42856-45-1Relevant academic research and scientific papers
Reaction between glutaric anhydride and N-benzylidenebenzylamine, and further transformations to new substituted piperidin-2-ones
Burdzhiev, Nikola T.,Stanoeva, Elena R.
, p. 8318 - 8326 (2006)
The reaction between glutaric anhydride (1) and N-benzylidenebenzylamine (3) was studied in detail by 1H NMR spectroscopy under different reaction conditions. The major product was (±)-trans-1-benzyl-6-oxo-2-phenylpiperidine-3-carboxylic acid (
Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: Application to the synthesis of vernakalant
Garad, Dnyaneshwar N.,Tanpure, Subhash D.,Mhaske, Santosh B.
supporting information, p. 1008 - 1016 (2015/08/18)
Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.
High affinity ligands and potent antagonists for the α1D- adrenergic receptor. Novel 3,8-disubstituted [1]benzothieno[3,2-d]pyrimidine derivatives
Romeo, Giuseppe,Salerno, Loredana,Pittalà, Valeria,Modica, Maria N.,Siracusa, Maria A.,Materia, Luisa,Buccioni, Michela,Marucci, Gabriella,Minneman, Kenneth P.
, p. 419 - 432 (2014/07/21)
A new series of high affinity ligands and antagonists for the α1D-adrenergic receptor (AR) has been discovered. New molecules present a [1]benzothieno[3,2-d]pyrimidin-2,4(1H,3H)-dione or a [1]benzothieno[3,2-d]pyrimidin-4(3H)-one scaffold and bear a 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl moiety in the 3-position and various amide substituents in the 8-position. In binding assays at the three human cloned α1A-, α1B-, and α1D-AR subtypes, they showed high affinity values, particularly for the α1D-AR subtype. Compound 22 (RX18), N1-methyl-N 5-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3, 4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N1-(phenylmethyl) pentanediamide, was the most interesting in the series displaying very high affinity (pKi = 10.25) and potent antagonism (pKb = 9.15) when tested in a functional assay at the α1D-AR.
Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin- 1(2H)-yl)methylidene]piperidine-2,6-dione
Bisset, Alexander A.,Shiibashi, Akira,Desmond, Jasmine L.,Dishington, Allan,Jones, Teyrnon,Clarkson, Guy J.,Ikariya, Takao,Wills, Martin
supporting information, p. 11978 - 11980 (2013/01/16)
The synthesis of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene] piperidine-2,6-dione 4 from N-benzylglutarimide was achieved in three steps. The asymmetric hydrogenation of 4 gave either the product of partial reduction (10) or full reduction (13), depending on the catalyst which was employed, in high ee in each case. Attempts at asymmetric transfer hydrogenation (ATH) of 4 resulted in formation of a racemic product. The Royal Society of Chemistry.
Chemoselective hydrogenation of imides catalyzed by Cp*Ru(PN) complexes and its application to the asymmetric synthesis of paroxetine
Ito, Masato,Sakaguchi, Ayaka,Kobayashi, Chika,Ikariya, Takao
, p. 290 - 291 (2008/04/18)
This work represents the first catalytic hydrogenation of imides into amides and primary alcohols, in which the unique chemoselectivity is originated from the bifunctional nature of ruthenium-NH moiety in the catalyst. Copyright
Rational Design of an Indolebutanoic Acid Derivative as a Novel Aldose Reductase Inhibitor Based on Docking and 3D QSAR Studies of Phenethylamine Derivatives
Sun, Won Suck,Park, Yoon Sun,Yoo, Jakyung,Park, Ki Duk,Kim, Sung Han,Kim, Jung-Han,Park, Hyun-Ju
, p. 5619 - 5627 (2007/10/03)
A series of 45 phenethylamine derivatives were synthesized and evaluated for their inhibitory activity against pig kidney aldose reductase (ALR2, EC 1.1.1.21). Their IC50 values ranged from 400 μM to 24 μM. The binding modes of compounds at the active site of ALR2 were examined using flexible docking. The results indicated that phenethylamine derivatives nicely fit into the active pocket of ALR2 by forming various hydrogen bonding and hydrophobic interactions. 3D-QSAR analysis was also conducted using FlexX-docked alignment of the compounds. The best prediction was obtained by CoMSIA combined with hydrophobic and hydrogen bond donor/acceptor field (q 2 = 0.557, r2 = 0.934). A new derivative, 4-oxo-4-(4-hydroxyindole)butanoic acid, was designed, taking into account the CoMSIA field and the binding mode derived by FlexX docking. This rationally designed compound exhibits an ALR2 inhibition with an IC50 value of 7.4 μM, which compares favorably to that of a well-known ALR2 inhibitor, tolrestat (IC50 = 16 μM) and represents a potency approximately 240-fold higher than that of an original phenethylamine lead compound, YUA001.
Inhibition of the HER2 tyrosine kinase and characterization of a hydrophobic site near the nucleotide binding domain
Maddry, Joseph A.,Kussner, Conrad,Truss, Jackie W.,Niwas, Shri,White, E. Lucile,Kwong, Cecil D.
, p. 2109 - 2114 (2007/10/03)
A series of compounds was prepared to investigate the hydrophobic character of the HER2 receptor tyrosine kinase active site, These bisubstrate analogs contained hydrophobic moieties in place of the polar triphosphate and nucleoside fragments of the natural ATP ligand. Despite these modifications, good affinity was observed as measured by inhibition of receptor autophosphorylation.
Specificity of DNA alkylation by 1-(2-chloroethyl)-3-alkyl-3- acyltriazenes depends on the structure of the acyl group: Kinetic and product studies
Smith,Schmidt,Czerwinski,Taneyhill,Snyder,Kline,Michejda,Smith Jr.
, p. 466 - 475 (2007/10/03)
The reactions of calf thymus DNA with ten 1-(2-chloroethyl)-3-alkyl-3- acyltriazenes of varying acyl side chain structure were studied alone, or in the presence of porcine liver esterase in pH 7.0 phosphate buffer. In several of the key triazenes, the acyl substituent contained a free carboxylic acid group. With esterase present in the reaction mixture, the resultant levels of DNA alkylation could be correlated with the kinetic rates of decomposition of the triazenes. Under these conditions, the predominant pathway of decomposition involved deacylation of the parent triazene and eventual production of an alkanediazonium ion. This intermediate subsequently alkylated DNA-guanine to give 7-alkylguanine as the principal reaction product. In the absence of esterase, the order of DNA alkylation for all of the acyltriazenes did not correlate with their respective rates of decomposition, leading to the conclusion that the triazenes did not decompose by the expected mode of uncatalyzed N(2)-N(3) heterolyic cleavage. The major DNA alkylation product from the N(3)-methyltriazenes was 7-methylguanine, instead of the expected 7-(chloroethyl)- and 7-(hydroxyethyl)guanine products, which suggested that the acyl group was being hydrolyzed. However, acyltriazenes with an N(3)-benzyl group rather than a methyl in this position produced very little 7-benzylguanine product, contrary to prediction. An alternative mechanism involving internally assisted hydrolysis of the side chain ester is proposed to explain these results. NMR product analysis and computational studies were carried out to lend support to the postulated mechanism.
