818-49-5Relevant academic research and scientific papers
Highly antiproliferative neutral Ru(ii)-arene phosphine complexes
Chotard, Florian,Dondaine, Lucile,Balan, Cédric,Betta?eb, Ali,Paul, Catherine,Le Gendre, Pierre,Bodio, Ewen
, p. 8105 - 8112 (2018/05/24)
Six ruthenium(ii)- and four gold(i)-phosphine based complexes were synthesized and fully characterized. Some of them displayed strong antiproliferative properties for several types of cancer including colon, breast, and lung. Notably, two of the Ru(ii) complexes displayed an IC50 of around 2 μM, which is exceptional for these types of complexes. The dramatic impact of the nature of the arene coordinated on the ruthenium center was clearly evidenced.
Isolation, structure elucidation, and synthesis of antiplasmodial quinolones from Crinum firmifolium
Presley, Christopher C.,Du, Yongle,Dalal, Seema,Merino, Emilio F.,Butler, Joshua H.,Rakotonandrasana, Stéphan,Rasamison, Vincent E.,Cassera, Maria B.,Kingston, David G.I.
, p. 4203 - 4211 (2017/07/05)
Antiplasmodial bioassay guided fractionation of a Madagascar collection of Crinum firmifolium led to the isolation of seven compounds. Five of the seven compounds were determined to be 2-alkylquinolin-4(1H)-ones with varying side chains. Compounds 1 and 4 were determined to be known compounds with reported antiplasmodial activities, while 5 was believed to be a new branched 2-alkylquinolin-4(1H)-one, however, it was isolated in limited quantities and in admixture and therefore was synthesized to confirm its structure as a new antiplasmodial compound. Along with 5, two other new and branched compounds 6 and 7 were synthesized as well. Accompanying the five quinolones were two known compounds 2 and 3 which are inactive against Plasmodium falciparum. The isolation, structure elucidation, total synthesis, and biological evaluation of these compounds are discussed in this article.
Volatile methyl esters of medium chain length from the bacterium Chitinophaga Fx7914
Nawrath, Thorben,Gerth, Klaus,Mueller, Rolf,Schulz, Stefan
experimental part, p. 2228 - 2253 (2011/05/17)
The analysis of the volatiles released by the novel bacterial isolate Chitinophaga Fx7914 revealed the presence of ca. 200 compounds including different methyl esters. These esters comprise monomethyl- and dimethyl-branched, saturated, and unsaturated fatty acid methyl esters that have not been described as bacterial volatiles before. More than 30 esters of medium C-chain length were identified, which belong to five main classes, methyl (S)-2-methylalkanoates (class A), methyl (S)-2,(ω-1)-dimethylalkanoates (class B), methyl 2,(ω-2)-dimethylalkanoates (class C), methyl (E)-2-methylalk-2-enoates (class D), and methyl (E)-2,(ω-1)-dimethylalk-2- enoates (class E). The structures of the compounds were verified by GC/MS analysis and synthesis of the target compounds as methyl (S)-2-methyloctanoate (28), methyl (S)-2,7-dimethyloctanoate ((S)-43), methyl 2,6-dimethyloctanoate (49), methyl (E)-2-methylnon-2-enoate (20a), and methyl (E)-2,7-dimethyloct-2- enoate (41a). Furthermore, the natural saturated 2-methyl-branched methyl esters showed (S)-configuration as confirmed by GC/MS experiments using chiral phases. Additionally, the biosynthetic pathway leading to the methyl esters was investigated by feeding experiments with labeled precursors. The Me group at C(2) is introduced by propanoate incorporation, while the methyl ester is formed from the respective carboxylic acid by a methyltransferase using S-adenosylmethionine (SAM).
Reductive ethylation of homoallyl alcohols with a disubstituted double bond with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide
Kulinkovich,Shevchuk,Isakov,Prokhorevich
, p. 659 - 664 (2007/10/03)
Homoallyl and bishomoallyl alcohols with a disubstituted double bond treated with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide are converted into the products of a reductive ethylation of the olefin fragment. Under similar conditions esters of β,γ-unsaturated carboxylic acids undergo a successive cyclopropanation of the ester group and reductive ethylation of the double carbon-carbon bond and yield 1-(3-ethylalkyl)cyclopropanols. The features of the observed reactions are explained in the framework of the carbometallation mechanism of the double carbon-carbon bond by the action of dialkoxytitanacyclopropane reagents. Pleiades Publishing, Inc. 2006.
Alkane oxygenation with H2O2 catalysed by FeCl 3 and 2,2′-bipyridine
Shul'pin, Georgiy B.,Golfeto, Camilla C.,Süss-Fink, Georg,Shul'pina, Lidia S.,Mandelli, Dalmo
, p. 4563 - 4567 (2007/10/03)
The H2O2-FeCl3-bipy system in acetonitrile efficiently oxidises alkanes predominantly to alkyl hydroperoxides. Turnover numbers attain 400 after 1 h at 60°C. It has been assumed that bipy facilitates proton abstraction from a H2O2 molecule coordinated to the iron ion (these reactions are stages in the catalytic cycle generating hydroxyl radicals from the hydrogen peroxide). Hydroxyl radicals then attack alkane molecules finally yielding the alkyl hydroperoxide.
Novel Caprolactones from a Marine Streptomycete
Stritzke, Katja,Schulz, Stefan,Laatsch, Hartmut,Helmke, Elisabeth,Beil, Winfried
, p. 395 - 401 (2007/10/03)
Two new caprolactones, (R)-10-methyl-6-undecanolide (1) and (6R,10S)-10-methyl-6-dodecanolide (2), were identified in the lipid extract of a marine streptomycete (isolate B6007). Their structures were proposed on the basis of GC-MS experiments and proved by synthesis. The absolute configuration of the compounds was established by comparison of the natural and synthetic stereoisomers using chiral gas chromatography. These caprolactones show a moderate phytotoxicity and a promising activity against cancer cells with concomitant low general cytotoxicity.
A SIMPLE PROCEDURE FOR THE SYNTHESIS OF THREE-CARBON HOMOLOGATED BORONATE ESTERS AND TERMINAL ALKENES VIA NUCLEOPHILIC DISPLACEMENT IN α-HALOALLYLBORONATE ESTER
Brown, Herbert C.,Rangaishenvi, Milind V.
, p. 7115 - 7118 (2007/10/02)
The transfer reactions of α-haloallylboronate ester 1 with representative organolithium and Grignard reagents provide α-alkyl- or α-aryl-substituted allylboronate esters, readily converted into three-carbon homologated boronate esters and terminal alkenes.
