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‣ Estudo de uma nova rota sintética para o fármaco (R)-baclofen; Investigation of a New Synthetic Route to (R)-Baclofen

Barazzone, Giovana Cappio
Fonte: Biblioteca Digitais de Teses e Dissertações da USP Publicador: Biblioteca Digitais de Teses e Dissertações da USP
Tipo: Tese de Doutorado Formato: application/pdf
Publicado em 06/12/2007 Português
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O objetivo principal deste trabalho foi a investigação da viabilidade de uma nova rota sintética para a obtenção do fármaco Baclofen em sua forma enantiopura. A etapa principal da rota sintética por nós proposta consiste na síntese de uma aziridina de estereoquímica cis, utilizando uma nova metodologia, desenvolvida em nosso laboratório pelo emprego da catálise de transferência de fase (CTF). Para a obtenção da aziridina apropriada, tornou-se necessário preparar de maneira estereosseletiva, a (2S, 3R)-(4-clorofenil)-serina. Este precursor seria adequado, uma vez que, em estudos preliminares, verificamos que o fechamento do aziridínico ocorre sem racemização dos estereocentros presentes na molécula. Inicialmente, tentamos obter o β-hidróxi-α-aminoácido desejado pela reação de adição aldólica de uma imina do éster terc-butílico da glicina com o 4-clorobenzaldeído, em condições de catálise de transferência de fase assimétrica. Tais reações não apresentaram estereosseletividade. Porém, apesar de gerarem dois produtos diastereoméricos racêmicos, estes são de interesse, uma vez que um deles é uma oxazolidina cis inédita. Para a obtenção da (2S, 3R)-(4-clorofenil)-serina...

‣ Síntese de um fragmento precursor do fármaco Indinavir; Synthesis of a precursor fragment of drug Indinavir

Vasconcelos, Leonardo de
Fonte: Biblioteca Digitais de Teses e Dissertações da USP Publicador: Biblioteca Digitais de Teses e Dissertações da USP
Tipo: Dissertação de Mestrado Formato: application/pdf
Publicado em 28/09/2012 Português
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Neste trabalho foram aprofundados nossos estudos para obtenção da (S)-2-terc-butilamida-4-(3-picolil)piperazina, pela abertura da (S)-2-terc-butilcarboxamida-N-p-tosilaziridina seguida de ciclização, em 78% de rendimento, com o triflato de vinildifenilsulfônio. A aziridina foi preparada por um processo de ciclização, em condições de transferência de fase, partindo-se da L-serina, um aminoácido natural de baixo custo. Esta rota sintética rendeu um material que apresenta a mesma estereoquímica S do fragmento piperazínico usado na síntese do Indinavir, podendo vir a constituir uma via alternativa para a obtenção deste fármaco.; In this work we performed a deeper study for obtaining (S)-2-tert-butylamide-4-(3-picolyl)piperazine by opening (S)-2-tert-butylcarboxamide-N-p-tosylaziridine followed by cyclization, in 78% yield, with diphenylvinylsulfonium trifluoromethanesulfonate. The aziridine were prepared by a cyclization process in phase transfer conditions, starting from L-serine, a low cost amino acid. This synthetic route yielded a material which has the same S piperazinic fragment stereochemistry used in the synthesis of Indinavir, and may constitute an alternative route for obtaining this drug.

‣ Metodologia AGOA: a modelagem de clusters de hidratação no complexo aziridina···ácido fluorídrico

Oliveira,Boaz G.; Araújo,Regiane C. M. U.; Carvalho,Antônio B.; Ramos,Mozart N.
Fonte: Sociedade Brasileira de Química Publicador: Sociedade Brasileira de Química
Tipo: Artigo de Revista Científica Formato: text/html
Publicado em 01/01/2009 Português
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We present a theoretical study of solvent effect on C2H5N···HF hydrogen-bonded complex through the application of the AGOA methodology. By using the TIP4P model to orientate the configuration of water molecules, the hydration clusters generated by AGOA were obtained through the analysis of the molecular electrostatic potential (MEP) of solute (C2H5N···HF). Thereby, it was calculated the hydration energies on positive and negative MEP fields, which are maxima (PEMmax) and minima (PEMmin) when represent the -CH2- methylene groups and hydrofluoric acid, respectively. By taking into account the higher and lower hydration energy values of -370.6 kJ mol-1 and -74.3 kJ mol-1 for PEMmax and PEMmin of the C2H5N···HF, our analysis shows that these results corroborate the open ring reaction of aziridine, in which the preferential attack of water molecules occurs at the methylene groups of this heterocyclic.

‣ Covalent HLA-B27/peptide complex induced by specific recognition of an aziridine mimic of arginine.

Weiss, G A; Valentekovich, R J; Collins, E J; Garboczi, D N; Lane, W S; Schreiber, S L; Wiley, D C
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em 01/10/1996 Português
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The class I major histocompatibility complex (MHC) glycoprotein HLA-B27 binds short peptides containing arginine at peptide position 2 (P2). The HLA-B27/peptide complex is recognized by T cells both as part of the development of the repertoire of T cells in the cellular immune system and during activation of cytotoxic T cells. Based on the three-dimensional structure of HLA-B27, we have synthesized a ligand with an aziridine-containing side chain designed to mimic arginine and to bind covalently in the arginine-specific P2 pocket of HLA-B27. Using tryptic digestion followed by mass spectrometry and amino acid sequencing, the aziridine-containing ligand is shown to alkylate specifically cysteine 67 of HLA-B27. Neither free cysteine in solution nor an exposed cysteine on a class II MHC molecule can be alkylated, showing that specific recognition between the anchor side-chain pocket of an MHC class I protein and the designed ligand (propinquity) is necessary to induce the selective covalent reaction with the MHC class I molecule.

‣ Reduction of the toxicity and mutagenicity of aziridine in mammalian cells harboring the Escherichia coli fpg gene.

Cussac, C; Laval, F
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em 01/05/1996 Português
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Aziridine (ethyleneimine) reacts with DNA in vitro, mainly at the N7 position of guanine and N3 of adenine, then imidazole ring opening of the modified guanine results in formation of formamidopyrimidine (FaPy) residues. The Escherichia coli fpg gene encodes a DNA glycosylase that removes FaPy residues from DNA. To determine whether aziridine produces FaPy lesions in mammalian cells we have expressed the E.coli fpg gene in CHO cells. The transfected cells, expressing high levels of the bacterial protein, are more resistant to the toxic and mutagenic effects of aziridine than the control population. Less DNA damage was measured by quantitative PCR analysis in transfected than in control cells treated with equimolar concentrations of aziridine. The results suggest that aziridine produces in vivo FaPy residues that could account for the deleterious effects of this compound.

‣ Inhibitory Effects of Mitomycin-Related Compounds Lacking the C1-C2 Aziridine Ring

Mercado, Carmen M.; Tomasz, Maria
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em /01/1972 Português
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Three chemical derivatives of mitomycin C cause loss of viability, inhibition of deoxyribonucleic acid synthesis, and inhibition of cell division in bacteria. Each of these drugs lacks the C1-C2 aziridine ring previously postulated to be essential for the bactericidal effect of mitomycin C.

‣ Aziridine-2,3-Dicarboxylates, Peptidomimetic Cysteine Protease Inhibitors with Antileishmanial Activity

Ponte-Sucre, Alicia; Vicik, Radim; Schultheis, Martina; Schirmeister, Tanja; Moll, Heidrun
Fonte: American Society for Microbiology Publicador: American Society for Microbiology
Tipo: Artigo de Revista Científica
Publicado em /07/2006 Português
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Chemotherapy of leishmaniasis is mainly based on antimonials. However, they are extremely toxic and cause serious side effects, and there is a worldwide increasing frequency of chemoresistance to antimonials. These issues emphasize the urgent need for affordable alternative drugs against leishmaniasis. Leishmania cysteine proteases are essential for parasite growth, differentiation, pathogenicity, and virulence and are thus attractive targets for combating leishmaniasis. Herein we demonstrate that the cysteine protease inhibitors aziridine-2,3-dicarboxylates 13b and 13e impaired promastigote growth at mid-micromolar concentrations and decreased the infection rate of peritoneal macrophages at concentrations 8- to 13-fold lower than those needed to inhibit parasite replication. Simultaneous treatment of infected cells with compound 13b and gamma interferon resulted in an even further reduction of the concentration needed for a significant decrease in macrophage infection rate. Notably, treatment with the compounds alone modulated the cytokine secretion of infected macrophages, with increased levels of interleukin-12 and tumor necrosis factor alpha. Furthermore, the decreased infection rate in the presence of compound 13b correlated with increased nitric oxide production by macrophages. Importantly...

‣ Occupational asthma and contact dermatitis in a spray painter after introduction of an aziridine cross-linker.

Leffler, C T; Milton, D K
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em /07/1999 Português
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A 23-year-old spray painter developed contact dermatitis and respiratory difficulty characterized by small airways obstruction shortly after the polyfunctional aziridine cross-linker CX-100 began to be used in his workplace as a paint activator. The symptoms resolved after he was removed from the workplace and was treated with inhaled and topical steroids. Painters may have an increased risk of asthma due to exposure to a variety of agents, such as isocyanates, alkyd resins, and chromates. This case illustrates the importance of using appropriate work practices and personal protective equipment to minimize exposure. Occupational asthma is diagnosed by a history of work-related symptoms and exposure to known causative agents. The diagnosis is confirmed by serial pulmonary function testing or inhalational challenge testing. The risk of asthma attributable to occupational exposures is probably underappreciated due to underreporting and to inappropriate use of narrow definitions of exposure in epidemiologic studies of attributable risk.

‣ Aziridine-2,3-Dicarboxylate-Based Cysteine Cathepsin Inhibitors Induce Cell Death in Leishmania major Associated with Accumulation of Debris in Autophagy-Related Lysosome-Like Vacuoles▿

Schurigt, Uta; Schad, Caroline; Glowa, Christin; Baum, Ulrike; Thomale, Katja; Schnitzer, Johannes K.; Schultheis, Martina; Schaschke, Norbert; Schirmeister, Tanja; Moll, Heidrun
Fonte: American Society for Microbiology (ASM) Publicador: American Society for Microbiology (ASM)
Tipo: Artigo de Revista Científica
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The papain-like cysteine cathepsins expressed by Leishmania play a key role in the life cycle of these parasites, turning them into attractive targets for the development of new drugs. We previously demonstrated that two compounds of a series of peptidomimetic aziridine-2,3-dicarboxylate [Azi(OBn)2]-based inhibitors, Boc-(S)-Leu-(R)-Pro-(S,S)-Azi(OBn)2 (compound 13b) and Boc-(R)-Leu-(S)-Pro-(S,S)-Azi(OBn)2 (compound 13e), reduced the growth and viability of Leishmania major and the infection rate of macrophages while not showing cytotoxicity against host cells. In the present study, we characterized the mode of action of inhibitors 13b and 13e in L. major. Both compounds targeted leishmanial cathepsin B-like cysteine cathepsin cysteine proteinase C, as shown by fluorescence proteinase activity assays and active-site labeling with biotin-tagged inhibitors. Furthermore, compounds 13b and 13e were potent inducers of cell death in promastigotes, characterized by cell shrinkage, reduction of mitochondrial transmembrane potential, and increased DNA fragmentation. Transmission electron microscopic studies revealed the enrichment of undigested debris in lysosome-like organelles participating in micro- and macroautophagy-like processes. The release of digestive enzymes into the cytoplasm after rupture of membranes of lysosome-like vacuoles resulted in the significant digestion of intracellular compartments. However...

‣ (2S)-2-[(2S*,5R*,6R*)-5,6-Dimeth­oxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethyl­ethylsulfon­yl]aziridine

Moragas Solà, Toni; Lewis, William; Bettigeri, Sampada V.; Stockman, Robert A.; Forbes, David C.
Fonte: International Union of Crystallography Publicador: International Union of Crystallography
Tipo: Artigo de Revista Científica
Publicado em 27/11/2010 Português
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The reaction of a sulfur ylide with a chiral non-racemic sulfinyl imine afforded the desired aziridine in excellent yield and subsequent oxidation of the sulfinyl moiety dissolved in anhydrous dichloro­methane using a 75% aqueous solution of 3-chloro­per­oxy­benzoic acid afforded the title compound, C14H27NO6S. The configuration of the newly formed stereogenic center at the point of attachment of the 1,4-dioxane ring to the aziridine ring is S. The configurations of the pre-existing sites 2-, 5-, and 6-positions of the 1,4-dioxane ring prior to reaction of sulfinyl imine with the sulfur ylide are S, R, and R, respectively. The C—N bond lengths of the aziridine are 1.478 (2) and 1.486 (2) Å.

‣ N,N-Diisopropyl-N-phosphonyl Imines Lead to Efficient Asymmetric Synthesis of Aziridine-2-Carboxylic Esters

Kattamuri, Padmanabha V.; Xiong, Yiwen; Pan, Yi; Li, Guigen
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em 28/05/2013 Português
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Highly diastereoselective asymmetric synthesis of chiral aziridine-2-carboxylic esters is reported for 20 examples with good yields (51–87%) and excellent diastereoselectivities (>99:1 dr for most cases). The modified N-phosphonyl imines are proven to be superior to previous imine auxiliaries for the aza Darzens reaction by using secondary isopropyl to replace primary benzyl group for N,N-diamino protection. In the meanwhile, a special operation by slowly adding the pre-cooled imine solution at −78 °C into the preformed β-bromo lithium enolate mixture at this temperature in the presence of 4 Å molecular sieves was found to be crucial in terms of yields and diastereoselectivity. The present method can provide an easy and general access to β-hydroxy α-amino acids and other important amino building blocks.

‣ rac-2-Phenyl-1-[(2,4,6-triiso­propyl­benzene)­sulfon­yl]aziridine

Golz, Christopher; Preut, Hans; Strohmann, Carsten
Fonte: International Union of Crystallography Publicador: International Union of Crystallography
Tipo: Artigo de Revista Científica
Publicado em 15/01/2014 Português
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In the title compound, C23H31NO2S, the geometry of the triiso­propyl­phenyl group is slightly distorted, with elongated C—C bonds at the ipso-C atom, and an S atom which deviates from the benzene ring plane by 0.228 (2) Å. This distortion is caused by the bulky substituents and, in comparison, an unbent geometry is observed in N-toluene­sulfonyl­aziridine [Zhu et al. (2006 ▶). Acta Cryst. E62, o1507–o1508]. π–π inter­actions between adjacent benzene rings [centroid–centroid distance = 3.7928 (11) Å] and are observed.

‣ Selectivity in the Addition Reactions of Organometallic Reagents to Aziridine-2-carboxaldehydes: The Effects of Protecting Groups and Substitution Patterns

Kulshrestha, Aman; Schomaker, Jennifer M.; Holmes, Daniel; Staples, Richard J.; Jackson, James E.; Borhan, Babak
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
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Good to excellent stereo-selectivity has been found in the addition reactions of Grignard and organo-zinc reagents to N-protected aziridine-2-carboxaldehydes. Specifically, high syn selectivity was obtained with benzyl-protected cis, tert-butyloxycar-bonyl-protected trans, and tosyl-pro-tected 2,3-disubstituted aziridine-2-car-boxaldehydes. Furthermore, rate and selectivity effects of ring substituents, temperature, solvent, and Lewis acid and base modifiers were studied. The diastereomeric preference of addition is dominated by the substrate aziri-dines’ substitution pattern and especially the electronic character and conformational preferences of the nitrogen protecting groups. To help rationalize the observed stereochemical outcomes, conformational and electronic structural analyses of a series of model systems representing the various substitution patterns have been explored by density functional calculations at the B3LYP/6–31G* level of theory with the SM8 solvation model to account for solvent effects.

‣ Efficient Regioselective Ring Opening of Activated Aziridine-2-Carboxylates with [18F]Fluoride

Schjoeth-Eskesen, Christina; Hansen, Paul Robert; Kjaer, Andreas; Gillings, Nic
Fonte: BlackWell Publishing Ltd Publicador: BlackWell Publishing Ltd
Tipo: Artigo de Revista Científica
Português
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Aziridines can undergo a range of ring-opening reactions with nucleophiles. The regio- and stereochemistry of the products depend on the substituents on the aziridine. Aziridine ring-opening reactions have rarely been used in radiosynthesis. Herein we report the ring opening of activated aziridine-2-carboxylates with [18F]fluoride. The aziridine was activated for nucleophilic attack by substitution of various groups on the aziridine nitrogen atom. Fluorine-18 radiolabelling was followed by ester hydrolysis and removal of the activation group. Totally regioselective ring opening and subsequent deprotection was achieved with tert-butyloxycarbonyl- and carboxybenzyl-activated aziridines to give α-[18F]fluoro-β-alanine in good radiochemical yield.

‣ Occupational Asthma and Contact Dermatitis in a Spray Painter after Introduction of an Aziridine Cross-Linker.

Leffler, C T; Milton, Donald Kirby
Fonte: The National Institute of Environmental Health Sciences Publicador: The National Institute of Environmental Health Sciences
Tipo: Artigo de Revista Científica
Português
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A 23-year-old spray painter developed contact dermatitis and respiratory difficulty characterized by small airways obstruction shortly after the polyfunctional aziridine cross-linker CX-100 began to be used in his workplace as a paint activator. The symptoms resolved after he was removed from the workplace and was treated with inhaled and topical steroids. Painters may have an increased risk of asthma due to exposure to a variety of agents, such as isocyanates, alkyd resins, and chromates. This case illustrates the importance of using appropriate work practices and personal protective equipment to minimize exposure. Occupational asthma is diagnosed by a history of work-related symptoms and exposure to known causative agents. The diagnosis is confirmed by serial pulmonary function testing or inhalational challenge testing. The risk of asthma attributable to occupational exposures is probably underappreciated due to underreporting and to inappropriate use of narrow definitions of exposure in epidemiologic studies of attributable risk.

‣ Réactions d’ouverture d’aziridines Troc-protégées

Ross, Karen
Fonte: Université de Montréal Publicador: Université de Montréal
Tipo: Thèse ou Mémoire numérique / Electronic Thesis or Dissertation
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Ce mémoire a comme sujet principal les réactions d’ouvertures d’aziridines et leur application synthétique. Notre groupe de recherche a récemment mis au point une méthode d’aziridination énantiosélective catalysée au cuivre à partir de N-tosyloxycarbamates qui permet d’obtenir une grande variété d’arylaziridines protégées avec un groupement carbamate. Or, même si le motif aziridine se retrouve dans certains produits naturels, l’intérêt de sa synthèse provient en partie de l’accès facile à différents composés contenant une fonction amine protégée qui peuvent être obtenus suite à l’ouverture d’aziridines par différents nucléophiles. L’ouverture nucléophile des aziridines fut largement explorée pour une variété de nucléophiles et d’aziridines. Toutefois, puisque les arylaziridines protégées par un groupement carbamate n’étaient auparavant pas disponibles, leur régio- et stéréosélectivité est encore méconnue. Nous présentons ici dans un premier temps, les résultats obtenus lors de l’ouverture de la p-nitrophénylaziridine protégée par un groupement Troc avec différents nucléophiles. Puis, suite à l’obtention de bonnes diastéréosélectivités lors de la synthèse d’aziridines avec le dérivé chiral PhTrocNHOTs...

‣ Investigation of regio- and sterochemistries of microbial biotransformation /

Zabic, Mirjana.
Fonte: Brock University Publicador: Brock University
Tipo: Electronic Thesis or Dissertation
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Epoxides can be hydrolyzed by fungi to produce chiral diols. The first part of this thesis presents an investigation of the microbial hydrolysis of aziridines comparable in structure to epoxide biotransformation substrates. Biotransformation of the aziridines 1 -methyl-2-phenyl aziridine, 2- phenylaziridine and N-methyl-7-aza bicyclo[4.1.0] heptane was studied using Beauveria sulfurescens, Aspergillus niger and Diplodia gossypina but no evidence for enzymic hydrolysis was obtained. The hydroxylation reaction performed by the fungus Beauveria sulfurescens ATCC 7159 has been studied for many years and several models describing the hydroxylating pattern exhibited by this fungus have been proposed. The second part of this thesis presents a test of the proposed models. The ability of Beauveria sulfurescens to hydroxylate thirty potential substrates was examined, and the data suggest that none of the earlier proposed models accounts for all of the bioconversion results. A possible explanation is proposed, suggesting that there is more than one enzyme responsible for the hydroxylation reactions performed by Beauveria sulfurescens.

‣ Aspects of organoselenium chemistry.

Ward, Virginia R.
Fonte: Universidade de Adelaide Publicador: Universidade de Adelaide
Tipo: Tese de Doutorado
Publicado em //2013 Português
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A range of β-amidoalkyl phenylselenides were prepared in order to explore their cyclisation via oxidation of the selenium moiety to the selenone followed by intramolecular displacement. At first, the β-amidoalkyl phenylselenides were prepared in one-step from the alkenes. However, the one-step preparation was complicated by side-reactions and a two-step method was found to give clean reactions and higher yields of a wide range of the desired amido selenides. Along with the expected oxazolines, isomeric N-acylaziridines were obtained from the cyclisation reaction. Formation of N-acylaziridines by cyclisation of amides is unusual, and variation of the conditions was explored in order to optimise this novel aziridine-forming reaction. It was found that conducting the oxidation reaction at low temperature favoured the aziridine products. In this way, the aziridines derived from all prepared β-amido selenides were obtained in good to excellent yield. From some substrates, the aziridine was obtained as the exclusive product. The low temperature generation of a selenone from the corresponding selenide had not been reported previously. Experiments were carried out which provided evidence for the supposition that the intermediate in the cyclisation reaction was the selenone. The preparation of β-amido selenides was also investigated using silver ion to sequester the halide of the selenium reagent...

‣ PURIFICATION AND KINETIC STUDIES OF ASPARTASE FROM ESCHERICHIA COLI AND EFFECT OF S-2,3-DICARBOXY AZIRIDINE ON FUMARASE FROM PIG HEART

GREENHUT, JOAN
Fonte: Universidade Rice Publicador: Universidade Rice
Tipo: Thesis; Text Formato: application/pdf
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Aspartase has been purified from E. coli B cells using high performance liquid ion exchange chromatography. This procedure allows rapid purification of the enzyme with >80% recovery of total activity. The kinetic mechanism of aspartase, determined from initial velocity experiments, is best described by the equilibrium ordered addition of a divalent metal cation to free enzyme followed by binding of aspartate. Following interconversion of the central complex, NH(,4)('+) and fumarate are randomly released. Michaelis constants for each substrate are: 85 mM for NH(,4)('+), 0.17 mM for fumarate, 0.6-1.0 mM for aspartate and 9.0 (mu)M for Mg('2+). From the results of inhibition studies using structural analogues of aspartate, it was determined that aspartase recognizes the (beta)-carboxylate group of aspartate. The (alpha)-amino group contributes very little to the binding of aspartate to the enzyme. Compounds having an -OH group in addition to the (beta)-carboxylate had no effect on the rate of deamination of aspartate, suggesting a restricted geometry at the active site. S-2,3-Dicarboxy aziridine was found to be a potent competitive inhibitor of aspartase (K(,i) = 0.1 (mu)M) and fumarase (K(,i) = 0.08 (mu)M). The aziridine did not inactivate either enzyme nor did it exhibit any observable substrate activity. It is likely that it functions as a transition state analogue mimicking the carbanion intermediate found in the normal catalytic reaction. The aziridine inhibited fumarate utilization in ruptured but not intact mitochondria.

‣ NSC50704; Aziridine, 1-(p-nitrobenzoyl)- (8CI); Aziridine, 1-(4-nitrobenzoyl)- (9CI); N-(p-Nitrobenzoyl)aziridine; 1-(p-Nitrobenzoyl)aziridine

US National Cancer Institute
Fonte: Unilever Center for Molecular Informatics, Cambridge University Publicador: Unilever Center for Molecular Informatics, Cambridge University
Tipo: Outros Formato: 3628 bytes; 4034 bytes; chemical/x-cml; chemical/x-cml
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