Zur direkten Nitrierung des Benzimidazolons und der Reduktion einiger dieser Nitrierungsprodukte

Schindlbauer, H.; Kwiecinski, Wlodzimierz

doi:10.1007/bf01153908

Cited by 11 publications

(2 citation statements)

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“…2,4,6-Trinitrophenyl-N-methyl-nitramine (tetryl) was obtained following the method [21]. The N-containing heterocyclic nitrocompounds 3,6-dinitro-9H-carbazole (DNC), 1,3,6,8-tetranitro-9H-carbazole (TNC), 4,5,6-trinitrobenzimidazol-2-one (TriNBO) and 4,5,6,7-tetranitrobenzimidazol-2-one (TNBO) were synthesized according to methods [22][23][24][25], 3-nitro-1,2,4-triazole and 4(5)-nitroimidazole compounds were obtained as described in [26][27]. Their purities and structures were verified by means of the melting points, and TLC, NMR and IR analysis.…”

Section: Methodsmentioning

confidence: 99%

The QSAR study for antibacterial activity of structurally diverse nitroaromatics

Šarlauskas¹,

Polmickaitė-Smirnova²,

Čėnas³

et al. 2019

chemija

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The antibacterial activity of a series of structurally diverse nitroaromatic compounds (NACs) (nitrobenzene and nitroheterocyclic derivatives) was estimated in terms of the minimum inhibitory concentrations (MICs) against Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli bacteria strains in vitro. The resultant log of 1/MICs (pMICs) was subjected to a quantitative structure–activity relationship analysis (QSAR) using a set of molecular descriptors of the compounds assessed by means of quantum mechanical computation and other methods. The estimated pMIC values of NACs tentatively increased with an increase in their electrophilic potency (in terms of LUMO energy) along with the LUMO–HOMO energy gap (or chemical hardness) towards both bacteria strains. No reliable contribution of lipophilicity (octanol/water log P) of nitroaromatics was found to both bacteria strains. The activity of NACs towards S. aureus increased with an increase in their molecular weight and van der Waals volume, and it also tended to increase with an increase in their polar surface area (PSA) and in the number of hydrogen bond-acceptors (HBAs), whereas using these descriptors against E. coli strain, no satisfactory correlations were obtained. The activity of NACs towards both bacteria strains showed a parabolic type dependence upon the highest positive values of molecular electrostatic potentials (VS, max) that might partially be associated with the non-specific interaction of nitroaromatics with the surfaces of the negatively charged envelopes of bacteria at the initial stage of NACs’ action.

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Section: Methodsmentioning

confidence: 99%

The QSAR study for antibacterial activity of structurally diverse nitroaromatics

Šarlauskas¹,

Polmickaitė-Smirnova²,

Čėnas³

et al. 2019

chemija

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“…The components were quantitated by the internal normalization technique using calibration factors. 5,6-Dinitro-2,3-dihydro-1H-benzimidazol-2-one (VI) and 4,5,6-trinitro-2,3-dihydro-1H-benzimidazol-2-one (V) were synthesized according to the procedures described in [1,18]. 1,4,5,6-Tetranitro-2,3-dihydro-1H-benzimidazol-2-one (I).…”

Section: Methodsmentioning

confidence: 99%

Nitro derivatives of 1,3-dihydrobenzimidazol-2-one: II. Rearrangement of N-nitrobenzimidazol-2-ones

et al. 2009

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N-Nitrobenzimidazol-2-ones readily undergo rearrangement to C-nitro derivatives on heating in various solvents (ethyl acetate, butyl acetate, acetonitrile, acetone, dioxane, o-dichlorobenzene, anisole, acetic acid). This rearrangement was used to develop a procedure for the synthesis of 4,5,6,7-tetranitro-1,3-dihydrobenzimidazol-2-one in high yield (90-96%) by nitration of 1,3-dihydrobenzimidazol-2-one, as well as of 5,6-dinitro-and 4,5,6-trinitro-1,3-dihydrobenzimidazol-2-ones, with a small excess of concentrated nitric acid in a mixture with acetic anhydride and acetic acid at 50-60°C.* For communication I, see [1].

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Dihydrobenzimidazoles, Benzimidazolones, Benzimidazolethiones, and Related Compounds

Smith¹

1981

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Zur direkten Nitrierung des Benzimidazolons und der Reduktion einiger dieser Nitrierungsprodukte

Cited by 11 publications

References 0 publications

The QSAR study for antibacterial activity of structurally diverse nitroaromatics

The QSAR study for antibacterial activity of structurally diverse nitroaromatics

Nitro derivatives of 1,3-dihydrobenzimidazol-2-one: II. Rearrangement of N-nitrobenzimidazol-2-ones

Dihydrobenzimidazoles, Benzimidazolones, Benzimidazolethiones, and Related Compounds

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