N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor.

A series of potent antagonists of the ion channel transient receptor potential A1 (TRPA1) was developed by modifying lead structure 16 that was discovered by high-throughput screening. Based on lead compound 16, a SAR was established, showing a narrow region at the nitro-aromatic R(1) moiety and at the warhead, while the R(2) side had a much wider scope including ureas and carbamates. Compound 16 inhibits Ca(2+)-activated TRPA1 currents reversibly in whole cell patch clamp experiments, indicating that under in vivo conditions, it does not react covalently, despite its potentially electrophilic ketone.

Benzyl isothiocyanate, a major component from the roots of Salvadora persica is highly active against Gram-negative bacteria.

Plants produce a number of antimicrobial substances and the roots of the shrub Salvadora persica have been demonstrated to possess antimicrobial activity. Sticks from the roots of S. persica, Miswak sticks, have been used for centuries as a traditional method of cleaning teeth.

Syntheses, characterizations, and biological activities of tetradeca-4,8-dien-1-yl acetates as sex attractants of leaf-mining moth of the genus Phyllonorycter (Lepidoptera: Gracillariidae).

The four possible isomers of tetradeca-4,8-dien-1-yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of (Z,E)- and (Z,Z)-isomers, and alkylation of terminal alkynes for the preparation of (E,E)- and (E,Z)-isomers as the key steps. Synthetic products were characterized by 13C- and 1H-NMR spectroscopy as well as mass-spectrometric methods. All four isomers gave distinctive mass spectra where m/z 81 fragments clearly dominated.

Simplified isolation procedure and interconversion of the diastereomers of nepetalactone and nepetalactol.

Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassénii.

Relative attractiveness of (10E)-dodecen-1-yl acetate and (4E,10E)-dodecadien-1-yl acetate to male spotted tentiform leafminers Phyllonorycter blancardella (F.).

The antennae of male spotted tentiform leafminers, Phyllonorycter blancardella, from Ontario, Canada, exhibited similar electroantennogram responses when stimulated with E10-12:Ac or E4,E10-12:Ac. In field trapping experiments, E10-12:Ac was two-fold or more attractive than E4,E10-12:Ac, and E4,E10-12:Ac did not enhance the attractiveness of E10-12:Ac. E4,E10-12:Ac has not been identified in the pheromone of P.

Neurochemical analysis of brain monoamines after L-histidine and chlorpheniramine administration in goldfish.

This study investigated the effects of chlorpheniramine (CPA) and L-histidine (LH) administration on catecholaminergic levels in goldfish brain using neurochemical analysis. Fifty-eight animals were used. After 20 min of i.

Electrophysiological studies and identification of possible sex pheromone components of Brazilian populations of the sugarcane borer, Diatraea saccharalis.

Virgin female gland extracts of sugarcane moth Diatraea saccharalis (Fabricius) (Lepidoptera: Pyralidae), from three locations in Brazil, have been analyzed. By GC-MS analysis and comparison of the chromatographic retention time of the components of the pheromone gland with those retention times of synthetic standards, we observed the presence of (Z)-hexadec-11-enal (1), hexadecanal (2), (9E,11Z)-hexadecadienal (4), (9Z,11Z)-hexadecadienal (5) and (9E,11E)-hexadecadienal (6), as minor components besides the major constituent (9Z,11E)-hexadecadienal (3) already reported. We found no variations in the composition of the gland extracts deriving from the three Brazilian populations and only two compounds, (Z)-hexadec-11-enal (1) and (9Z,11E)-hexadecadienal (3), elicited antennal responses (GC-EAD).

Identification, syntheses, and characterization of the geometric isomers of 9,11-hexadecadienal from female pheromone glands of the sugar cane borer Diatraea saccharalis.

Chemical analysis of the pheromone glands of the sugar cane borer Diatraea saccharalis has shown the presence of the four geometric isomers of 9,11-hexadecadienal (1-4), in addition to hexadecanal and (Z)-hexadec-11-enal. We here report the syntheses and characterization of compounds 1-4. One starting material, 9-decen-1-ol, has been used to obtain all of them via divergent synthetic routes.

Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis.

A short synthetic route to asymmetric iridoids was developed. The three key steps were an intramolecular [4 + 2] cycloaddition reaction of an enamine derivative of 8-oxocitral (2), a dynamic acetylation, and an enzymatic resolution of the gastrolactyl acetates 5a and 5b, iridoids with three stereocenters. Some regio- and stereoselective heterogeneous catalytic hydrogenations of double bonds in iridoid aglucones were discussed.

Facilitatory effect of substance P on learning and memory in the inhibitory avoidance test for goldfish.

The aim of this study was to investigate if substance P (SP) can improve learning and memory processes in goldfish, using an inhibitory avoidance test. A two-compartment aquarium with a central sliding door was used. The animals were placed in the white compartment, and after 20 s the door was opened.

Substance P facilitates memory in goldfish in an appetitively motivated learning task.

The aim of this study was to investigate if the neuropeptide substance P (SP) can improve learning and memory in goldfish (Carassius auratus). Four groups of fish were trained for seven days to find food in one out of two compartments until discrimination was achieved. On the last training day, they were injected (intra-abdominal) with haloperidol or vehicle before the training, and with SP or vehicle immediately after the training session.