782-08-1Relevant articles and documents
Capture of benzhydryl chloride ion pairs by cobalt nitrate
Diaz,Assamunt
, p. 797 - 800 (1974)
A case is presented where a transition metal salt, Co(NO3)2, intervenes in the solvolysis of benzhydryl chloride, after the rate determining ionization step. This is in contrast to the behavior of other salts which intervene early and promote the ionization reaction. This novel behavior of Co(NO3)2 permits for the first time the detection of two ion pair intermediates in the solvolysis of an alkyl chloride which generates an open carbonium ion.
Discovery, Optimization, and Characterization of Novel Chlorcyclizine Derivatives for the Treatment of Hepatitis C Virus Infection
He, Shanshan,Xiao, Jingbo,Dulcey, Andrés E.,Lin, Billy,Rolt, Adam,Hu, Zongyi,Hu, Xin,Wang, Amy Q.,Xu, Xin,Southall, Noel,Ferrer, Marc,Zheng, Wei,Liang, T. Jake,Marugan, Juan J.
, p. 841 - 853 (2016/02/23)
Recently, we reported that chlorcyclizine (CCZ, Rac-2), an over-the-counter antihistamine piperazine drug, possesses in vitro and in vivo activity against hepatitis C virus. Here, we describe structure-activity relationship (SAR) efforts that resulted in the optimization of novel chlorcyclizine derivatives as anti-HCV agents. Several compounds exhibited EC50 values below 10 nM against HCV infection, cytotoxicity selectivity indices above 2000, and showed improved in vivo pharmacokinetic properties. The optimized molecules can serve as lead preclinical candidates for the treatment of hepatitis C virus infection and as probes to study hepatitis C virus pathogenesis and host-virus interaction.
Phosphine functionalized polyphosphazenes: soluble and re-usable polymeric reagents for highly efficient halogenations under Appel conditions
K?nig, Michael,Linhardt, Anne,Brüggemann, Oliver,Teasdale, Ian
, p. 1575 - 1582 (2016/08/16)
In this paper we present the preparation and application of a novel soluble phosphine functionalized polyphosphazene (poly[3-(diphenylphosphino)propylamino]phosphazene) and investigate its application as a polymeric reagent. Upon chlorination of the pendant phosphine groups, the polymer was found to facilitate the rapid and efficient transformation of alcohols to the corresponding chlorides and bromides under Appel-type conditions. Reaction times followed by 31P NMR spectroscopy are shown to be rapid (several minutes) and the yields for the transformation of alcohols to the corresponding halides are in the range 80–99?%. The facile recovery of the oxidized polymeric agent by precipitation is also described, offering a significant advantage over notoriously difficult to remove small molecule phosphine oxide by-products. Furthermore the regeneration of the reactive phosphine chloride pendant groups is demonstrated, which could be efficiently re-used in a further chlorination reaction. Graphical abstract: [Figure not available: see fulltext.]