52889-89-1Relevant articles and documents
Preparation of Functionalized Aryl, Heteroaryl, and Benzylic Potassium Organometallics Using Potassium Diisopropylamide in Continuous Flow
Harenberg, Johannes H.,Knochel, Paul,Weidmann, Niels
supporting information, p. 12321 - 12325 (2020/05/04)
We report the preparation of lithium-salt-free KDA (potassium diisopropylamide; 0.6 m in hexane) complexed with TMEDA (N,N,N′,N′-tetramethylethylenediamine) and its use for the flow-metalation of (hetero)arenes between ?78 °C and 25 °C with reaction times between 0.2 s and 24 s and a combined flow rate of 10 mL min?1 using a commercial flow setup. The resulting potassium organometallics react instantaneously with various electrophiles, such as ketones, aldehydes, alkyl and allylic halides, disulfides, Weinreb amides, and Me3SiCl, affording functionalized (hetero)arenes in high yields. This flow procedure is successfully extended to the lateral metalation of methyl-substituted arenes and heteroaromatics, resulting in the formation of various benzylic potassium organometallics. A metalation scale-up was possible without further optimization.
Aminoadamantanes with persistent in vitro efficacy against H1N1 (2009) influenza A
Kolocouris, Antonios,Tzitzoglaki, Christina,Johnson, F. Brent,Zell, Roland,Wright, Anna K.,Cross, Timothy A.,Tietjen, Ian,Fedida, David,Busath, David D.
, p. 4629 - 4639 (2014/07/07)
A series of 2-adamantanamines with alkyl adducts of various lengths were examined for efficacy against strains of influenza A including those having an S31N mutation in M2 proton channel that confer resistance to amantadine and rimantadine. The addition of as little as one CH2 group to the methyl adduct of the amantadine/rimantadine analogue, 2-methyl-2-aminoadamantane, led to activity in vitro against two M2 S31N viruses A/Calif/07/2009 (H1N1) and A/PR/8/34 (H1N1) but not to a third A/WS/33 (H1N1). Solid state NMR of the transmembrane domain (TMD) with a site mutation corresponding to S31N shows evidence of drug binding. But electrophysiology using the full length S31N M2 protein in HEK cells showed no blockade. A wild type strain, A/Hong Kong/1/68 (H3N2) developed resistance to representative drugs within one passage with mutations in M2 TMD, but A/Calif/07/2009 S31N was slow (>8 passages) to develop resistance in vitro, and the resistant virus had no mutations in M2 TMD. The results indicate that 2-alkyl-2-aminoadamantane derivatives with sufficient adducts can persistently block p2009 influenza A in vitro through an alternative mechanism. The observations of an HA1 mutation, N160D, near the sialic acid binding site in both 6-resistant A/Calif/07/2009(H1N1) and the broadly resistant A/WS/33(H1N1) and of an HA1 mutation, I325S, in the 6-resistant virus at a cell-culture stable site suggest that the drugs tested here may block infection by direct binding near these critical sites for virus entry to the host cell.
Synthesis of novel thermally reversible photochromic spiro[adamantane-2,7′(6′H)-benzothiophene]
Yokoyama, Yasushi,Nagashima, Hitoshi,Man, Sujen,Yokoyama, Shrestha Yayoi,Takada, Kensaku
, p. 355 - 361 (2007/10/03)
A new thermally reversible photochromic compound, 4′,5′-hexafluoropropano-6′-phenylspiro[adamantane-2, 7′(6′H)-benzothiophene], derived from UV-irradiation of 2-(1-adamantylidene-1-phenylmethyl)-3,3,4,4,5,5-hexafluoro-1- (3-thienyl)cyclopentene via the ph
