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Chemical Compound Review:

PubChem9020 1H-benzoimidazol-2-amine

Synonyms: SureCN9098, zlchem 194, AGN-PC-0D1DA2, CHEMBL305513, SureCN444778, ...

Mor, M. et al., Sandahl, M. et al., Backlund, M. et al., Stratford, R.E. et al., Jing-Liang, X. et al., et al.

Mor, Bordi, Silva, Rivara, Zuliani, Vacondio, Rivara, Barocelli, Bertoni, Ballabeni, Magnanini, Impicciatore, Plazzi, Stratford, Clay, Heinz, Kuhfeld, Osborne, Phillips, Sweetana, Tebbe, Vasudevan, Zornes, Lindstrom, de Dios, Shih, López de Uralde, Sánchez, del Prado, Martín Cabrejas, Pleite, Blanco-Urgoiti, Lorite, Nevill, Bonjouklian, York, Vieth, Wang, Magnus, Campbell, Anderson, McCann, Giera, Lee, Schultz, Li, Johnson, Wolos, Backlund, Weidolf, Ingelman-Sundberg,

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Disease relevance of NSC7628

Previous studies in rats and humans demonstrated poor oral bioavailability of potent in vitro 2-aminobenzimidazole inhibitors of rhinovirus replication due to significant first-pass elimination and possibly also to poor aqueous solubility [1].

High impact information on NSC7628

Design of potent and selective 2-aminobenzimidazole-based p38alpha MAP kinase inhibitors with excellent in vivo efficacy [2].
Structure-activity relationship analysis indicated the importance in its structure of a substituted 2-aminobenzimidazole [3].
On-line supported liquid membrane (SLM) extraction and microporous membrane liquid-liquid extraction (MMLLE) techniques for sample preparation of natural water samples have been developed for the determination of thiophanate-methyl (TM), carbendazim (MBC) and 2-aminobenzimidazole (2-AB) using reversed-phase HPLC [4].
In addition, hydroxyomeprazole, 2-aminobenzimidazole and 2-mercapto-5-nitro-benzimidazole caused a notable increase in CYP1A1 protein expression, whereas 5-O-desmethylomeprazole, 2-hydroxybenzimidazole, 2-benzimidazole propionic acid and 5-benzimidazole carboxylic acid were ineffective [5].
High-pressure liquid chromatography-mass spectrometry (HPLC-MS) analysis showed the presence of 2-aminobenzimidazole, benzimidazole, and an unknown metabolite with molecular ions (M(+)) of m/z 104.8 and 118 [6].

Biological context of NSC7628

Synthesis, biological activity, QSAR and QSPR study of 2-aminobenzimidazole derivatives as potent H3-antagonists [7].
In fact, methylation of the exocyclic NH group maintained high affinity for the tri-methylene 2-aminobenzimidazole derivative, while a drop in affinity was observed for the annular N-methylation [8].

Anatomical context of NSC7628

Immunotropic properties of 2-aminobenzimidazole derivatives in cultures of human peripheral blood cells, Part 5 [9].

Associations of NSC7628 with other chemical compounds

We report the design, synthesis, QSPR and QSAR of a new class of H(3)-antagonists, having a 2-aminobenzimidazole moiety connected to the 4(5) position of an imidazole ring through di- or tri-methylene chains [7].
Benomyl and Carbendazim are extracted with ethyl acetate, saponified and determined as 2-aminobenzimidazole by thin-layer chromatography [10].

References

Application of oral bioavailability surrogates in the design of orally active inhibitors of rhinovirus replication. Stratford, R.E., Clay, M.P., Heinz, B.A., Kuhfeld, M.T., Osborne, S.J., Phillips, D.L., Sweetana, S.A., Tebbe, M.J., Vasudevan, V., Zornes, L.L., Lindstrom, T.D. Journal of pharmaceutical sciences. (1999) [Pubmed]
Design of potent and selective 2-aminobenzimidazole-based p38alpha MAP kinase inhibitors with excellent in vivo efficacy. de Dios, A., Shih, C., López de Uralde, B., Sánchez, C., del Prado, M., Martín Cabrejas, L.M., Pleite, S., Blanco-Urgoiti, J., Lorite, M.J., Nevill, C.R., Bonjouklian, R., York, J., Vieth, M., Wang, Y., Magnus, N., Campbell, R.M., Anderson, B.D., McCann, D.J., Giera, D.D., Lee, P.A., Schultz, R.M., Li, L.C., Johnson, L.M., Wolos, J.A. J. Med. Chem. (2005) [Pubmed]
Heterocyclic bis-cations as starting hits for design of inhibitors of the bifunctional enzyme histidine-containing protein kinase/phosphatase from Bacillus subtilis. Ramström, H., Bourotte, M., Philippe, C., Schmitt, M., Haiech, J., Bourguignon, J.J. J. Med. Chem. (2004) [Pubmed]
Determination of thiophanate-methyl and its metabolites at trace level in spiked natural water using the supported liquid membrane extraction and the microporous membrane liquid-liquid extraction techniques combined on-line with high-performance liquid chromatography. Sandahl, M., Mathiasson, L., Jönsson, J.A. Journal of chromatography. A. (2000) [Pubmed]
Structural and mechanistic aspects of transcriptional induction of cytochrome P450 1A1 by benzimidazole derivatives in rat hepatoma H4IIE cells. Backlund, M., Weidolf, L., Ingelman-Sundberg, M. Eur. J. Biochem. (1999) [Pubmed]
Isolation and characterization of a carbendazim-degrading Rhodococcus sp. djl-6. Jing-Liang, X., Xiang-Yang, G., Biao, S., Zhi-Chun, W., Kun, W., Shun-Peng, L. Curr. Microbiol. (2006) [Pubmed]
Synthesis, biological activity, QSAR and QSPR study of 2-aminobenzimidazole derivatives as potent H3-antagonists. Mor, M., Bordi, F., Silva, C., Rivara, S., Zuliani, V., Vacondio, F., Rivara, M., Barocelli, E., Bertoni, S., Ballabeni, V., Magnanini, F., Impicciatore, M., Plazzi, P.V. Bioorg. Med. Chem. (2004) [Pubmed]
The role of HB-donor groups in the heterocyclic polar fragment of H3-antagonists. I. Synthesis and biological assays. Zuliani, V., Bordi, F., Rivara, M., Silva, C., Vacondio, F., Morini, G., Rivara, S., Barocelli, E., Ballabeni, V., Bertoni, S., Magnanini, F., Plazzi, P.V. Farmaco (2003) [Pubmed]
Immunotropic properties of 2-aminobenzimidazole derivatives in cultures of human peripheral blood cells, Part 5. Nawrocka, W., Zimecki, M., Kuznicki, T., Kowalska, M.W. Arch. Pharm. (Weinheim) (1999) [Pubmed]
Determination of benomyl, carbendazim and 2-aminobenzimidazole (2-ab) in plant materials. Part I: Apples, red-currants, grapes, kale and sugar beets. Polzhofer, K. Zeitschrift für Lebensmittel-Untersuchung und -Forschung. (1977) [Pubmed]

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