85514-85-8Relevant articles and documents
Synthesis of a tetra-deuterium-labeled derivative of potent and selective anticancer agent AA005
Liu, Hai-Xia,Yao, Zhu-Jun
, p. 3525 - 3528 (2005)
Annonaceous acetogenins are a series of potent naturally occurring anticancer agents, which act as inhibitors of complex I in mitochondria. AA005, a mimicry of acetogenins, has been found as active as those natural products and to present high selectivities between cancer and normal cells. In order to investigate the further cell-based mechanism induced by AA005, a d 4-labeled derivative of AA005 (AA005-d4) was designed to detect the drug permeation ability into the membranes. In this letter, the synthesis is reported of this deuterium-labeled compound, wherein a ethylene-d4 glycol unit is incorporated efficiently into the molecule skeleton by simple etherifications.
2-{(4a′S,6a′S,10a′R,10b′R)-Octahydrospiro[1,3-dioxolane-2,2′-pyrano[2,3-c]chromen]-6a′(1′H)-yloxy}ethanol in the Synthesis of (2S)- and (2R)-Dodecane-1,2-diols
Faizullina, L. Kh.,Petrova, S. F.,Salikhov, Sh. M.,Tagirov, A. R.,Valeev, F. A.
, p. 1840 - 1843 (2020/12/01)
Abstract: Michael adduct of levoglucosenone and cyclohexanone, 1,6-anhydro-3,4-dideoxy-4-C-(2-oxocyclohexan-1-yl)-β-D-erythrohexo-2-ulose, was treated with ethylene glycol in the presence of oxalic acid, and the resulting mixed ketal, 2-{(4a′S,6a′S,10a′R,10b′R)-octahydrospiro[1,3-dioxolane-2,2′-pyrano[2,3-c]chromen]-6a′(1′H)-yloxy}ethanol, was used a chiral auxiliary in the synthesis of vicinal diols.
Synthesis and enantioselective transport studies of both enantiomers of new chiral proton-ionizable crown ethers containing a diarylphosphinic acid unit
Szabó-Szentjóbi, Hajnalka,Bagi, Péter,Müller, Judit,Balogh, Gy?rgy Tibor,Tóth, Tünde,Huszthy, Péter
, p. 1275 - 1281 (2019/01/30)
The synthesis of four new enantiopure crown ethers containing a diarylphosphinic acid unit has been carried out. As a continuation of our work in this field, the enantioselective transport ability of these ligands for chiral amines has been studied in an
Lipase-catalyzed stereoresolution of long-chain 1,2-alkanediols: A screening of preferable reaction conditions
Parve, Jaan,Reile, Indrek,Aid, Tiina,Kudrja?ova, Marina,Müürisepp, Aleksander-Mati,Vallikivi, Imre,Villo, Ly,Aav, Riina,Pehk, T?nis,Vares, Lauri,Parve, Omar
, p. 60 - 69 (2015/04/14)
Scalable lipase-catalytic method for the kinetic resolution of long-chain 1,2-alkanediol enantiomers via stereoselective cleavage of esters was developed. The influence of lipase, reaction medium, nucleophile, temperature and the structure of the acyl group on the reaction velocity, the stereopreference and the stereoselectivity of the deacylation was studied. In addition, the rate of the spontaneous intramolecular migration of different acyl groups was determined for the intermediate 2-monoesters. The acyl group migration may diminish the apparent stereoselectivity of the two-step process if fast migrating acyl groups are used. It was found that the migration rate of different acyl groups differs by up to two orders of magnitude, being faster for acetyl and isobutyryl and much slower for butyryl and benzoyl groups. The best results were obtained by the sequential methanolysis of bis-butyryl-1,2-alkanediols in an acetonitrile/methanol mixture catalyzed by Candida antarctica lipase B (CALB) at 20 °C, affording (S)-1,2-alkanediols. Stereo- and chemoselective crystallization of the deacylated (S)-1,2-alkanediols from the reaction mixture complements the enzymatic process improving the stereochemical purity to up to ee > 99.8%. (R)-1,2-Alkanediol 2-monoesters were separated from the mother liquor and enriched stereochemically by repeated incubation with CALB, then separated, hydrolyzed with alkali and crystallized to afford (R)-alkanediols of ee > 99.8%.
Synthesis and transport studies of new enantiopure lipophilic crown ethers containing a diarylphosphinic acid unit
Szab, Tams,Hirsch, Edit,Tth, Tünde,Huszthy, Pter
, p. 1443 - 1449 (2015/02/05)
The synthesis of new enantiopure lipophilic crown ethers (S,S)-6, (R,R)-6 and (S,S)-7 containing a diarylphosphinic acid unit has been carried out. The transport ability of these ligands has been studied in an aqueous source phase/lipophilic organic bulk liquid membrane/aqueous receiving phase system controlled by the pH of the media. The transport of metal ions and amines has also been studied. These studies showed high selectivity for protonated amines.
An NMR and MD modeling insight into nucleation of 1,2-alkanediols: Selective crystallization of lipase-catalytically resolved enantiomers from the reaction mixtures
Parve, Omar,Reile, Indrek,Parve, Jaan,Kasvandik, Sergo,Kudrjasova, Marina,Tamp, Sven,Metsala, Andrus,Villo, Ly,Pehk, Tonis,Jarvet, Jueri,Vares, Lauri
, p. 12795 - 12801 (2014/01/17)
The work on developing a scalable lipase-catalytic method for the kinetic resolution of long-chain 1,2-alkanediols, complemented by crystallization of the pure enantiomers from the reaction mixtures, offered the possibility of a more detailed study of the aggregation of such diols. MD modeling, mass spectrometry, 1H NMR, and DOSY studies provided a novel insight into the nucleation process. An efficient protocol for stereo- and chemoselective crystallization of (S)-1,2-dodecanediol and related compounds from the crude bioconversion mixtures was developed.
Synthesis of linear aza and thio analogues of acetogenins and evaluation of their cytotoxicity
Villo, Piret,Toom, Lauri,Eriste, Elo,Vares, Lauri
, p. 6886 - 6899 (2013/11/06)
We report the stereoselective synthesis of thio and aza analogues of Annonaceous acetogenins. The synthetic route allows easy variation of the stereochemistry and of the thio- and aza-fragments. Kinetic resolution of terminal bis-epoxides was used to set two remote stereocentres with high enantio- and diastereoselectivities in one step. The cytotoxicity of the analogues was assessed using the HeLa cell line. Four aza and two thio analogues of Annonaceous acetogenins were synthesized according to a general synthetic route. Two remote stereocentres in the analogues were set with high enantio- and diastereoselectivity in one step by hydrolytic kinetic resolution of a terminal bis-epoxide. Copyright
AMINOALCOHOL LIPIDOIDS AND USES THEREOF
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Page/Page column 160, (2010/06/11)
Aminoalcohol lipidoids are prepared by reacting an amine with an epoxide-terminated compound are described. Methods of preparing aminoalcohol lipidoids from commercially available starting materials are also provided. Aminoalcohol lipidoids may be prepare
Highly diastereoselective synthesis of orthoquinone monoketals through λ13-iodane-mediated oxidative dearomatization of phenols
Pouysegu, Laurent,Chassaing, Stefan,Dejugnac, Delphine,Lamidey, Anne-Marie,Miqueu, Karinne,Sotiropoulos, Jean-Marc,Quideau, Stephane
supporting information; experimental part, p. 3552 - 3555 (2009/02/07)
(Chemical Equation Presented) Versatile chiral substrates for asymmetric synthesis are formed through the spiroketalization of phenols with a chiral substituted ethanol unit O-tethered to the ortho position upon treatment with PhI-(OAc)2 (see example; TFE = 2,2,2-tri-fluoroethanol). Intermediates with a six-membered iodine(III)-containing ring (the natural localized molecular orbitals associated with the I-C6 bond are shown) undergo ligand coupling to give the spiroketals.
Studies on mimicry of naturally occurring annonaceous acetogenins: Non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells
Zeng, Bu-Bing,Wu, Yikang,Jiang, Sheng,Yu, Qian,Yao, Zhu-Jun,Liu, Zhong-Hai,Li, Hong-Yan,Li, Yan,Chen, Xiao-Guang,Wu, Yu-Lin
, p. 282 - 290 (2007/10/03)
A class of structurally simplified analogues of the naturally occurring annonaceous acetogenins were developed, amongst which some non-THF analogues showed remarkable cytotoxicities against tumor cell lines, as well as good selectivity between human tumor cells and normal cells. The synthetic routes were significantly shortened because of the removal of the chiral centers bearing the THF rings on the natural templates. This simplification also provides access to the parallel synthesis of these mimics by a combinatorial strategy. The remaining stereogenic centers at the positions α to the ethereal links were introduced by the Chiron approach from the easily accessible chiral building blocks 6a and/or 6b, made in turn from L-ascorbic acid or Dmannitol, while the one in the butenolide segment was taken from L-lactate. All four diastereomeric non-THF analogues 2a-2d showed remarkable activity against the HCT-8 cell line, and better differentiation was found when testing against the HT-29 cell line. It was also discovered that both the butenolide and ethylene glycol subunits play essential roles in the cytotoxicities against tumor cell lines, while the 10-substituted hydroxy group and the absolute configuration of methyl group at the butenolide moiety are less important for their activity.
