Base de dados : MEDLINE
Pesquisa : D03.661 [Categoria DeCS]
Referências encontradas : 15 [refinar]
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  1 / 15 MEDLINE  
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[PMID]:26729078
[Au] Autor:Slawinski J; Grzonek A; Zolnowska B; Kawiak A
[Ad] Endereço:Department of Organic Chemistry, Medical University of Gdansk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland. jaroslaw@gumed.edu.pl.
[Ti] Título:Synthesis of Novel Pyrido[4,3-e][1,2,4]triazino[3,2-c][1,2,4]thiadiazine 6,6-dioxide Derivatives with Potential Anticancer Activity.
[So] Source:Molecules;21(1):E41, 2015 Dec 29.
[Is] ISSN:1420-3049
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:A series of novel 3-/2,3-substituted pyrido[4,3-e][1,2,4]triazino[3,2-c][1,2,4]thiadiazine 6,6-dioxides 4-28 have been synthesized by the reaction of 3-amino-2-(4-thioxo-1,4-dihydropyridin-3-yl-sulfonyl)guanidine with either 2-oxoalkanoic acids and its esters, or phenylglyoxylic hydrates in glacial acetic acid. Some of them exhibited reasonable or moderate anticancer activity toward human cancer cell lines, HCT-116, MCF-7 and HeLa. The structure of this novel heterocyclic ring system was confirmed by ¹D-NMR and ²D-NMR spectroscopic data including COSY, ROESY and HMBC, elemental analyses and MS spectrometry.
[Mh] Termos MeSH primário: Antineoplásicos/farmacologia
Óxidos Heterocíclicos/síntese química
Tiadiazinas/síntese química
[Mh] Termos MeSH secundário: Antineoplásicos/síntese química
Proliferação Celular/efeitos dos fármacos
Sobrevivência Celular/efeitos dos fármacos
Células HCT116
Células HeLa
Óxidos Heterocíclicos/farmacologia
Seres Humanos
Células MCF-7
Relação Estrutura-Atividade
Tiadiazinas/farmacologia
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Heterocyclic Oxides); 0 (Thiadiazines)
[Em] Mês de entrada:1610
[Cu] Atualização por classe:161230
[Lr] Data última revisão:
161230
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160106
[St] Status:MEDLINE


  2 / 15 MEDLINE  
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[PMID]:23445181
[Au] Autor:Porter NA
[Ad] Endereço:Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, USA. n.porter@vanderbilt.edu
[Ti] Título:A perspective on free radical autoxidation: the physical organic chemistry of polyunsaturated fatty acid and sterol peroxidation.
[So] Source:J Org Chem;78(8):3511-24, 2013 Apr 19.
[Is] ISSN:1520-6904
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:This Perspective describes advances from the author's laboratory on the free radical reactions of organic compounds with molecular oxygen. Polyunsaturated fatty acids (PUFAs) and sterols are particularly prone to undergo radical chain oxidation, and evidence suggests that this process, known as lipid peroxidation, occurs in vivo under a variety of conditions that are the result of an oxidative stress. Cyclic peroxides, hydroperoxides, and epoxy alcohols are major products formed from peroxidation, and the basic mechanisms of product formation are now reasonably well understood. These mechanisms include reversible addition of oxygen to carbon radicals, rearrangement and cyclization of allyl and pentadienyl peroxyl radicals, and homolytic substitution of carbon radicals on the peroxide bond. A physical organic approach to the problem of free radicals in biology and medicine is highlighted in this Perspective with stereochemical, kinetic, and extrathermodynamic probes applied to the study of mechanism. A radical clock permits the determination of free radical propagation rate constants, and 7-dehydrocholesterol, the immediate biosynthetic precursor of cholesterol, is found by this clock to be one of the most oxidizable lipids known. The consequences of the extreme reactivity of 7-dehydrocholesterol on human health is the focus of a current research theme in the author's laboratory.
[Mh] Termos MeSH primário: Ácidos Graxos Insaturados/química
Radicais Livres/química
Óxidos Heterocíclicos/química
Peróxidos/química
Esteróis/química
[Mh] Termos MeSH secundário: Química Física
Desidrocolesteróis
Seres Humanos
Estresse Oxidativo
[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 (Dehydrocholesterols); 0 (Fatty Acids, Unsaturated); 0 (Free Radicals); 0 (Heterocyclic Oxides); 0 (Peroxides); 0 (Sterols); BK1IU07GKF (7-dehydrocholesterol)
[Em] Mês de entrada:1308
[Cu] Atualização por classe:170220
[Lr] Data última revisão:
170220
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:130301
[St] Status:MEDLINE
[do] DOI:10.1021/jo4001433


  3 / 15 MEDLINE  
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[PMID]:21192645
[Au] Autor:Zhou YQ; Wang NX; Zhou SB; Huang Z; Cao L
[Ad] Endereço:Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, China, 100190.
[Ti] Título:[4 + 3] Cycloaddition of aromatic α,ß-unsaturated aldehydes and ketones with epoxides: one-step approach to synthesize seven-membered oxacycles catalyzed by Lewis acid.
[So] Source:J Org Chem;76(2):669-72, 2011 Jan 21.
[Is] ISSN:1520-6904
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:A novel intermolecular [4 + 3] cycloaddition method to construct 1,4-dioxide seven-membered oxacycles was developed. This one-step method was carried out in the presence of catalytic amount of (C(2)H(5))(2)OBF(3) under mild conditions. Seven-membered oxacycles and some natural compounds could be easily synthesized via this protocol. Control experiments were carried out and possible mechanism for the reaction was proposed. Asymmetric reactions were proceeded and 3e was obtained with moderate ee value.
[Mh] Termos MeSH primário: Aldeídos/química
Óxidos Heterocíclicos/química
Óxidos Heterocíclicos/síntese química
Cetonas/química
Ácidos de Lewis/química
[Mh] Termos MeSH secundário: Catálise
Ciclização
Estrutura Molecular
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Aldehydes); 0 (Heterocyclic Oxides); 0 (Ketones); 0 (Lewis Acids)
[Em] Mês de entrada:1105
[Cu] Atualização por classe:110114
[Lr] Data última revisão:
110114
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110104
[St] Status:MEDLINE
[do] DOI:10.1021/jo101669t


  4 / 15 MEDLINE  
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[PMID]:19724815
[Au] Autor:Xie YX; Yan ZY; Qian B; Deng WY; Wang DZ; Wu LY; Liu XY; Liang YM
[Ad] Endereço:State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
[Ti] Título:A novel iodine-mediated tandem cyclization-cycloaddition reaction leading to polyoxacyclic ring systems.
[So] Source:Chem Commun (Camb);(36):5451-3, 2009 Sep 28.
[Is] ISSN:1364-548X
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:A novel iodine-catalyzed tandem cyclization-cycloaddition reaction of ortho-alkynyl-substituted benzaldehydes leading to polyoxacyclic ring systems has been developed, which represents a useful approach towards the synthesis of the oxabicyclo-[3.2.1]octane ring skeleton found in a variety of natural products.
[Mh] Termos MeSH primário: Óxidos Heterocíclicos/síntese química
Iodo/química
Compostos Policíclicos/síntese química
[Mh] Termos MeSH secundário: Alquinos/química
Benzaldeídos/química
Catálise
Cristalografia por Raios X
Ciclização
Óxidos Heterocíclicos/química
Modelos Químicos
Conformação Molecular
Compostos Policíclicos/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alkynes); 0 (Benzaldehydes); 0 (Heterocyclic Oxides); 0 (Polycyclic Compounds); 9679TC07X4 (Iodine)
[Em] Mês de entrada:1002
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:090903
[St] Status:MEDLINE
[do] DOI:10.1039/b910232a


  5 / 15 MEDLINE  
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[PMID]:17964796
[Au] Autor:Lin Y; Liu X; Yan R; Li J; Pannecouque C; Witvrouw M; De Clercq E
[Ad] Endereço:Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, Jinan 250012, China.
[Ti] Título:Synthesis and anti-HIV evaluation of novel 1,3-disubstituted thieno[3,2-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxides(TTDDs).
[So] Source:Bioorg Med Chem;16(1):157-63, 2008 Jan 01.
[Is] ISSN:1464-3391
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:A series of novel 1,3-disubstituted thieno[3,2-c] [1,2,6]thiadiazin-4(3H)-one 2,2-dioxides (TTDDs), designed as non-nucleoside reverse transcriptase inhibitors (NNRTIs), was synthesized, structurally confirmed by spectral analysis and evaluated for their anti-HIV-1 activities by inhibition of HIV-1(IIIB)-induced cytopathogenicity in MT-4 cell culture. The results showed that TTDD analogues exhibited marked potency as anti-HIV-1 agents. The most active and selective compound was 1-(3-cyano)benzyl-3-benzyl-thieno[3,2-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxide (5f) with a 50% effective concentration (EC(50)) of 4.0 microM and a selectivity index (SI) of >76. The structure-activity relationship (SAR) is discussed.
[Mh] Termos MeSH primário: HIV-1/efeitos dos fármacos
Inibidores da Transcriptase Reversa/química
Tiadiazinas/farmacologia
[Mh] Termos MeSH secundário: Linhagem Celular
HIV-1/patogenicidade
Óxidos Heterocíclicos/química
Óxidos Heterocíclicos/farmacologia
Seres Humanos
Concentração Inibidora 50
Estrutura Molecular
Inibidores da Transcriptase Reversa/farmacologia
Relação Estrutura-Atividade
Tiadiazinas/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Heterocyclic Oxides); 0 (Reverse Transcriptase Inhibitors); 0 (Thiadiazines)
[Em] Mês de entrada:0801
[Cu] Atualização por classe:080114
[Lr] Data última revisão:
080114
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:071030
[St] Status:MEDLINE


  6 / 15 MEDLINE  
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[PMID]:16901140
[Au] Autor:Pchalek K; Hay MP
[Ad] Endereço:Auckland Cancer Society Research Centre, Faculty of Medical and Health Sciences, The University of Auckland, Auckland, New Zealand.
[Ti] Título:Stille coupling reactions in the synthesis of hypoxia-selective 3-alkyl-1,2,4-benzotriazine 1,4-dioxide anticancer agents.
[So] Source:J Org Chem;71(17):6530-5, 2006 Aug 18.
[Is] ISSN:0022-3263
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The introduction of a 3-alkyl substituent is a key step in the synthesis of 1,2,4-benzotriazine 1,4-dioxide hypoxia-selective anticancer agents, such as SN29751. The Stille reaction of 3-chloro-1,2,4-benzotriazine 1-oxides (BTOs) 5 was inhibited by the presence of electron donating substituents on the benzo ring, thus limiting the range of compounds available for SAR studies. The use of 3-iodo-BTOs 8 did not provide a significant improvement in the yields of 3-ethyl-BTOs 6. Microwave-assisted Stille coupling of chlorides 5 gave dramatically improved yields, which were consistently superior to those from the corresponding iodides 8. The application of microwave-assisted synthesis extended the range of substituted BTOs available for SAR studies and provided an efficient, scalable synthesis of the investigational anticancer agent, SN29751 (1).
[Mh] Termos MeSH primário: Antineoplásicos/síntese química
Óxidos Heterocíclicos/síntese química
Oxigênio/química
Triazinas/síntese química
[Mh] Termos MeSH secundário: Antineoplásicos/química
Catálise
Cloretos/química
Óxidos Heterocíclicos/química
Temperatura Alta
Iodetos/química
Micro-Ondas
Estrutura Molecular
Triazinas/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Chlorides); 0 (Heterocyclic Oxides); 0 (Iodides); 0 (Triazines); S88TT14065 (Oxygen)
[Em] Mês de entrada:0706
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:060812
[St] Status:MEDLINE


  7 / 15 MEDLINE  
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[PMID]:12735985
[Au] Autor:Martinez A; Gil C; Castro A; Pérez C; Prieto C; Otero J
[Ad] Endereço:Instituto de Qui;mica Médica (CSIC), Juan de la Cierva 3, 28006, Madrid, Spain. amartinez@neuropharma.es
[Ti] Título:Benzothiadiazine dioxides (BTD) derivatives as non-nucleoside human cytomegalovirus (HCMV) inhibitors. study of structural requirements for biological activity.
[So] Source:Bioorg Med Chem;11(11):2395-402, 2003 May 29.
[Is] ISSN:0968-0896
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Two new series of BTD derivatives have been synthesised allowing to explore the steric requirements for their biological activity. The N3-alkylBTD compounds have shown antiviral activity in the same order or lower than previously prepared compounds. However, the cytotoxicity values observed prevent this new series of BTD derivatives from its potential therapeutic application. Concerning BTD derivatives with the modified linker attached to N1 position, we have obtained new non-nucleoside anti-HCMV derivatives. The activity against HCMV is shown at concentrations that were 10-fold lower than the concentration that was toxic for the host cells, which confirm that these derivatives show a specific antiviral effect against HCMV. SAR conclusions derived from these last compounds have provided new knowledge about the structural requirements of BTD showing certain positions that could be modified for enhancing the anti-HCMV action.
[Mh] Termos MeSH primário: Antivirais/química
Antivirais/farmacologia
Benzotiadiazinas/química
Benzotiadiazinas/farmacologia
Citomegalovirus/efeitos dos fármacos
Óxidos Heterocíclicos/química
Óxidos Heterocíclicos/farmacologia
[Mh] Termos MeSH secundário: Antivirais/síntese química
Benzotiadiazinas/síntese química
Efeito Citopatogênico Viral
Óxidos Heterocíclicos/síntese química
Seres Humanos
Modelos Moleculares
Conformação Molecular
Ressonância Magnética Nuclear Biomolecular
Relação Estrutura-Atividade
Ensaio de Placa Viral
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antiviral Agents); 0 (Benzothiadiazines); 0 (Heterocyclic Oxides)
[Em] Mês de entrada:0402
[Cu] Atualização por classe:111117
[Lr] Data última revisão:
111117
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:030509
[St] Status:MEDLINE


  8 / 15 MEDLINE  
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[PMID]:12175197
[Au] Autor:Huang Y; Rawal VH
[Ad] Endereço:Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
[Ti] Título:Hydrogen-bond-promoted hetero-Diels-Alder reactions of unactivated ketones.
[So] Source:J Am Chem Soc;124(33):9662-3, 2002 Aug 21.
[Is] ISSN:0002-7863
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:We report the first examples of hydrogen-bond-promoted acceleration of hetero-Diels-Alder reactions and the use of such catalysis for the hetero-Diels-Alder reactions of simple, unactivated ketones. Several spiro-fused dihydropyans were synthesized in good yields using this procedure. This activation protocol represents an attractive and operationally simple alternative to conventional, Lewis acid catalysis.
[Mh] Termos MeSH primário: Cicloexanonas/química
Óxidos Heterocíclicos/síntese química
[Mh] Termos MeSH secundário: Alcenos/química
Benzaldeídos/química
Clorofórmio/química
Ligações de Hidrogênio
Cinética
Solventes/química
Termodinâmica
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T; RESEARCH SUPPORT, U.S. GOV'T, P.H.S.
[Nm] Nome de substância:
0 (Alkenes); 0 (Benzaldehydes); 0 (Cyclohexanones); 0 (Heterocyclic Oxides); 0 (Solvents); 5QOR3YM052 (cyclohexanone); 7V31YC746X (Chloroform); 9PA5V6656V (4-anisaldehyde)
[Em] Mês de entrada:0210
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:020815
[St] Status:MEDLINE


  9 / 15 MEDLINE  
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[PMID]:11123958
[Au] Autor:Reznik R; Greer A
[Ad] Endereço:Department of Chemistry, Graduate School, and University Center, The City University of New York, Brooklyn College, Brooklyn, New York 11210, USA.
[Ti] Título:An adjacent thioester provides apical-directed stabilization to 3-isothiazolidinone 1-oxide heterocycles.
[So] Source:Chem Res Toxicol;13(12):1193-8, 2000 Dec.
[Is] ISSN:0893-228X
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The structural and energetic features of the attractive intramolecular through-space S-X interaction [X being oxygen (O) or sulfur (S)] of thioester containing 3-isothiazolidinone 1-oxide heterocycles are described. Density functional theoretical and semiempirical calculations are used to explain the previous X-ray data on 3-isothiazolidinone 1-oxides 5 and 6 [Kanda, Y., Ashizawa, T. , Kakita, S., Takahashi, Y., Kono, M., Yoshida, M., Saitoh, Y., and Okabe, M. (1999) J. Med. Chem. 42, 1330-1332] and implicate a mechanism where the adjacent thioester participates in an apical-directed stabilization of the sulfur heterocycle. A key factor that distinguishes the S-O interaction from the S-S interaction is the stronger through-space interaction of the former, which is a consequence of the greater electronegativity of apical O compared to apical S. Reaction field theory reveals that the conversion of the S-O interaction to the S-S interaction is more facile compared to gas phase computations, which suggest a reduced importance of the 1,5-S-X interactions in solution. The conversion of the S-O interaction to the S-S interaction gives an isothiazolidinone oxide that places the reacting sulfurs in proximity with an orientation presumably suitable for bond formation and access to the dithiolanone oxide surface. Factors that influence the through-space S-X interactions may represent important issues in identifying target 3-isothiazolidinone 1-oxide prodrugs capable of rearranging to 1,2-dithiolan-3-one 1-oxide drugs.
[Mh] Termos MeSH primário: Antibióticos Antineoplásicos/química
Óxidos Heterocíclicos/química
Lactamas
Pró-Fármacos/química
Tiazóis/química
Tionas
[Mh] Termos MeSH secundário: Macrolídeos
Oxigênio/química
Compostos de Sulfidrila
Enxofre/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (3-isothiazolidinone-1-oxide); 0 (Antibiotics, Antineoplastic); 0 (Heterocyclic Oxides); 0 (Lactams); 0 (Macrolides); 0 (Prodrugs); 0 (Sulfhydryl Compounds); 0 (Thiazoles); 0 (Thiones); 120500-15-4 (leinamycin); 70FD1KFU70 (Sulfur); S88TT14065 (Oxygen)
[Em] Mês de entrada:0103
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:001222
[St] Status:MEDLINE


  10 / 15 MEDLINE  
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[PMID]:10552795
[Au] Autor:Bonaccorsi IL; McNair HM; Brunner LA; Dugo P; Dugo G
[Ad] Endereço:Università di Messina, Dipartimento Farmaco-chimico Facoltà di Farmacia, Messina, Italy.
[Ti] Título:Fast HPLC for the analysis of oxygen heterocyclic compounds of citrus essential oils.
[So] Source:J Agric Food Chem;47(10):4237-9, 1999 Oct.
[Is] ISSN:0021-8561
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:A fast HPLC method for the determination of the oxygen heterocyclic compounds of citrus essential oils was developed. Five different oils were analyzed under identical conditions, by reversed-phase HPLC with photodiode array detector, for a direct comparison of the composition of their oxygen heterocyclic fraction. Analysis time was 7 min. The oils analyzed were lemon, bergamot, mandarin, sweet orange, and bitter orange. The method developed is good for rapid screening or fingerprinting of these essential oils; a slightly slower method is recommended for higher resolution and better quantitative results.
[Mh] Termos MeSH primário: Cromatografia Líquida de Alta Pressão
Citrus/química
Óxidos Heterocíclicos/análise
Óleos Vegetais/química
[Mh] Termos MeSH secundário: Cromatografia Líquida de Alta Pressão/métodos
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Heterocyclic Oxides); 0 (Plant Oils)
[Em] Mês de entrada:0002
[Cu] Atualização por classe:001218
[Lr] Data última revisão:
001218
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:991210
[St] Status:MEDLINE



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