124909-02-0Relevant articles and documents
Total Synthesis of Gelsemoxonine through a Spirocyclopropane Isoxazolidine Ring Contraction
Diethelm, Stefan,Carreira, Erick M.
, p. 6084 - 6096 (2015)
Plants of the species Gelsemium have found application in traditional Asian medicine for over a thousand years. Gelsemoxonine represents a novel constituent of this plant incorporating a highly functionalized azetidine at its core. We herein report a full
Synthesis and anticancer profile of novel sphingoid base-like compounds with a quaternary stereocentre
Jacková, Dominika,Brunderová, Mária,Fábian, Martin,Martinková, Miroslava,Gonda, Jozef,Pilátová, Martina Bago
, (2019/11/16)
The synthesis of novel sphingoid base-like compounds with a quaternary stereocentre was achieved in a sequence featuring [3,3]-sigmatropic rearrangements and olefin cross-metathesis transformation as the key reaction steps, which were accompanied by the rational selection of suitable functional group transformations. The stereochemistry of the desired tetra-substituted carbon bearing nitrogen functionality was determined via NOESY experiments of the advanced oxazolidine-2-thiones. Cell viability experiments revealed significant antiproliferative/cytotoxic activity of the target compounds 7, ent-7 and 29 against the Jurkat cell line, with the IC50 values of 6.6 μM, 5.6 μM and 6.1 μM, respectively.
Production of optically active 2 - vinylcyclopropane - 1, 1 - dicarboxylic acid ester
-
Paragraph 0058, (2018/03/31)
Provided is a method for producing an optically active 1-amino-2-vinylcyclopropane-1-carboxylic acid ester and 2-vinylcyclopropane-1,1-dicarboxylic acid ester, which do not isomerize during a reaction, with an inexpensive and easily obtainable optically a
Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation Dedicated to Associated Professor Ladislav Knie?o on the occasion of his 70th birthday
Martinková, Miroslava,Mezeiová, Eva,Fabi?íková, Milica,Gonda, Jozef,Pilátová, Martina,Moj?i?, Ján
, p. 6 - 24 (2015/02/05)
Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group
Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation Dedicated to Associated Professor Ladislav Knieo on the occasion of his 70th birthday
Martinkov, Miroslava,Mezeiov, Eva,Fabikov, Milica,Gonda, Jozef,Piltov, Martina,Moji, Jn
, p. 6 - 24 (2015/02/19)
Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group
Reaction of (2S,3S)-2-benzyloxybutane-1,2,4-triol with N,N′-carbonyldiimidazole
Selezneva,Khasanova,Egorov,Gimalova,Ovchinnikov, M. Yu.,Miftakhov
, p. 910 - 914 (2015/08/25)
(2S,3S)-2-Benzyloxybutane-1,2,4-triol reacted with N,N′-carbonyldiimidazole to give a mixture of the expected 1,2-carbonate and the corresponding bis-carbonate.
Facile synthesis of (2R,3S)-2-benzyloxy-3-hydroxybutyrolactone
El-Batta, Amer
, p. 2457 - 2463 (2013/07/25)
The heterocyclic diols derived from L-dimethyl tartrate are important chiral synthons in organic synthesis. In particular, L-threosolactone and L-threosolactam structures are versatile precursors for the synthesis of biologically active molecules. Structu
Preparation of enantioenriched tetraols and triolamines from a common epoxide
Kaviani-Joupari, Makan,Schramm, Michael P.
supporting information, p. 5014 - 5017 (2013/09/02)
We identify a silylcyclopentene oxide that is amenable to several distinct asymmetric catalytic transformations providing access to enantio-enriched tetraol and triol-amines. The sequence employed allows for selective protection of one amine or alcohol from the four heteroatoms that are introduced into the carbon scaffold.
Development of diacyltetrol lipids as activators for the C1 domain of protein kinase C
Mamidi, Narsimha,Gorai, Sukhamoy,Mukherjee, Rakesh,Manna, Debasis
experimental part, p. 1275 - 1285 (2012/06/04)
The protein kinase C (PKC) family of serine/threonine kinases is an attractive drug target for the treatment of cancer and other diseases. Diacylglycerol (DAG), phorbol esters and others act as ligands for the C1 domain of PKC isoforms. Inspection of the crystal structure of the PKCδ C1b subdomain in complex with phorbol-13-O-acetate shows that one carbonyl group and two hydroxyl groups play pivotal roles in recognition of the C1 domain. To understand the importance of two hydroxyl groups of phorbol esters in PKC binding and to develop effective PKC activators, we synthesized DAG like diacyltetrols (DATs) and studied binding affinities with C1b subdomains of PKCδ and PKC. DATs, with the stereochemistry of natural DAGs at the sn-2 position, were synthesized from (+)-diethyl l-tartrate in four to seven steps as single isomers. The calculated EC50 values for the short and long chain DATs varied in the range of 3-6 μM. Furthermore, the fluorescence anisotropy values of the proteins were increased in the presence of DATs in a similar manner to that of DAGs. Molecular docking of DATs (1b-4b) with PKCδ C1b showed that the DATs form hydrogen bonds with the polar residues and backbone of the protein, at the same binding site, as that of DAG and phorbol esters. Our findings reveal that DATs represent an attractive group of C1 domain ligands that can be used as research tools or further structurally modified for potential drug development.
Studies of intramolecular alkylidene carbene reactions; an approach to heterocyclic nucleoside bases
Hobley, Gerard,Stuttle, Keith,Wills, Martin
, p. 4739 - 4748 (2007/10/03)
A series of investigations into the applications of intramolecular cyclisations of alkylidene carbenes are described. The insertion reaction of the carbene generated from 1,4-di(tert-butyldimethylsilyloxy)-3-benzyloxy-butane-2-one to the benzylic position