167216-30-0Relevant articles and documents
Novel metabolically stable and functionally active mimetic of spermidine
Khomutov,Hyvoenen,Simonian,Vepsaelaeinen,Alhonen,Kochetkov,Keinaenen
, p. 225 - 230 (2011)
Earlier unknown 1,8-diamino-3-methyl-4-azanonane (γ-MeSpd) was synthesized. The analogue was a substrate of neither spermine/spermidine N 1-acetyltransferase nor spermine synthase, but was capable to support the growth of DU145 cells having depleted polyamine pools. Such a combination of γ-MeSpd properties discloses novel opportunities to study cellular functions of catabolically unstable and easily interconvertible spermine and spermidine.
Oxa-Michael Addition to α,β-Unsaturated Nitriles: An Expedient Route to γ-Amino Alcohols and Derivatives
Guo, Beibei,Zijlstra, Douwe S.,de Vries, Johannes G.,Otten, Edwin
, p. 2868 - 2872 (2018)
Water addition to α,β-unsaturated nitriles would give facile access to the β-hydroxy-nitriles, which in turn can be hydrogenated to the γ-amino alcohols. We have previously shown that alcohols readily add in 1,4-fashion to these substrates using Milstein's Ru(PNN) pincer complex as catalyst. However, attempted water addition to α,β-unsaturated nitriles gave the 3-hydroxynitriles in mediocre yields. On the other hand, addition of benzyl alcohol proceeded in excellent yields for a variety of β-substituted unsaturated nitriles. Subsequent treatment of the benzyl alcohol addition products with TMSCl/FeCl3 resulted in the formation of 3-hydroxy-alkylnitriles. The 3-benzyloxy-alkylnitriles obtained from oxa-Michael addition also could be hydrogenated directly in the presence of acid to give the amino alcohols as their HCl salts in excellent yields. Hydrogenation under neutral conditions gave a mixture of the secondary and tertiary amines. Hydrogenation in the presence of base and Boc-anhydride gave the orthogonally bis-protected amino alcohols, in which the benzyl ether can subsequently be cleaved to yield Boc-protected amino alcohols. Thus, a variety of molecular scaffolds with a 1,3-relationship between O- and N-functional group is accessible starting from oxa-Michael addition of benzyl alcohol to α,β-unsaturated nitriles.
INHIBITORS OF HISTONE DEMETHYLASES
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Page/Page column 112; 114, (2014/04/18)
The present application discloses compounds capable of modulating the activity of histone demethylases (HDMEs), which are useful for prevention and/or treatment of diseases in which genomic dysregulation is involved in the pathogenesis, such as e.g. cancer. The present application also discloses pharmaceutical compositions comprising said compounds and the use of such compounds as a medicament. The compounds take the form (I).
Construction of the 5,10b-phenanthridine skeleton using [3+2]-cycloaddition of a non-stabilized azomethine ylide: Total synthesis of (±)-maritidine and (±)-crinine alkaloids
Pandey, Ganesh,Gupta, Nishant R.,Gadre, Smita R.
body text, p. 740 - 750 (2011/03/22)
Vicinal quaternary and tertiary stereocenters of the 5,10b-phenanthridine skeleton 1 are constructed simultaneously in one step by the [3+2]-cycloaddition of non-stabilized azomethine ylide 9, generated by sequential double desilylation of 10 utilizing silver(I) fluoride as a one-electron oxidant. The regio- as well as stereochemical origin of this cycloaddition reaction is explained through a favorable transition state 9″. The strategy is successfully applied for the total synthesis of the biologically active alkaloids (±)-maritidine (1a), (±)-crinine (1b), and their analogues (1d, 1e, and 1f). The synthesis features construction of the BD ring with concomitant installation of a quarternary and tertiary carbon in a single operation by employing intramolecular 1,3-dipolar cycloaddition of a non-stabilizedazomethine ylide. Oxo-maritidine and oxo-crinine were found to be advanced and efficient intermediates for the synthesis of natural products of this class.
HETEROCYCLIC COMPOUNDS CONTAINING A PYRROLOPYRIDINE OR BENZIMIDAZOLE CORE
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Page/Page column 55, (2011/06/26)
The present invention relates to compounds of Formula (I) and pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5 and n are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.
HETEROCYCLIC COMPOUNDS CONTAINING AN INDOLE CORE
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Page/Page column 55, (2011/06/26)
Disclosed are novel compounds which inhibit RSK, methods of making such compounds and pharmaceutical compositions comprising such compounds. Also disclosed are methods of treating RSK2 regulated disorders using compounds of the invention.
Stereoselective one-step construction of vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton: Total synthesis of (±)-maritidine
Pandey, Ganesh,Gupta, Nishant R.,Pimpalpalle, Tukaram M.
supporting information; experimental part, p. 2547 - 2550 (2009/10/18)
The challenging vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton are created in a single step utilizing intramolecular [3 + 2]-cycloaddition of nonstabilized azomethine ylide as the key step. The application of the
Ornithine decarboxylase inhibiting branched aminooxy amino alkane derivatives
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, (2008/06/13)
Compounds of formula (I) in which (a) four of the radicals R1, R2, R3, R4, R5 and R6 are hydrogen and the others independently of one another are in each case C1 -C2 alkyl, these groups being bonded to the same carbon atom or to two different carbon atoms, or (b) five of the radicals R1, R2, R3, R4, R5 and R6 are hydrogen and the other radical is C1 -C2 alkyl or hydroxymethyl, or salts thereof, are described. The compounds of formula (I) and their salts are ornithine decarboxylase inhibitors.
