72599-99-6Relevant articles and documents
Oxynitrilase-catalyzed transformation of substituted aldehydes: The case of (±)-2-phenylpropionaldehyde and of (±)-3-phenylbutyraldehyde
Danieli, Bruno,Barra, Carlo,Carrea, Giacomo,Riva, Sergio
, p. 1675 - 1682 (1996)
The influence of a stereocenter already present in the molecule on the selectivity displayed by almond oxynitrilase has been addressed, considering the substituted aldehydes (±)-2-phenylpropionaldehyde 1 and (±)-3- phenylbutyraldehyde 2 as model substrates. Only when the stereocenter was adjacent to the aldehyde group (as in 1) a strong influence on the selectivity of this enzyme was observed, resulting in the formation of the four possible cyanohydrins although in different ratio. On the other hand, the cyanohydrins obtained from 2 had the expected 2R configuration.
Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents
Donslund, Aske S.,Neumann, Karoline T.,Corneliussen, Nicklas P.,Grove, Ebbe K.,Herbstritt, Domenique,Daasbjerg, Kim,Skrydstrup, Troels
supporting information, p. 9856 - 9860 (2019/07/09)
Herein, we report a nickel-catalyzed carbonylative coupling of α-bromonitriles and alkylzinc reagents with near stoichiometric carbon monoxide to give β-ketonitriles in good yields. The reaction is catalyzed by a readily available and stable nickel(II) pincer complex. The developed protocol tolerates substrates bearing a variety of functional groups, which would be problematic or incompatible with previous synthetic methods. Additionally, we demonstrate the suitability of the method for carbon isotope labeling by the synthesis of 13C-labeled β-ketonitriles and their transformation into isotopically labeled heterocycles.
Mechanism-Based inactivation of human cytochrome p450 3A4 by two piperazine-Containing compounds
Bolles, Amanda K.,Fujiwara, Rina,Briggs, Erran D.,Nomeir, Amin A.,Furge, Laura Lowe
, p. 1471 - 1475 (2014/12/11)
Human cytochrome P450 3A4 (CYP3A4) is responsible for the metabolism of more than half of pharmaceutic drugs, and inactivation of CYP3A4 can lead to adverse drug-drug interactions. The substituted imidazole compounds 5-fluoro-2-[4-[(2-phenyl-1H-imidazol-5-yl) methyl]-1-piperazinyl]pyrimidine (SCH 66712) and 1-[(2-ethyl-4-methyl-1H-imidazol-5-yl)methyl]-4-[4-(trifluoromethyl)-2-pyridinyl]piperazine (EMTPP) have been previously identified as mechanism-based inactivators (MBI) of CYP2D6. The present study shows that both SCH 66712 and EMTPP are also MBIs of CYP3A4. Inhibition of CYP3A4 by SCH 66712 and EMTPP was determined to be con-centration, time, and NADPH dependent. In addition, inactivation of CYP3A4 by SCH 66712 was shown to be unaffected by the presence of electrophile scavengers. SCH 66712 displays type I binding to CYP3A4 with a spectral binding constant (Ks) of 42.9 ± 2.9 μM. The partition ratios for SCH 66712 and EMTPP were 11 and 94, respectively. Whole protein mass spectrum analysis revealed 1:1 binding stoichiometry of SCH 66712 and EMTPP to CYP3A4 and a mass increase consistent with adduction by the inactivators without addition of oxygen. Heme adduction was not apparent. Multiple monooxygenation products with each inactivator were observed; no other products were apparent. These are the first MBIs to be shown to be potent inactivators of both CYP2D6 and CYP3A4.
Catalyst-free Strecker reaction in water: A simple and efficient protocol using acetone cyanohydrin as cyanide source
Galletti, Paola,Pori, Matteo,Giacomini, Daria
experimental part, p. 3896 - 3903 (2011/09/12)
A simple, convenient, and practical method for the synthesis of α-amino nitriles through a one-pot, three-component Strecker reaction of a carbonyl compound, amine, and acetone cyanohydrin in water has been developed. Reactions proceed very efficiently without any catalyst at room temperature with high chemoselectivity and give, in some cases, the expected α-amino nitrile pure after direct separation from water. The protocol is particularly efficient for both aliphatic and aromatic aldehydes, and cyclic ketones, in combination with primary and secondary amines. An unusual application of the Strecker reaction to 1,2-diamines to obtain 1,2-diamino nitriles, and to cyclic secondary amines is reported. Copyright
Cyanobenzoylation and hydrocyanation of aldehydes with benzoyl cyanide using no catalyst
Watahiki, Tsutomu,Ohba, Sayoko,Oriyama, Takeshi
, p. 2679 - 2681 (2007/10/03)
(Matrix presented) In the presence of MS 4A in DMSO, cyanobenzoylation of various aldehydes with benzoyl cyanide proceeded very smoothly to give the corresponding cyanohydrin benzoates in high to excellent yields without an acid or a base. On the other hand, reaction of aldehydes with BzCN in DMSO-H2O also occurred readily to afford the corresponding free cyanohydrins exclusively.
Asymmetric trimethylsilylcyanation of aldehydes utilizing chiral bismuth compounds. A frontier in bismuth mediated synthetic reactions
Wada, Makoto,Takahashi, Toshikazu,Domae, Terutomo,Fukuma, Tomohiro,Miyoshi, Norikazu,Smith, Keith
, p. 3939 - 3946 (2007/10/03)
Bismuth(III) chloride (BiCl3) was found to work efficiently as a versatile catalyst for cyanation of aldehydes with trimethylsilyl cyanide to afford the corresponding cyanohydrins in high yields. Triphenylbismuthan (Ph3Bi) is also effective. The reaction has been applied to the asymmetric cyanation of a variety of aldehydes in high yields with moderate to good enantioselectivities by use of a chiral bismuth catalyst prepared in situ from BiCl3 and (2R,3R)-(+)-diethyl tartrate.
