Cytotoxicity of 3,4-dihalogenated 2(5H)-furanones

Mucohalogen acids have been used for the preparation of a variety of 3,4-clihalogenated 2(5H)-furanones. In one synthetic step the carbarnates 2a-c and the pseudoanhydrides 4a-e were prepared using isocyanates and acid anhydrides. A series of 5-alkoxylated 3,4-dichloro-2(5H)-furanones 5a-o have been synthesized with a wide range of lipophilicity, using the hydroxy-form of mucohalogen acids 1a and 1b. The 5-allyl-3,4-dichloro-2(5H)-furanone 5f was derived into the dihydro-isoxazol 6 and the oxirane 7. The methyl ester 5a was converted with ammonia into the tetramic acid chloride 11. The pseudo acid chloride 3 was reacted further into the bis aziricline 8. Reduction of the mucochloric acid 1a furnished the trichlorofuranone 3. The cytotoxicity of these simple and bis-cyclic butenolides have been evaluated in tissue culture on MAC13 and MAC16 cancer cell lines using the MTT cytotoxicity assay. The ester 5g, the acetate 4b and the carbamate 2b displayed a cytotoxicity in the low micromolar range. Further, an IC50 (50% inhibitory concentration) of 50 nM and 30 nm was determined forthe epoxide 7 and the aziridine 18. © 2004 The Authors Recieved.

Organic reactions in ionic liquids: ionic liquid-promoted efficient synthesis of N-alkyl and N-arylimides

In the ionic liquids [Bmim][PF6] or [Bmim][BF4], a series of succinimide, maleimide and phthalimide derivatives were synthesized from corresponding anhydrides with a variety of primary amines in excellent yield.

Novel tear film supplements:a potential application for synthetic protein-phospholipid complexes

Purpose: Surfactant proteins A, B, C and D complex with (phospho)lipids to produce surfactants which provide low interfacial tensions. It is likely that similar complexation occurs in the tear film and contributes to its low surface tension. Synthetic protein-phospholipid complexes, with styrene maleic anhydrides (SMAs) as the protein analogue, have been shown to have similarly low surface tensions. This study investigates the potential of modified SMAs and/or SMA-phospholipid complexes, which form under physiological conditions, to supplement natural tear film surfactants. Method: SMAs were modified to provide structural variants which can form complexes under varying conditions. Infrared spectroscopy and Nuclear Magnetic Resonance were used to confirm SMA structure. Interfacial behaviour of the SMA and SMA-phospholipid complexes was studied using Langmuir trough, du Nûoy ring and pulsating bubblemethods. Factors which affect SMA-phospholipid complex formation, such as temperature and pH, were also investigated. Results: Structural manipulation of SMAs allows control over complex formation, including under physiological conditions (e.g. partial SMAesterfication allowed complexation with dimyristoylphosphatidylcholine, at pH7). The low surface tensions of the SMAs (42mN/m for static (du Nûoy ring) and 34mN/m for dynamic (Langmuir) techniques) demonstrate their surface activity at the air-aqueous interface. SMA-phospholipid complexes provide even lower surface tensions (~2 mN/m), approaching that of lung surfactant, as measured by the pulsating bubblemethod. Conclusions: Design of the molecular architecture of SMAs allows control over their surfactant properties. These SMAs could be used as novel tear films supplements, either alone to complex with native tear film phospholipids or delivered as synthetic protein-phospholipid complexes.

Aditivo polimérico derivado de fonte renovável para aplicação em cimento asfáltico de petróleo

This study evaluated the effects of incorporating an additive from an agro-industrial residue, after some chemical modification reactions, to petroleum asphalt cement (CAP) through the polymerization reaction of a viscous polyol obtained by bagasse biomass oxypropylation reaction sugarcane with anhydrides. The polyol is obtained by biomass oxypropylation reaction with propylene oxide, the reaction was performed in an autoclave sealed with pressure and temperature control using 25 mL of OP for every 5 grams of biomass 200°C, which time reaction was two hours. The reaction is revealed by varying the system pressure, initially at atmospheric pressure to reach a maximum pressure value and its subsequent return to atmospheric pressure. For the choice of the most suitable reaction time for polymerization of the polyol with pyromellitic anhydride, the reaction was also conducted in an autoclave sealed with temperature controller (150 ° C) using 20 g of polyol, 1 g of sodium acetate (catalyst) and 8 g of pyromellitic anhydride with the times 30 and 60 minutes. The polymerized materials with different times were characterized by determining the relative viscosity and percentage content of extractable in cyclohexane / ethanol. Given the results with the polymerized material 30 minutes showed the lowest percentage content of extractives and an increased viscosity relative indicating that this time is highlighted with respect to time 60 minutes, because the material is possibly in the form of a crosslinked polymer. Given the choice of time of 30 minutes other polymerization reactions were performed with various anhydrides and other conditions employed different proportions by mass of polyol anhydrides we were referred to as condition I (20 g anhydride and 8 g of polyol), II (20 g anhydride and 20 g of polyol) and III (8 g anhydride and 20 g of polyol). The FTIR spectra of polymeric materials with different polymerization conditions used to prove the occurrence of chemical modification due to the appearance of a characteristic band ester groups (1750 cm-1) present in the polymerized material. He chose to work with the condition III, as is the condition which employs a larger amount of polyol, and even with the smaller amount of anhydride used FTIR spectra revealed that the polymerization reaction was performed. Among the various anhydrides (phthalic, maleic and pyromellitic) of the different conditions used that stood out before the solubility test with solvents analyzed was polymerized material with pyromellitic anhydride because the polymerized material likely in the form of a crosslinked polymer because it was insoluble or poorly soluble in the solvents tested. Polymerization of the polyol with pyromellitic anhydride using condition III, that is, BCPP30, CSPP30, PCPP30 e BCPPG30, provided an increase in thermal stability relative to material in the form of polyol. Applicability tests concerning the incorporation of 16% m / m BCPP30, CSPP30, PCPP30 e BCPPG30 additive in relation to the mass of 600 g CAP showed through characterization tests used, softening point, elastic recovery and marshall dosage, it is possible to use BCPP30 as an additive the conventional CAP, because even with the incorporation of this new additive modified CAP met the specifications of the appropriate standard.