- Iodine-mediated aryl transfer reaction from arylhydrazine hydrochlorides to nitriles
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An iodine-promoted, metal-, base-, and solvent-free cross-coupling reaction was developed for the synthesis of various useful secondary amides via an aryl N-addition reaction of aryl groups to cyano groups. This aryl transfer reaction proceeds with arylhydrazine hydrochlorides serving as the aryl donors. A labelling experiment shows that the N atom in the product comes from the cyano group of the nitriles, which are low in cost. A plausible radical-driven mechanism is also proposed.
- Zhang, Zhiguo,Li, Xiang,Li, Yinghua,Guo, Yan,Zhao, Xunan,Yan, Yan,Sun, Kai,Zhang, Guisheng
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supporting information
p. 3628 - 3635
(2019/05/29)
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- Hypervalent Iodine(III)-Promoted Phenyl Transfer Reaction from Phenyl Hydrazides to Nitriles
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A useful transformation of nitriles to N-phenyl amides has been achieved through a novel intermolecular phenyl transfer reaction from phenyl hydrazides and N-addition to nitriles in the presence of PIFA under mild and solvent-free conditions. This cross-coupling reaction includes the oxidative cleavage of sp2 C-N bonds of phenyl hydrazides to form a phenyl radical and the subsequent N-addition to cyanos to form new sp2 C-N bonds and provides efficient access to various N-phenyl amides in moderate to good yields under mild reaction conditions.
- Yan, Yan,Zhang, Zhiguo,Wan, Yameng,Zhang, Guisheng,Ma, Nana,Liu, Qingfeng
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supporting information
p. 7957 - 7963
(2017/08/14)
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- Structure-Based Design and Biological Characterization of Selective Histone Deacetylase 8 (HDAC8) Inhibitors with Anti-Neuroblastoma Activity
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Histone deacetylases (HDACs) are important modulators of epigenetic gene regulation and additionally control the activity of non-histone protein substrates. While for HDACs 1-3 and 6 many potent selective inhibitors have been obtained, for other subtypes much less is known on selective inhibitors and the consequences of their inhibition. The present report describes the development of substituted benzhydroxamic acids as potent and selective HDAC8 inhibitors. Docking studies using available crystal structures have been used for structure-based optimization of this series of compounds. Within this study, we have investigated the role of HDAC8 in the proliferation of cancer cells and optimized hits for potency and selectivity, both in vitro and in cell culture. The combination of structure-based design, synthesis, and in vitro screening to cellular testing resulted in potent and selective HDAC8 inhibitors that showed anti-neuroblastoma activity in cellular testing.
- Heimburg, Tino,Kolbinger, Fiona R.,Zeyen, Patrik,Ghazy, Ehab,Herp, Daniel,Schmidtkunz, Karin,Melesina, Jelena,Shaik, Tajith Baba,Erdmann, Frank,Schmidt, Matthias,Romier, Christophe,Robaa, Dina,Witt, Olaf,Oehme, Ina,Jung, Manfred,Sippl, Wolfgang
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p. 10188 - 10204
(2018/01/10)
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- Discovery of the first histone deacetylase 6/8 dual inhibitors
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We disclose the first small molecule histone deacetylase (HDAC) inhibitor (3, BRD73954) capable of potently and selectively inhibiting both HDAC6 and HDAC8 despite the fact that these isoforms belong to distinct phylogenetic classes within the HDAC family of enzymes. Our data demonstrate that meta substituents of phenyl hydroxamic acids are readily accommodated upon binding to HDAC6 and, furthermore, are necessary for the potent inhibition of HDAC8.
- Olson, David E.,Wagner, Florence F.,Kaya, Taner,Gale, Jennifer P.,Aidoud, Nadia,Davoine, Emeline L.,Lazzaro, Fanny,We?wer, Michel,Zhang, Yan-Ling,Holson, Edward B.
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p. 4816 - 4820
(2013/07/19)
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- Variable Regioselectivity in Reactions of N-Lithio-N-vinylaniline with Arenedicarboxylates and α,β-Unsaturated Esters
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Regioselectivity patterns for the reactions of N-lithio-N-vinylaniline with several arenedicarboxylates and esters of α,β-unsaturated esters are reported.N-Lithio-N-vinylaniline reacted at both of its ambient anionic sites, to give β-enamino ketones and amide derivatives.A bridgehead compound resulting from cycloaddition involving N-lithio-N-vinylaniline was also formed in the reactions with ethyl cinnamate and ethyl phenylpropiolate.The structures of all compounds formed were fully characterized by NMR techniques.
- Katrizky, Alan R.,Oniciu, Daniela C.,Mancheno, Balbino,Barcolk, Richard A.
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p. 113 - 119
(2007/10/02)
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- KINETICS OF ACYLATION OF ANILINE BY AROYL CHLORIDES IN N,N-DIMETHYLACETAMIDE
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The rate constants and activation energies were determined for the acylation of aniline by ring-monosubstituted benzoyl chlorides in N,N-dimethylacetamide at 0-25 deg C.The isoparametric relationships between the effect of the substituent and the temperature were established by means of a crossed correlation.
- Kuz'min, N. I.,Zhizdyuk, B. I.
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p. 121 - 123
(2007/10/02)
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