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

• The crucial tetrahydropyran ring was formed by a highly stereoselective cationic cyclization [4].
• Key features of the unified synthetic scheme included the stereocontrolled construction of the cis-2,6-disubstituted tetrahydropyran via a modified Petasis-Ferrier rearrangement, a highly convergent assembly of the macrocyclic domain, and, in the case of zampanolide, a Curtius rearrangement/acylation tactic to install the N-acyl hemiaminal [5].
• Two cyclic ethers, tetrahydrofuran (THF) and tetrahydropyran (THP), were intercalated into vanadyl phosphate and characterized by X-ray powder diffraction, thermogravimetry, and IR and Raman spectroscopy [6].
• A solvolysis reaction is used to demonstrate that a tetrahydropyranyl cation is a common intermediate for Prins cyclizations, 2-oxonia-Cope rearrangements, and Grob fragmentations of tetrahydropyran rings [7].
• A stereoselective allyl transfer reaction was used in the synthesis of enol ether 18 followed by a TFA-mediated cyclization to create the three new asymmetric centers in the tetrahydropyran with complete stereocontrol in a single-pot process [8].

Biological context of tetrahydropyran

• Catalytic asymmetric alkylation reactions of branched racemic carbonates 1a and 1b with sodium dimethyl malonate, promoted by molybdenum and ligand 5, proceed by a kinetic resolution in toluene, THF, tetrahydropyran, i-PrOAc, 1,2-dichloroethane, and MeCN with k(rel) of 7-16 [9].
• Data showed that the lactone and tetrahydropyran portions of the molecule were both susceptible to hydroxylation, and the hydroxylated tetrahydropyran was further oxidized to the hydroxy acid [10].

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