42235-38-1Relevant academic research and scientific papers
A Facile and Efficient Method for the Synthesis of Labeled and Unlabeled Very Long Chain Polyunsaturated Fatty Acids
Hamberg, Mats
, p. 489 - 494 (2021/04/19)
Several methods are available for elongation of fatty acid acyl chains. The present paper describes adaptation to the fatty acid field of a previously published protocol for manganese-based Wurtz type coupling of alkyl bromides. 22-Bromo-3(Z),6(Z),9(Z),12(Z),15(Z),18(Z)-docosahexaene, easily prepared from 4(Z),7(Z),10(Z),13(Z),16(Z),19(Z)-docosahexaenoic acid, was coupled to homologous ω-bromoesters by stirring for 4 hours at 40°C in the presence of manganese powder, a nickel catalyst and terpyridine. This afforded in yields of 70–75% a series of ω3-hexaenoates of chain lengths of 32–40 carbons. The corresponding fatty acids of >98% purity were obtained following saponification and final purification. By using methyl [2,2,3,3,4,4-2H6]10-bromodecanoate as coupling partner it was possible to prepare a very long chain fatty acid in isotopically labeled form, i.e., [2,2,3,3,4,4-2H6]14(Z),17(Z),20(Z),23(Z),26(Z),29(Z)-dotriacontahexaenoic acid. Also prepared were the monounsaturated long chain fatty acids 15(Z)-octadecenoic acid and 15(Z)-tetracosenoic acid. Very long chain fatty acids have been isolated from retina and other tissues and are of biological relevance. The methodology described will assist in further analytical and biological studies in this field.
Cysteine-Targeted Insecticides against A. gambiae Acetylcholinesterase Are Neither Selective nor Reversible Inhibitors
Gorecki, Lukas,Andrys, Rudolf,Schmidt, Monika,Kucera, Tomas,Psotka, Miroslav,Svobodova, Barbora,Hrabcova, Veronika,Hepnarova, Vendula,Bzonek, Petr,Jun, Daniel,Kuca, Kamil,Korabecny, Jan,Musilek, Kamil
supporting information, p. 65 - 71 (2019/12/25)
Acetylcholinesterase cysteine-targeted insecticides against malaria vector Anopheles gambia and other mosquitos have already been introduced. We have applied the olefin metathesis for the preparation of cysteine-targeted insecticides in high yields. The prepared compounds with either a succinimide or maleimide moiety were evaluated on Anopheles gambiae and human acetylcholinesterase with relatively high irreversible inhibition of both enzymes but poor selectivity. The concept of cysteine binding was not proved by several methods, and poor stability was observed of the chosen most potent/selective compounds in a water/buffer environment. Thus, our findings do not support the proposed concept of cysteine-targeted selective insecticides for the prepared series of succinimide or maleimide compounds.
Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species
Kovács, Ervin,Sághy, Péter,Turczel, Gábor,Tóth, Imre,Lendvay, Gy?rgy,Domján, Attila,Anastas, Paul T.,Tuba, Róbert
supporting information, p. 213 - 217 (2017/09/12)
Cross-metathesis (CM) of conjugated polyenes, such as 1,6-diphenyl-1,3,5-hexatriene (1) and α-eleostearic acid methyl ester (2) with several olefins, including 1-hexene, dimethyl maleate and cis-stilbene as model compounds has been carried out using (1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)-dichloro(o-isopropoxyphenylmethylene)ruthenium (Hoveyda-Grubbs 2nd generation, HG2) catalyst. The feasibility of these reactions is demonstrated by the observed high conversions and reasonable yields. Thus, regardless of the relatively low electron density, =CH–CH= conjugated units of molecules, including compound 2 as a sustainable, non-foodstuff source, can be utilized as building blocks for the synthesis of various value-added chemicals via olefin metathesis. DFT-studies and the product spectrum of the self-metathesis of 1,6-diphenyl-1,3,5-hexatriene suggest that a Ru η1-allylidene complex is the active species in the reaction.
Synthesis of [3]rotaxanes that utilize the catalytic activity of a macrocyclic phenanthroline-Cu complex: Remarkable effect of the length of the axle precursor
Yamashita, Yoshiaki,Mutoh, Yuichiro,Yamasaki, Ryu,Kasama, Takeshi,Saito, Shinichi
supporting information, p. 2139 - 2145 (2015/02/19)
[3]Rotaxanes, which consist of one macrocyclic phenanthroline compound and two axle components, were prepared by the oxidative dimerization of an alkyne compound with bulky tris[4'-cyclohexyl-(1,1'-biphenyl)-4-yl]methyl blocking group. The catalytic activ
Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer's agent
Zhang, Hong-Yan,Yamakawa, Yu-Ichiro,Matsuya, Yuji,Toyooka, Naoki,Tohda, Chihiro,Awale, Suresh,Li, Feng,Kadota, Shigetoshi,Tezuka, Yasuhiro
, p. 604 - 608 (2014/01/23)
In order to develop new drugs for Alzheimer's disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)- octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on Aβ(25-35)-treated rat cortical neurons, which activities were comparable to that of a positive control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity.
Dynamic assessment of bilayer thickness by varying phospholipid and hydraphile synthetic channel chain lengths
Weber, Michelle E.,Schlesinger, Paul H.,Gokel, George W.
, p. 636 - 642 (2007/10/03)
A library of "hydraphile" synthetic ion channel analogues that differ in overall length from ～28-58 A has been prepared. A new and convenient ion-selective electrode (ISE) method was used to assay Na+ release. Liposomes were formed from three d
