16292-88-9Relevant academic research and scientific papers
PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS
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Page/Page column 78, (2012/02/01)
Compounds of the formula I or II: wherein X, m, Ar, R1 and R2 are as defined herein. The subject compounds are useful for treatment of IRAK-mediated conditions.
Highly chemoselective nitration of aromatic amines using the Ph3P/Br2/AgNO3 system
Iranpoor, Nasser,Firouzabadi, Habib,Nowrouzi, Najmeh,Firouzabadi, Dena
, p. 6879 - 6881 (2007/10/03)
The use of PPh3/Br2/AgNO3 provides a new reagent system for the novel and highly chemoselective nitration of aromatic amines under mild reaction conditions.
A Combined Experimental and Theoretical Approach toward the Development of Optimized Luminescent Carbostyrils
Strohmeier, Gernot A.,Fabian, Walter M. F.,Uray, Georg
, p. 215 - 226 (2007/10/03)
The synthesis and photophysical data of new carbostyrils (quinoline-2(1H)-ones) with the longest hitherto observed absorption- and emission wavelengths are described. Introduction of 6-amino, 7-MeO, and 4-(CF3) substituents enabled us to rise the absorption and fluorescence maxima up to 414 and 557 nm, respectively. Supported by semi-empirical and ab initio calculations, the 6,7-(1,4-diazine)-fused carbostyril 23b displayed absorption maxima at up to 440 nm, with quantum yields of up to 0.9 and large Stokes shifts (> 100 nm), comparable to the best coumarin chromophores known. The new fluorophore is neither pH-sensitive between pH 6 and 10 nor susceptible to O2 quenching. At pH 3, the emitted light appears greenish-white, which arises from three different stages of protonation.
Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides
Makosza, Mieczyslaw,Bialecki, Maciej
, p. 4878 - 4888 (2007/10/03)
A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.
Amination of Nitroarenes with Sulfenamides via Vicarious Nucleophilic Substitution of Hydrogen
Makosza, Mieczyslaw,Bialecki, Maciej
, p. 4784 - 4785 (2007/10/02)
Nitroarenes react with sulfenamides RSNH2 in the presence of strong bases to give p- and o-nitroanilines.
Potential Antitumor Agents. 48. 3'-Dimethylamino Derivatives of Amsacrine: Redox Chemistry and in Vivo Tumor Activity
Atwell, Graham J.,Rewcastle, Gordon W.,Baguley, Bruce C.,Denny, William A.
, p. 652 - 658 (2007/10/02)
Structure-activity relationships for a series of acridine-substituted 3'-N(CH3)2 derivatives of the clinical antileukemic drug amsacrine (1) are reported.The parent (unsubstituted) compound 3 has activity against the Lewis lung solid tumor that is superior to amsacrine(1), the new clinical amsacrine analogue 4, and the recently developed 3'-NHCH3 derivative 2.Although the compounds generally bind less well to DNA and are less dose potent in vivo than either their amsacrine (3'-OCH3) or 3'-NHCH3 analogues, they show very high levels of antitumor activity, with the 4-OCH3 derivative capable of effecting 100percent cures of the Lewis lung solid tumor.The broad structure-activity relationships for acridine substitution more closely resemble those of the amsacrine than the 3'-NHCH3 series, with 4-substituted and 4,5-disubstituted compounds showing the highest activity.
Benzidine Rearrangements. 19. The Concerted Nature of the One-Proton Rearrangement of 2,2'-Dimethoxyhydrazobenzene
Shine, Henry J.,Park, Koon Ha,Brownawell, Marilyn L.,Filippo, Joseph San
, p. 7077 - 7082 (2007/10/02)
Kinetic isotope effects (KIE) in the acid-catalyzed, one-proton rearrangement of 2,2'-dimethoxyhydrazobenzene (1) into 3,3'-dimethoxybenzidine (2) have been measured.Nitrogen KIE were determined on the bis(trifluoroacetyl) derivative of 2 which was isolated from low and 100percent conversions of mixtures of 1 and 1 under kinetic conditions.The ratio of masses M(438)/M(436) as determined by whole-ion mass spectrometric techniques led to the result k(14N)/k(15N)=1.0289 (for two nitrogens).Similar measurements on the derivative of 2 isolated from conversions of mixtures of 1 and 1 led to the result k(12C)/k(13C)=1.0286 (for two carbons).These results show that the formation of 2 is a concerted process and, thus, that the acid-cytylyzed rearrangement of 1 is a 5,5-sigmatropic shift.Rearrangement via a ?-complex intermediate or a solvent-caged, radical/radical-ion pair is excluded.That bonding in the 4,4' positions of 1 is part of the rate-determining step in this rearrangement was confirmed by measurement of an inverse secondary deuterium KIE (kH/kD=0.929 for two deuteriums).This result was obtained from ratios of M(244)/M(242) which were measured on 2,2'-dimethoxyazobenzene (3), obtained by oxidizing the hydrazo substrate remaining after high conversions of mixtures of 1 and 1.
