33425-91-1Relevant articles and documents
Enantioseparation and determination of orphenadrine in rat plasma and its application to a stereoselective pharmacokinetic study
Liu, Yanru,Ding, Yushan,Song, Yongbo,Guo, Xingjie
, p. 5428 - 5436 (2021)
A simple, sensitive, and enantioselective HPLC-MS/MS method has been developed for the determination of orphenadrine (ORP) enantiomers in rat plasma for the first time. The method used diphenhydramine as the internal standard (IS), and plasma samples were extracted by liquid-liquid extraction with satisfactory recovery. Chiral separation of the ORP enantiomers was obtained on a Chiralcel OD-RH column (150 mm × 4.6 mm, 5 μm). The mobile phase consists of acetonitrile-ammonium bicarbonate buffer (30 mM, pH 9.0) (80?:?20, v/v). Sufficient resolution (Rs= 3.562) was achieved in a short analysis time (7 min). The multiple reaction monitoring (MRM) mode was used for the detection of ORP enantiomers and IS. The transitions ofm/z270.0 → 181.1 and 256.2 → 167.1 were chosen for monitoring the ORP enantiomers and IS, respectively. Linearity was confirmed in the range of 0.1-50.0 ng mL?1with the lower limit of quantification of 0.1 ng mL?1for both ORP enantiomers in plasma. After validation, the method was applied to the enantioselective pharmacokinetic study of ORP enantiomers in rat plasma following oral administration of 10 mg kg?1racemic ORP. Significant differences (Pmax, AUC,t1/2, CL,Vd, MRT, and VRT, which indicated that enantioselective pharmacokinetic behavior of ORP enantiomers was present in rats.
Chiral Lithium Amido Aryl Zincates: Simple and Efficient Chemo- and Enantio-Selective Aryl Transfer Reagents
Chaumont-Olive, Pauline,Rouen, Mathieu,Barozzino-Consiglio, Gabriella,Ben Abdeladhim, Amel,Maddaluno, Jacques,Harrison-Marchand, Anne
supporting information, p. 3193 - 3197 (2019/01/25)
An enantioselective aryl transfer is promoted using chiral tricoordinated lithium amido aryl zincates that are easily accessible reagents and whose chiral appendage is simply recovered for reuse. The arylation reaction is run in good yields (60 % average on twenty substrates) and high enantiomeric excesses (95 % ee average). This occurs whatever the ortho, meta, or para substituent borne by the substrate and a complete chemoselectivity is observed with respect to the aldehyde function. Sensitive groups such as nitriles, esters, ketones, and enolisable substrates resist to the action of the ate reagent, warranting a large scope to this methodology.
CuII-catalyzed asymmetric hydrosilylation of diaryl- and aryl heteroaryl ketones: Application in the enantioselective synthesis of orphenadrine and neobenodine
Sui, Yao-Zong,Zhang, Xi-Chang,Wu, Jun-Wen,Li, Shijun,Zhou, Ji-Ning,Li, Min,Fang, Wenjun,Chan, Albert S. C.,Wu, Jing
, p. 7486 - 7492 (2012/07/27)
With certain amounts of sodium tert-butoxide and tert-butanol as additives, catalytic amounts of an inexpensive and easy-to-handle copper source Cu(OAc)2·H2O, a commercially available and air-stable non-racemic dipyridylphosphine ligand, as well as the stoichiometric desirable hydride donor polymethylhydrosiloxane (PMHS), formed a versatile in situ catalyst system for the enantioselective reduction of a broad spectrum of prochiral diaryl and aryl heteroarylketones in air, in high yields and with good to excellent enantioselectivities (up to 96 %). In particular, the practical viability of this process was evinced by its successful applications in the asymmetric synthesis of optically enriched potent antihistaminic drugs orphenadrine and neobenodine. Copyright
