1159999-75-3Relevant academic research and scientific papers
1,3-Bis(ethyl-amino)-2-nitro-benzene, 1,3-bis-(n-octylamino)-2-nitro- benzene and 4-ethylamino-2-methyl-1H-benz-imid-azole
Walczak, Christopher P.,Yonkey, Matthew M.,Squattrito, Philip J.,Mohanty, Dillip K.,Kirschbaum, Kristin
, p. o248-o251 (2008)
1,3-Bis(ethyl-amino)-2-nitro-benzene, C10H15N3O2, (I), and 1,3-bis-(n-octylamino)-2-nitro-benzene, C22H39N3O2, (II), are the first structurally characterized 1,3-bis-(n-alkyl-amino)-2-nitro-benzenes. Both mol-ecules are bis-ected though the nitro N atom and the 2-C and 5-C atoms of the ring by twofold rotation axes. Both display intra-molecular N - H...O hydrogen bonds between the amine and nitro groups, but no inter-molecular hydrogen bonding. The nearly planar mol-ecules pack into flat layers ca 3.4 A apart that inter-act by hydro-phobic inter-actions involving the n-alkyl groups rather than by π-π inter-actions between the rings. The intra- and inter-molecular inter-actions in these mol-ecules are of inter-est in understanding the physical properties of polymers made from them. Upon heating in the presence of anhydrous potassium carbonate in dimethyl-acetamide, (I) and (II) cyclize with formal loss of hydrogen peroxide to form substituted benzimidazoles. Thus, 4-ethylamino-2-methyl-1H-benzimidazole, C10H13N3, (III), was obtained from (I) under these reaction conditions. Compound (III) contains two independent mol-ecules with no imposed inter-nal symmetry. The mol-ecules are linked into chains via N - H...N hydrogen bonds involving the imidazole rings, while the ethylamino groups do not participate in any hydrogen bonding. This is the first reported structure of a benzimidazole derivative with 4-amino and 2-alkyl substituents.
Secondary amines containing one aromatic nitro group: Preparation, nitrosation, sustained nitric oxide release, and the synergistic effects of released nitric oxide and an arginase inhibitor on vascular smooth muscle cell proliferation
Curtis, Brandon,Payne, Thomas J.,Ash, David E.,Mohanty, Dillip K.
, p. 1123 - 1135 (2013/03/14)
Atherosclerosis, a leading cause of death worldwide, is associated with the excessive proliferation of vascular smooth muscle cells. Nitrogen monoxide, more commonly known as nitric oxide, inhibits this uncontrolled proliferation. Herein we report the preparation of two families of nitric oxide donors; beginning with the syntheses of secondary amine precursors, obtained through the reaction between 2 equiv of various monoamines with 2,4 or 2,6- difluoronitrobenzene. The purified secondary amines were nitrosated then subjected to a Griess reagent test to examine the slow and sustained nitric oxide release rate for each compound in both the absence and presence of reduced glutathione. The release rate profiles of these two isomeric families of NO-donors were strongly dependent on the number of side chain methylene units and the relative orientations of the nitro groups with respect to the N-nitroso moieties. The nitrosated compounds were then added to human aortic smooth muscle cell cultures, individually and in tandem with S-2-amino-6-boronic acid (ABH), a potent arginase inhibitor. Cell viability studies indicated a lack of toxicity of the amine precursors, in addition to anti-proliferative effects exhibited by the nitrosated compounds, which were enhanced in the presence of ABH.
