SYNTHESIS AND BIOLOGICAL ACTIVITY OF NEW SERIES OF ORGANOTIN(IV) ESTERS WITH N,N-DIACETYLGLYCINE

A bioactive N,N-diacetylglycine (NNDAG) and new organotin(IV) complexes (OTCs) (1-7) were synthesized. Spectroscopic techniques were employed to characterize NNDAG and OTCs. FTIR was employed to verify N,N protection of glycine by acetyl groups. The disappearance of υ(OH) at 3000-2600 cm-1 showed de-protonation of free ligand. The Δυ 150<200 cm-1 of OTCs 4-7 verified bidentate coordination with tetrahedral geometry. The Δυ of OTCs1 and 3 was <200 cm-1 exhibitingtrans -octahedral geometry while OTC 2 dimer was assigned a unique sinusoidal view. The 1H NMR spectra of OTCs verified their synthesis by de-protonation of NNDAG and no chemical shift was found downfield for carboxylic acid proton. The 13C, 119Sn NMR and Mass spectrometric data also supported FTIR and 1H NMR descriptions. The OTCs 4, 5, 6 and7 (500 ppm) proved twice as active against Escherichia coli as the standard antibiotic enoxacin (1000 ppm). The promising property of the OTCs (4, 5, 6 and7) is clearly due to their tetrahedral. The OTCs 4and 5 exhibited excellent activity against M. minimum and good activity against T. castaneum.LD50 of all the compounds were determined and OTCs4, 5 and 7 were found to be active.

Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

Propolis is a sticky, gummy, resinous substance collected by honeybees (Apis mellifera L.) from various plant sources, which has excellent medicinal properties. This paper describes the isolation and identification of triterpenoids and anacardic acid derivatives from Brazilian propolis and their antibacterial activity. Their structures were elucidated by ¹H and 13C NMR, including uni- and bidimensional techniques; in addition, comparisons were made with data from academic literature. These compounds were identified as: cardanols (1a + 1b), cardols (2a + 2b), monoene anacardic acid (3), a-amirine (4), b-amirine (5), cycloartenol (6), 24-methylene-cycloartenol (7) and lupeol (8). The determination of the position of the double bond after a reaction with Dimethyl disulfide (DMDS) is described for the phenol derivatives. The ethanolic extract was tested in vitro for antimicrobial activity by using the disc diffusion method and it showed significant results against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Shigella spp.

Synthesis and characterization of solid 2-methoxycinnamylidenepyruvic acid

The 2-methoxycinnamylidenepyruvic acid (2-MeO-HCP) was synthesized and characterized for nuclear magnetic resonance (¹H and 13C NMR), mass spectrometry (MS), Infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC). The application of DSC for purity determination is well documented in literature and is used in the analysis of pure organic compounds. The molecular geometry and vibrational frequencies of 2-MeO-HCP have been calculated.

Phytosterols isolated from endophytic fungus Colletotrichum gloeosporioides(Melanconiaceae)

ABSTRACTEndophytic fungi are fungi that colonize internal tissues of plants. There are few studies of compounds isolated from endophytic fungi of Amazon plants. Thus, the aim this study was the isolation and structural identification of sitosterol (1), stigmasterol (2), sitostenone (3), squalene (4), ergosterol (5) and ergosterol peroxide (6) from fungus Colletotrichum gloeosporioidesisolated as endophytic from Virola michelli, a typical Amazon plant, used in folk medicine against skin infection. Compounds were isolated by chromatography column on silica and identified by 1H and 13C NMR and MS. The presence of phytosterols in fungi is rare and this is the first report of the isolation of the phytosterols sitosterol, stigmasterol and sitostenone from the genus Colletotrichum.

Contribution of humic substances from different composts to the synthesis of humin in a tropical soil

The contribution of humic substances of different composts to the synthesis of humin in a tropical soil was evaluated. Increasing doses (0, 13, 26, 52, and 104 Mg ha-1) of five different composts consisting of agroinpowderrial residues were applied to a Red-Yellow Latosol. These composts were chemically characterized and 13C NMR determined and the quantity of the functional alkyl groups of humic acids applied to the soil as compost was estimated. Thirty days after application of the treatments, organic matter samples were collected for fractionation of humic acids (HA), fulvic acids (FA) and humin (HU), from which the ratios HA/FA and (HA + FA)/HU were calculated. The application of the composts based on castor cake resulted in the highest HU levels in the soil; alkyl groups of the HA fraction of the composts were predominant in the organic components added to the HU soil fraction.

Evaluation of preoperative computed tomography angiography in association with conventional angiography versus computed tomography angiography only, in the endovascular treatment of aortic diseases

Objective To evaluate the association of conventional angiography (AG) with computed tomography angiography (CTA) as compared with CTA only, preoperatively, in the treatment of aortic diseases. Materials and Methods Retrospective study involving patients submitted to endovascular treatment of aortic diseases, in the period from January 2009 to July 2010, with use of preoperative CTA + conventional AG or CTA only. The patients were divided into two groups, namely: G1 – thoracic aortic diseases; and G2 – abdominal aortic diseases. G1 was subdivided into 1A (preoperative AG + CTA) and 1B (preoperative CTA). G2 was subdivided into 2C (CTA + AG) and 2D (CTA only). Results The authors evaluated 156 patients. In subgroups 1A and 1B, the rate of technical success was, respectively, 100% and 94.7% (p = 1.0); and the rate of therapeutic success was, respectively, 81% and 58% (p = 0.13). A higher number of complications were observed in subgroup 1B (p = 0.057). The accuracy in the calculation of the prosthesis was higher in subgroup 1A (p = 0.065). In their turn, the rate of technical success in subgroups 2C and 2D was, respectively, 92.3% and 98.6% (p = 0.17). The rate of therapeutic success was 73% and 98.6% (p = 0.79). Conclusion Preoperative conventional AG should be reserved for cases where CTA cannot provide all the information in the planning of a therapeutic intervention.

Determinação da Estereoquímica Relativa de Pimaradienos Através de Produtos de Oxidação

Pimaradienes, including isopimaradienes, with an endocyclic double bond between C-9 and C-11 are uncommon compounds in nature. The diterpenoid pimar-9(11),15-dien-19-oic acid (1) was isolated from Mikania triangularis (Asteraceae) and the correct stereochemistry of 1was established by ¹H and 13C NMR studies of several oxidative products, mainly epoxides, of this compound and its double bond isomers.

Isolamento e caracterização de acil-tiossemicarbazidas como intermediários na síntese de compostos mesoiônicos

1,3,4-thiadiazolium-2-aminides and their isomers 1,3,4-triazolium-2-thiolates have been synthesized via anhydroacylation reactions. This work presents a study by infrared monitoring of the reaction between substituted aroyl acid chlorides and 1,4-diphenylthiosemcarbazide. The intermediates and products were isolated, purified and charaterized by IR and 13C NMR spectroscopy. The increasing or decreasing in intensity of characteristic stretching bands indicated the rate dependence on the electronic nature of substituents. The results also demonstrate that 1,3,4-triazolium-2-thiolates are obtained in anhydrous conditions whereas presence of water leads to a mixture of the isomers.

Triterpenos isolados de Eschweilera longipes miers (Lecythidaceae)

The phytochemical studies of Eschweilera longipes have led to the identification of ten triterpenoids: fridelin, fridelinol, alpha-amirin, beta-amirin, 3beta-O-cinamoyl-alpha-amirin, 3beta-O-cinamoyl-beta-amirin, alpha-amirenone, beta-amirenone, 3-alpha-hidroxi-lupeol, 3-alpha-hidroxi-taraxasterol, along with b-sitosterol, stigmasterol, alpha -tocopherol and tocotrienol. The structures of these compounds were identified by analysis of IR, ¹H and 13C NMR data and comparison with values of literature.

Identificação de componentes de óleos voláteis: Análise espectroscópica de misturas de sesquiterpenos

This paper describes a chromatographic method to fractionate volatile oils and to identify their sesquiterpenic constituents. The fractionation process includes flash chromatography over silica gel and chromatography over silica gel/AgNO3, utilising pentane, CH2Cl2 and/or acetone as eluents. GC chromatograms were obtained in order to get the relative percentage of each constituent in the volatile oils, to get the retention time value of them as well as to analyse and combine the fractions eluted from the columns. Such procedure afford mixtures of sesquiterpenes which are analysed by GC/MS, 13C and ¹H NMR.

Química orgânica experimental: integração de teoria, experimento e análise

A new approach for teaching in basic experimental organic chemistry is presented. Experimental work goes on parallel to theoretical lectures leading to an immediate application of theoretical concepts transmitted therein. One day/week is dedicated exclusively to the organic laboratory. Reactions are proposed as problems to be solved; the student has to deduce the structure of the product on the basis of his observations, the analytical data and his mechanistical knowledge. 70 different experiments, divided in 7 thematical chapters, are presented. All experiments require the analysis and discussion of 1H and 13C NMR, IR and UV spectra. Additional questions about each reaction have to be answered by the student in his written report. Laboratory safety is garanteed by the exclusion or substitution of hazardous and toxic reagents. Microscale preparations are adopted in most cases to lower the cost of materials and the amount of waste. Recycling of many reaction products as starting materials in other experiments reduces the need for commercial reagents and allows the execution of longer reaction sequences. Only unexpensive standard laboratory equipment and simple glassware are required. All experiments include instructions for the save treatment or disposal of chemical waste.

Síntese de aminoglicosídeos, precursores de pseudo-dissacarídeos potencialmente ativos

This work describes the syntheses of O-protected aminoglycosides as an important block building for the preparation of potential bioactive pseudodisaccharide. The new O-protected methyl 3-amino-3-deoxy-alpha-D-glycopyranoside 4 and methyl 2-amino-2-deoxy-alpha-D-glycopyranoside 5 were prepared, respectively, in five and four steps. All compounds were obtained in good yield and characterized by spectral data (¹H and 13C NMR, MS, IR) and elemental analysis.

Synthesis of 2-(alkylamino)-1-phenylethane-1-thiosulfuric acids, potential schistosomicides

The total synthesis of seven here-to-fore unreported aromatic aminoalkanethiosulfuric acids, their physical properties and those of the aminoalcohol and bromoalkanamine intermediates are reported. All structures were established by including ¹H and 13C NMR, IR and MS spectroscopy and elemental analysis.

Interação tensoativo/hidrótropo em sistemas aquosos, utilizando ressonância magnética nuclear de ¹H e 13C

In this work, it was studied the behavior of the nonionic surfactant aqueous solutions, containing or not a hydrotropic agent, by resonance magnetic nuclear (NMR). We have studied monofunctional diblock copolymers of poly(propylene oxide-ethylene oxide) (R-PPO-PEO-OH, where R length is linear C4) as nonionic surfactant and sodium p-toluenesulfonate (NaPTS) as hydrotropic agent. The critical micelle concentration (CMC) of the aqueous copolymer solution was obtained from ¹H-NMR. The preliminary study of the interaction between the copolymer, under the unimer and micelle forms, and the hydrotrope, in aqueous solutions, was evaluated by ¹H-NMR and 13C-NMR.

Constituintes químicos de Gustavia augusta L. (Lecythidaceae)

Gustavia augusta is used in the folk medicine against leishmaniosis and showed anti-inflammatory action. The phytochemical studies of the plant stem bark have led to the isolation of (22E)-stigmasta-7,22-dien-3beta-ol, 24alpha(S)-ethyl-5alpha-colesta-7,trans-22-dien-3-one, D-friedoolean-14-en-3beta-ol, D-friedoolean-14-en-3-one and D-friedoolean-14-en-3alpha-ol along with stigmasterol, alpha-amyrin, beta-amyrin, lupeol, 3alpha-hidroxi-lupeol and betulinic acid. The structures of these compounds were identified by IR, GC/MS, ¹H and 13C NMR spectral analysis and comparison with literature data.