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Chemical Compound Review

AG-F-54252     dioxolane

Synonyms: AC1L3CAG, CTK4I7625, 1,2-Dioxolane, 4362-13-4, 3H-1,2-Dioxole, dihydro-
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Disease relevance of dioxolane


High impact information on dioxolane

  • Amdoxovir ((-)-beta-D-2,6-diaminopurine dioxolane), the prodrug of dioxolane guanosine (DXG), is currently in phase I/II clinical development for the treatment of HIV-1 infection [6].
  • Steady-state plasma concentrations of DAPD and dioxolane guanosine followed linear kinetics [7].
  • The differential effects of relatively thick monoglyceride bilayers on proton transfer in both dioxolane-linked gA channels must relate to distinct interactions between the bilayers and the SS and RR dioxolanes [8].
  • Modulation of proton transfer in the water wire of dioxolane-linked gramicidin channels by lipid membranes [9].
  • D- and L-Oxathiolane and -dioxolane derivatives 13, 16, 20, 21, and 29-34 were prepared by glycosylation reaction of the oxathiolane and dioxolane intermediates with silylated uracil analogues using TMSI as the coupling agent [10].

Chemical compound and disease context of dioxolane

  • Triangle Pharmaceuticals is developing DAPD, a prodrug of the viral replication inhibitor dioxolane guanosine, as a potential therapy for HIV and HBV infection [11].

Biological context of dioxolane


Anatomical context of dioxolane


Associations of dioxolane with other chemical compounds


Gene context of dioxolane

  • The submillisecond closing events (flickers) and the single channel conductances to protons (g(H)) were studied in native gramicidin A (gA) and in the SS and RR diastereoisomers of dioxolane-linked gA channels in planar bilayers [22].
  • With the exception of dioxolane, 4-methyldioxolane and 4-ethyldioxolane, these compounds interacted with ferric cytochrome P-450 to give complexes exhibiting type I optical difference spectra, and, after incubation with NADPH, spectra with peaks at about 430 nm [23].
  • After preseparation in a C18 and a silica gel column, nineteen pyrone and dioxolane derivatives and two aliphatic esters are obtained, respectively [24].
  • Both dioxolane derivatives represent NMDA receptor antagonists, which possess high affinity to the phencyclidine binding site within the NMDA receptor associated ion channel [25].
  • The gingkolide terpene, BN 52021 and the dioxolane-based compound BN 52115 had no effect on benzodiazepine binding or chloride channel binding in cortical membrane preparations [26].

Analytical, diagnostic and therapeutic context of dioxolane


  1. Amdoxovir versus placebo with enfuvirtide plus optimized background therapy for HIV-1-infected subjects failing current therapy (AACTG A5118). Gripshover, B.M., Ribaudo, H., Santana, J., Gerber, J.G., Campbell, T.B., Hogg, E., Jarocki, B., Hammer, S.M., Kuritzkes, D.R. Antivir. Ther. (Lond.) (2006) [Pubmed]
  2. L- and D-enantiomers of 2',3'-dideoxycytidine 5'-triphosphate analogs as substrates for human DNA polymerases. Implications for the mechanism of toxicity. Kukhanova, M., Liu, S.H., Mozzherin, D., Lin, T.S., Chu, C.K., Cheng, Y.C. J. Biol. Chem. (1995) [Pubmed]
  3. The new dioxolane, (-)-2'-deoxy-3'-oxacytidine (BCH-4556, troxacitabine), has activity against pancreatic human tumor xenografts. Weitman, S., Marty, J., Jolivet, J., Locas, C., Von Hoff, D.D. Clin. Cancer Res. (2000) [Pubmed]
  4. In vitro susceptibilities of wild-type or drug-resistant hepatitis B virus to (-)-beta-D-2,6-diaminopurine dioxolane and 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil. Chin, R., Shaw, T., Torresi, J., Sozzi, V., Trautwein, C., Bock, T., Manns, M., Isom, H., Furman, P., Locarnini, S. Antimicrob. Agents Chemother. (2001) [Pubmed]
  5. Absence of mutagenicity of trioxane and dioxolane in Salmonella typhimurium. Kowalski, Z., Spiechowicz, E., Barański, B. Mutat. Res. (1984) [Pubmed]
  6. Dioxolane guanosine 5'-triphosphate, an alternative substrate inhibitor of wild-type and mutant HIV-1 reverse transcriptase. Steady state and pre-steady state kinetic analyses. Jeffrey, J.L., Feng, J.Y., Qi, C.C., Anderson, K.S., Furman, P.A. J. Biol. Chem. (2003) [Pubmed]
  7. Short-term safety and pharmacodynamics of amdoxovir in HIV-infected patients. Thompson, M.A., Kessler, H.A., Eron, J.J., Jacobson, J.M., Adda, N., Shen, G., Zong, J., Harris, J., Moxham, C., Rousseau, F.S. AIDS (2005) [Pubmed]
  8. Proton transfer in gramicidin channels is modulated by the thickness of monoglyceride bilayers. Chernyshev, A., Armstrong, K.M., Cukierman, S. Biophys. J. (2003) [Pubmed]
  9. Modulation of proton transfer in the water wire of dioxolane-linked gramicidin channels by lipid membranes. de Godoy, C.M., Cukierman, S. Biophys. J. (2001) [Pubmed]
  10. Structure-activity relationships of (E)-5-(2-bromovinyl)uracil and related pyrimidine nucleosides as antiviral agents for herpes viruses. Choi, Y., Li, L., Grill, S., Gullen, E., Lee, C.S., Gumina, G., Tsujii, E., Cheng, Y.C., Chu, C.K. J. Med. Chem. (2000) [Pubmed]
  11. DAPD (Emory University/Triangle Pharmaceuticals/Abbott Laboratories). Corbett, A.H., Rublein, J.C. Current opinion in investigational drugs (London, England : 2000) (2001) [Pubmed]
  12. Chiral dioxolane inhibitors of leukotriene biosynthesis: structure-activity relationships and syntheses using asymmetric dihydroxylation. Crawley, G.C., Briggs, M.T. J. Med. Chem. (1995) [Pubmed]
  13. Pharmacokinetics of (-)-beta-D-2-aminopurine dioxolane and (-)-beta-D-2-amino-6-chloropurine dioxolane and their antiviral metabolite (-)-beta-D-dioxolane guanine in rhesus monkeys. Chen, H., Boudinot, F.D., Chu, C.K., Mcclure, H.M., Schinazi, R.F. Antimicrob. Agents Chemother. (1996) [Pubmed]
  14. Inhibition of N-methyl-D-aspartate evoked sodium flux by MK-801. Ransom, R.W., Stec, N.L. Brain Res. (1988) [Pubmed]
  15. Transdermal delivery of drugs with differing lipophilicities using azone analogs as dermal penetration enhancers. Phillips, C.A., Michniak, B.B. Journal of pharmaceutical sciences. (1995) [Pubmed]
  16. Inhalation toxicity of Dioxole and Dioxolane compounds in the rat. Kennedy, G.L., O'Neill, A.J., Valentine, R. Drug and chemical toxicology. (2001) [Pubmed]
  17. Determination of dissociation constants and relative efficacies of some potent muscarinic agonists at postjunctional muscarinic receptors. Grana, E., Lucchelli, A., Zonta, F., Boselli, C. Naunyn Schmiedebergs Arch. Pharmacol. (1987) [Pubmed]
  18. Genotoxic effects of dioxolane and trioxane in mice evaluated by the micronucleus test. Przybojewska, B., Dziubałtowska, E., Kowalski, Z. Toxicol. Lett. (1984) [Pubmed]
  19. Beta-3 adrenoceptor selectivity of the dioxolane dicarboxylate phenethanolamines. Dolan, J.A., Muenkel, H.A., Burns, M.G., Pellegrino, S.M., Fraser, C.M., Pietri, F., Strosberg, A.D., Largis, E.E., Dutia, M.D., Bloom, J.D. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  20. Applications of the Chiralpak AD and Chiralcel OD chiral columns in the enantiomeric separation of several dioxolane compounds by supercritical fluid chromatography. Toribio, L., Bernal, J.L., del Nozal, M.J., Jiménez, J.J., Nieto, E.M. Journal of chromatography. A. (2001) [Pubmed]
  21. Antifungal sordarins. Synthesis and structure-activity relationships of 3',4'-fused dioxolane and dioxane derivatives. Bueno, J.M., Cuevas, J.C., Fiandor, J.M., García-Ochoa, S., Gómez de las Heras, F. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  22. On the origin of closing flickers in gramicidin channels: a new hypothesis. Armstrong, K.M., Cukierman, S. Biophys. J. (2002) [Pubmed]
  23. The interaction of aliphatic analogs of methylene-dioxyphenyl compounds with cytochromes P-450 and P-420. Dahl, A.R., Hodgson, E. Chem. Biol. Interact. (1979) [Pubmed]
  24. Separation and identification of volatile components in the fermentation broth of Trichoderma atroviride by solid-phase extraction and gas chromatography-mass spectrometry. Keszler, A., Forgács, E., Kótai, L., Vizcaíno, J.A., Monte, E., García-Acha, I. Journal of chromatographic science. (2000) [Pubmed]
  25. Relationships between the structure of dexoxadrol and etoxadrol analogues and their NMDA receptor affinity. Sax, M., Wünsch, B. Current topics in medicinal chemistry. (2006) [Pubmed]
  26. Platelet activating factor antagonists interact with GABAA receptors. Miller, L.G., Bazan, N.G., Roy, R.B., Clostre, F., Gaver, A., Braquet, P. Res. Commun. Chem. Pathol. Pharmacol. (1991) [Pubmed]
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