21626-41-5Relevant academic research and scientific papers
Water-promoted dehydrative coupling of 2-aminopyridines in heptane: Via a borrowing hydrogen strategy
Azumaya, Isao,Hikawa, Hidemasa,Kikkawa, Shoko,Nakayama, Taku
, p. 23144 - 23150 (2021/07/21)
A synthetic method for dehydrative N-benzylation promoted by water molecules in heptane using a π-benzylpalladium system has been developed. The presence of water significantly accelerates carbon-nitrogen bond formation, which is accomplished in an atom-economical process to afford the corresponding N-monobenzylated products. A crossover experiment afforded H/D scrambled products, which is consistent with a borrowing hydrogen mechanism. Kinetic isotope effect measurements revealed that benzylic carbon-hydrogen bond cleavage was the rate-determining step.
Discovery of Aromatic Carbamates that Confer Neuroprotective Activity by Enhancing Autophagy and Inducing the Anti-Apoptotic Protein B-Cell Lymphoma 2 (Bcl-2)
Kinarivala, Nihar,Patel, Ronak,Boustany, Rose-Mary,Al-Ahmad, Abraham,Trippier, Paul C.
, p. 9739 - 9756 (2017/12/26)
Neurodegenerative diseases share certain pathophysiological hallmarks that represent common targets for drug discovery. In particular, dysfunction of proteostasis and the resultant apoptotic death of neurons represent common pathways for pharmacological intervention. A library of aromatic carbamate derivatives based on the clinically available drug flupirtine was synthesized to determine a structure-activity relationship for neuroprotective activity. Several derivatives were identified that possess greater protective effect in human induced pluripotent stem cell-derived neurons, protecting up to 80% of neurons against etoposide-induced apoptosis at concentrations as low as 100 nM. The developed aromatic carbamates possess physicochemical properties desirable for CNS therapeutics. The primary known mechanisms of action of the parent scaffold are not responsible for the observed neuroprotective activity. Herein, we demonstrate that neuroprotective aromatic carbamates function to increase the Bcl-2/Bax ratio to an antiapoptotic state and activate autophagy through induction of beclin 1.
C-N bond formation by the oxidative alkylamination of azines: Comparison of AgPy2MnO4 versus KMnO4 as oxidant
Gulevskaya, Anna V.,Maes, Bert U. W.,Meyers, Caroline,Herrebout, Wouter A.,Van Der Veken, Benjamin J.
, p. 5305 - 5314 (2007/10/03)
Reports on the successful oxidative alkylamination of azines by the S NH-reaction, with the use of alkylamines other than methylamine, are very scarce. Hitherto, the experimental limitation to extend oxidative animation of azines wit
Substitution reactions of 5-nitropyridine-2-sulfonic acid. A new pathway to 2,5-disubstituted pyridines
Bakke, Jan M.,Sletvold, Ingrid
, p. 2710 - 2715 (2007/10/03)
We have investigated reactions of 5-nitropyridine-2-sulfonic acid and its potassium salt in which substitution of the sulfonate group by oxygen, nitrogen and halogen nucleophiles has been attempted. By this approach, 2-methoxy-(95% yield), 2-ethoxy- (97%), 2-isopropoxy- (65%), 2-amino- (92%), 2- butylamino- (76%), 2-diethylamino- (62%), 2-ethylamino- (32%), 2-benzylamino- (77%), 2-(R-1-phenylethylamino)- (71%) and 2-chloro-5-nitropyridine (87%) have been obtained. No reactions were observed with phenols or anilines. With t-BuOH, 2-hydroxy-5-nitropyridine was formed together with 2-methylpropene.
Substituted 4-oxo-napthyridine-3-carboxamides: GABA brain receptor ligands
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, (2008/06/13)
The present invention encompasses structures of the Formula or the pharmaceutically acceptable non-toxic salts thereof wherein: x is hydrogen, halogen, (un)substituted alkyl, (un)substituted alkoxy or amino; and Y is (un)substituted alkyl, aryl, or heteroaryl, which compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compounds are useful in the diagnosis and treatment of anxiety, Down Syndrome, sleep, cognitive and seizure disorders, and overdose with benzodiazepine drugs and for enhancement of alertness.
