- Synthesis of novel chiral TBBt derivatives with hydroxyl moiety. Studies on inhibition of human protein kinase CK2α and cytotoxicity properties
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The efficient method for the synthesis of novel 4,5,6,7-tetrabromo-1H- benzotriazole (TBBt) derivatives bearing a single stereogenic center has been developed. New compounds with a variety of substituents at the meta- and para-position of the phenyl ring are reported. All of the presented compounds were obtained using classical synthetic methods, such as bromination of benzotriazole, and its subsequent alkylation by monotosylated arylpropane-1,3-diols, which in turn have been synthesized through reduction of the corresponding prochiral β-keto esters, and the selective monotosylation of the primary hydroxyl group. The influence of the new and previously reported N-hydroxyalkyl TBBt derivatives on the activity of human protein kinase CK2α catalytic subunit was examined. The most active were derivatives with N-hydroxyalkyl substituents (IC50 in 0.80-7.35 μM range). A binding mode of (R)-1-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)butan-3-ol 7b to hCK2α has been proposed based on in silico docking studies. Additionally, MTT-based cytotoxicity tests demonstrated high activities of novel 1-aryl-3-TBBt-propan-1-ol and 3-TBBt-propan-1,2-diol derivatives against human peripheral blood T lymphoblast (CCRF-CEM), and moderate anti-tumor activities against human breast adenocarcinoma (MCF7) cell lines.
- Borowiecki, Pawe?,Wawro, Adam M.,Wińska, Patrycja,Wielechowska, Monika,Bretner, Maria
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supporting information
p. 364 - 374
(2014/08/05)
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- Nickel-catalyzed reductive cyclization of organohalides
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A mild and convenient nickel-catalyzed method for free-radical cyclization of organohalides is described. The use of a NiCl2DME/Pybox complex as the catalyst and zinc powder in methanol efficiently promotes the reductive cyclization of various
- Kim, Hyejin,Lee, Chulbom
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supporting information; experimental part
p. 2050 - 2053
(2011/06/25)
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- Tandem alkylation - Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,6-tetrasubstituted tetrahydropyrans
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A stereoselective method for the synthesis of substituted tetrahydropyran derivatives employing a tandem SN2-Michael addition sequence to vinylogous carbonates is developed. The method is extended to the synthesis of bicyclic ether motifs present in polyether ladder toxins.
- Gharpure, Santosh J.,Reddy, S. Raja Bhushan
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supporting information; scheme or table
p. 2519 - 2522
(2009/10/18)
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- Selective nosylation of 1-phenylpropane-1,3-diol and perchloric acid mediated Friedel-Crafts alkylation: Key steps for the new and straightforward synthesis of tolterodine
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We have developed a new and straightforward synthesis of racemic tolterodine [N,N-diisopropyl-3-(2-hydroxy-5-methyl-phenyl)-3-phenylpropanamine]. The synthesis involves selective nosylation on the primary alcohol of 1-phenylpropane-1,3-diol using 4-nitrob
- De Castro, Kathlia A.,Rhee, Hakjune
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experimental part
p. 1841 - 1844
(2009/04/04)
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- Pd-catalyzed kinetic resolution of benzylic alcohols: A practical synthesis of (R)-tomoxetine and (S)-fluoxetine hydrochlorides
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A convenient synthetic route to (R)-tomoxetine hydrochloride (90% ee) and (S)-fluoxetine hydrochloride (84% ee) is described. (S)-3-Phenyl-3-hydroxypropyl p-toluenesulphonate, the key intermediate, is obtained by the oxidative kinetic resolution of the corresponding racemic 3-phenyl-3-hydroxypropyl p-toluenesulphonate using (-)-sparteine/Pd(II)/O2 (1 atm) catalytic system.
- Ali, Iliyas Sayyed,Sudalai, Arumugam
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p. 5435 - 5436
(2007/10/03)
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- Dibutyltin oxide catalyzed selective sulfonylation of α-chelatable primary alcohols
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(equation presented) The reaction of substituted glycols with catalytic dibutyltin oxide, stoichiometric p-toluenesulfonyl chloride, and triethylamine in CH2Cl2 resulted in the complete and rapid sulfonylation at the primary alcohol. The α-heterosubstituted primary alcohol moiety appeared optimal for best results, supporting the intermediacy of a five-membered chelate. The role of the amine is discussed, in addition to catalyst requirements and solvent effects.
- Martinelli, Michael J.,Nayyar, Naresh K.,Moher, Eric D.,Dhokte, Ulhas P.,Pawlak, Joseph M.,Vaidyanathan, Rajappa
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p. 447 - 450
(2008/02/11)
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