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  • 74 Reads
Nitroquinolines as dienophiles in polar Diels-Alder reactions. Influences of molecular solvents and ionic liquids
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5- and 8-nitroquinolines are studied as dienophiles in polar thermal Diels-Alder reactions whit normal electron demand using several and structural different dienes, and chloroform as solvent media. A very strong electron-acceptor group, such as nitro group, push the dienophilic character of these heterocyclic compounds and owing to this substituent is easily extruded under thermal conditions. When the cited dienophiles were reacted with isoprene, 1-trimethylsilyloxy-1,3-butadiene and de Danishesfky diene, under different reaction conditions they showedtheir dienophilic character taking part in a normal demand DA cycloaddition reactions. These cycloaddition reactions were analyzed in presence of ionic liquids (IL´s). In this sense was used ethyl ammonium nitrate (NEA) as protic IL´s and another composed by 1-butyl-3-methyl-imidazolium [bmim] as the cation and tetrafluoroborate as the anion [BMIM] [BF4]. The presence of IL´s improved the yields and the reaction conditions are softer.
  • Open access
  • 80 Reads
A Triterpenoid Saponin from the Seeds of Ricinus communis
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novel oleanen type triterpenoid, has been isolated from butanolic extract of the seeds of Ricinus communis. Its structure was elucidated as 3-O-[β -D-glucoronopyranosyl-(1→ 3)-α –L-rhamnopyranosyl-(1→ 2)β-D-glucopyranosyl]-4α,20α-hydroxy methyl olean-12-ene-28-oic acid on the basis of spectral evidences i.e. FTIR, 1H NMR, 13C NMR and FAB-MS data. The isolated saponin was tested for its antibacterial and antifungal activity, where the growth of microbes was found to be inverse function of concentration of saponin. The MIC value for E.coli was found to be 260µg/mL and that of Staphylococcus aureus was 350µg/mL
  • Open access
  • 90 Reads
SYNTHESIS, CHARACTERIZATION and ANTIMICROBIAL PROPERTIES OF THIOSEMICARBAZONEDERIVED FROM α-CHLORALOSE
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1,2-O-(R)-Trichloroethylidene-α-D-xylo-1,4-furanodialdose hydrate was obtained fromα-chloralose via conventional sodium metaperiodate cleavage-oxidation reaction. 1,2-O-(R)-trichloroethylidene-α-D-xylo-1,4-furanodialdose thiosemicarbazonewas obtained from the reaction of 1,2-O-(R)-trichloroethylidene-α-D-xylo-1,4-furanodialdose hydrate with thiosemicarbazide in the presence of an acid catalyst. The structure of thiosemicarbazone product was characterized with NMR and FTIR spectroscopic methods. This new compound (5) was evaluated for its antimicrobial activity against Gram-positive, Gram-negative bacteria and C. albicans using the well diffusion and microdilution method. The thiosemicarbazone product shows significant growth inhibitory activity against bacteria Staphylococcus aureus, Escherichia coli, Kocuria rhizophila, Bacillus cereus, Enterobacter aerogenes and showed moderate activity against Candida albicans. The minimal inhibitory concentrations (MIC) experiments revealed that tested compound exhibited variable MICs and selective antimicrobial activity, depending on the microbial strains.
  • Open access
  • 69 Reads
Synthesis of 3-chlorohimachal-7-one
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The title compound, 3-chlorohimacha-3-one has been synthesized by catalytic oxidation with ruthenium trichloride and sodium periodate of 3-chlorhimachl-6,13-ene(1). .The structure of this new compound was confirmed by elemental analysis, IR, 1H-NMR, 13C-NMR and EI-Ms spectral analysis.
  • Open access
  • 39 Reads
The Reactions of Mitomycin C with Dithiols I. Reductive Activation
We report that the clinically used antitumor drug mitomycin C is reductively activated in vitro by simple thiols; a mechanism for this activation is proposed based on kinetic data and the identification of mitosene metabolites. The biological implications of these findings are discussed.
  • Open access
  • 55 Reads
The Reactions of Mitomycin C with Dithiols II. Formation of Dithiol Cross-Links
We report that the clinically used antitumor drug mitomycin C reacts with excess dithiols to give dithiol cross-links as major products. Mechanistic studies reveal that three dithiol molecules participate at different stages of the reaction: in the reductive activation of mitomyicin C, in an alkylation at C1, and in an additional reduction that activates C10 for the second-arm alkylation by the dithiol. We hypothesize that the reactions reported here indicate that mitomycin C could act as a mechanism-based inhibitor of enzymes containing a dithiol active site.
  • Open access
  • 75 Reads
The Reactions of Mitomycin C with Dithiols III. Mysterious Reactions
We report two unexpected findings ocurring after treatment of the antitumor drug mitomycin C with dithiols. The first finding relates to the reaction of mitomycin C with exactly one molar equivalent of dithiol to form a mitosene-like material with unusual physico-chemical properties. The second finding was the formation of unexpected dimeric mitosenes when the reaction of MC with dithiols was quenched at short reaction times. We hypothesize that both events are originated by an unprecedetended deaziridination reaction.
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