- Structural analogues of quinoline alkaloids: Straightforward route to [1,3]dioxolo[4,5-c]quinolines with antibacterial properties
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Compounds bearing [1,3]dioxolo-quinoline scaffolds have been found in quinoline-based natural products; the only exception is the [1,3]dioxolo[4,5-c]quinoline moiety with a rare occurrence in both natural and synthetic derivatives. In this article, we report the preparation of diversely substituted and functionalized [1,3]dioxolo[4,5-c]quinolines using [1,3]dioxolo[4,5-c]quinoline-4-carbaldehyde (DQC) as the common intermediate. DQC was synthesized on a large scale from anthranilic acid and chloroacetone as the starting materials, with the rearrangement of acetonyl-anthranilate as the key step. The developed method allows for the simple preparation of [1,3]dioxolo[4,5-c]quinolines with various C2 substituents on the quinoline scaffold. Additionally, the synthetic route was successfully applied to the preparation of 3-hydroxyquinoline-4(1H)-ones. The target compounds were tested against representative Gram-positive/negative bacteria, and two derivatives exhibited submicromolar minimum inhibitory concentrations against Micrococcus luteus.
- ?am?ulová, Veronika,Funk, Petr,Grepl, Martin,Horák, Radim,Hradil, Pavel,Ko?istek, Kamil,Kvapil, Lubomír,Slaninová, Ludmila,Soural, Miroslav
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- Synthesis, characterization and behavior in water/DMSO solution of Ru(II) arene complexes with bioactive carboxylates
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The reactions of [RuCl(μ-Cl)(η6-p-cymene)]2 with sodium carboxylates, in methanol or acetonitrile solution, afforded the complexes [RuCl(κ2O-RCO2)(η6-p-cymene)] (RCO2 = valproate, 1; aspirinate, 2; diclofenate, 3), in 79–96% yields. Analogously, [RuCl(κ2O-dfCO2)(η6-benzene)], 4, was obtained in admixture with minor by-products from [RuCl(μ-Cl)(η6-benzene)]2 and sodium/silver diclofenate. The sequential reaction of [RuCl(μ-Cl)(η6-p-cymene)]2 with sodium salicylate and PPh3 gave [Ru(κ2O,O′-salCO2)(PPh3)(η6-p-cymene)], 5, in 70% yield. The hydride complex [Ru2Cl2(μ-Cl)(μ-H)(η6-p-cymene)2], 6, was produced in 36% yield from [RuCl(μ-Cl)(η6-p-cymene)]2 and sodium formate. An optimization of the experimental work-up allowed to isolate [RuCl(μ-Cl)(η6-p-cymene)]2 with an improved yield respect to the literature (98% vs. 65%). The bidentate coordination mode of the carboxylato ligands in 1–5 was unambiguously ascertained by IR and NMR spectroscopy, moreover the solid state structure of 1 was elucidated by single crystal X-ray diffraction. Complexes 1–3 experience rapid and quantitative dissociation of the carboxylato anion in DMSO/water/NaCl mixtures, mainly converting into [RuCl2(DMSO)(η6-p-cymene)], 7.
- Biancalana, Lorenzo,Pampaloni, Guido,Zacchini, Stefano,Marchetti, Fabio
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supporting information
p. 201 - 211
(2018/07/06)
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