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Chemical Compound Review

Oxane     oxane

Synonyms: Oxacyclohexane, PubChem9509, AC1LAZGD, SureCN13487, HSDB 126, ...
 
 
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Disease relevance of tetrahydropyran

  • The formation of the tetrahydropyran is more likely with an amino function of low nucleophilicity, whereas dehydration to an imine leading to a dihydropyridine is favored with an amino function of higher nucleophilicity [1].
  • In peripheral models of inflammation and hyperalgesia, tetrahydropyran derivative significantly reduced nociceptive effect induced by acetic acid or formalin in mice [2].
  • Using a simplified structure (2-(tetrahydropyran-2-yloxy) tetrahydropyran) as a model we have calculated the energy and 13C magnetic shielding parameters as a function of the two glycosidic torsion angles [3].
 

High impact information on tetrahydropyran

 

Biological context of tetrahydropyran

 

Anatomical context of tetrahydropyran

  • Studies conducted with microsomes from genetically engineered human cell lines expressing individual cytochrome P450s indicated that the isozyme responsible for the metabolism at the tetrahydropyran ring, was P4503A4 [10].
 

Associations of tetrahydropyran with other chemical compounds

  • Reductive cyclizations of hydroxysulfinyl ketones: enantioselective access to tetrahydropyran and tetrahydrofuran derivatives [11].
  • The stereoselective synthesis of methyl monate C 2 is described using as a key step an ene-intramolecular modified Sakurai cyclization (IMSC) reaction to prepare tetrahydropyran 5 [12].
  • [structure: see text] The ABC tristetrahydropyran substructure 1 of the natural products thyrsiferol (2) and venustatriol (3) has been synthesized in 14 steps from farnesyl acetate, with effective control of all aspects of regio- and stereoselectivity in the formation of each tetrahydropyran ring [13].
  • A tetrahydropyran-based inhibitor (2) of mammalian ribonucleotide reductase (mRR) has been designed and synthesized based on the heptapeptide, N-AcFTLDADF (1), corresponding to the C-terminus of the R2 subunit of mRR [14].
  • A tetrahydropyran ring-containing fatty acid-combined taurine (tetrathermoyltaurine) was found in the taurolipid fraction of Tetrahymena thermophila [15].
 

Gene context of tetrahydropyran

  • Specific tetrahydropyrane analogues modeled on PheArgTrp as a truncated version of the melanocortin receptor message sequence, showed activity at the melanocortin receptors MC4R and MC1R [16].
  • The substitution of an acetyl or an ethoxycarbonyl group for the amine N-ethoxycarbonyl-7-oxostaurosporine moiety on the tetrahydropyran ring of staurosporine decreased inhibition of both protein kinases, but increased selectivity for C-kinase by further modification of the lactam moiety to the imide (NA-382) [17].
 

Analytical, diagnostic and therapeutic context of tetrahydropyran

  • The first total synthesis of the reported structure of the sponge metabolite clavosolide A is described using a Prins cyclisation to assemble the tetrahydropyran core followed by manipulation of the side-chain, dimerisation and finally glycosidation [18].

References

  1. 2,6-diarylaminotetrahydropyrans from reactions of glutaraldehyde with anilines: models for biomolecule cross-linking. Henderson, A.P., Bleasdale, C., Clegg, W., Golding, B.T. Chem. Res. Toxicol. (2004) [Pubmed]
  2. Antinociceptive action of (+/-)-cis-(6-ethyl-tetrahydropyran-2-yl)-formic acid in mice. Marinho, B.G., Miranda, L.S., Gomes, N.M., Matheus, M.E., Leit??o, S.G., Vasconcellos, M.L., Fernandes, P.D. Eur. J. Pharmacol. (2006) [Pubmed]
  3. Solid-state 13C NMR investigations of the glycosidic linkage in alpha-alpha' trehalose. Zhang, P., Klymachyov, A.N., Brown, S., Ellington, J.G., Grandinetti, P.J. Solid state nuclear magnetic resonance. (1998) [Pubmed]
  4. Toward the synthesis of the carbacylic ansa antibiotic kendomycin. Mulzer, J., Pichlmair, S., Green, M.P., Marques, M.M., Martin, H.J. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  5. Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy. Smith, A.B., Safonov, I.G., Corbett, R.M. J. Am. Chem. Soc. (2002) [Pubmed]
  6. Intercalation of cyclic ethers into vanadyl phosphate. Zima, V., Melánová, K., Benes, L., Capková, P., Trchová, M., Matejka, P. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  7. Solvolysis of a tetrahydropyranyl mesylate: mechanistic implications for the prins cyclization, 2-oxonia-cope rearrangement, and grob fragmentation. Jasti, R., Rychnovsky, S.D. Org. Lett. (2006) [Pubmed]
  8. Stereoselective synthesis of the tetrahydropyran core of polycarvernoside A. Barry, C.S., Bushby, N., Harding, J.R., Willis, C.L. Org. Lett. (2005) [Pubmed]
  9. Solvent-dependent dynamic kinetic asymmetric transformation/kinetic resolution in molybdenum-catalyzed asymmetric allylic alkylations. Hughes, D.L., Palucki, M., Yasuda, N., Reamer, R.A., Reider, P.J. J. Org. Chem. (2002) [Pubmed]
  10. In vitro and in vivo biotransformations of the naphthalenic lignan lactone 5-lipoxygenase inhibitor, L-702,539. Chauret, N., Li, C., Ducharme, Y., Trimble, L.A., Yergey, J.A., Ramachandran, C., Nicoll-Griffith, D.A. Drug Metab. Dispos. (1995) [Pubmed]
  11. Reductive cyclizations of hydroxysulfinyl ketones: enantioselective access to tetrahydropyran and tetrahydrofuran derivatives. Carreño, M.C., Des Mazery, R., Urbano, A., Colobert, F., Solladié, G. J. Org. Chem. (2003) [Pubmed]
  12. Stereoselective synthesis of methyl monate C. Innis, L., Plancher, J.M., Mark??, I.E. Org. Lett. (2006) [Pubmed]
  13. Concise, regioselective synthesis of the ABC tristetrahydropyran of thyrsiferol and venustatriol. McDonald, F.E., Wei, X. Org. Lett. (2002) [Pubmed]
  14. Design and synthesis of a tetrahydropyran-based inhibitor of mammalian ribonucleotide reductase. Smith, A.B., Sasho, S., Barwis, B.A., Sprengeler, P., Barbosa, J., Hirschmann, R., Cooperman, B.S. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  15. Tetrahydropyran ring-containing fatty acid-combined taurine (tetrathermoyltaurine) in the taurolipid fraction of Tetrahymena thermophila. Kaya, K., Sano, T., Shiraishi, F. Biochim. Biophys. Acta (1992) [Pubmed]
  16. Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors. Mazur, A.W., Kulesza, A., Mishra, R.K., Cross-Doersen, D., Russell, A.F., Ebetino, F.H. Bioorg. Med. Chem. (2003) [Pubmed]
  17. Effect of staurosporine derivatives on protein kinase activity and vinblastine accumulation in mouse leukaemia P388/ADR cells. Miyamoto, K., Inoko, K., Ikeda, K., Wakusawa, S., Kajita, S., Hasegawa, T., Takagi, K., Koyama, M. J. Pharm. Pharmacol. (1993) [Pubmed]
  18. Total synthesis of a diastereomer of the marine natural product clavosolide A. Barry, C.S., Bushby, N., Charmant, J.P., Elsworth, J.D., Harding, J.R., Willis, C.L. Chem. Commun. (Camb.) (2005) [Pubmed]
 
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