13203-73-1Relevant articles and documents
Synthesis and antibacterial activity of fused Mannich ketones
Lóránd, Tamás,Kocsis, Béla,Sohár, Pál,Nagy, Gergely,József, Pál,Kispál, Gyula,László, Renáta,Prókai, László
, p. 803 - 812 (2002)
New Mannich ketones of fused bicyclic ketones as 1-indanones and 1-tetralones were prepared using the classical acid-catalysed Mannich reaction. Known members of this family were used in comparative biological tests. Antibacterial activity of these new water-soluble compounds was reported against Pseudomonas aeruginosa, Escherichia coli, E. coli ReD31m4, Salmonella minnesota Re595, Shigella sonnei Re4350, Staphylococcus aureus, Staphylococcus saprophyticus, Micrococcus luteus and Bacillus subtilis standard strains. Human cytotoxicity of our new compounds was evaluated against HeLa cell line. Some compounds showed low cytotoxicity (56.738 nM mL-1 for 24, 47.497 nM mL-1 for 31 and 48.379 nM mL-1 for 26) and proved to be efficient antibacterial agents against the Gram-positive and partly against E. coli strains. Minimum inhibitory concentrations (MIC) changed in the range of 1.56->200 μg mL-1. The deep rough mutants showed (generally eight times) higher sensitivity toward the compounds than the smooth E. coli. Hence, the permeability of Gram-negative outer membrane can influence the MIC values of our compounds. A preliminary quantitative structure-activity relationship (QSAR) study indicated the maximum positive charge (MaxQ+) as the parameter that most significantly affected antibacterial activity against E. coli. In B. subtilis, the influence of a topological descriptor (first-order valence-connectivity index, XV1) was also revealed; however, other strains did not yield meaningful QSAR with the set of descriptors employed.
Solvent-Dependent Reaction Pathways Operating in Copper(II) Tetrafluoroborate Promoted Oxidative Ring-Opening Reactions of Cyclopropyl Silyl Ethers
Hasegawa, Eietsu,Nemoto, Kazuki,Nagumo, Ryosuke,Tayama, Eiji,Iwamoto, Hajime
, p. 2692 - 2703 (2016)
(Figure Presented) Oxidative ring-opening reactions of benzene-fused bicyclic cyclopropyl silyl ethers, promoted by copper(II) tetrafluoroborate, were investigated. The regioselectivity of cyclopropane ring-opening as well as product distributions were found to be highly dependent on the nature of the solvent. In alcohols, dimeric substances arising from external bond cleavage are major products. Radical rearrangement products are also formed in solvents such as ether and ethyl acetate. On the contrary, nucleophile addition to carbocation intermediates, generated by internal bond cleavage, occurs mainly in reactions taking place in acetonitrile. It is proposed that the observed solvent effects that govern the reaction pathways followed are a consequence of varying solvation of copper intermediates, which governs their reactivity and redox properties. In addition, the influence of counteranions of the copper salts, organonitriles, cyclic dienes, and substrate structures on the pathways followed in these reactions was also examined.
Synthesis of 1,3-Aminoalcohols and Spirocyclic Azetidines via Tandem Hydroxymethylation and Aminomethylation Reaction of β-Keto Phosphonates with N-Nosyl- O-(2-bromoethyl)hydroxylamine
Chen, Hongbing,Gao, Min,Gong, Xiangnan,Hu, Lin,Wu, Binyu
supporting information, p. 4152 - 4157 (2021/06/27)
An unprecedented tandem α-hydroxymethylation and α-aminomethylation reaction of aromatic cyclic β-keto phosphonates with N-nosyl-O-(2-bromoethyl)hydroxylamine in the presence of DBU base has been developed, affording a range of 1,3-aminoalcohols in good y
A New Fragmentation Reaction of γ-Oxosulfonium Methylides
Watanabe, Yoshihiko,Takeda, Toyonori,Anbo, Keiji,Ueno, Yoshio,Toru, Takeshi
, p. 159 - 162 (2007/10/02)
Reactions of sulfonium methylides attached to a 5- or 6-membered cycloalkanone undergo the ring-fission as a major reaction course to give α-methylene-ω-(phenylthio)carboxylates, whereas sulfonium methylides attached to a larger ring give α-methylenecycloalkanones predominantly.Reactions of the acyclic compounds are also examined.
