- PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS
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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.
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Page/Page column 78
(2012/02/01)
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- Highly chemoselective nitration of aromatic amines using the Ph3P/Br2/AgNO3 system
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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.
- Iranpoor, Nasser,Firouzabadi, Habib,Nowrouzi, Najmeh,Firouzabadi, Dena
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p. 6879 - 6881
(2007/10/03)
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- A Combined Experimental and Theoretical Approach toward the Development of Optimized Luminescent Carbostyrils
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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.
- Strohmeier, Gernot A.,Fabian, Walter M. F.,Uray, Georg
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p. 215 - 226
(2007/10/03)
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- Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides
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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.
- Makosza, Mieczyslaw,Bialecki, Maciej
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p. 4878 - 4888
(2007/10/03)
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- Amination of Nitroarenes with Sulfenamides via Vicarious Nucleophilic Substitution of Hydrogen
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Nitroarenes react with sulfenamides RSNH2 in the presence of strong bases to give p- and o-nitroanilines.
- Makosza, Mieczyslaw,Bialecki, Maciej
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p. 4784 - 4785
(2007/10/02)
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- Potential Antitumor Agents. 48. 3'-Dimethylamino Derivatives of Amsacrine: Redox Chemistry and in Vivo Tumor Activity
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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.
- Atwell, Graham J.,Rewcastle, Gordon W.,Baguley, Bruce C.,Denny, William A.
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p. 652 - 658
(2007/10/02)
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- Benzidine Rearrangements. 19. The Concerted Nature of the One-Proton Rearrangement of 2,2'-Dimethoxyhydrazobenzene
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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.
- Shine, Henry J.,Park, Koon Ha,Brownawell, Marilyn L.,Filippo, Joseph San
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p. 7077 - 7082
(2007/10/02)
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