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Chemical Compound Review

Dithiane     dithiane

Synonyms: o-Dithiane, CHEBI:47844, NSC-521078, CTK1G9893, NSC521078, ...
 
 
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Disease relevance of dithiane

 

High impact information on dithiane

  • For vinyl epoxides, the steric nature of the dithiane anion is critical; sterically unencumbered dithiane anions afford S(N)2 adducts, whereas encumbered anions lead primarily to SN2' adducts [2].
  • Several dithiane derivatives, prepared as intermediates for compounds structurally related to the therapeutically useful antimuscarinic agent oxybutynin, were effective inhibitors of calcium ion induced contraction of guinea pig ileal strips and of KCl-induced calcium entry into neuronal cells [3].
  • [reaction: see text] Double deprotection of dithiane aldol equivalents is feasible under mild conditions with ZnBr(2) and suitably placed MEM, BOM, and SEM groups which function as protecting, activating, and regiodirecting groups [4].
  • Alkylation with a model epoxide demonstrates that (-)-3 is a competent dithiane for further elaboration of the macrolide skeleton [5].
  • Dithiane analogues of tiapamil are highly active as modifiers of P-glycoprotein mediated multidrug resistance (MDR) in vitro [6].
 

Anatomical context of dithiane

  • The first steps have been taken in using the NCB site for affinity chromatography of the GABAA receptor in CHAPS-solubilized bovine brain membranes with the dithiane-biotin probe and an avidin-acrylic bead system or with an analogous dithiane-agarose/ sepharose column eluting with GABA or dithiane as above (R = OH) [7].
 

Associations of dithiane with other chemical compounds

  • To study the activity of the different desaturases present in the pheromone biosynthetic pathway of the Egyptian armyworm, Spodoptera littoralis, we prepared a series of mono- and gem-difluorinated analogs of myristic acid with halogen substitution at the C8-C11 positions of the aliphatic chain via specifically positioned dithiane precursors [8].
 

Gene context of dithiane

  • Dithiane additions to vinyl epoxides: steric control over the SN2 and SN2' manifolds [9].
 

Analytical, diagnostic and therapeutic context of dithiane

  • 2-(Methyl 6-deoxy-2,3-O-isopropylidene-5-O-methyl-alpha-D-mannofuranosid- 6-yl)-1,3-dithiane was converted into the lithiated anion, which after treatment with alkyl halide afforded the corresponding 2-alkyl-C-(methyl 6-deoxy-2,3-O-isopropylidene-5-O-methyl-alpha-D-mannofuranosid-6-y l)-1,3- dithiane [10].

References

  1. Inhibition of multiple phases of human immunodeficiency virus type 1 replication by a dithiane compound that attacks the conserved zinc fingers of retroviral nucleocapsid proteins. Rice, W.G., Baker, D.C., Schaeffer, C.A., Graham, L., Bu, M., Terpening, S., Clanton, D., Schultz, R., Bader, J.P., Buckheit, R.W., Field, L., Singh, P.K., Turpin, J.A. Antimicrob. Agents Chemother. (1997) [Pubmed]
  2. Multicomponent linchpin couplings. Reaction of dithiane anions with terminal epoxides, epichlorohydrin, and vinyl epoxides: efficient, rapid, and stereocontrolled assembly of advanced fragments for complex molecule synthesis. Smith, A.B., Pitram, S.M., Boldi, A.M., Gaunt, M.J., Sfouggatakis, C., Moser, W.H. J. Am. Chem. Soc. (2003) [Pubmed]
  3. Aminoalkynyldithianes. A new class of calcium channel blockers. Adams, T.C., Dupont, A.C., Carter, J.P., Kachur, J.F., Guzewska, M.E., Rzeszotarski, W.J., Farmer, S.G., Noronha-Blob, L., Kaiser, C. J. Med. Chem. (1991) [Pubmed]
  4. Chelation, activation, and proximity effects in the deprotection of dithianes with ZnBr(2): applications in the polyketide field. Vakalopoulos, A., Hoffmann, H.M. Org. Lett. (2001) [Pubmed]
  5. Synthesis of tedanolide and 13-deoxytedanolide. Assembly of a common C(1)-C(11) subtarget. Smith, A.B., Lodise, S.A. Org. Lett. (1999) [Pubmed]
  6. Novel dithiane analogues of tiapamil with high activity to overcome multidrug resistance in vitro. Eliason, J.F., Ramuz, H., Yoshikubo, T., Ishikawa, T., Yamamoto, T., Tsuruo, T. Biochem. Pharmacol. (1995) [Pubmed]
  7. Affinity probes for the GABA-gated chloride channel: 5e-tert-butyl-2e-[4-(substituted-ethynyl)phenyl]-1,3-dithianes with photoactivatable, fluorescent, biotin, agarose and protein substituents. Li, Q.X., Casida, J.E. Bioorg. Med. Chem. (1995) [Pubmed]
  8. Synthesis of fluorinated analogs of myristic acid as potential inhibitors of Egyptian armyworm (Spodoptera littoralis) delta11 desaturase. Abad, J.L., Villorbina, G., Fabriàs, G., Camps, F. Lipids (2003) [Pubmed]
  9. Dithiane additions to vinyl epoxides: steric control over the SN2 and SN2' manifolds. Smith, A.B., Pitram, S.M., Gaunt, M.J., Kozmin, S.A. J. Am. Chem. Soc. (2002) [Pubmed]
  10. A new 6-C-alkylation from an alkyl mannofuranoside 5,6-cyclic sulfate. Gourlain, T., Wadouachi, A., Beaupère, D. Carbohydr. Res. (2000) [Pubmed]
 
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