An additional methylene group driving the conformation and assembly of two arylsulfonamidepara-alkoxychalcone hybrids

Abstract

The structures of two arylsulfonamide para-alkoxychalcones, namely, N-{4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C22H19NO4S, (I), and N-{4-[(E)-3-(4-ethoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C23H21NO4S, (II), reveal the effect of the inclusion of one -CH2- group between the CH3 branch and the alkoxy O atom on the conformation and crystal structure. Although the molecular conformations and one-dimensional chain motifs are the same in both structures, their crystallographic symmetry, number of independent molecules and crystal packing are different. The crystal packing of (I) is stabilized by weak C-H...π and π-π interactions, while only C-H...π contacts occur in the structure of (II). The role of the additional methylene group in the crystal packing can also be seen in the fact that the alkoxy O atom is an acceptor in nonclassical hydrogen bonds only in the para-ethoxy analogue, (II). The remarkable similarity between the crystal packing features of (I) and (II) lies in the formation of N-H...O hydrogen-bonded ribbons, a synthon commonly found in related compounds.

Synthesis, Characterization and Evaluation of in vitro Antitumor Activities of Novel Chalcone-Quinolinone Hybrid Compounds

“…In recent years, our research group has been dedicated to synthesis, characterization and antitumor evaluation of chalcone derivatives. [29][30][31][32][33][34] The bioactivity of these compounds is associated with cellular thiols as glutathione reduced (GSH). Therefore, our group reported the reaction of Mannich bases and hydroxychalcone with GSH and the stereochemistry of non-enzyme nucleophilic addition of GSH to hydroxychalcone and Mannich base derivative at different pH.…”

“…32,33 Among these derivatives, the sulfonamide chalcones have been synthesized and evaluated against several strains of human cancer with relevant results. [29][30][31] The synthesis of 3-(p-nitrobenzylidene) quinolinone, with nitro group in rings B and C, reported by de Castro et al, 31 motivated the subsequent study of chalcone-quinolinones. Therefore, the aim of this work was the development of a synthetic route for chalcone-quinolinone synthesis in such a way as to incorporate different substituents in B and C rings and evaluate the antitumor activity of these compounds against HCT-116 (colon) human tumor cell lines.…”

Conformational Variability in Sulfonamide Chalcone Hybrids: Crystal Structure and Cytotoxicity

“…More details for synthesis carried out at Instituto de Química from Universidade Federal de Goiás, yield and melting point of 5 and 6 can be found in another related paper. 26 Full characterization of synthesized compounds can be found in the Supplementary Information. …”

“…This phenomenon has been previously reported in one related chalcone sulfonamide. 26 Here, the absence of para-nitro group at ring C is related to the conformational variability in compounds 1 and 2 as described in sequence. In 4, this phenomenon seems to be related to crystallization of ethyl alcohol came from synthetic procedure and its different interaction modes with each sulfonamide chalcone conformer (see crystal packing description below).…”

“…Its crystal structure was the only one reported for this compound series 25 before we were interested in their crystallographic characterization. In sequence, crystal structure of two TSAHC analogs, which cytotoxicity is reported here (compounds 5 and 6), 26 were elucidated by our research group. Not so much similar to TSAHC and its analogs, all of them owing arylsulfonamide moiety attached in the 1-phenyl group from chalcone scaffold in the para-position, crystal structure of some other related compound with arylsulfonamide bonded in the ortho-position of either 1-phenyl (two compounds) 27,28 or 3-phenyl (six compounds) [29][30][31][32][33][34] ring from chalcone core has been also determined.…”