37075-68-6Relevant academic research and scientific papers
Effect of sulfonamidoethylenediamine substituents in RuII arene anticancer catalysts on transfer hydrogenation of coenzyme NAD+ by formate
Chen, Feng,Soldevila-Barreda, Joan J.,Romero-Canelón, Isolda,Coverdale, James P. C.,Song, Ji-Inn,Clarkson, Guy J.,Kasparkova, Jana,Habtemariam, Abraha,Brabec, Viktor,Wolny, Juliusz A.,Schünemann, Volker,Sadler, Peter J.
supporting information, p. 7178 - 7189 (2018/06/04)
A series of neutral pseudo-octahedral RuII sulfonamidoethylenediamine complexes [(η6-p-cym)Ru(N,N′)Cl] where N,N′ is N-(2-(R1,R2-amino)ethyl)-4-toluenesulfonamide (TsEn(R1,R2)) R1,R2 = Me,H (1); Me,Me (2); Et,H (3); benzyl,H (Bz, 4); 4-fluorobenzyl,H (4-F-Bz, 5) or naphthalen-2-ylmethyl,H (Naph, 6), were synthesised and characterised including the X-ray crystal structure of 3. These complexes catalyse the reduction of NAD+ regioselectively to 1,4-NADH by using formate as the hydride source. The catalytic efficiency depends markedly on the steric and electronic effects of the N-substitutent, with turnover frequencies (TOFs) increasing in the order: 1 -1 for 4 with a 95% yield of 1,4-NADH. The reduction rate was highest between pH? (deuterated solvent) 6 and 7.5 and improved with an increase in formate concentration (TOF of 18.8 h-1, 140 mM formate). The calculations suggested initial substitution of an aqua ligand by formate, followed by hydride transfer to RuII and then to NAD+, and indicated specific interactions between the aqua complex and both NAD+ and NADH, the former allowing a preorganisation involving interaction between the aqua ligand, formate anion and the pyridine ring of NAD+. The complexes exhibited antiproliferative activity towards A2780 human ovarian cancer cells with IC50 values ranging from 1 to 31 μM, the most potent complex, [(η6-p-cym)Ru(TsEn(Bz,H))Cl] (4, IC50 = 1.0 ± 0.1 μM), having a potency similar to the anticancer drug cisplatin. Co-administration with sodium formate (2 mM), increased the potency of all complexes towards A2780 cells by 20-36%, with the greatest effect seen for complex 6.
Cooperative catalysis through noncovalent interactions
Tang, Weijun,Johnston, Steven,Iggo, Jonathan A.,Berry, Neil G.,Phelan, Marie,Lian, Luyun,Bacsa, John,Xiao, Jianliang
supporting information, p. 1668 - 1672 (2013/04/24)
One of four: A chiral phosphoric acid enables asymmetric hydrogenation of imines with an achiral iridium catalyst by virtue of noncovalent interactions. These interactions lead to the formation of a highly organized ternary complex, and the hydride is transferred highly enantioselectively. Copyright
Cooperative catalysis: Combining an achiral metal catalyst with a chiral Br?nsted acid enables highly enantioselective hydrogenation of imines
Tang, Weijun,Johnston, Steven,Li, Chaoqun,Iggo, Jonathan A.,Bacsa, John,Xiao, Jianliang
supporting information, p. 14187 - 14193 (2013/11/06)
Asymmetric hydrogenation of imines leads directly to chiral amines, one of the most important structural units in chemical products, from pharmaceuticals to materials. However, highly effective catalysts are rare. This article reveals that combining an ac
Design of base metal extractants. Part 1. Inter-ligand hydrogen bonding in the assembly of pseudo-macrocyclic bis(aminosulfonamidato)M(ii) complexes
Squires, Clare,Baxter, Christopher W.,Campbell, John,Lindoy, Leonard F.,McNab, Hamish,Parkin, Andrew,Parsons, Simon,Tasker, Peter A.,Wei, Gang,White, David J.
, p. 2026 - 2034 (2007/10/03)
Monosulfonyl derivatives of simple 1,2- and 1,3-diamines (R 2HN-R-NHSO2R1 = L) have been shown to be easily deprotonated to give neutral 2: 1 complexes, [M(L - H)2], with Co(ii), Ni(ii), Cu(ii) or Zn(ii). The Ni
