oxepins

Summary

Summary: Compounds based on a 7-membered heterocyclic ring including an oxygen. They can be considered a medium ring ether. A natural source is the MONTANOA plant genus. Some dibenzo-dioxepins, called depsidones, are found in GARCINIA plants.

Top Publications

  1. Cayetanot F, Deprez J, Aujard F. Calbindin D28K protein cells in a primate suprachiasmatic nucleus: localization, daily rhythm and age-related changes. Eur J Neurosci. 2007;26:2025-32 pubmed
    ..These changes may affect the ability of the SCN to transmit rhythmic information to other SCN cells and thereby modify the synchronization of the different cell populations in the SCN. ..
  2. Olanow C, Schapira A, LeWitt P, Kieburtz K, Sauer D, Olivieri G, et al. TCH346 as a neuroprotective drug in Parkinson's disease: a double-blind, randomised, controlled trial. Lancet Neurol. 2006;5:1013-20 pubmed
  3. Miller R, Bradley W, Cudkowicz M, Hubble J, Meininger V, Mitsumoto H, et al. Phase II/III randomized trial of TCH346 in patients with ALS. Neurology. 2007;69:776-84 pubmed
    ..The trial revealed no evidence of a beneficial effect of TCH346 on disease progression in patients with ALS. ..
  4. Erb M, Meinen S, Barzaghi P, Sumanovski L, Courdier Fruh I, Ruegg M, et al. Omigapil ameliorates the pathology of muscle dystrophy caused by laminin-alpha2 deficiency. J Pharmacol Exp Ther. 2009;331:787-95 pubmed publisher
    ..These data qualify omigapil, which is in late phase of clinical development for human use, as a drug candidate for the treatment of MDC1A. ..
  5. Belforte J, Pazo J. Striatal inhibition of nociceptive responses evoked in trigeminal sensory neurons by tooth pulp stimulation. J Neurophysiol. 2005;93:1730-41 pubmed
    ..These results indicate that the striatum could be involved in the modulation of nociceptive inputs and confirm the role of the basal ganglia in the processing of nociceptive information. ..
  6. Puttachary S, Trailovic S, Robertson A, Thompson D, Woods D, Martin R. Derquantel and abamectin: effects and interactions on isolated tissues of Ascaris suum. Mol Biochem Parasitol. 2013;188:79-86 pubmed publisher
    ..42, CI 0.13-1.36?M). Our study demonstrates that abamectin and derquantel interact at nicotinic acetylcholine receptors on the somatic muscle and suggested synergism can occur. ..
  7. Chen G, Wang Y, Zhang L, Zhou J. Age- and sex-related disturbance in a battery of sensorimotor and cognitive tasks in Kunming mice. Physiol Behav. 2004;83:531-41 pubmed
    ..These results suggest that disturbance of spatial learning and memory, as well as selective impairment of non-spatial learning and memory, existed in older female KM mice. ..
  8. Jenkins J, Tanner J. High-resolution structure of human D-glyceraldehyde-3-phosphate dehydrogenase. Acta Crystallogr D Biol Crystallogr. 2006;62:290-301 pubmed
    ..These results are discussed in the context of the recently discovered NO-S-nitrosylation-GAPDH-Siah1 apoptosis cascade. ..
  9. Vannam R, Peczuh M. A practical and scalable synthesis of carbohydrate based oxepines. Org Biomol Chem. 2016;14:3989-96 pubmed publisher
    ..The practicality of the method make it amenable to scale up as demonstrated by the gram-scale synthesis of the d-glucose derived oxepine. ..

More Information

Publications104 found, 100 shown here

  1. Markad S, Xia S, Snyder N, Surana B, Morton M, Hadad C, et al. Stereoselectivity in the epoxidation of carbohydrate-based oxepines. J Org Chem. 2008;73:6341-54 pubmed publisher
    ..Considered together, these factors should generally predict facial selectivity in the DMDO-epoxidation of cyclic enol ethers. ..
  2. Liao R, Siegbahn P. Mechanism and selectivity of the dinuclear iron benzoyl-coenzyme A epoxidase BoxB. Chem Sci. 2015;6:2754-2764 pubmed publisher
    ..The first step is rate-limiting with a barrier of only 10.8 kcal mol-1. Further experimental studies are encouraged to verify our results. ..
  3. Li N, Yao B, Wang C, Meng Q, Hou G. Synthesis, crystal structure and activity evaluation of novel 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives as protein-tyrosine kinase (PTK) inhibitors. Acta Crystallogr C Struct Chem. 2017;73:1003-1009 pubmed publisher
    ..This may be because (9) and (10) could effectively bind to the active pockets of the protein through intermolecular interactions...
  4. Kurokawa M, Uno H, Nakamura H, Sato F, Naruto S. Synthesis and antiinflammatory activity of cis- and trans-6,6a,7,8,9,10,10a,11-octahydro-11-oxodibenzo[b,e]thiepinacetic and -oxepinacetic acids. J Med Chem. 1990;33:504-9 pubmed
    ..The phenethyl ester (25) is the most favorable compound with high antiinflammatory activity and little ulcerogenicity. ..
  5. Carlile G, Chalmers Redman R, Tatton N, Pong A, Borden K, Tatton W. Reduced apoptosis after nerve growth factor and serum withdrawal: conversion of tetrameric glyceraldehyde-3-phosphate dehydrogenase to a dimer. Mol Pharmacol. 2000;57:2-12 pubmed
    ..These actions on GAPDH, rather than MAO-B inhibition, may contribute to the improvements in Parkinson's and Huntington's diseases found with DEP treatment. ..
  6. Gan L, Johnson D, Johnson J. Keap1-Nrf2 activation in the presence and absence of DJ-1. Eur J Neurosci. 2010;31:967-77 pubmed publisher
    ..These findings indicate that activation of the Nrf2-ARE pathway is independent of DJ-1, and Nrf2 activation is a potential therapeutic target to prevent neurodegeneration in sporadic and DJ-1 familial Parkinson's disease. ..
  7. Lu L, Tsai J, Liu J. Novel Pharmacologic Candidates for Treatment of Primary Open-Angle Glaucoma. Yale J Biol Med. 2017;90:111-118 pubmed
    ..This study aims to systematically review and summarize the most recent developments in clinical trials for new pharmacologic options for the treatment of primary open-angle glaucoma. ..
  8. Cartas Rosado R, Castro M. Theoretical study of reaction mechanisms of OH radical with toluene 1,2-epoxide/2-methyloxepin. J Phys Chem A. 2007;111:13088-98 pubmed
    ..The study of the oxide/oxepin mechanism is relevant because, aside from its relatively high concentration in the troposphere, this compound has carcinogenic and mutagenic properties. ..
  9. Sureram S, Wiyakrutta S, Ngamrojanavanich N, Mahidol C, Ruchirawat S, Kittakoop P. Depsidones, aromatase inhibitors and radical scavenging agents from the marine-derived fungus Aspergillus unguis CRI282-03. Planta Med. 2012;78:582-8 pubmed publisher
    ..0 and < 15.6 µM, respectively. Compounds 1 and 3- 7 were mostly inactive or showed only weak cytotoxic activity against HuCCA-1, HepG2, A549, and MOLT-3 cancer cell lines. ..
  10. Orendt A, Roberts S, Rainier J. The role of asynchronous bond formation in the diastereoselective epoxidation of cyclic enol ethers: a density functional theory study. J Org Chem. 2006;71:5565-73 pubmed
    ..Apparent only from the calculations is that the degree of synchronicity in the transition state is important in the diastereoselectivity. ..
  11. Sun T, Kuang R, Chen G, Qin S, Wang C, Hu D, et al. Three Pairs of New Isopentenyl Dibenzo[b,e]oxepinone Enantiomers from Talaromyces flavus, a Wetland Soil-Derived Fungus. Molecules. 2016;21: pubmed publisher
    ..The structures of isolated compounds were determined by detailed spectroscopic analysis. In addition, the absolute configurations of these three pairs of new enantiomers were determined by quantum chemical ECD calculations. ..
  12. Abbott J, Kent S, Levay E, Tucker R, Penman J, Tammer A, et al. The effects of calorie restriction olfactory cues on conspecific anxiety-like behaviour. Behav Brain Res. 2009;201:305-10 pubmed publisher
    ..This may have implications for the development of more efficacious novel treatments for anxiety disorders. ..
  13. Ozgo M, Skrzypczak W, Drzezdzon D, Lepczynski A, Dratwa Chalupnik A, Michalek K, et al. Urinary excretion of low molecular weight proteins in goats during the neonatal period. J Physiol Pharmacol. 2009;60 Suppl 3:119-25 pubmed
    ..The urinary LMW protein pool may also contain proteins resulting from the hydrolysis in the tubular cells. ..
  14. Ponce Monter H, Campos Lara G, Pedron N, De la Torre L, Villaneuva T, Gallegos A, et al. The zoapatle. XV. Activity of 16 alpha-hydroxy-ent-kauran-19-oic acid isolated from Montanoa hibiscifolia, and its methyl ester on rat and guinea pig uterus. J Ethnopharmacol. 1988;24:127-34 pubmed
    ..Such effects were observed using bath concentrations of 6, 15, 30 and 60 microM of each compound. ..
  15. Perrine S, Schroeder J, Unterwald E. Behavioral sensitization to binge-pattern cocaine administration is not associated with changes in protein levels of four major G-proteins. Brain Res Mol Brain Res. 2005;133:224-32 pubmed
    ..These results suggest that alterations in the level of G-proteins are not necessary for the development of cocaine-induced sensitization. ..
  16. Mu L, Li J, Yang J, Zhang D. New dibenz[b, f]oxepins from Cercis chinensis Bunge. J Asian Nat Prod Res. 2007;9:649-53 pubmed
    Three new dibenz[b,f]oxepins: 6-methoxy-7-methyl-8-hydroxydibenz[b, f]oxepin (1), 1,8-dimethoxy-6-hydroxy-7-methyldibenz[b, f]oxepin (2), and 1-hydroxy-6,8-dimethoxy-7-methyldibenz[b,f]oxepin (3), along with two known dibenz[b,f]oxepins ..
  17. Wu Y, Zhang Y, Toyn J, Macor J, Thompson L. Synthesis of pyrimido[4,5-c]azepine- and pyrimido[4,5-c]oxepine-based γ-secretase modulators. Bioorg Med Chem Lett. 2016;26:1554-1557 pubmed publisher
    ..These chlorides were applied to the synthesis of several potent γ-secretase modulators (GSMs). ..
  18. Tandon V, Kumar M, Awasthi A, Saxena H, Goswamy G. Potential hypotensive agents: synthesis and hypotensive activity of oxime ethers derived from 1-naphthoxepines and related compounds. Bioorg Med Chem Lett. 2004;14:3177-80 pubmed
    ..The hypotensive activity of oximino-ethers 1 and 2 was evaluated on anaesthetized cats. The results indicated that 1c caused a fall of 80 mm/Hg for >100' at a dose of 5mg/kg iv in anaesthetized cats. ..
  19. Ankisetty S, ElSohly H, Li X, Khan S, Tekwani B, Smillie T, et al. Aromatic constituents of Uvaria grandiflora. J Nat Prod. 2006;69:692-4 pubmed
    ..Only compound 1 exhibited antileishmanial activity, with IC(50)/IC(90) values of 0.7/1.5 microg/mL. The positive controls pentamidine and amphotericin B had IC(50)/IC(90) values of 1.6/6.6 and 0.17/0.34 microg/mL, respectively. ..
  20. Hara M, Thomas B, Cascio M, Bae B, Hester L, Dawson V, et al. Neuroprotection by pharmacologic blockade of the GAPDH death cascade. Proc Natl Acad Sci U S A. 2006;103:3887-9 pubmed
    ..In mice treated with the dopamine neuronal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), low doses of deprenyl prevent binding of GAPDH and Siah1 in the dopamine-enriched corpus striatum...
  21. Hayashida M, Ishizaki M, Hara H. Investigation of selective mono-deallylation of O,O'-diallylcatechols and 3-methylene-1,5-benzodioxepanes. Chem Pharm Bull (Tokyo). 2006;54:1299-303 pubmed
    ..On the other hand, an electron-donating group did not cause any selectivity. ..
  22. Lohézic Le Dévéhat F, Tomasi S, Elix J, Bernard A, Rouaud I, Uriac P, et al. Stictic acid derivatives from the lichen Usnea articulata and their antioxidant activities. J Nat Prod. 2007;70:1218-20 pubmed
    ..The depsidones 4 and 5 showed better superoxide anion scavenging activity (IC50 = 566 and 580 microM, respectively) than quercetin (IC50 = 754 microM)...
  23. Asami Y, Jang J, Soung N, He L, Moon D, Kim J, et al. Protuboxepin A, a marine fungal metabolite, inducing metaphase arrest and chromosomal misalignment in tumor cells. Bioorg Med Chem. 2012;20:3799-806 pubmed publisher
    ..These results indicate that protuboxepin A has a potential of being a new and effective anti-cancer drug. ..
  24. Rossington S, Hadfield J, Shnyder S, Wallace T, Williams K. Tubulin-binding dibenz[c,e]oxepines: Part 2. Structural variation and biological evaluation as tumour vasculature disrupting agents. Bioorg Med Chem. 2017;25:1630-1642 pubmed publisher
  25. Hamilton K, Harris A, Gewirtz J, Sparber S, Schrott L. HPA axis dysregulation following prenatal opiate exposure and postnatal withdrawal. Neurotoxicol Teratol. 2005;27:95-103 pubmed
    ..These results suggest that prenatal opiate exposure followed by postnatal withdrawal dysregulated the HPA axis response to stressors in the neonate and adult and differentially affected adult anxiety-like behavior in males and females. ..
  26. Trabanco A, Alonso J, Cid J, Font L, Megens A. Synthesis of 2-N,N-dimethylaminomethyl-2,3,3a,12b-tetrahydrodibenzo[b,f]furo[2,3-d]oxepine derivatives as potential anxiolytic agents. Part 2: substitutions by methyl groups on the tetrahydrofuran ring. Farmaco. 2005;60:241-8 pubmed
    ..Preliminary pharmacological data of the newly synthesised compounds are also communicated. ..
  27. Fujiwara H, Kurogi T, Okaya S, Okano K, Tokuyama H. Total synthesis of (-)-acetylaranotin. Angew Chem Int Ed Engl. 2012;51:13062-5 pubmed publisher
    ..Acetylaranotin is obtained in 22 steps from commercially available L-Cbz-tyrosine (Cbz=benzyloxycarbonyl). ..
  28. Zimmermann K, Roggo S, Kragten E, Furst P, Waldmeier P. Synthesis of tools for target identification of the anti-apoptotic compound CGP 3466; Part I. Bioorg Med Chem Lett. 1998;8:1195-200 pubmed
  29. LeWitt P. Clinical trials of neuroprotection for Parkinson's disease. Neurology. 2004;63:S23-31 pubmed
  30. Kamei S, Oga K, Matsuura M, Tanaka N, Kojima T, Arakawa Y, et al. Correlation between quantitative-EEG alterations and age in patients with interferon-alpha-treated hepatitis C. J Clin Neurophysiol. 2005;22:49-52 pubmed
    ..0001). The alterations of EEG occurring during IFN-alpha treatment were marked in older patients. ..
  31. Sonda S, Katayama K, Fujio M, Sakashita H, Inaba K, Asano K, et al. 1,5-Benzodioxepin derivatives as a novel class of muscarinic M3 receptor antagonists. Bioorg Med Chem Lett. 2007;17:925-31 pubmed
    ..These compounds displayed selectivity for the bladder over the salivary gland. ..
  32. Fu L, Wang S, Wang X, Wang P, Zheng Y, Yao D, et al. Crystal structure-based discovery of a novel synthesized PARP1 inhibitor (OL-1) with apoptosis-inducing mechanisms in triple-negative breast cancer. Sci Rep. 2016;6:3 pubmed publisher
    ..These findings highlight a new small-molecule PAPR1 inhibitor (OL-1) that has the potential to impact future TNBC therapy. ..
  33. Laufer S, Ahrens G, Karcher S, Hering J, Niess R. Design, synthesis, and biological evaluation of phenylamino-substituted 6,11-dihydro-dibenzo[b,e]oxepin-11-ones and dibenzo[a,d]cycloheptan-5-ones: novel p38 MAP kinase inhibitors. J Med Chem. 2006;49:7912-5 pubmed
    ..Synthesis, p38 inhibition, and CYP-inhibition of selected compounds are described. ..
  34. Castaldi M, Troast D, Porco J. Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations. Org Lett. 2009;11:3362-5 pubmed publisher
    ..The synthesis of spirocyclic oxindole pyran and oxepene frameworks using highly stereoselective Prins cyclizations of homoallylic and bis-homoallylic alcohols and isatin ketals is described. ..
  35. de Paz G, Raggio J, Gómez Serranillos M, Palomino O, González Burgos E, Carretero M, et al. HPLC isolation of antioxidant constituents from Xanthoparmelia spp. J Pharm Biomed Anal. 2010;53:165-71 pubmed publisher
  36. McDonald F, Wang X, Do B, Hardcastle K. Synthesis of oxepanes and trans-fused bisoxepanes via biomimetic, endo-regioselective tandem oxacyclizations of polyepoxides. Org Lett. 2000;2:2917-9 pubmed
    ..A mechanism for these biomimetic oxacyclizations is proposed in which the epoxides act as both electrophilic and nucleophilic reaction partners. ..
  37. Teufel R, Gantert C, Voss M, Eisenreich W, Haehnel W, Fuchs G. Studies on the mechanism of ring hydrolysis in phenylacetate degradation: a metabolic branching point. J Biol Chem. 2011;286:11021-34 pubmed publisher
    ..Apparently, bacteria made a virtue out of the necessity of disposing the dead-end product with ring hydrolysis as a metabolic branching point...
  38. Pan C, Liu F, Ji Q, Wang W, Drinkwater D, Vivilecchia R. The use of LC/MS, GC/MS, and LC/NMR hyphenated techniques to identify a drug degradation product in pharmaceutical development. J Pharm Biomed Anal. 2006;40:581-90 pubmed
    ..The combination approach is critical for unambiguous impurity structure elucidation in drug degradation studies of pharmaceutical drug products. ..
  39. Frey S, Funnell M, Gerry V, Gazzaniga M. A dissociation between the representation of tool-use skills and hand dominance: insights from left- and right-handed callosotomy patients. J Cogn Neurosci. 2005;17:262-72 pubmed
    ..This effect is not attributable to differences at the conceptual level, as the left and right hemispheres are equally and highly competent at associating tools with observed pantomimes (Experiment 4). ..
  40. Wagner A, Cloos P, Bergholdt R, Boissy P, Andersen T, Henriksen D, et al. Post-translational protein modifications in type 1 diabetes: a role for the repair enzyme protein-L-isoaspartate (D-aspartate) O-methyltransferase?. Diabetologia. 2007;50:676-81 pubmed
    ..05 for high-dose vs control group) in the treated animals. The results support a role for post-translational modifications and PIMT in the development of type 1 diabetes in the diabetes-prone BB rat, and perhaps also in humans. ..
  41. Xiong X, Zhao D, Bu P, Liu Y, Ren J, Wang J, et al. CoMFA, CoMSIA and eigenvalue analysis on dibenzodioxepinone and dibenzodioxocinone derivatives as cholesteryl ester transfer protein inhibitors. Molecules. 2008;13:1822-39 pubmed
    ..These derived models may help us to gain a deeper understanding of the binding interaction of these lactone-based compounds and aid in the design of new potent compounds against CETP. ..
  42. Ban C, Twigg S, Franjic B, Brooks B, Celermajer D, Yue D, et al. Serum MMP-7 is increased in diabetic renal disease and diabetic diastolic dysfunction. Diabetes Res Clin Pract. 2010;87:335-41 pubmed publisher
    ..How increased circulating MMP-7 is associated with these diabetic microvascular complications and the significance of these findings will require prospective studies. ..
  43. Codelli J, Puchlopek A, REISMAN S. Enantioselective total synthesis of (-)-acetylaranotin, a dihydrooxepine epidithiodiketopiperazine. J Am Chem Soc. 2012;134:1930-3 pubmed publisher
    ..We anticipate that the approach described herein will serve as a general strategy for the synthesis of additional members of the dihydrooxepine ETP family. ..
  44. George S, George A, Stein P, Rolfe P, Hosking B, Seewald W. The comparative efficacy of abamectin, monepantel and an abamectin/derquantel combination against fourth-stage larvae of a macrocyclic lactone-resistant Teladorsagia spp. isolate infecting sheep. Vet Parasitol. 2012;188:190-3 pubmed publisher
  45. Geurden T, Hodge A, Noé L, Winstanley D, Bartley D, Taylor M, et al. The efficacy of a combined oral formulation of derquantel-abamectin against anthelmintic resistant gastro-intestinal nematodes of sheep in the UK. Vet Parasitol. 2012;189:308-16 pubmed publisher
    ..circumcincta was the most abundant worm species after treatment (52-99% of the larvae). The results of these studies confirm the high efficacy of the DQL+ABA combination formulation against anthelmintic resistant nematodes in the UK. ..
  46. Sager H, Bapst B, Strehlau G, Kaminsky R. Efficacy of monepantel, derquantel and abamectin against adult stages of a multi-resistant Haemonchus contortus isolate. Parasitol Res. 2012;111:2205-7 pubmed publisher
    ..While monepantel resulted in 100 % elimination, derquantel in combination with abamectin resulted in efficacies <95 % (faecal egg counts and worm counts). ..
  47. Trabanco A, Alonso J, Andrés J, Cid J, Fernandez J, Iturrino L, et al. Synthesis of 2-N,N-dimethylaminomethyl-2,3,3a,12b-tetrahydrodibenzo-[b,f]furo[2,3-d]oxepin derivatives as potential anxiolytic agents. Chem Pharm Bull (Tokyo). 2004;52:262-5 pubmed
    ..According to preliminary data these novel tetracycles can be useful intermediates for the preparation of potential new therapeutic agents. ..
  48. Heine V, Zareno J, Maslam S, Joels M, Lucassen P. Chronic stress in the adult dentate gyrus reduces cell proliferation near the vasculature and VEGF and Flk-1 protein expression. Eur J Neurosci. 2005;21:1304-14 pubmed
    ..This demonstrates that changes in angiogenic factors are implicated in the decreased adult proliferation found after chronic stress. ..
  49. Stuber G, Wightman R, Carelli R. Extinction of cocaine self-administration reveals functionally and temporally distinct dopaminergic signals in the nucleus accumbens. Neuron. 2005;46:661-9 pubmed
  50. Amewu R, Stachulski A, Berry N, Ward S, Davies J, Labat G, et al. Synthesis of 1,2,4-trioxepanes via application of thiol-olefin co-oxygenation methodology. Bioorg Med Chem Lett. 2006;16:6124-30 pubmed
    ..FMO calculations clearly show that the sigma* orbital of the peroxide moiety of 1,2,4-trioxane derivatives 4a and 14b are lower in energy and more accessible to attack by Fe(II) compared to their trioxepane analogues 8b and 9b. ..
  51. Musthapa I, Juliawaty L, Syah Y, Hakim E, Latip J, Ghisalberti E. An oxepinoflavone from Artocarpus elasticus with cytotoxic activity against P-388 cells. Arch Pharm Res. 2009;32:191-4 pubmed publisher
    ..The structure of the new compound was identified by spectroscopic methods. Upon cytotoxic evaluation against murine leukemia P-388 cells, the new compound showed IC(50) 5.0 microg/mL...
  52. Chen J, Zhang H, Chen L, Wu B. New stress metabolite from Bulbophyllum kwangtungense. Nat Prod Commun. 2011;6:53-4 pubmed
    ..The structure of 1 was established by spectroscopic and spectrometric means. ..
  53. Peczuh M, Snyder N, Sean Fyvie W. Synthesis, crystal structure, and reactivity of a D-xylose based oxepine. Carbohydr Res. 2004;339:1163-71 pubmed
    ..Spectroscopic data of methyl 2,3,4,5-tetra-O-acetyl-alpha-D-idoseptanoside, derived from the methanolysis product 11, was compared to data of its enantiomer, the known methyl 2,3,4,5-tetra-O-acetyl-alpha-L-idoseptanoside. ..
  54. Fyvie W, Morton M, Peczuh M. Synthesis of 2-iodo-2-deoxy septanosides from a D-xylose-based oxepine: intramolecular cyclization in the absence of a glycosyl acceptor. Carbohydr Res. 2004;339:2363-70 pubmed
    ..When limited equivalents of a glycosyl acceptor were used, or in the absence of a glycosyl acceptor, an intramolecular cyclization predominated to form 1,6-anhydro-3,4-di-O-benzyl-2-deoxy-2-iodo-alpha-D-idopyranose (10). ..
  55. Ji J, Dheen S, Kumar S, He B, Tay S. Expressions of cytokines and chemokines in the dorsal motor nucleus of the vagus nerve after right vagotomy. Brain Res Mol Brain Res. 2005;142:47-57 pubmed
    ..However, it warrants further investigation to understand the neurodestructive and neuroprotective mechanisms that determine the fate of the vagal motoneurons after vagotomy. ..
  56. Sabatino D, Damha M. Synthesis and properties of oligonucleotides containing a 7-membered (oxepane) sugar ring. Nucleosides Nucleotides Nucleic Acids. 2007;26:1185-8 pubmed
    ..Coli RNase H. Thus the oxepane nucleic acids reported here are one of only a handful of DNA mimics capable of activating RNase H when bound to RNA. ..
  57. Batchelor R, Harvey J, Northcote P, Teesdale Spittle P, Hoberg J. Heptanosides from galactose-derived oxepenes via stereoselective addition reactions. J Org Chem. 2009;74:7627-32 pubmed publisher
    ..The 3,4-anhydroheptanose used in this study is obtained from the ring-expansion of a cyclopropanated galactal and thus demonstrates the synthetic utility of heptanose synthesis via cyclopropanated carbohydrates. ..
  58. Hewitt R, Harvey J. Synthesis of oxepines and 2-branched pyranosides from a d-glucal-derived gem-dibromo-1,2-cyclopropanated sugar. J Org Chem. 2010;75:955-8 pubmed publisher
    ..In contrast, cyclopropane ring cleavage under basic conditions leads to 2-C-branched pyranosides, not the 2-bromooxepine structures assigned in an earlier report. ..
  59. Wassman C, Baronio R, Demir O, Wallentine B, Chen C, Hall L, et al. Computational identification of a transiently open L1/S3 pocket for reactivation of mutant p53. Nat Commun. 2013;4:1407 pubmed publisher
    ..These results indicate the L1/S3 pocket as a target for pharmaceutical reactivation of p53 mutants. ..
  60. Yu Q, Sali A, van der Meulen J, Creeden B, Gordish Dressman H, Rutkowski A, et al. Omigapil treatment decreases fibrosis and improves respiratory rate in dy(2J) mouse model of congenital muscular dystrophy. PLoS ONE. 2013;8:e65468 pubmed publisher
    ..1 mg/kg) improved respiratory rate and decreased skeletal and respiratory muscle fibrosis in dy(2J) mice. These results support a putative role for the use of omigapil in laminin deficient congenital muscular dystrophy patients. ..
  61. Braca A, Cioffi G, Morelli I, Venturella F, Pizza C, De Tommasi N. Two new sesquiterpene lactones from Montanoa tomentosa ssp. microcephala. Planta Med. 2001;67:774-6 pubmed
    ..in La Llave et Lex ssp. microcephala (Sch. Bip. In K. Koch) V.A. Funk (Asteraceae). The structures of all compounds were established on the basis of 1D, 2D NMR, and EIMS analysis. ..
  62. Taillier C, Bellosta V, Cossy J. Total synthesis of natural (+)-(2's,3'r)-zoapatanol. Org Lett. 2004;6:2149-51 pubmed
  63. Groeneveld G, van Muiswinkel F, de Leeuw van Weenen J, Blauw H, Veldink J, Wokke J, et al. CGP 3466B has no effect on disease course of (G93A) mSOD1 transgenic mice. Amyotroph Lateral Scler Other Motor Neuron Disord. 2004;5:220-5 pubmed
    ..We also did not observe a significant effect on the number of motor neurons due to CGP 3466B. We conclude that in high-copy G93A mSOD1 mice, chronic subcutaneous treatment with CGP 3466B offers no clinical benefit. ..
  64. Leonard S, Alizadeh Naderi R, Stokes K, Ferkin M. The role of prolactin and testosterone in mediating seasonal differences in the self-grooming behavior of male meadow voles, Microtus pennsylvanicus. Physiol Behav. 2005;85:461-8 pubmed
    ..In contrast, the endocrine tissues that underlie self-grooming in SP male meadow voles appear to be refractory to the effects of LP-equivalent titers of PRL and T. ..
  65. Boeck C, Kroth E, Bronzatto M, Jardim F, Souza D, Vendite D. Effects of glutamate transporter and receptor ligands on neuronal glutamate uptake. Neurosci Res. 2005;53:77-83 pubmed
    ..The possible involvement of this modulation after certain neurotoxicity insults is discussed. ..
  66. Kalin N, Shelton S, Davidson R. Role of the primate orbitofrontal cortex in mediating anxious temperament. Biol Psychiatry. 2007;62:1134-9 pubmed
    ..Because of the similarities between rhesus monkey threat-induced freezing and childhood behavioral inhibition, these findings are relevant to understanding mechanisms underlying anxious temperament in humans. ..
  67. Morgan J, Greenberg A. Insights into the formation and isomerization of the benzene metabolite muconaldehyde and related molecules: comparison of computational and experimental studies of simple, benzo-annelated, and bridged 2,3-epoxyoxepins. J Org Chem. 2010;75:4761-8 pubmed publisher
    ..The results are compared with published experimental data. The markedly different fates of these three molecules suggest a means for testing the postulated metabolic pathway. ..
  68. Meinen S, Lin S, Thurnherr R, Erb M, Meier T, Ruegg M. Apoptosis inhibitors and mini-agrin have additive benefits in congenital muscular dystrophy mice. EMBO Mol Med. 2011;3:465-79 pubmed publisher
  69. Lin H, Xu L, Liu H, Sun Q, Chen Z, Yuan G, et al. KLF4 promotes the odontoblastic differentiation of human dental pulp cells. J Endod. 2011;37:948-54 pubmed publisher
    ..Our findings suggest that KLF4 is able to promote odontoblastic differentiation of hDPCs and inhibit proliferation of hDPCs. ..
  70. Arakawa K, Endo Y, Kimura M, Yoshida T, Kitaoka T, Inakazu T, et al. Multifunctional anti-angiogenic activity of the cyclic peroxide ANO-2 with antitumor activity. Int J Cancer. 2002;100:220-7 pubmed
  71. Crimmins M, DeBaillie A. Enantioselective total synthesis of (+)-rogioloxepane A. Org Lett. 2003;5:3009-11 pubmed
    ..The key steps in the synthesis are an asymmetric glycolate alkylation leading to the diene 2 and a subsequent ring-closing metathesis to construct the oxepene core. ..
  72. Abbott C, Monteiro M, Small C, Sajedi A, Smith K, Parkinson J, et al. The inhibitory effects of peripheral administration of peptide YY(3-36) and glucagon-like peptide-1 on food intake are attenuated by ablation of the vagal-brainstem-hypothalamic pathway. Brain Res. 2005;1044:127-31 pubmed
    ..These findings suggest that the vagal-brainstem-hypothalamic pathway may also play a role in the effects of circulating PYY(3-36) and GLP-1 on food intake. ..
  73. Barnes S, Hua J, Pinel J, Takahashi A, Wig G. Conditioned effects of kindling three different sites in the hippocampal complex of the rat. Behav Neurosci. 2005;119:1572-9 pubmed
  74. Castro S, Cherney E, Snyder N, Peczuh M. Synthesis of substituted septanosyl-1,2,3-triazoles. Carbohydr Res. 2007;342:1366-72 pubmed
    ..Hydrogenolysis of benzyl protecting groups gave substituted septanosyl-1,2,3-triazoles. The new septanose-based structures were then evaluated as potential glycosidase inhibitors. ..
  75. Ognibene E, Adriani W, Caprioli A, Ghirardi O, Ali S, Aloe L, et al. The effect of early maternal separation on brain derived neurotrophic factor and monoamine levels in adult heterozygous reeler mice. Prog Neuropsychopharmacol Biol Psychiatry. 2008;32:1269-76 pubmed publisher
    ..The modulatory effects of a chronic treatment with the atypical antipsychotic olanzapine (OLZ, 1.5 mg/kg for 40 days) were also investigated...
  76. Golding B, Barnes M, Bleasdale C, Henderson A, Jiang D, Li X, et al. Modeling the formation and reactions of benzene metabolites. Chem Biol Interact. 2010;184:196-200 pubmed publisher
    ..The observations presented may be relevant to the toxicology of benzene oxide-oxepin and other arene oxide-oxepins as we have previously shown that (E,Z)-muconaldehyde, analogously to (Z,Z)-muconaldehyde, affords pyrrole adducts ..
  77. Arruda Carvalho M, Sakaguchi M, Akers K, Josselyn S, Frankland P. Posttraining ablation of adult-generated neurons degrades previously acquired memories. J Neurosci. 2011;31:15113-27 pubmed publisher
    ..These retrograde effects suggest that adult-generated neurons form a critical and enduring component of hippocampal memory traces. ..
  78. Pedron N, Wens M, García Pineda J, Estrada A, Ponce Monter H, Gallegos A. The zoapatle XIV--the effect of oral administration of zoapatle upon progesterone plasma levels in pregnant rabbits. Contraception. 1988;38:373-9 pubmed
    ..Pregnancy and delivery were similar in controls and zoapatle-treated animals. ..
  79. Nasveschuk C, Rovis T. Stereoselective Lewis acid mediated [1,3] ring contraction of 2,5-dihydrooxepins as a route to polysubstituted cyclopentenes. Angew Chem Int Ed Engl. 2005;44:3264-7 pubmed
  80. Kobayashi S, Hori M, Hirama M. Synthesis of trans-fused tetrahydrooxepins: stereoselective allylation of sulfur or fluoro-substituted tetrahydrooxepins. Carbohydr Res. 2008;343:443-52 pubmed
  81. Krohn K, Kouam S, Kuigoua G, Hussain H, Cludius Brandt S, Flörke U, et al. Xanthones and oxepino[2, 3-b]chromones from three endophytic fungi. Chemistry. 2009;15:12121-32 pubmed publisher
    ..Preliminary studies indicated that 1, 2, and enone 7 showed antibacterial, fungicidal, and algicidal properties. ..
  82. Learmount J, Taylor M, Bartram D. A computer simulation study to evaluate resistance development with a derquantel-abamectin combination on UK sheep farms. Vet Parasitol. 2012;187:244-53 pubmed publisher
  83. Nicolaou K, Yu R, Shi L, Cai Q, Lu M, Heretsch P. General synthetic approach to functionalized dihydrooxepines. Org Lett. 2013;15:1994-7 pubmed publisher
    ..This approach features a regioselective Baeyer-Villiger oxidation and subsequent functionalization via the corresponding enol phosphate intermediate. ..
  84. Muhammad A, Sirat H. Potent microbial and tyrosinase inhibitors from stem bark of Bauhinia rufescens (Fabaceae). Nat Prod Commun. 2013;8:1435-7 pubmed
    ..In the tyrosinase inhibition assay, a-amyrin acetate was found to be moderately active against tyrosinase with an inhibition of 62% at 0.1 mg/mL. This activity was lower than that of the positive control, kojic acid (85%)...
  85. Wang J, He W, Huang X, Tian X, Liao S, Yang B, et al. Antifungal New Oxepine-Containing Alkaloids and Xanthones from the Deep-Sea-Derived Fungus Aspergillus versicolor SCSIO 05879. J Agric Food Chem. 2016;64:2910-6 pubmed publisher
    ..4 ?g/mL). The results of antifungal experiments indicated that versicoloids A and B may be regarded as candidate agents of antifungal agrochemicals. ..
  86. Waldmeier P, Spooren W, Hengerer B. CGP 3466 protects dopaminergic neurons in lesion models of Parkinson's disease. Naunyn Schmiedebergs Arch Pharmacol. 2000;362:526-37 pubmed
    ..In addition, treatment with CGP 3466 resulted in improved skilled motor performance in 6-OHDA-lesioned rats. ..
  87. Rodrigues J, Abramovitch R, de Sousa J, Leiva G. Diastereoselective synthesis of cularine alkaloids via enium ions and an easy entry to isoquinolines by aza-Wittig electrocyclic ring closure. J Org Chem. 2004;69:2920-8 pubmed
    ..We now report the full details of the syntheses of (+)-O-demethylcularine, (+)-cularine, (+)-sarcocapnidine, (+)-sarcocapnine, and (+)-crassifoline and describe different methods of synthesis of their precursors. ..
  88. Medina A, Krahe T, Ramoa A. Early alcohol exposure induces persistent alteration of cortical columnar organization and reduced orientation selectivity in the visual cortex. J Neurophysiol. 2005;93:1317-25 pubmed
    ..These findings indicate that alcohol exposure during a brief period of development disrupts cortical processing of sensory information at a later age and suggest a neurobiological substrate for some types of sensory deficits in FAS. ..
  89. Babot Z, Cristofol R, Suñol C. Excitotoxic death induced by released glutamate in depolarized primary cultures of mouse cerebellar granule cells is dependent on GABAA receptors and niflumic acid-sensitive chloride channels. Eur J Neurosci. 2005;21:103-12 pubmed
  90. Luo W, Yu Q, Holloway H, Parrish D, Greig N, Brossi A. Syntheses of tetrahydrofurobenzofurans and dihydromethanobenzodioxepines from 5-hydroxy-3-methyl-3H-benzofuran-2-one. Rearrangement and ring expansion under reductive conditions on treatment with hydrides. J Org Chem. 2005;70:6171-6 pubmed
    ..Specific carbamates of phenols, 10 and 14, have shown impressive inhibitory activities against human acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) ex vivo. ..
  91. Boyd D, Sharma N, Harrison J, Malone J, McRoberts W, Hamilton J, et al. Enzyme-catalysed synthesis and reactions of benzene oxide/oxepine derivatives of methyl benzoates. Org Biomol Chem. 2008;6:1251-9 pubmed publisher
  92. Yuan T, Yang S, Zhang H, Liao S, Wang W, Wu Y, et al. Phenolic compounds with cell protective activity from the fruits of Livistona chinensis. J Asian Nat Prod Res. 2009;11:243-9 pubmed publisher
    ..The structures of the new compounds were determined by spectroscopic methods. Compounds 1, 4-6 exhibited remarkable cell protective activities against H(2)O(2)-induced SH-SY5Y cell damage. ..