Nematicidal activity of furanoeremophilenes against Meloidogyne incognita and Nacobbus aberrans.

Background: While searching for novel small molecules for new organic pesticide agents against plant-parasitic nematodes, we found that the hexane extract from the roots of Senecio sinuatos and its main secondary metabolite, 3β-angeloyloxy-6β-hydroxyfuranoeremophil-1(10)-ene (1), possess nematicidal activity against the second stage juvenile (J2) of Meloidogyne incognita and Nacobbus aberrans. Both species reduce yield of various vegetable crops. These results encouraged us to synthesize esters 3-9 formed by diol 2, obtained by alkaline hydrolysis of 1 and acetic anhydride, benzoic acid, 2-nitrobenzoic acid, 2-bromobenzoic acid, 4-nitrobenzoic acid, 4-bromobenzoic acid, and 4-methoxybenzoic acid, respectively.

TiCl catalyzed cleavage of (25R)-22-oxo-23-spiroketals. Synthesis of sapogenins with furostanol and pyranone E rings on the side chain.

The regioselective opening of the F ring of 22-oxo-23-spiroketals 7a-d using TiCl in acetic anhydride yielded the novel furostanols 11a-d along with cholestanic derivatives 8a-d with pyranone E ring. The structures of the new derivatives thus obtained were established using one- (DEPT) and two-dimensional H, C NMR experiments (COSY, HSQC, HMBC, NOESY). The 22α-hydroxyl orientation in compounds 11a-d was proposed by comparison of the C chemical shifts with those of other aglycone members of this family, and confirmed by combined NOESY and X-ray diffraction analysis of compound 11a.

In search of safe pain relief: The analgesic and anti-inflammatory activity of phytosteryl ibuprofenates.

β-Sitosteryl (S)-ibuprofenate (2), stigmasteryl (S)-ibuprofenate (3), ergosteryl (S)-ibuprofenate (4), and cholesteryl (S)-ibuprofenate (5) were prepared in 70-75% yields by Steglich esterification and were characterized by 1D and 2D NMR, as well as by MS. The new esters were evaluated in in vivo pain models of antinociception and anti-inflammation using the writhing, formalin, and carrageenan tests, in mice and rats, and the results were compared with those of (S)-ibuprofen (1). Damage to the gastric mucosa of animals was also assessed.

Synthesis of 2-Tetrazolylmethyl-isoindolin-1-ones via a One-Pot Ugi-Azide/(N-Acylation/-Diels-Alder)/Dehydration Process.

A series of fifteen 2-tetrazolylmethyl-isoindolin-1-one linked-type bis-heterocycles were synthesized in 10-76% yields under mild conditions via a one-pot Ugi-azide/(Nacylation/-Diels-Alder)/dehydration process from furan-2-ylmethanamine, aldehydes, isocyanides, azidotrimethylsilane, and maleic anhydride. Density functional theory calculations were performed using the polarizable continuum model (toluene)-M06-2X-D3/6-311+G(d)//M06-2X-D3/6-31G(d) level of theory to obtain the full energy profile when investigating over eight possible pathways. An anthracene-containing analogue displayed a distribution of its highest occupied molecular orbital-lowest unoccupied molecular orbital throughout both cyclic moieties.

Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane.

Triethylborane (TEB) was found to be a mild, efficient, and acid catalyst in electrophilic substitution reaction of indoles with aldehydes compounds to afford the corresponding bis(indolyl)methanes. Vibrindole and bis(indolyl)methanes derivatives and were synthesized using this methodology. Compound is an intermediary in the synthesis of the natural bisindoles arsindoline and streptindole .

Crystal structure of 2-(2-amino-phen-yl)-1,3-benzoxazole.

Crystals of the title compound, C13H10N2O, were grown from a di-chloro-methane/ketone/methanol solvent mixture. It crystallizes with two mol-ecules, A and B, in the asymmetric unit with very similar almost planar conformations [dihedral angles between the ring planes = 0.74 (8) and 0.

O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl-oxazolidin-3-yl]propan-2-yl} carbonodi-thio-ate.

In the title compound, C15H17NO4S2, synthesized by addition of O-ethylxanthic acid potassium salt to a diastereomeric mixture of (4R)-3-(2-chloro-propano-yl)-4-phenyl-oxazolidin-2-one, the oxazolidinone ring has a twist conformation on the C-C bond. The phenyl ring is inclined to the mean plane of the oxazolidinone ring by 76.4 (3)°.

2-(4-Hy-droxy-phen-yl)-1H-benzimidazol-3-ium chloride monohydrate.

The title mol-ecular salt, C13H11N2O(+)·Cl(-)·H2O, crystallizes as a monohydrate. In the cation, the phenol and benzimidazole rings are almost coplanar, making a dihedral angle of 3.18 (4)°.

π-stacking and C-X...D (X = H, NO2; D = O, π) interactions in the crystal network of both C-H...N and π-stacked dimers of 1,2-bis(4-bromophenyl)-1H-benzimidazole and 2-(4-bromophenyl)-1-(4-nitrophenyl)-1H-benzimidazole.

Molecules of 1,2-bis(4-bromophenyl)-1H-benzimidazole, C19H12Br2N2, (I), and 2-(4-bromophenyl)-1-(4-nitrophenyl)-1H-benzimidazole, C19H12BrN3O2, (II), are arranged in dimeric units through C-H...

Coupling of internal alkynes in tp(me2)ir derivatives: selective oxidation of a noncoordinated double bond of the resulting iridacycloheptatrienes.

The reaction of different Tp(Me2)Ir derivatives and dimethylacetylene dicarboxylate (DMAD) allows the preparation of three different metallacycloheptatriene complexes and an unusual allyl-terminated metallacycle. The C atoms of distant C=C bonds in the metallacycles, including aromatic ones, can be converted selectively to the corresponding keto functionality under mild conditions.

Facile preparation of [4.4]metacyclophane- and [5.5]paracyclophane-type macrocycles from arylboronic acids and salicylideneaminoaryl alcohols.

Four different salicylideneaminoaryl alcohols have been treated with arylboronic acids in order to prepare air-stable cyclophane-type macrocyclic systems. In two cases, this objective could be realized with the high-yield formation of [4.4]metacyclophane and [5.