21971-24-4Relevant academic research and scientific papers
Construction of 1,4-benzodiazepine skeleton from 2-(arylamino)benzamides through PhI(OAc)2-mediated oxidative C-N bond formation
Li, Xuming,Yang, Liu,Zhang, Xiang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
, p. 955 - 962 (2014/03/21)
New compounds involving the biologically important 1,4-benzodiazepine skeleton were conveniently constructed from 2-(arylamino)benzamides through PhI(OAc)2-mediated oxidative C-N bond formation. The attractive features of this new synthetic strategy include mild reaction conditions, the heavy-metal-free characteristic of the oxidative coupling process, and the flexibility to tolerate a broad scope of substrates.
Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N -phenyl-aminobenzoates and their structure-activity relationships
Adeniji, Adegoke O.,Twenter, Barry M.,Byrns, Michael C.,Jin, Yi,Chen, Mo,Winkler, Jeffrey D.,Penning, Trevor M.
supporting information; experimental part, p. 2311 - 2323 (2012/05/04)
Aldo-keto reductase 1C3 (AKR1C3; type 5 17β-hydroxysteroid dehydrogenase) is overexpressed in castration resistant prostate cancer (CRPC) and is implicated in the intratumoral biosynthesis of testosterone and 5α-dihydrotestosterone. Selective AKR1C3 inhibitors are required because compounds should not inhibit the highly related AKR1C1 and AKR1C2 isoforms which are involved in the inactivation of 5α-dihydrotestosterone. NSAIDs, N-phenylanthranilates in particular, are potent but nonselective AKR1C3 inhibitors. Using flufenamic acid, 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid, as lead compound, five classes of structural analogues were synthesized and evaluated for AKR1C3 inhibitory potency and selectivity. Structure-activity relationship (SAR) studies revealed that a meta-carboxylic acid group relative to the amine conferred pronounced AKR1C3 selectivity without loss of potency, while electron withdrawing groups on the phenylamino B-ring were optimal for AKR1C3 inhibition. Lead compounds did not inhibit COX-1 or COX-2 but blocked the AKR1C3 mediated production of testosterone in LNCaP-AKR1C3 cells. These compounds offer promising leads toward new therapeutics for CRPC.
An inexpensive and efficient copper catalyst for N-arylation of amines, amides and nitrogen-containing heterocycles
Guo, Xun,Rao, Honghua,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
, p. 2197 - 2202 (2007/10/03)
An inexpensive and efficient catalyst system has been developed for the N-arylation of nitrogen-containing compounds including a variety of amines, amides, indole and imidazole. This simple protocol uses CuI as the catalyst, commercial available pipecolinic acid as the new ligand, K2CO 3 as the base and DMF as the solvent.
Scope and Limitations of the Pd/BINAP-Catalyzed Amination of Aryl Bromides
Wolfe, John P.,Buchwald, Stephen L.
, p. 1144 - 1157 (2007/10/03)
Mixtures of Pd2(dba)3 or Pd(OAc)2 and BINAP catalyze the cross-coupling of amines with a variety of aryl bromides. Primary amines are arylated in high yield, and certain classes of secondary amines are also effectively transformed. The process tolerates the presence of several functional groups including methyl and ethyl esters, enolizable ketones, and nitro groups provided that cesium carbonate is employed as the base. Most reactions proceed to completion with 0.5-1.0 mol % of the palladium catalyst; in some cases, catalyst levels as low as 0.05 mol % Pd may be employed. Reactions are considerably faster if Pd(OAc)2 is employed as the precatalyst, and the order in which reagents are added to the reaction has a substantial effect on reaction rate. It is likely that the catalytic process proceeds via bis(phosphine)palladium complexes as intermediates. These complexes are less prone to undergo undesirable side reactions which lead to diminished yields or catalyst deactivation than complexes of the corresponding monodentate triarylphosphines.
An improved method for the palladium-catalyzed amination of aryl triflates
Ahman, Jens,Buchwald, Stephen L.
, p. 6363 - 6366 (2007/10/03)
Aryl triflates are coupled with amines using catalytic amounts of Pd(OAc)2 and BINAP and Cs2CO3 as a stoichiometric base. This protocol allows for the efficient amination of electron-poor as well as electron-rich aryl triflates and the reaction conditions are compatible with a wide variety of functional groups.
Improved functional group C compatibility in the palladium-catalyzed amination of aryl bromides
Wolfe, John P.,Buchwald, Stephen L.
, p. 6359 - 6362 (2007/10/03)
Aryl bromides are coupled with amines in the presence of a palladium catalyst and a stoichiometric amount of cesium carbonate. Using these conditions base-sensitive functional groups, which were incompatible with our previously reported catalytic-amination reaction conditions, are well tolerated.
