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Chemical Compound Review

m-Dioxane     1,3-dioxane

Synonyms: meta-Dioxane, SureCN22744, ACMC-1ASQC, CCRIS 5911, LS-147, ...
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High impact information on meta-Dioxane

  • Individual members of the 1,3-dioxane library have activity in a variety of phenotypic and protein-binding assays [1].
  • This evaluation of a portion of the 1,3-dioxane library suggests that many additional probes for chemical genetics will be identified as the entire library becomes biologically annotated [2].
  • Compounds such as 13a bearing simple alkyl or hydroxymethyl substituents at the 5-position of the 1,3-dioxane ring are potent bioavailable inhibitors of the rat hepatic microsomal enzyme in vitro (IC50 < 100 nM) but are only weak inhibitors of the human hepatic enzyme [3].
  • Representative structures from this library were tested for inhibitory activity and the 1,3-dioxane structure was shown to be compatible with HDAC inhibition [4].
  • Acrylated phosphonate esters containing 1,3-dioxane and 1,3-dioxolane moieties as adhesion-promoting agents for dentin and hard tissues, I [5].

Biological context of meta-Dioxane


Gene context of meta-Dioxane

  • The CD spectra are reported for a series of 1,3-dioxane-type 4,6-O-(2'-naphthyl)methylene acetals of carbohydrates with and without interacting aromatic protective groups on the C-1, C-2, and C-3 hydroxy groups [7].
  • The 1,3-dioxane ring has a distorted chair conformation with puckering parameters Q = 0.516 A, phi = 90.9, and theta = 11.0 degrees [8].

Analytical, diagnostic and therapeutic context of meta-Dioxane


  1. Split--pool synthesis of 1,3-dioxanes leading to arrayed stock solutions of single compounds sufficient for multiple phenotypic and protein-binding assays. Sternson, S.M., Louca, J.B., Wong, J.C., Schreiber, S.L. J. Am. Chem. Soc. (2001) [Pubmed]
  2. Modular synthesis and preliminary biological evaluation of stereochemically diverse 1,3-dioxanes. Wong, J.C., Sternson, S.M., Louca, J.B., Hong, R., Schreiber, S.L. Chem. Biol. (2004) [Pubmed]
  3. Acyl-CoA:Cholesterol O-acyltransferase (ACAT) inhibitors. 2. 2-(1,3-Dioxan-2-yl)-4,5-diphenyl-1H-imidazoles as potent inhibitors of ACAT. Astles, P.C., Ashton, M.J., Bridge, A.W., Harris, N.V., Hart, T.W., Parrott, D.P., Porter, B., Riddell, D., Smith, C., Williams, R.J. J. Med. Chem. (1996) [Pubmed]
  4. Synthesis of 7200 small molecules based on a substructural analysis of the histone deacetylase inhibitors trichostatin and trapoxin. Sternson, S.M., Wong, J.C., Grozinger, C.M., Schreiber, S.L. Org. Lett. (2001) [Pubmed]
  5. Acrylated phosphonate esters containing 1,3-dioxane and 1,3-dioxolane moieties as adhesion-promoting agents for dentin and hard tissues, I. Cabasso, I., Sahni, S. J. Biomed. Mater. Res. (1990) [Pubmed]
  6. Metabolism of the antimicrobial agent nibroxane, 5-bromo-2-methyl-5-nitro-m-dioxane, in the rat. Sullivan, H.R., Marshall, F.J., Bopp, R.J. Xenobiotica (1978) [Pubmed]
  7. Circular dichroism of 1,3-dioxane-type (2'-naphthyl)methylene acetals of glycosides. Kurtán, T., Borbás, A., Szabó, Z.B., Lipták, A., Bényei, A., Antus, S. Chirality. (2004) [Pubmed]
  8. The crystal and molecular structure of 1,2-O-isopropylidene-alpha-D-xylo-pentodialdo-1,4-furanose. A dimeric form in the crystalline state. Shalaby, M.A., Fronczek, F.R., Younathan, E.S. Carbohydr. Res. (1994) [Pubmed]
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