Abstract
The title compound, C19H20N4O3S, was synthesized by refluxing equimolar amounts of 1-phenyl-3-methyl-4-propionylpyrazol-5-one and benzene-sulfonyl hydrazide in ethanol. The compound crystallizes in the keto form and the carbonyl O atom forms an intra-molecular N-H⋯O hydrogen bond with the neighbouring NH group. There is also C-H⋯O short contact involving the neighbouring phenyl ring. Probably as a result of this, the phenyl ring is inclined to the pyrazolone ring by only 7.58 (12)°. The dihedral angle between the phenyl ring and the benzene-sulfonyl ring is 22.78 (11)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R (2) 2(14) ring motif. The dimers are linked via pairs of C-H⋯O hydrogen bonds, forming chains propagating along [100].
Highlights
The title compound, C19H20N4O3S, was synthesized by refluxing equimolar amounts of 1-phenyl-3-methyl-4-propionylpyrazol-5-one and benzenesulfonyl hydrazide in ethanol
The compound crystallizes in the keto form and the carbonyl O atom forms an intramolecular N—H O hydrogen bond with the neighbouring NH group
We have devoted our efforts to the design and synthesis of 4-acyl pyrazolone derivatives and their transition metal complexes (Zhang et al, 2004; Xu et al, 2013; Yi et al, 2014; Li et al, 2013)
Summary
Many pyrazolones and their derivatives possess biological and pharmaceutical activities, such as anticancer, antitumor and antifungal activities as well as the inhibition of lipid peroxidation (Wang et al, 1991; Yu et al, 1993; Padhyé & Kauffman, 1985; Yang et al, 1992). We have devoted our efforts to the design and synthesis of 4-acyl pyrazolone derivatives and their transition metal complexes (Zhang et al, 2004; Xu et al, 2013; Yi et al, 2014; Li et al, 2013). Such 4-acyl pyrazolone derivatives can form different types of complexes due to the multiple coordination sites and the tautomeric enol-to-keto effect. May be a promising drug for cancer chemotherapy (Wang et al, 2007) This has encouraged us to investigate more 4-acyl pyrazolone derivatives and we report on the synthesis and crystal structure of the title compound
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