Cytotoxic and Antimicrobial Activity of Dehydrozingerone based Cyclopropyl Derivatives

Abstract

A small series of 1-acetyl-2-(4-alkoxy-3-methoxyphenyl)cyclopropanes was prepared, starting from dehydrozingerone (4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one) and its O-alkyl derivatives. Their microbiological activities toward some strains of bacteria and fungi were tested, as well as their in vitro cytotoxic activity against some cancer cell lines (HeLa, LS174 and A549). All synthesized compounds showed significant antimicrobial activity and expressed cytotoxic activity against tested carcinoma cell lines, but they showed no significant influence on normal cell line (MRC5). Butyl derivative is the most active on HeLa cells (IC = 8.63 μm), while benzyl one is active against LS174 and A549 cell lines (IC = 10.17 and 12.15 μm, respectively).

Synthesis, Anti-inflammatory, and Antioxidant Activity of Mannich Bases of Dehydrozingerone Derivatives

“…2,4,[9][10][11] However, the substitution in the aromatic ring of the compound with an aminomethyl group via Mannich reaction has not been reported yet. In this study, a series of five novel Mannich bases of DHZ (2a-e) was synthesized.…”

“…[1][2][3][4][5][6][7][8] Various chemical modification of DHZ has been performed to exploit for diverse biological activities of DHZ derivatives, such as esterification or alkylation of OH phenolic group, replacement of OH with other substituents, substitution of the methoxy group, reduction of double bond, cyclization of α,β-unsaturated carbonyl, and substitution of hydrogen atom bound to the carbonyl α-carbon. 2,4,[9][10][11] Some Mannich bases of DHZ have been synthesized and reported to have better anti-inflammatory activity compared to DHZ and fairly good anti-inflammatory activity compared to indomethacin. However, the aminomethyl group was substituted at the carbonyl α-carbon of the compound.…”

Synthesis of <em>N</em>-acetyl and <em>N</em>-formyl pyrazoline derivatives from vanillin and their antigenotoxic activity

“…Alkylation/ allylation of the phenol group of the vanillin was achieved by a standard procedure [8][9][10] using an alkyl/allyl halide to yield the corresponding phenoxy compounds 1(a-j). Starting from our previous results in dehydrozingerone derivatives transformation 11,12 we decided to prepare some dehydrozingerone analogues, with rigid cyclopropane ring fragment instead of methyl one, in reaction O-alkyl vanillines and methyl cyclopropyl ketone. On this way, chalcone like compounds 2(a-j), (E)-1-cyclopropyl-3-(4-alkoxy-3methoxyphenyl)prop-2-en-1-ones were synthesized.…”

Antimicrobial, antioxidant and DNA-binding studies of palladium(II) complexes with different chelate ligands containing nitrogen donor atoms

“…Previous research of antimicrobial activity led to different conclusions with most of the studies evidencing markedly lower antifungal activity, 7,26 although a study conducted in 2012 determined that palladium(II) complexes with a derivative of thiosalicylic acid as ligand showed significantly higher antifungal activity towards species from the Aspergillus genus (A. fumigatus, A. flavus and A. restrictus) than the positive control, fluconazole. 6 Garoufis et al explored the antifungal and antibacterial activity of Pd(II) complexes with various ligands (sulphur and nitrogen donor ligands, Schiff bases and ligands used as drugs), and found that they had promising antibacterial but weak antifungal activity.…”

“…Special attention is paid to the study of the antimicrobial activity of complex compounds with different metal ions. [4][5][6][7] The chemical behaviour in solution of structurally analogous Pt(II) and Pd(II) complexes is very similar. 8 Since the antitumor activity of certain Pd(II) complexes has been demonstrated, the idea arose to examine several structurally different Pd(II) complexes for their antimicrobial activity as well as their interaction with calf thymus DNA (CT-DNA).…”