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[PMID]:27151143
[Au] Autor:Bunsupa S; Yamazaki M; Saito K
[Ad] Endereço:Department of Molecular Biology and Biotechnology, Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan.
[Ti] Título:Lysine-derived Alkaloids: Overview and Update on Biosynthesis and Medicinal Applications with Emphasis on Quinolizidine Alkaloids.
[So] Source:Mini Rev Med Chem;17(12):1002-1012, 2017.
[Is] ISSN:1875-5607
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: Plants produce a vast variety of specialized metabolites which can be a rich source for lead compounds for the development of new drugs. Alkaloids are one the largest groups of plant specialized metabolites important for natural product based pharmaceuticals. Of these, lysine (Lys)-derived alkaloids exhibit a wide range of pharmacological properties which are beneficial for humans. For instance they have anticancer, anti-Alzheimer's disease, anti-inflammatory, hypocholesterolemic and antiarrhtymic effects. Lys-derived alkaloids are widely distributed throughout the plant kingdom: they can be found in various species from clubmosses to flowering plants. Lys is one of the most essential amino acids for humans and livestock and is synthesized in the plastids of land plants. Lys-derived alkaloids can be divided into four major groups including quinolizidine, lycopodium, piperidine, and indolizidine alkaloids. Despite the importance of these compounds, the biosynthetic pathways of Lys-derived alkaloids are not well understood. With the exception of indolizidine alkaloids, Lys decarboxylase (LDC) is the enzyme involved in the first committed step of the biosynthesis by catalyzing the transformation of L-Lys into cadaverine. Cadaverine is then oxidized by copper amine oxidase (CuAO) and spontaneously cyclized to Δ1-piperideine Schiff base which is a universal intermediate for the production of various Lys-derived alkaloids. CONCLUSION: In this review, we briefly summarize the recent understanding about the structures, occurrences, analytical procedures, biosyntheses, and potential health effects and medical applications of Lys-derived alkaloids with emphasis on quinolizidine alkaloids (QAs).
[Mh] Termos MeSH primário: Alcaloides/biossíntese
Lisina/química
Quinolizidinas/química
[Mh] Termos MeSH secundário: Alcaloides/química
Indolizidinas/química
Lycopodium/química
Lycopodium/metabolismo
Piperidinas/química
Plantas/química
Plantas/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (Alkaloids); 0 (Indolizidines); 0 (Piperidines); 0 (Quinolizidines); 67I85E138Y (piperidine); K3Z4F929H6 (Lysine)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170912
[Lr] Data última revisão:
170912
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160507
[St] Status:MEDLINE
[do] DOI:10.2174/1389557516666160506151213


  2 / 120 MEDLINE  
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[PMID]:27509489
[Au] Autor:Pereira NA; Sureda FX; Pérez M; Amat M; Santos MM
[Ad] Endereço:Instituto de Investigação do Medicamento (iMed.ULisboa), Faculdade de Farmácia, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal. nalpereira@ff.ulisboa.pt.
[Ti] Título:Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists.
[So] Source:Molecules;21(8), 2016 Aug 06.
[Is] ISSN:1420-3049
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:Enantiopure tryptophanol is easily obtained from the reduction of its parent natural amino acid trypthophan (available from the chiral pool), and can be used as chiral auxiliary/inductor to control the stereochemical course of a diastereoselective reaction. Furthermore, enantiopure tryptophanol is useful for the syntheses of natural products or biological active molecules containing the aminoalcohol functionality. In this communication, we report the development of a small library of indolo[2,3-a]quinolizidines and evaluation of their activity as N-Methyl d-Aspartate (NMDA) receptor antagonists. The indolo[2,3-a]quinolizidine scaffold was obtained using the following key steps: (i) a stereoselective cyclocondensation of (S)- or (R)-tryptophanol with appropriate racemic δ-oxoesters; (ii) a stereocontrolled cyclization on the indole nucleus. The synthesized enantiopure indolo[2,3-a]quinolizidines were evaluated as NMDA receptor antagonists and one compound was identified to be 2.9-fold more potent as NMDA receptor blocker than amantadine (used in the clinic for Parkinson's disease). This compound represents a hit compound for the development of novel NMDA receptor antagonists with potential applications in neurodegenerative disorders associated with overactivation of NMDA receptors.
[Mh] Termos MeSH primário: Quinolizidinas/síntese química
Quinolizidinas/farmacologia
Receptores de N-Metil-D-Aspartato/antagonistas & inibidores
[Mh] Termos MeSH secundário: Ciclização
Indóis/síntese química
Indóis/química
Indóis/farmacologia
Estrutura Molecular
Quinolizidinas/química
Bibliotecas de Moléculas Pequenas/síntese química
Bibliotecas de Moléculas Pequenas/química
Bibliotecas de Moléculas Pequenas/farmacologia
Estereoisomerismo
Triptofano/análogos & derivados
Triptofano/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Indoles); 0 (Quinolizidines); 0 (Receptors, N-Methyl-D-Aspartate); 0 (Small Molecule Libraries); 526-53-4 (tryptophanol); 8DUH1N11BX (Tryptophan)
[Em] Mês de entrada:1704
[Cu] Atualização por classe:170418
[Lr] Data última revisão:
170418
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160811
[St] Status:MEDLINE


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[PMID]:27460668
[Au] Autor:Zhou Y; Nie T; Zhang Y; Song M; Li K; Ding M; Ding K; Wu D; Xu Y
[Ad] Endereço:Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou 510530, China; University of Chinese Academy of Sciences, No. 19 Yuquan Road, Beijing 100049, China.
[Ti] Título:The discovery of novel and selective fatty acid binding protein 4 inhibitors by virtual screening and biological evaluation.
[So] Source:Bioorg Med Chem;24(18):4310-4317, 2016 Sep 15.
[Is] ISSN:1464-3391
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Adipocyte fatty acid binding protein (AFABP, FABP4) has been proven to be a potential therapeutic target for diabetes, atherosclerosis and inflammation-related diseases. In this study, a series of new scaffolds of small molecule inhibitors of FABP4 were identified by virtual screening and were validated by a bioassay. Fifty selected compounds were tested, which led to the discovery of seven hits. Structural similarity-based searches were then performed based on the hits and led to the identification of one high affinity compound 33b (Ki=0.29±0.07µM, ΔTm=8.5°C). This compound's effective blockade of inflammatory response was further validated by its ability to suppress pro-inflammatory cytokines induced by lipopolysaccharide (LPS) stimulation. Molecular dynamics simulation (MD) and mutagenesis studies validated key residues for its inhibitory potency and thus provide an important clue for the further development of drugs.
[Mh] Termos MeSH primário: Ácidos Carboxílicos/farmacologia
Proteínas de Ligação a Ácido Graxo/antagonistas & inibidores
Quinolizidinas/farmacologia
[Mh] Termos MeSH secundário: Animais
Ácidos Carboxílicos/química
Linhagem Celular
Descoberta de Drogas
Proteína 3 Ligante de Ácido Graxo
Proteínas de Ligação a Ácido Graxo/genética
Ligações de Hidrogênio
Interleucina-6/metabolismo
Ligantes
Camundongos
Simulação de Acoplamento Molecular
Simulação de Dinâmica Molecular
Mutagênese Sítio-Dirigida
Quinolizidinas/química
Relação Estrutura-Atividade
Fator de Necrose Tumoral alfa/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Carboxylic Acids); 0 (Fabp3 protein, mouse); 0 (Fabp4 protein, mouse); 0 (Fatty Acid Binding Protein 3); 0 (Fatty Acid-Binding Proteins); 0 (Interleukin-6); 0 (Ligands); 0 (Quinolizidines); 0 (Tumor Necrosis Factor-alpha); 0 (interleukin-6, mouse)
[Em] Mês de entrada:1707
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160728
[St] Status:MEDLINE


  4 / 120 MEDLINE  
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[PMID]:27381554
[Au] Autor:Uys M; Shahid M; Sallinen J; Dreyer W; Cockeran M; Harvey BH
[Ad] Endereço:Division of Pharmacology, North-West University (Potchefstroom Campus), Potchefstroom 2520, South Africa. Electronic address: madeleine.erasmus@gmail.com.
[Ti] Título:The α2C-adrenoceptor antagonist, ORM-10921, has antipsychotic-like effects in social isolation reared rats and bolsters the response to haloperidol.
[So] Source:Prog Neuropsychopharmacol Biol Psychiatry;71:108-16, 2016 Nov 03.
[Is] ISSN:1878-4216
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Early studies suggest that selective α2C-adrenoceptor (AR)-antagonism has anti-psychotic-like and pro-cognitive properties. However, this has not been demonstrated in an animal model of schizophrenia with a neurodevelopmental construct. The beneficial effects of clozapine in refractory schizophrenia and associated cognitive deficits have, among others, been associated with its α2C-AR modulating activity. Altered brain-derived neurotrophic factor (BDNF) has been linked to schizophrenia and cognitive deficits. We investigated whether the α2C-AR antagonist, ORM-10921, could modulate sensorimotor gating and cognitive deficits, as well as alter striatal BDNF levels in the social isolation reared (SIR) model of schizophrenia, comparing its effects to clozapine and the typical antipsychotic, haloperidol, the latter being devoid of α2C-AR-activity. Moreover, the ability of ORM-10921 to augment the effects of haloperidol on the above parameters was also investigated. Animals received subcutaneous injection of either ORM-10921 (0.01mg/kg), clozapine (5mg/kg), haloperidol (0.2mg/kg), haloperidol (0.2mg/kg)+ORM-10921 (0.01mg/kg) or vehicle once daily for 14days, followed by assessment of novel object recognition (NOR), prepulse inhibition (PPI) of startle response and striatal BDNF levels. SIR significantly attenuated NOR memory as well as PPI, and reduced striatal BDNF levels vs. social controls. Clozapine, ORM-10921 and haloperidol+ORM-10921, but not haloperidol alone, significantly improved SIR-associated deficits in PPI and NOR, with ORM-10921 also significantly improving PPI deficits vs. haloperidol-treated SIR animals. Haloperidol+ORM-10921 significantly reversed reduced striatal BDNF levels in SIR rats. α2C-AR-antagonism improves deficits in cognition and sensorimotor gating in a neurodevelopmental animal model of schizophrenia and bolsters the effects of a typical antipsychotic, supporting a therapeutic role for α2C-AR-antagonism in schizophrenia.
[Mh] Termos MeSH primário: Antipsicóticos/uso terapêutico
Benzofuranos/uso terapêutico
Haloperidol/uso terapêutico
Quinolizidinas/uso terapêutico
Esquizofrenia/tratamento farmacológico
Psicologia do Esquizofrênico
Isolamento Social/psicologia
[Mh] Termos MeSH secundário: Estimulação Acústica
Animais
Fator Neurotrófico Derivado do Encéfalo/metabolismo
Corpo Estriado/efeitos dos fármacos
Corpo Estriado/metabolismo
Modelos Animais de Doenças
Sinergismo Farmacológico
Masculino
Inibição Pré-Pulso/efeitos dos fármacos
Ratos
Ratos Sprague-Dawley
Recognição (Psicologia)/efeitos dos fármacos
Esquizofrenia/patologia
Estatísticas não Paramétricas
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antipsychotic Agents); 0 (Benzofurans); 0 (Brain-Derived Neurotrophic Factor); 0 (ORM-10921); 0 (Quinolizidines); J6292F8L3D (Haloperidol)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:170830
[Lr] Data última revisão:
170830
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160707
[St] Status:MEDLINE


  5 / 120 MEDLINE  
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[PMID]:27285814
[Au] Autor:Jan S; Kamili AN; Parray JA; Bedi YS; Ahmad P
[Ad] Endereço:Centre of Research for Development, University of Kashmir, Srinagar 190006, India.
[Ti] Título:Microclimatic variation in UV perception and related disparity in tropane and quinolizidine alkaloid composition of Atropa acuminata, Lupinus polyphyllus and Hyoscyamus niger.
[So] Source:J Photochem Photobiol B;161:230-5, 2016 Aug.
[Is] ISSN:1873-2682
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:The aim of current research was to evaluate the physiological adjustment in three medicinal herbs viz., Atropa acuminata, Lupinus polyphyllus and Hyoscyamus niger to the winter period characterised by intense UV flux in Kashmir valley across the North Western Himalaya. Quinolizidine (QA) and tropane alkaloid (TA) concentrations were analysed in these herbs thriving at two different altitudes via GC-MS and correlated by PCA analysis. This study investigated the hypothesis that UV reflectance and absorbance at low temperatures are directly related to disparity in alkaloid accumulation. Among QAs in L. polyphyllus, ammodendrine and lupanine accumulated at higher concentration and exhibited significant variation of 186.36% and 95.91% in ammodendrine and lupanine respectively in both sites. Tetrahydrohombifoline displayed non-significant variation of about 9.60% irrespective of sites. Among tropane alkaloid (TA), hyoscyamine was recorded as the most abundant constituent irrespective of the plant and site while apotropine accumulated in lesser quantity in A. acuminata than H. niger. However, apotropine demonstrated significant variation of 175% among both sites. The final concentration of quinolizidine (QA) and tropane alkaloid (TA) reflects the interplay between reflectance and absorbance of UV radiation response field. These findings suggest that spectral response of UV light contributes directly to alkaloid biosynthesis.
[Mh] Termos MeSH primário: Alcaloides/análise
Atropa/química
Hyoscyamus/química
Lupinus/química
Raios Ultravioleta
[Mh] Termos MeSH secundário: Alcaloides/biossíntese
Atropa/metabolismo
Cromatografia Gasosa-Espectrometria de Massas
Hyoscyamus/metabolismo
Lupinus/metabolismo
Piperidinas/análise
Extratos Vegetais/química
Folhas de Planta/química
Folhas de Planta/metabolismo
Análise de Componente Principal
Piridinas/análise
Quinolizidinas/química
Esparteína/análogos & derivados
Esparteína/análise
Temperatura Ambiente
Tropanos/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkaloids); 0 (Piperidines); 0 (Plant Extracts); 0 (Pyridines); 0 (Quinolizidines); 0 (Tropanes); 183KU7535A (lupanine); 298897D62S (Sparteine); 494-15-5 (ammodendrine)
[Em] Mês de entrada:1703
[Cu] Atualização por classe:170313
[Lr] Data última revisão:
170313
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160611
[St] Status:MEDLINE


  6 / 120 MEDLINE  
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[PMID]:27077446
[Au] Autor:Zheng H; Dong Y; Li L; Sun B; Liu L; Yuan H; Lou H
[Ad] Endereço:Department of Natural Products Chemistry, Key Laboratory of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, ‡Department of Biochemistry and Molecular Biology, School of Medicine, and §National Glycoengineering Research Center, Shandong University , No.44 Western Wenhua
[Ti] Título:Novel Benzo[a]quinolizidine Analogs Induce Cancer Cell Death through Paraptosis and Apoptosis.
[So] Source:J Med Chem;59(10):5063-76, 2016 May 26.
[Is] ISSN:1520-4804
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Paraptosis is nonapoptotic cell death characterized by massive endoplasmic reticulum (ER)- or mitochondria-derived vacuoles. Induction of paraptosis offers significant advantages for the treatment of chemotherapy-resistant tumors compared with anticancer drugs that rely on apoptosis. Because some natural alkaloids induce paraptotic cell death, a novel series of benzo[a]quinolizidine derivatives were synthesized, and their antiproliferative activity and ability to induce cytoplasmic vacuolation were analyzed. Structural optimization led to the identification of the potent compound 22b, which inhibited cancer cell proliferation in vitro and in vivo and profoundly facilitated paraptosis-like cell death and induced caspase-dependent apoptosis. Further investigation revealed that 22b-mediated vacuolation originated from persistent ER stress and upregulation of LC3B. Paraptosis induced by benzo[a]quinolizidine derivatives thus represents an alternative strategy for cancer chemotherapy.
[Mh] Termos MeSH primário: Apoptose/efeitos dos fármacos
Neoplasias/patologia
Quinolizidinas/farmacologia
[Mh] Termos MeSH secundário: Animais
Proliferação Celular/efeitos dos fármacos
Relação Dose-Resposta a Droga
Desenho de Drogas
Ensaios de Seleção de Medicamentos Antitumorais
Seres Humanos
Camundongos
Estrutura Molecular
Quinolizidinas/síntese química
Quinolizidinas/química
Relação Estrutura-Atividade
Células Tumorais Cultivadas
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Quinolizidines)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170529
[Lr] Data última revisão:
170529
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160415
[St] Status:MEDLINE
[do] DOI:10.1021/acs.jmedchem.6b00484


  7 / 120 MEDLINE  
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[PMID]:26777309
[Au] Autor:Michael JP
[Ad] Endereço:Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, Gauteng, South Africa. Electronic address: joseph.michael@wits.ac.za.
[Ti] Título:Simple Indolizidine and Quinolizidine Alkaloids.
[So] Source:Alkaloids Chem Biol;75:1-498, 2016.
[Is] ISSN:1099-4831
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:This review of simple indolizidine and quinolizidine alkaloids (i.e., those in which the parent bicyclic systems are in general not embedded in polycyclic arrays) is an update of the previous coverage in Volume 55 of this series (2001). The present survey covers the literature from mid-1999 to the end of 2013; and in addition to aspects of the isolation, characterization, and biological activity of the alkaloids, much emphasis is placed on their total synthesis. A brief introduction to the topic is followed by an overview of relevant alkaloids from fungal and microbial sources, among them slaframine, cyclizidine, Steptomyces metabolites, and the pantocins. The important iminosugar alkaloids lentiginosine, steviamine, swainsonine, castanospermine, and related hydroxyindolizidines are dealt with in the subsequent section. The fourth and fifth sections cover metabolites from terrestrial plants. Pertinent plant alkaloids bearing alkyl, functionalized alkyl or alkenyl substituents include dendroprimine, anibamine, simple alkaloids belonging to the genera Prosopis, Elaeocarpus, Lycopodium, and Poranthera, and bicyclic alkaloids of the lupin family. Plant alkaloids bearing aryl or heteroaryl substituents include ipalbidine and analogs, secophenanthroindolizidine and secophenanthroquinolizidine alkaloids (among them septicine, julandine, and analogs), ficuseptine, lasubines, and other simple quinolizidines of the Lythraceae, the simple furyl-substituted Nuphar alkaloids, and a mixed quinolizidine-quinazoline alkaloid. The penultimate section of the review deals with the sizable group of simple indolizidine and quinolizidine alkaloids isolated from, or detected in, ants, mites, and terrestrial amphibians, and includes an overview of the "dietary hypothesis" for the origin of the amphibian metabolites. The final section surveys relevant alkaloids from marine sources, and includes clathryimines and analogs, stellettamides, the clavepictines and pictamine, and bis(quinolizidine) alkaloids.
[Mh] Termos MeSH primário: Alcaloides/química
Indolizidinas/química
Quinolizidinas/química
[Mh] Termos MeSH secundário: Animais
Biologia Marinha
Plantas/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (Alkaloids); 0 (Indolizidines); 0 (Quinolizidines)
[Em] Mês de entrada:1605
[Cu] Atualização por classe:160118
[Lr] Data última revisão:
160118
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160119
[St] Status:MEDLINE


  8 / 120 MEDLINE  
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[PMID]:26492086
[Au] Autor:N V G M; Dyapa R; Pansare SV
[Ad] Endereço:Department of Chemistry, Memorial University , St. John's, Newfoundland, Canada A1B 3X7.
[Ti] Título:Formal Synthesis of (+)-Lasubine II and (-)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α-Nitrostyrene.
[So] Source:Org Lett;17(21):5312-5, 2015 Nov 06.
[Is] ISSN:1523-7052
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The first examples of an organocatalytic Michael addition of a ketone to in situ generated α-nitrostyrenes are reported. A suitably functionalized γ-nitroketone obtained from the organocatalyzed Michael addition was converted into (+)-2-epi-lasubine II, the immediate synthetic precursor of (+)-lasubine II and (-)-subcosine II (enantiomers of the natural quinolizidine alkaloids). Two of the three stereocenters in (+)-2-epi-lasubine II are set by the Michael reaction.
[Mh] Termos MeSH primário: Alcaloides/síntese química
Cetonas/química
Nitrocompostos/química
Quinolizidinas/síntese química
Quinolizinas/síntese química
Estirenos/química
[Mh] Termos MeSH secundário: Alcaloides/química
Estrutura Molecular
Piperidinas/química
Quinolizidinas/química
Quinolizinas/química
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alkaloids); 0 (Ketones); 0 (Nitro Compounds); 0 (Piperidines); 0 (Quinolizidines); 0 (Quinolizines); 0 (Styrenes); 0 (lasubin I); 0 (subcosine II)
[Em] Mês de entrada:1603
[Cu] Atualização por classe:151106
[Lr] Data última revisão:
151106
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:151023
[St] Status:MEDLINE
[do] DOI:10.1021/acs.orglett.5b02677


  9 / 120 MEDLINE  
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[PMID]:26429714
[Au] Autor:Perez M; Espadinha M; Santos MM
[Ti] Título:Indolo[2,3-a]quinolizidines and Derivatives: Bioactivity and Asymmetric Synthesis.
[So] Source:Curr Pharm Des;21(38):5518-46, 2015.
[Is] ISSN:1873-4286
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Corynantheine alkaloids with a tetracyclic indole[2,3-a]-quinolizidine motif are an important issue in academia and in the life science industries due to their broad bioactivity profile. In particular, the main biological effects described for indoloquinolizidines include analgesic, anti-inflammatory, antihypertensive, and antiarrhythmic activities, as well as inhibition of multiple ion channels, affinity for opioid receptors, and activity against Leishmania. For that reason, in the last decades, numerous efforts have been invested in the development of novel synthetic strategies to obtain the indole[2,3-a]-quinolizidine system. This review focuses on the synthetic methodologies developed to target the most important alkaloids of this family, and highlights the potential use of these alkaloids or analogs to treat several diseases, ranging from cancer to neurodegenerative disorders.
[Mh] Termos MeSH primário: Indóis/química
Indóis/metabolismo
Quinolizidinas/química
Quinolizidinas/metabolismo
[Mh] Termos MeSH secundário: Animais
Anti-Inflamatórios/química
Anti-Inflamatórios/metabolismo
Anti-Inflamatórios/uso terapêutico
Anti-Hipertensivos/química
Anti-Hipertensivos/metabolismo
Anti-Hipertensivos/uso terapêutico
Antineoplásicos/química
Antineoplásicos/metabolismo
Antineoplásicos/uso terapêutico
Seres Humanos
Indóis/uso terapêutico
Neoplasias/tratamento farmacológico
Neoplasias/metabolismo
Doenças do Sistema Nervoso/tratamento farmacológico
Doenças do Sistema Nervoso/metabolismo
Quinolizidinas/uso terapêutico
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T; REVIEW
[Nm] Nome de substância:
0 (Anti-Inflammatory Agents); 0 (Antihypertensive Agents); 0 (Antineoplastic Agents); 0 (Indoles); 0 (Quinolizidines)
[Em] Mês de entrada:1609
[Cu] Atualização por classe:151117
[Lr] Data última revisão:
151117
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:151003
[St] Status:MEDLINE


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[PMID]:26375043
[Au] Autor:Chio FK; Guesné SJ; Hassall L; McGuire T; Dobbs AP
[Ad] Endereço:School of Biological & Chemical Sciences, Queen Mary University of London , Mile End Road, London E1 4NS, United Kingdom.
[Ti] Título:Synthesis of Azabicycles via Cascade Aza-Prins Reactions: Accessing the Indolizidine and Quinolizidine Cores.
[So] Source:J Org Chem;80(20):9868-80, 2015 Oct 16.
[Is] ISSN:1520-6904
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The first detailed studies of intramolecular aza-Prins and aza-silyl-Prins reactions, starting from acyclic materials, are reported. The methods allow rapid and flexible access toward an array of [6,5] and [6,6] aza-bicycles, which form the core skeletons of various alkaloids. On the basis of our findings on the aza-Prins and aza-silyl-Prins cyclizations, herein we present simple protocols for the intramolecular preparation of the azabicyclic cores of the indolizidines and quinolizidines using a one-pot cascade process of N-acyliminium ion formation followed by aza-Prins cyclization and either elimination or carbocation trapping. It is possible to introduce a range of different substituents into the heterocycles through a judicial choice of Lewis acid and solvent(s), with halo-, phenyl-, and amido-substituted azabicyclic products all being accessed through these highly diastereoselective processes.
[Mh] Termos MeSH primário: Indolizidinas/síntese química
Quinolizidinas/síntese química
[Mh] Termos MeSH secundário: Ciclização
Indolizidinas/química
Modelos Moleculares
Estrutura Molecular
Quinolizidinas/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Indolizidines); 0 (Quinolizidines)
[Em] Mês de entrada:1603
[Cu] Atualização por classe:151016
[Lr] Data última revisão:
151016
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150917
[St] Status:MEDLINE
[do] DOI:10.1021/acs.joc.5b01301



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