18772-11-7Relevant academic research and scientific papers
Synthesis and activity of benzimidazole-1,3-dioxide inhibitors of separase
Do, Ha T.,Zhang, Nenggang,Pati, Debananda,Gilbertson, Scott R.
, p. 4446 - 4450 (2016)
Due to the oncogenic activity of cohesin protease, separase in human cancer cells, modulation of separase enzymatic activity could constitute a new therapeutic strategy for targeting resistant, separase-overexpressing aneuploid tumors. Herein, we report the synthesis, structural information, and structure–activity relationship (SAR) of separase inhibitors based on modification of the lead molecule 2,2-dimethyl-5-nitro-2H-benzimidazole-1,3-dioxide, named Sepin-1, (1) identified from a high-throughput-screen. Replacement of –NO2at C5 with other functional groups reduce the inhibitory activity in separase enzymatic assay. Substitution of the two methyl groups with other alkyl chains at the C2 moderately improves the effects on the inhibitory activity of those compounds. Modifications on 2H-benzimidazole-1,3-dioxide or the skeleton have variable effect on inhibition of separase enzymatic activity. Density-functional theory (DFT) calculations suggest there may be a correlation between the charges on the oxide moieties on these compounds and their activity in inhibiting separase enzyme.
Straightforward one-pot synthesis of benzofuroxans from o-halonitrobenzenes in ionic liquids
Sheremetev, Aleksei B.,Aleksandrova, Nataliya S.,Ignat'Ev, Nikolai V.,Schulte, Michael
scheme or table, p. 95 - 97 (2012/07/03)
Treatment of o-halonitrobenzenes with sodium azide in a [empyrr][BF4]/Bu4NBr/H2O system gives benzofuroxans in high yields, with the recovery and reuse of the ionic liquid for at least ten times.
A new cyclization involving the diazonium and ortho-(tert-butyl)-NNO-azoxy groups - Synthesis of 1,2,3,4-benzotetrazine 1-oxides
Lipilin, Dmitry L.,Smirnov, Oleg Yu.,Churakov, Aleksandr M.,Strelenko, Yuri A.,Ioffe, Sema L.,Tartakovsky, Vladimir A.
, p. 3435 - 3446 (2007/10/03)
The synthesis of 1,2,3,4-benzotetrazine 1-oxides (BTOs) is described. Bromo-BTOs 4b-d were prepared by the intramolecular cyclization of diazonium salts bearing an ortho-(tert-butyl)-NNO-azoxy group. BTOs bearing electron-releasing substituents were obtained by nucleophilic displacements of bromine in 4b-d. The formation of the BTO cyclic system involves the intermediate 2-(tert-butyl)-1,2,3,4-benzotetrazinium 4-oxides, which arise from an N,N-[1,21-shift of the tert-butyl group. Decomposition of BTOs involves opening of the tetrazine ring to afford ortho-azidonitroso derivatives, followed by their cyclization with the evolution of the N2 molecule to give benzofurazans. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
New approach to the synthesis of benzo[e][1,2,3,4]tetrazine 1,3-dioxides
Frumkin,Churakov,Strelenko,Tartakovsky
, p. 482 - 486 (2007/10/03)
A new approach to the synthesis of benzo[e][1,2,3,4]tetrazine 1,3-dioxides involves the treatment of N-nitroanilines containing an ortho-(tert-butyl-NNO-azoxy) group with phosphoric anhydride or phosphorus pentachloride. The reaction is supposed to procee
Thermal Stability Studies on a Homologous Series of Nitroarenes
Oxley, Jimmie C.,Smith, James L.,Ye, Hong,McKenney, Robert L.,Bolduc, Paul R.
, p. 9593 - 9602 (2007/10/02)
The thermal stabilities of a number of nitroarenes were examined in solution and in condensed phase.In general, increasing the number of nitro groups decreased thermal stability.Changing the substituent on 1-X-2,4,6-trinitrobenzene from X = H to NH2 to CH3 to OH accelerated decomposition; this effect was attributed to increased ease of intramolecular proton transfer to an ortho nitro group, thus weakening the carbon-nitrogen bond.In solution, the effect of increasing substitution from n = 1 to n = 3 on Xn(NO2)3C6H3-n was uniformly that of decreasing the thermal stability of the species.However, in condensed phase, results suggested that crystal habit may be more important than molecular structure; for X = Br, CH3, and NH2, the more substituted species was the more stable.
