunologia
Lipopolissacarídeos/imunologia
Macrófagos/efeitos dos fármacos
Camundongos
Modelos Moleculares
Células RAW 264.7
Fator de Necrose Tumoral alfa/imunologia
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alkadienes); 0 (Anti-Inflammatory Agents); 0 (Interleukin-6); 0 (Lipopolysaccharides); 0 (Tumor Necrosis Factor-alpha); IT942ZTH98 (Curcumin)
[Em] Mês de entrada:1707
[Cu] Atualização por classe:171124
[Lr] Data última revisão:
171124
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170313
[St] Status:MEDLINE


  4 / 1109 MEDLINE  
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[PMID]:27631524
[Au] Autor:Herrera H; Barros-Parada W; Flores MF; Francke W; Fuentes-Contreras E; Rodriguez M; Santis F; Zarbin PH; Bergmann J
[Ad] Endereço:Instituto de Química, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.
[Ti] Título:Identification of a Novel Moth Sex Pheromone Component from Chilecomadia valdiviana.
[So] Source:J Chem Ecol;42(9):908-918, 2016 Sep.
[Is] ISSN:1573-1561
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Chilecomadia valdiviana (Philippi) (Lepidoptera: Cossidae) is an insect native to Chile. The larval stages feed on the wood of economically important fruit tree species such as apple, pear, olive, cherry, and avocado, and also on eucalyptus. This causes weakening and, in case of severe infestation, death of the tree. We report identification of the sex pheromone produced by females of this species. Hexane extracts of the abdominal glands of virgin females were analyzed by gas chromatography (GC) with electroantennographic detection, GC coupled with mass spectrometry, and GC coupled to infrared spectroscopy. The major pheromone component was identified as (7Z,10Z)-7,10-hexadecadienal (Z7,Z10-16:Ald), and minor components present in the extracts were (Z)-7-hexadecenal and (Z)-9-hexadecenal, hexadecanal, and (9Z,12Z)-9,12-octadecadienal. Structural assignments were carried out by comparison of analytical data of the natural products and their dimethyl disulfide adducts with those of authentic reference samples. In field tests, traps baited with Z7,Z10-16:Ald captured significantly more males than control traps.
[Mh] Termos MeSH primário: Mariposas/química
Atrativos Sexuais/análise
[Mh] Termos MeSH secundário: Aldeídos/análise
Aldeídos/metabolismo
Alcadienos/análise
Alcadienos/metabolismo
Animais
Cromatografia Gasosa
Feminino
Cromatografia Gasosa-Espectrometria de Massas
Masculino
Mariposas/metabolismo
Atrativos Sexuais/metabolismo
Espectrofotometria Infravermelho
Árvores/parasitologia
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (9-hexadecenal); 0 (Aldehydes); 0 (Alkadienes); 0 (Sex Attractants); 96883-53-3 ((Z,Z)-7,11-hexadecadienal)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:171027
[Lr] Data última revisão:
171027
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160916
[St] Status:MEDLINE


  5 / 1109 MEDLINE  
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[PMID]:27608302
[Au] Autor:Kang BK; Kim MJ; Kim KB; Ahn DH
[Ad] Endereço:Department of Food Science & Technology/Institute of Food Science, Pukyong National University, Busan 608-737, Republic of Korea.
[Ti] Título:In vivo and in vitro inhibitory activity of an ethanolic extract of Sargassum fulvellum and its component grasshopper ketone on atopic dermatitis.
[So] Source:Int Immunopharmacol;40:176-183, 2016 Nov.
[Is] ISSN:1878-1705
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:The present study investigated the effect of Sargassum fulvellum ethanol extract (SFEE) on 2,4-dinitrochlorobenzene (DNCB)-induced atopic dermatitis (AD)-like skin lesions in BALB/c mice. The severity of skin dermatitis, production of cytokines, and total IgE content were measured, and the histopathological features were analyzed. SFEE decreased the severity of DNCB-induced dermatitis and suppressed the serum levels of total immunoglobulin E (IgE), tumor necrosis factor (TNF)-α, and interleukin (IL)-4. In addition, SFEE reduced the production of IL-4, IL-5, and IL-13 in mice splenocytes. However, the levels of IL-10 and interferon (IFN)-γ significantly increased in mice sera and splenocytes. Histological examination revealed decreased dermal thickness and infiltration by mast cells after treatment with SFEE. Furthermore, grasshopper ketone, a compound isolated from SFEE, was found to significantly decrease cytokine production in concanavalin A-stimulated splenocytes from BALB/c mice with no cytotoxicity. Taken together, these results indicate that SFEE and the isolated grasshopper ketone have an inhibitory effect on AD by regulating immune mediators and cells and may be a potential effective alternative therapy for AD.
[Mh] Termos MeSH primário: Alcadienos/uso terapêutico
Cicloexanóis/uso terapêutico
Dermatite Atópica/tratamento farmacológico
Extratos Vegetais/uso terapêutico
Sargassum
[Mh] Termos MeSH secundário: Alcadienos/farmacologia
Animais
Concanavalina A/farmacologia
Cicloexanóis/farmacologia
Citocinas/sangue
Dermatite Atópica/sangue
Dermatite Atópica/imunologia
Dermatite Atópica/patologia
Etanol/química
Imunoglobulina E/sangue
Masculino
Camundongos Endogâmicos BALB C
Mitógenos/farmacologia
Fitoterapia
Extratos Vegetais/farmacologia
Pele/patologia
Solventes/química
Baço/citologia
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkadienes); 0 (Cyclohexanols); 0 (Cytokines); 0 (Mitogens); 0 (Plant Extracts); 0 (Solvents); 0 (grasshopper ketone); 11028-71-0 (Concanavalin A); 37341-29-0 (Immunoglobulin E); 3K9958V90M (Ethanol)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170515
[Lr] Data última revisão:
170515
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160909
[St] Status:MEDLINE


  6 / 1109 MEDLINE  
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[PMID]:27591085
[Au] Autor:Wang J; Gibbert L; Djudjaj S; Alidousty C; Rauen T; Kunter U; Rembiak A; Enders D; Jankowski V; Braun GS; Floege J; Ostendorf T; Raffetseder U
[Ad] Endereço:Department of Nephrology and Clinical Immunology, University Hospital RWTH-Aachen, Aachen, Germany.
[Ti] Título:Therapeutic nuclear shuttling of YB-1 reduces renal damage and fibrosis.
[So] Source:Kidney Int;90(6):1226-1237, 2016 Dec.
[Is] ISSN:1523-1755
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Virtually all chronic kidney diseases progress towards tubulointerstitial fibrosis. In vitro, Y-box protein-1 (YB-1) acts as a central regulator of gene transcription and translation of several fibrosis-related genes. However, it remains to be determined whether its pro- or antifibrotic propensities prevail in disease. Therefore, we investigated the outcome of mice with half-maximal YB-1 expression in a model of renal fibrosis induced by unilateral ureteral obstruction. Yb1 animals displayed markedly reduced tubular injury, immune cell infiltration and renal fibrosis following ureteral obstruction. The increase in renal YB-1 was limited to a YB-1 variant nonphosphorylated at serine 102 but phosphorylated at tyrosine 99. During ureteral obstruction, YB-1 localized to the cytoplasm, directly stabilizing Col1a1 mRNA, thus promoting fibrosis. Conversely, the therapeutic forced nuclear compartmentalization of phosphorylated YB-1 by the small molecule HSc025 mediated repression of the Col1a1 promoter and attenuated fibrosis following ureteral obstruction. Blunting of these effects in Yb1 mice confirmed involvement of YB-1. HSc025 even reduced tubulointerstitial damage when applied at later time points during maximum renal damage. Thus, phosphorylation and subcellular localization of YB-1 determines its effect on renal fibrosis in vivo. Hence, induced nuclear YB-1 shuttling may be a novel antifibrotic treatment strategy in renal diseases with the potential of damage reversal.
[Mh] Termos MeSH primário: Alcadienos/uso terapêutico
Nefroesclerose/metabolismo
Fatores de Transcrição/metabolismo
[Mh] Termos MeSH secundário: Animais
Avaliação Pré-Clínica de Medicamentos
Masculino
Camundongos Endogâmicos C57BL
Camundongos Knockout
Nefroesclerose/etiologia
Nefroesclerose/prevenção & controle
Obstrução Ureteral/complicações
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkadienes); 0 (HSc025); 0 (Transcription Factors); 0 (YB-1 protein, mouse)
[Em] Mês de entrada:1711
[Cu] Atualização por classe:171103
[Lr] Data última revisão:
171103
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160904
[St] Status:MEDLINE


  7 / 1109 MEDLINE  
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[PMID]:27479320
[Au] Autor:Meng F; Li X; Torker S; Shi Y; Shen X; Hoveyda AH
[Ad] Endereço:Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
[Ti] Título:Catalytic enantioselective 1,6-conjugate additions of propargyl and allyl groups.
[So] Source:Nature;537(7620):387-393, 2016 09 15.
[Is] ISSN:1476-4687
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Conjugate (or 1,4-) additions of carbanionic species to α,ß-unsaturated carbonyl compounds are vital to research in organic and medicinal chemistry, and there are several chiral catalysts that facilitate the catalytic enantioselective additions of nucleophiles to enoates. Nonetheless, catalytic enantioselective 1,6-conjugate additions are uncommon, and ones that incorporate readily functionalizable moieties, such as propargyl or allyl groups, into acyclic α,ß,γ,δ-doubly unsaturated acceptors are unknown. Chemical transformations that could generate a new bond at the C6 position of a dienoate are particularly desirable because the resulting products could then be subjected to further modifications. However, such reactions, especially when dienoates contain two equally substituted olefins, are scarce and are confined to reactions promoted by a phosphine-copper catalyst (with an alkyl Grignard reagent, dialkylzinc or trialkylaluminium compounds), a diene-iridium catalyst (with arylboroxines), or a bisphosphine-cobalt catalyst (with monosilyl-acetylenes). 1,6-Conjugate additions are otherwise limited to substrates where there is full substitution at the C4 position. It is unclear why certain catalysts favour bond formation at C6, and-although there are a small number of catalytic enantioselective conjugate allyl additions-related 1,6-additions and processes involving a propargyl unit are non-existent. Here we show that an easily accessible organocopper catalyst can promote 1,6-conjugate additions of propargyl and 2-boryl-substituted allyl groups to acyclic dienoates with high selectivity. A commercially available allenyl-boron compound or a monosubstituted allene may be used. Products can be obtained in up to 83 per cent yield, >98:2 diastereomeric ratio (for allyl additions) and 99:1 enantiomeric ratio. We elucidate the mechanistic details, including the origins of high site selectivity (1,6- versus 1,4-) and enantioselectivity as a function of the catalyst structure and reaction type, by means of density functional theory calculations. The utility of the approach is highlighted by an application towards enantioselective synthesis of the anti-HIV agent (-)-equisetin.
[Mh] Termos MeSH primário: Fármacos Anti-HIV/síntese química
Compostos de Boro/química
Técnicas de Química Sintética/métodos
Química Farmacêutica/métodos
Cobre/química
Compostos Organometálicos/química
Pirrolidinonas/síntese química
Tetra-Hidronaftalenos/síntese química
[Mh] Termos MeSH secundário: Alcadienos/química
Alcenos/química
Fármacos Anti-HIV/química
Catálise
Pirrolidinonas/química
Estereoisomerismo
Tetra-Hidronaftalenos/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL; RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.
[Nm] Nome de substância:
0 (Alkadienes); 0 (Alkenes); 0 (Anti-HIV Agents); 0 (Boron Compounds); 0 (Organometallic Compounds); 0 (Pyrrolidinones); 0 (Tetrahydronaphthalenes); 4AV0LZ8QKB (propadiene); 57749-43-6 (equisetin); 789U1901C5 (Copper)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:170224
[Lr] Data última revisão:
170224
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160802
[St] Status:MEDLINE
[do] DOI:10.1038/nature19063


  8 / 1109 MEDLINE  
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[PMID]:27427398
[Au] Autor:Das S; Dixit M; Major DT
[Ad] Endereço:Department of Chemistry and the Lise Meitner-Minerva Center of Computational Quantum Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel.
[Ti] Título:First principles model calculations of the biosynthetic pathway in selinadiene synthase.
[So] Source:Bioorg Med Chem;24(20):4867-4870, 2016 Oct 15.
[Is] ISSN:1464-3391
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Terpenes comprise the largest class of natural products currently known. These ubiquitous molecules are synthesized by terpene synthases via complex carbocationic reactions, incorporating highly reactive intermediates. In the current study, we present a mechanistic investigation of the biosynthetic pathway for the formation of selina-4(15),7(11)-diene. We employ density functional theory to study a model carbocation system in the gas-phase, and delineate the energetic feasibility of a plausible reaction path. Our results suggests that during formation of selina-4(15),7(11)-diene, the substrate is likely folded in a conformation conducive to sequential cyclizations. We propose that a required proton transfer cannot occur intramolecularly in the gas-phase due to a high free energy barrier, and that enzyme assistance is essential for this step. Hybrid quantum mechanics-molecular mechanics docking studies suggest that enzyme intervention could be realized through electrostatic guidance.
[Mh] Termos MeSH primário: Alcadienos/metabolismo
Alquil e Aril Transferases/metabolismo
Teoria Quântica
[Mh] Termos MeSH secundário: Alcadienos/química
Alquil e Aril Transferases/química
Vias Biossintéticas
Modelos Moleculares
Conformação Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkadienes); EC 2.5.- (Alkyl and Aryl Transferases); EC 2.5.1.- (terpene synthase)
[Em] Mês de entrada:1707
[Cu] Atualização por classe:170910
[Lr] Data última revisão:
170910
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160719
[St] Status:MEDLINE


  9 / 1109 MEDLINE  
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[PMID]:27373635
[Au] Autor:Yasuda S; Yokosawa H; Mukai C
[Ad] Endereço:Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University.
[Ti] Título:Construction of Azabicyclo[6.4.0]dodecatrienes Based on Rhodium(I)-Catalyzed Intramolecular [6+2] Cycloaddition between Azetidine, Allene, and Alkynes.
[So] Source:Chem Pharm Bull (Tokyo);64(7):805-10, 2016.
[Is] ISSN:1347-5223
[Cp] País de publicação:Japan
[La] Idioma:eng
[Ab] Resumo:Treatment of the allenylazetidine-alkynes with a catalytic amount of [RhCl(CO)dppp]2 (dppp: 1,3-bis(diphenylphosphino)propane) effected the intramolecular hetero-[6+2]-type ring-closing reaction via the C-C bond cleavage of the azetidine ring to produce azabicyclo[6.4.0]dodecatriene derivatives in good to excellent yields. The formation of the oxa analogue could also be achieved.
[Mh] Termos MeSH primário: Alcadienos/química
Alquinos/química
Compostos Azabicíclicos/síntese química
Azetidinas/química
Ródio/química
[Mh] Termos MeSH secundário: Compostos Azabicíclicos/química
Catálise
Ciclização
Estrutura Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkadienes); 0 (Alkynes); 0 (Azabicyclo Compounds); 0 (Azetidines); 37S883XDWR (azetidine); 4AV0LZ8QKB (propadiene); DMK383DSAC (Rhodium)
[Em] Mês de entrada:1701
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160705
[St] Status:MEDLINE
[do] DOI:10.1248/cpb.c16-00178


  10 / 1109 MEDLINE  
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[PMID]:27300505
[Au] Autor:Uehara T; Kitahara H; Naka H; Matsuyama S; Ando T; Honda H
[Ad] Endereço:National Institute of Agrobiological Sciences (NIAS), Ohwashi 1-2, Tsukuba, Ibaraki, 305-8634, Japan. tue@affrc.go.jp.
[Ti] Título:Single-Component Pheromone Consisting of Bombykal in a Diurnal Hawk Moth, Neogurelca himachala sangaica.
[So] Source:J Chem Ecol;42(6):517-22, 2016 Jun.
[Is] ISSN:1573-1561
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Recent work has suggested that hawk moths share pheromone components but are sexually separated by qualitative and quantitative differences in their pheromone blends. During field assays on the sex pheromones of other species, a diurnal hawk moth, Neogurelca himachala sangaica (Lepidoptera: Sphingidae), was frequently captured, but the composition of the sex pheromone of this species was not known. Analysis of hexane extracts of the pheromone glands of calling female by gas chromatography (GC) using an electroantennographic detector (EAD) revealed two components that elicited EAD responses from male moth antennae. These components were identified by their mass spectra and retention indices on two GC columns as (10E,12Z)-10,12-hexadecadienal (E10,Z12-16:Ald) and a trace of its (10E,12E)-isomer (E10,E12-16:Ald) in 98:2 ratio. In field experiments, E10,Z12-16:Ald alone attracted male moths, and addition of E10,E12-16:Ald significantly reduced the attractiveness, even at the naturally-occurring ratio. Analysis of the data using a generalized linear mixed model showed that E10,Z12-16:Ald positively contributed to attractiveness, whereas E10,E12-16:Ald did so negatively, and it was concluded that the sex pheromone of N. himachala sangaica consists solely of E10,Z12-16:Ald, bombykal. The negative effect of E10,E12-16:Ald on attractiveness could promote the species-specificity of this single-component pheromone system.
[Mh] Termos MeSH primário: Alcadienos/análise
Alcadienos/farmacologia
Mariposas/efeitos dos fármacos
Atrativos Sexuais/análise
Atrativos Sexuais/farmacologia
[Mh] Termos MeSH secundário: Animais
Bioensaio
Feminino
Masculino
Comportamento Sexual Animal/efeitos dos fármacos
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkadienes); 0 (Sex Attractants); 63024-98-6 (bombykal)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:171027
[Lr] Data última revisão:
171027
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160615
[St] Status:MEDLINE
[do] DOI:10.1007/s10886-016-0714-y



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