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Chemical Compound Review

AG-G-15317     2,3-dinitroaniline

Synonyms: NSC-37400, NSC37400, CTK5B1119, UN1596, ZINC03852563, ...
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Disease relevance of UN1596


High impact information on UN1596


Biological context of UN1596

  • A 3D pharmacophore was generated to describe the antileishmanial activity of dinitroaniline sulfonamides by CATALYST 3D-QSAR methodology, and this pharmacophore was used to search the Maybridge database [8].
  • 3,5-Dinitro-4-chloro-alpha,alpha,alpha-trifluorotoluene (DNCTT) is an intermediate in the synthesis of dinitroaniline herbicides and was involved in an episode of ground water pollution in 1977 [9].
  • Moreover, a dinitroaniline-resistant biotype of goosegrass (Eleusine indica (L) Gaertn) with a point mutation in alpha-tubulin showed cross-resistance against CA1 and CA2 [10].

Anatomical context of UN1596


Associations of UN1596 with other chemical compounds


Gene context of UN1596

  • Molecular characterization of four beta-tubulin genes from dinitroaniline susceptible and resistant biotypes of Eleusine indica [12].
  • Furthermore, to investigate how dinitroanilines affect tubulin dynamics, molecular dynamics simulations of Leishmania alpha-tubulin with and without a bound dinitroaniline are performed [11].
  • A simple and rapid method for extraction of seven dinitroaniline herbicides from human whole blood and urine using Sep-Pak C18 cartridges is presented [13].
  • Structural modeling of the interaction of plant alpha-tubulin with dinitroaniline and phosphoroamidate herbicides [14].
  • The headspace SPME yielded clean extracts of dinitroaniline herbicides from urine, blood or water, which could be directly analyzed by GC-ECD without further purification [15].

Analytical, diagnostic and therapeutic context of UN1596


  1. Efficacy of oryzalin and associated histological changes in Cryptosporidium-infected neonatal rats. Armson, A., Menon, K., O'Hara, A., MacDonald, L.M., Read, C.M., Sargent, K., Thompson, R.C., Reynoldson, J.A. Parasitology (2002) [Pubmed]
  2. Developmental toxicity of dinitroaniline herbicides in rats and rabbits. I. Trifluralin. Byrd, R.A., Markham, J.K., Emmerson, J.L. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1995) [Pubmed]
  3. Inhibition of leishmanias but not host macrophages by the antitubulin herbicide trifluralin. Chan, M.M., Fong, D. Science (1990) [Pubmed]
  4. The plastid of Toxoplasma gondii is divided by association with the centrosomes. Striepen, B., Crawford, M.J., Shaw, M.K., Tilney, L.G., Seeber, F., Roos, D.S. J. Cell Biol. (2000) [Pubmed]
  5. Dinitroaniline herbicide-resistant transgenic tobacco plants generated by co-overexpression of a mutant alpha-tubulin and a beta-tubulin. Anthony, R.G., Reichelt, S., Hussey, P.J. Nat. Biotechnol. (1999) [Pubmed]
  6. Alpha-tubulin missense mutations correlate with antimicrotubule drug resistance in Eleusine indica. Yamamoto, E., Zeng, L., Baird, W.V. Plant Cell (1998) [Pubmed]
  7. Dinitroanilines bind alpha-tubulin to disrupt microtubules. Morrissette, N.S., Mitra, A., Sept, D., Sibley, L.D. Mol. Biol. Cell (2004) [Pubmed]
  8. Activity of and initial mechanistic studies on a novel antileishmanial agent identified through in silico pharmacophore development and database searching. Delfín, D.A., Bhattacharjee, A.K., Yakovich, A.J., Werbovetz, K.A. J. Med. Chem. (2006) [Pubmed]
  9. Hematotoxic effects in the rat of a toluene dinitro derivative after short-term exposure. Guastadisegni, C., Mantovani, A., Ricciardi, C., Stazi, A.V., Maffi, D., Salvati, A.M. Ecotoxicol. Environ. Saf. (1989) [Pubmed]
  10. Herbicidal cyanoacrylates with antimicrotubule mechanism of action. Tresch, S., Plath, P., Grossmann, K. Pest Manag. Sci. (2005) [Pubmed]
  11. Binding and interaction of dinitroanilines with apicomplexan and kinetoplastid alpha-tubulin. Mitra, A., Sept, D. J. Med. Chem. (2006) [Pubmed]
  12. Molecular characterization of four beta-tubulin genes from dinitroaniline susceptible and resistant biotypes of Eleusine indica. Yamamoto, E., Baird, W.V. Plant Mol. Biol. (1999) [Pubmed]
  13. Capillary gas chromatography with four different detectors for dinitroaniline herbicides in human body fluids. Kumazawa, T., Sato, K., Seno, H., Ishii, A., Suzuki, O. Journal of analytical toxicology. (1995) [Pubmed]
  14. Structural modeling of the interaction of plant alpha-tubulin with dinitroaniline and phosphoroamidate herbicides. Blume, Y.B., Nyporko, A.Y., Yemets, A.I., Baird, W.V. Cell Biol. Int. (2003) [Pubmed]
  15. Headspace solid-phase microextraction and gas chromatographic determination of dinitroaniline herbicides in human blood, urine and environmental water. Guan, F., Watanabe, K., Ishii, A., Seno, H., Kumazawa, T., Hattori, H., Suzuki, O. J. Chromatogr. B Biomed. Sci. Appl. (1998) [Pubmed]
  16. Analysis of trifluralin and other dinitroaniline herbicide residues by zero-order and derivative ultraviolet spectrophotometry. Traore, S., Aaron, J.J. The Analyst. (1989) [Pubmed]
  17. Microtubules in Plasmodium falciparum merozoites and their importance for invasion of erythrocytes. Fowler, R.E., Fookes, R.E., Lavin, F., Bannister, L.H., Mitchell, G.H. Parasitology (1998) [Pubmed]
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