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Several series of 45 acetophenone derivatives bearing various alkyl or benzyl substituents were conveniently synthesized and their structures characterized by 1H and 13C NMR spectroscopy, HRMS and single-crystal X-ray analysis. Their in vitro antifungal activities against a panel of phytopathogenic fungi were evaluated by mycelial growth rate assay. Of them, 12 derivatives (e.g., 3a-c, 4c and 4e) exhibited more potent antifungal effects on some phytopathogens than a commercial fungicide hymexazol as positive control. In particular, compound 3b with IC50 values of 10-19 μg/mL was found to be the most active in this series and might be a potential lead structure for further optimization. The preliminary structure-activity relationship (SAR) studies of a series of acetophenones are also discussed. [ABSTRACT FROM AUTHOR]

A new C18-ceramide congener named pecipamide ( 1), together with the known ergosta-4,6,8(14),22-tetraen-3-one ( 2), was isolated from the solid fermentations of the basidiomycetous fungus Polyporus picipes. The structure of the new metabolite was established as (2′ R,2 S,3 R)- N-2′-hydroxyheptadecanoyl-2-amino-octadecane-1,3-diol on the basis of spectroscopic data, including 1D- and 2D- nuclear magnetic resonance spectroscopy (NMR) experiments, as well as by means of mass spectrometric measurements (MS). [ABSTRACT FROM AUTHOR]

The title compound, C(10)H(13)ClN(2)O, was obtained as a by-product in the reaction of 2-chloro-methyl-1H-benzimidazole, dimethyl sulfate and toluene to synthesise 2-chloro-methyl-1-methyl-benzimidazole. The dihedral angle between the benzene ring and the acetamide group is 89.72  (6)° while that between the aromatic ring and the chloracetyl group is 84.40 (4)°. In the crystal, adjacent mol-ecules are linked by pairs of N-H⋯O hydrogen bonds into inversion dimers.

The title compound, C(15)H(14)O(3), has been obtained from the reaction of 2,4-dihy-droxy-acetophenone, potassium carbonate and benzyl bromide. The remaining hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond. In the crystal, inter-molecular C-H⋯O contacts occur.

The title compound, C(16)H(14)Cl(2)O(4)S, was obtained by the reaction of eugenol (4-allyl-2-meth-oxy-phenol) and 3,4-dichloro-benzene-sulfonyl chloride. The dihedral angle between the benzene rings in the mol-ecule is 40.53 (4)°. No significantly short inter-molecular contacts are observed in the crystal structure.

The title compound, C(13)H(11)Cl(2)N(3)O(2), was obtained by the reaction of eugenol and cyanuric chloride. The dihedral angle between the benzene and triazine rings is 87.56 (4)°. Two C atoms of the allyl group are disordered over two sites in a 0.72 (2):0.28 (2) ratio.

The title compound, C(15)H(12)F(2)O(3), has been obtained by the reaction of 2,4-dihy-droxy-lacetonephenone, potassium carbonate and 3,5-difluoro-benzyl bromide. The hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond in each of the two independent mol-ecules in the asymmetric unit. The dihedral angle between the aromatic rings is 0.5 (2)° in one molecule and 1.9 (2)° in the other. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into tetra-meric units aligned perpendicular to b.

In the title compound, C(15)H(12)F(2)O(2), the dihedral angle between the aromatic rings is 70.43 (4)°. The crystal packing exhibits no significantly short inter-molecular contacts.

The title compound, C(11)H(13)ClO(3), has been obtained in the reaction of 2, 4-dihydroxy-lacetonephenone, potassium carbonate and 1-bromo-3-chloro-hexane. The hydr-oxy group is involved in an intra-molecular O-H⋯O hydrogen bond. The crystal packing exhibits no significantly short inter-molecular contacts.