22968-45-2Relevant academic research and scientific papers
Synthesis and Substrate Evaluation of (E)-5-[(3-Selenophene-2-Carboxamido)Prop-1-en-1-yl]-Uridine-5′- O -Triphosphate for RNA Polymerase
Kore, Anilkumar R.,Yang, Bo,Thiyagarajan, Samaraj S.,Srinivasan, Balasubramanian
, p. 866 - 876 (2015)
Design, synthesis and T7 RNA polymerase substrate evaluation of (E)-5-[(3-selenophene-2-carboxamido)prop-1-en-1-yl]-uridine-5′-O-triphosphate is reported. The title compound is shown to be a good substrate for RNA polymerase by RNA labeling through in vitro transcription. pTRI-plasmid DNA with β-actin gene sequence (～300 base pairs) with T7 promoter was used as a template for the in vitro transcription. Transcribed product is characterized for incorporation by gel assay and for integrity, full length and size by bioanalyzer. The title compound will be very useful in biophysical techniques to obtain information on dynamics and recognition properties in real time as well as 3D structure of nucleic acids.
Effect of s–se bioisosteric exchange on affinity and intrinsic efficacy of novel n-acylhydrazone derivatives at the adenosine a2a receptor
Barreiro, Eliezer J.,No?l, Fran?ois G.,Pedreira, Júlia Galvez Bulh?es,Silva, Rafaela Ribeiro
, (2021/12/17)
In this work, we evaluated the conformational effect promoted by the isosteric exchange of sulfur by selenium in the heteroaromatic ring of new N-acylhydrazone (NAH) derivatives (3–8, 13, 14), analogues of the cardioactive compounds LASSBio-294 (1) and LASSBio-785 (2). NMR spectra analysis demonstrated a chemical shift variation of the iminic Csp2 of NAH S/Se-isosters, suggesting a stronger intramolecular chalcogen interaction for Se-derivatives. To investigate the pharmacological profile of these compounds at the adenosine A2A receptor (A2AR), we performed a previously validated functional binding assay. As expected for bioisosteres, the isosteric-S/Se replacement affected neither the affinity nor the intrinsic efficacy of our NAH derivatives (1–8). However, the N-methylated compounds (2, 6–8) presented a weak partial agonist profile at A2AR, contrary to the non-methylated counterparts (1, 3–5), which appeared as weak inverse agonists. Additionally, retroisosterism between aromatic rings of NAH on S/Se-isosters mimicked the effect of the N-methylation on intrinsic efficacy at A2AR, while meta-substitution in the phenyl ring of the acyl moiety did not. This study showed that the conformational effect of NAH-N-methylation and aromatic rings retroisosterism changed the intrinsic efficacy on A2AR, indicating the S/Se-chalcogen effect to drive the conformational behavior of this series of NAH.
Bioisosteric Replacement of Arylamide-Linked Spine Residues with N-Acylhydrazones and Selenophenes as a Design Strategy to Novel Dibenzosuberone Derivatives as Type i 1/2 p38α MAP Kinase Inhibitors
Pedreira, Júlia G. B.,Nahidino, Philipp,Kudolo, Mark,Pantsar, Tatu,Berger, Benedict-Tilman,Forster, Michael,Knapp, Stefan,Laufer, Stefan,Barreiro, Eliezer J.
supporting information, p. 7347 - 7354 (2020/09/11)
The recent disclosure of type I 1/2 inhibitors for p38α MAPK demonstrated how the stabilization of the R-spine can be used as a strategy to greatly increase the target residence time (TRT) of inhibitors. Herein, for the first time, we describe N-acylhydrazone and selenophene residues as spine motifs, yielding metabolically stable inhibitors with high potency on enzymatic, NanoBRET, and whole blood assays, improved metabolic stability, and prolonged TRT.
NOVEL HYDROPHILIC DERIVATIVES OF 2-ARYL-4-QUINOLONES AS ANTICANCER AGENTS
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Page/Page column 23-24, (2008/12/06)
2-aryl-4-quinolones are converted into phosphates by reacting with tetrabenzyl pyrophosphate to form dibenzyl phosphates thereof, which are then subject to hydrogenation to replace dibenzyl groups with H, followed by reacting with Amberlite IR-120(Na+ form) to form disodium salts. The results of preliminary screening revealed that these phosphates showed significant anti-cancer activity. A novel intermediate, 2-selenophene 4-quinolone and Λ/, Λ/-dialkylaminoalkyl derivatives of 2-phenyl-4-quinolones are also synthesized. These novel intermediates exhibited significant anticancer activities.
Thermodynamics of Protonation of Some Five-membered Heteroarylcarboxylates, -alkanoates and -trans-propenoates
Arena, Giuseppe,Cali, Rosario,Maccarone, Emanuele,Passerini, Amedeo
, p. 1941 - 1946 (2007/10/02)
Thermodynamic parameters for the proton complex formation of some five-membered heteroaryl-carboxylates, -alkanoates and -trans-propenoates have been determined in aqueous solution at 25 deg C and I = 0.10 mol dm-3 (KNO3) by means of potentiometric and calorimetric measurements.The acidity of heteroarylcarboxylic acids follows the order 2-furoic > 2-thenoic > selenophene-2-carboxylic > 3-furoic > 3-thenoic > pyrrole-2-carboxylic > N-methylpyrrole-2-carboxylic.Such a sequence agrees with the different effects of the heteroaryl groups on the carboxylic side chain.A similar trend is observed for the corresponding furyl- and thienyl-alkanoic acids, even though polar effects of heteroatoms on the acidity are less pronounced owing to the presence of the methylenic spacers.The pK values of trans-heteroarylpropenoic acids turn out to be independent of both the heteroatom and the carboxylic group position.Enthalpic and entropic changes are typical of a "hard-hard" interaction.
