3095-95-2Relevant articles and documents
Synthesis of phosphonoacetate analogues of the second messenger adenosine 5′-diphosphate ribose (ADPR)
Baszczyňski, Ond?ej,Watt, Joanna M.,Rozewitz, Monika D.,Fliegert, Ralf,Guse, Andreas H.,Potter, Barry V. L.
, p. 1776 - 1785 (2020)
Adenosine 5′-diphosphate ribose (ADPR) is an intracellular signalling molecule generated from nicotinamide adenine dinucleotide (NAD+). Synthetic ADPR analogues can shed light on the mechanism of activation of ADPR targets and their downstream effects. Such chemical biology studies, however, are often challenging due to the negatively charged pyrophosphate that is also sensitive to cellular pyrophosphatases. Prior work on an initial ADPR target, the transient receptor potential cation channel TRPM2, showed complete pyrophosphate group replacement to be a step too far in maintaining biological activity. Thus, we designed ADPR analogues with just one of the negatively charged phosphate groups removed, by employing a phosphonoacetate linker. Synthesis of two novel phosphonoacetate ADPR analogues is described via tandem N,N′-dicyclohexylcarbodiimide coupling to phosphonoacetic acid. Neither analogue, however, showed significant agonist or antagonist activity towards TRPM2, underlining the importance of a complete pyrophosphate motif in activation of this particular receptor.
Composition comprising a chloroquinoline based α,β-unsaturated amide derivative as an active ingredient for preventing and treating malaria infection
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Paragraph 0090-0093, (2017/02/28)
The present invention relates to an antimalarial agent containing a chloroquine-based andalpha;,andbeta;-unsaturated amide derivative compound having a novel structure as an active component. According to the present invention, an experiment, in order to analyze antimalarial activities of the chloroquine-based andalpha;,andbeta;-unsaturated amide derivative compounds having the novel structure, has been conducted by testing cytotoxicity in the growth of Hela cells and also by measuring inhibitory activities on the growth of P. falciparum strain. Accordingly, the novel compounds have shown excellence in antimalarial activities. Thus, the composition can be useful for pharmaceutical compositions for preventing and treating malaria.COPYRIGHT KIPO 2016
Synthesis of orthogonally protected (2S)-2-amino-adipic acid (α-AAA) and (2S,4 R)-2-amino-4-hydroxyadipic acid (Ahad)
Yadav, Saroj,Taylor, Carol M.
, p. 5401 - 5409 (2013/07/26)
(2S,4R)-2-Amino-4-hydroxyadipic acid (Ahad) building block 45 was synthesized in 11 steps and 6.5% overall yield from commercially available materials. Key steps in stereocontrol were an asymmetric conjugate addition employing a proline-based catalyst and a syn-selective intramolecular-conjugate addition of an oxygen nucleophile to an α,β-unsaturated ester. To enable incorporation of α-amino-adipic acid (α-AAA) and Ahad into peptides, a truly orthogonal protecting group scheme was developed, encompassing an allyloxycarbonyl (Alloc) carbamate for Nα, a tert-butyl ester for the δ-COOH, an acetol ester for the α-COOH, and a tert- butyldimethylsilyl ether for the γ-hydroxy group of Ahad.
