1-Methyl-2-methylsulfanyl-6-nitro-1<i>H</i>-benzimidazole

Ghozlani, Mohamed El; Rakib, El Mostapha; Medaghri-Alaoui, A.; Saadi, Mohamed; Ammari, Lahcen El

doi:10.1107/s1600536814004723

Cited by 3 publications

(3 citation statements)

References 10 publications

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“…However, the more thermodynamically stable form (orthorhombic, Pna2 1 ) exhibits C-HÁ Á Á interactions with an HÁ Á Ábenzene-centroid distance of 2.64 Å (Dik-Edixhoven et al, 1973;Escande & Galigné, 1974;Stibrany et al, 2001), whereas the form (orthorhombic, Pccn) exhibitsstacking with an interplanar distance of 3.418 (8) Å (Krawczyk & Gdaniec, 2005). An examination of the reported solid-state structures of 2-substituted and 1,2disubstituted benzimidazoles reveals that both C-HÁ Á Á and aromatic interactions are common (for example, see: Geiger & Isaac, 2014;El Ghozlani et al, 2014;Yeong et al, 2013;Fathima et al, 2013;.…”

Section: Introductionmentioning

confidence: 99%

Structure determination of three furan-substituted benzimidazoles and calculation of π–π and C—H...π interaction energies

Geiger

Deck

2014

Acta Crystallogr C

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The synthesis and structural characterization of 2-(furan-2-yl)-1-(furan-2-ylmethyl)-1H-benzimidazole [C16H12N2O2, (I)], 2-(furan-2-yl)-1-(furan-2-ylmethyl)-1H-benzimidazol-3-ium chloride monohydrate [C16H13N2O2(+)·Cl(-)·H2O, (II)] and the hydrobromide salt 5,6-dimethyl-2-(furan-2-yl)-1-(furan-2-ylmethyl)-1H-benzimidazol-3-ium bromide [C18H17N2O2(+)·Br(-), (III)] are described. Benzimidazole (I) displays two sets of aromatic interactions, each of which involves pairs of molecules in a head-to-tail arrangement. The first, denoted set (Ia), exhibits both intermolecular C-H···π interactions between the 2-(furan-2-yl) (abbreviated as Fn) and 1-(furan-2-ylmethyl) (abbreviated as MeFn) substituents, and π-π interactions involving the Fn substituents between inversion-center-related molecules. The second, denoted set (Ib), involves π-π interactions involving both the benzene ring (Bz) and the imidazole ring (Im) of benzimidazole. Hydrated salt (II) exhibits N-H···OH2···Cl hydrogen bonding that results in chains of molecules parallel to the a axis. There is also a head-to-head aromatic stacking of the protonated benzimidazole cations in which the Bz and Im rings of one molecule interact with the Im and Fn rings of adjacent molecules in the chain. Salt (III) displays N-H···Br hydrogen bonding and π-π interactions involving inversion-center-related benzimidazole rings in a head-to-tail arrangement. In all of the π-π interactions observed, the interacting moieties are shifted with respect to each other along the major molecular axis. Basis set superposition energy-corrected (counterpoise method) interaction energies were calculated for each interaction [DFT, M06-2X/6-31+G(d)] employing atomic coordinates obtained in the crystallographic analyses for heavy atoms and optimized H-atom coordinates. The calculated interaction energies are -43.0, -39.8, -48.5, and -55.0 kJ mol(-1) for (Ia), (Ib), (II), and (III), respectively. For (Ia), the analysis was used to partition the interaction energies into the C-H···π and π-π components, which are 9.4 and 24.1 kJ mol(-1), respectively. Energy-minimized structures were used to determine the optimal interplanar spacing, the slip distance along the major molecular axis, and the slip distance along the minor molecular axis for 2-(furan-2-yl)-1H-benzimidazole.

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Section: Introductionmentioning

confidence: 99%

Structure determination of three furan-substituted benzimidazoles and calculation of π–π and C—H...π interaction energies

Geiger

Deck

2014

Acta Crystallogr C

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“…For the Im ring, the closest approach is H16AÁ Á ÁC7 ii = 2.99 Å [C16Á Á ÁC7 ii = 3.839 (2) Å and C16-H16AÁ Á ÁC7 ii = 144 ], with a 2.93 Å H16A-to-ring plane distance. Contrary to expectations, there are no significantinteractions, as have been found in other benzimidazole derivatives Geiger, Geiger & Deck, 2014;Krawczyk & Gdaniec, 2005;Geiger & Isaac, 2014;El Ghozlani et al, 2014;Yeong et al, 2013;Fathima et al, 2013;Krishnamurthy et al, 2013;Yeong et al, 2013). The closest CgÁ Á ÁCg distance is Cg(Ph)Á Á ÁCg(Bz) ii of 5.0499 (14) Å .…”

Section: Figurementioning

confidence: 55%

Synthesis and characterization of a novel long-alkyl-chain ester-substituted benzimidazole gelator and its octan-1-ol solvate

et al. 2017

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The synthesis of a novel benzimidazole derivative with a long-chain-ester substituent, namely methyl 8-[4-(1H-benzimidazol-2-yl)phenoxy]octanoate, (3), is reported. Ester (3) shows evidence of aggregation in solution and weak gelation ability with toluene. The octan-1-ol solvate, methyl 8-[4-(1H-benzimidazol-2-yl)phenoxy]octanoate octan-1-ol monosolvate, CHNO·CHO, (4), exhibits a four-molecule hydrogen-bonded motif in the solid state, with N-H...O hydrogen bonds between benzimidazole molecules and O-H...N hydrogen bonds between the octan-1-ol solvent molecules and the benzimidazole unit. The alkyl chains of the ester and the octan-1-ol molecules are in unfolded conformations. The phenylene ring is canted by 10.27 (6)° from the plane of the benzimidazole ring system. H...C contacts make up 20.7% of the Hirshfeld surface coverage. Weak C-H...π interactions involving the benzimidazole alkyl chain and three aromatic rings are observed.

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“…Benzimidazole, as the one of the earliest nitrogen‐containing heterocyclic compounds ever found, has a flat ring system in which benzene rings are thickly combined on the 4, 5th position of the imidazole ring (Alzhrani et al, 2021). This special aromatic system makes it easy to form hydrogen bonds with receptors and enzymes in organisms, electrostatic action with metal ions and π–π interactions with other aromatic groups (El Ghozlani et al, 2014; Sahay & Ghalsasi, 2019). In this paper, recent progress of the anti‐tumor agents which contains benzimidazole with different mechanisms of actions were introduced.…”

Section: Introductionmentioning

confidence: 99%

Recent progress of research on anti‐tumor agents using benzimidazole as the structure unit

Peng

Chen

et al. 2022

Chem Biol Drug Des

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With the development of exploration for disease‐related proteins or receptors, more and more novel structural lead compounds are required to designed and synthesized. The benzimidazole is an effective structural unit in which the benzene ring is fused at the 4 and 5 positions of the imidazole ring and wildly used in drug design. Here, we introduce some recent progress of research for anti‐tumor agents which was target to various target proteins such as DNA topoisomerase, angiogenesis, serine/threonine protein kinase, and tyrosine protein kinase. These anti‐tumor agents are all introduced benzimidazole as the structure unit. Further docking study showed that the benzimidazole group was not only act as a skeleton to expand the structure of molecule but also as an excellent ligand unit to form hydrogen bond or π–π conjugation and hydrophobic interaction with target proteins or receptors. We expect that introducing benzimidazole in the chemical structure could be a reasonable and priority strategy in novel anti‐tumor agents' design.

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1-Methyl-2-methylsulfanyl-6-nitro-1H-benzimidazole

Cited by 3 publications

References 10 publications

Structure determination of three furan-substituted benzimidazoles and calculation of π–π and C—H...π interaction energies

Structure determination of three furan-substituted benzimidazoles and calculation of π–π and C—H...π interaction energies

Synthesis and characterization of a novel long-alkyl-chain ester-substituted benzimidazole gelator and its octan-1-ol solvate

Recent progress of research on anti‐tumor agents using benzimidazole as the structure unit

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