370554-92-0Relevant academic research and scientific papers
Synthesis of highly substituted 2-13c-imidazolium salts and metal NHC complexes for the investigation of electronic unsymmetry by NMR
Emsermann, Jens,Arduengo, Anthonyj.,Opatz, Till
, p. 2251 - 2264 (2013/09/02)
Complexes of unsymmetrically substituted N-heterocyclic carbenes with NMR-active metals (Ag, Hg, Pt) with or without a 13C-label in the 2-position were synthesized by aldimine cross coupling and analyzed with respect to the scalar couplings between the metal center or C2 and the other ring atoms. Georg Thieme Verlag Stuttgart. New York.
Racemase activity of B. cepacia lipase leads to dual-function asymmetric dynamic kinetic resolution of α-aminonitriles
Vongvilai, Pornrapee,Linder, Mats,Sakulsombat, Morakot,Svedendahl Humble, Maria,Berglund, Per,Brinck, Tore,Ramstroem, Olof
supporting information; experimental part, p. 6592 - 6595 (2011/09/15)
Applaudable promiscuity: Racemase-type activity discovered for B. cepacia lipase with N-substituted α-aminonitriles is proposed to involve a C-C bond-breaking/forming mechanism in the hydrolase site of the enzyme, as supported by experimental data and calculations. This promiscuous activity in combination with the transacylation activity of the enzyme enabled the asymmetric synthesis of N-methyl α-aminonitrile amides in high yield (see scheme). Copyright
Dynamic asymmetric multicomponent resolution: Lipase-mediated amidation of a double dynamic covalent system
Vongvilai, Pornrapee,Ramstroem, Olof
supporting information; experimental part, p. 14419 - 14425 (2010/02/16)
The Strecker reaction is one of the most important multicomponent reactions developed, leading to R-aminonitriles that are versatile substrates for many synthetic applications. In the present study, this reaction type has been applied to a double dynamic covalent resolution protocol, leading to efficient C-C- and C-N-bond generation as well as chiral discrimination. The combination of transimination with iminecyanation enabled the dynamic exchange in more than one direction around a single stereogenic center of restricted structure. This multiple exchange process could generate a vast range of compounds from a low number of starting materials in very short time. The resulting double dynamic covalent systems, created under thermodynamic control, were subsequently coupled in a one-pot process with kinetically controlled lipase-mediated transacylation. This resulted in complete resolution of the dynamic systems, yielding the optimal N-acyl-α-aminonitriles for the enzyme, where the individual chemoenzymatic reactions could produce enantiomerically pure acylated N-substituted α-aminonitriles in good yields.
Synthesis and central nervous system properties of 2-[(alkoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines
Weinhardt,Beard,Dvorak,Marx,Patterson,Roszkowski,Schuler,Unger,Wagner,Wallach
, p. 616 - 627 (2007/10/02)
A series of 2-[(alkoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines was prepared and evaluated for central nervous system (CNS) effects (antidepressant, anticonvulsant, muscle relaxant, and depressant) in animal models. Some separation of those CNS activities was achieved through substitutions on the phenyl and imidazoline moieties. Halo-substituted phenyl compounds were among the most potent antidepressants in this series, while imidazole N-alkylation produced compounds with increased depressant effects (loss of righting reflex, mouse behavior). Comparison of in vitro and in vivo data for pairs of 2-[(methoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines and their parent, 2-amino-4(5)-phenyl-2-imidazolines, suggests that the title compounds were prodrugs for the 2-amino-4(5)-phenyl-2-imidazolines in inhibition of norepinephrine reuptake.
