99522-34-6

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 540-38-5 p-Iodophenol 
• 182281-01-2 4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid 

Downstream Products

• 119754-13-1 1-[(tetrahydro-2H-pyran-2-yl)oxy]-4-[3-hydroxy-3-methylbut-1-ynyl]benzene 
• 150508-72-8 trimethyl{[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]ethynyl}silane 
• 864757-75-5 4-(benzyloxy)-1-[4-(tetrahydro-2H-pyran-2-yloxy)-phenyl]pyridin-2(1H)-one 
• 134142-88-4 2-[(4-trifluoromethyl)phenoxy]tetrahydro-2H-pyrane 
• 618913-07-8 4-[(2,3,4-tridodecyloxy)phenylethynyl]-O-(tetrahydropyran-2-yl)phenol 
• 312624-89-8 (4-{2,5-dihexyl-4-[4-(tetrahydro-pyran-2-yloxy)-phenylethynyl]-phenylethynyl}-2,5-dihexyl-phenylethynyl)-triisopropyl-silane 
• 312624-88-7 {2,5-dihexyl-4-[4-(tetrahydro-pyran-2-yloxy)-phenylethynyl]-phenylethynyl}-triisopropyl-silane 

Relevant academic research and scientific papers

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable ipso-iododeboronation procedure that uses NIS in the non-toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter-expressing tumours.

Effect of isouronium/guanidinium substitution on the efficacy of a series of novel anti-cancer agents

Considering our hypothesis that the guanidinium moiety in the protein kinase type III inhibitor 1 interacts with a phosphate of ATP within the hinge region, the nature of the interactions established between a model isouronium and the phosphate groups of ATP was computationally analysed indicating that an isouronium derivative of 1 will interact in a similar manner with ATP. Thus, a number of compounds were prepared to assess the effect of the guanidinium/isouronium substitution on cancer cell growth; additionally, the molecular shortening and conformational change induced by replacing the di-substituted guanidine-linker of 1 by an amide was explored. The effect of these compounds on cell viability was tested in human leukaemia, breast cancer and cervical cancer cell lines and the resulting IC50 values were compared with those of the lead compound 1. Replacement of the di-substituted guanidine-linker by an amide results in the loss of cytotoxicity; however, substitution of the mono-substituted guanidinium by an isouronium cation seems to be beneficial for cell growth inhibition. Additionally, the effect of these compounds on the MAPK/ERK pathway was studied by means of Western blotting and the results indicate that the isouronium derivative 2 decreases the levels of phosphorylated, and thus activated, ERK (pERK) both in leukaemia and breast cancer cells, whereas lead compound 1 only shows an effect on pERK levels in breast cancer cells. This confirms that both compounds could interfere with the MAPK/ERK pathway although other targets cannot be ruled out.

Synthesis and spectroscopic properties of photochromic dithienylethene-functionalized subphthalocyanine conjugate

A subphthalocyanine-dithienylethene dyad has been synthesized and characterized by 1H-, 13C-NMR, HR-MS, UV-visible and emission spectroscopy. The results show that photoinduced isomerization of dithienylethene moiety from close-form to opened form can be achieved under visible light using subphthalocyanine as a light-harvesting unit and the fluorescence properties of subphthalocyanine could be modulated by the isomerization state of the dithienylethene moiety.

Polymerizable liquid crystal compound

PROBLEM TO BE SOLVED: To provide a polymerizable compound giving high refractive index anisotropy, a wide liquid crystal phase temperature range and high storage stability to a liquid crystal composition and producing a polymer film having high pattern resolution, high heat resistance, and little haze and white irregularity when polymerizing the liquid crystal composition. SOLUTION: The polymerizable compound is represented by general formula (I). The polymerizable liquid crystal composition contains the polymerizable compound as a structural member. COPYRIGHT: (C)2013,JPOandINPIT

Synthesis, structure, and SAR of tetrahydropyran-based LpxC inhibitors

In the search for novel Gram-negative agents, we performed a comprehensive search of the AstraZeneca collection and identified a tetrahydropyran-based matrix metalloprotease (MMP) inhibitor that demonstrated nanomolar inhibition of UDP-3-O-(acyl)-N-acetylglucosamine deacetylase (LpxC). Crystallographic studies in Aquifex aeolicus LpxC indicated the tetrahydropyran engaged in the same hydrogen bonds and van der Waals interactions as other known inhibitors. Systematic optimization of three locales on the scaffold provided compounds with improved Gram-negative activity. However, the optimization of LpxC activity was not accompanied by reduced inhibition of MMPs. Comparison of the crystal structure of the native product, UDP-3-O-(acyl)-glucosamine, in Aquifex aeolicus to the structure of a tetrahydropyran-based inhibitor indicates pathways for future optimization.

Solvent-free NaHSO4-SiO2-catalyzed efficient tetrahydropyranylation of alcohols and phenols

A simple and efficient tetrahydropyranylation of alcohols and phenols has been developed using NaHSO4-SiO2 (0.5 mol%) as a catalyst under solvent-free conditions to yield corresponding tetrahydropyranyl ethers in excellent yields.

NOVEL ARYLALKENE DERIVATIVES AND USE THEREOF AS SELECTIVE ESTROGEN RECEPTOR MODULATORS

The invention provides novel ethylene derivatives represented by Formula I, which may be used as selective estrogen receptor modulators (SERMs) and useful in the prophylaxis and/or treatment of estrogen-dependent conditions or conditions.

Simple and efficient method for tetrahydropyranylation of alcohols and phenols by using silica supported sodium hydrogen sulphate as a catalyst

A Simple and efficient process for tetrahydropyranylation of alcohols and phenols has been developed by reacting with dihydropyran at room temperature in presence of catalytic amount of silica supported sodium hydrogen sulphate.

Synthesis and characterization of light-driven dithienylcyclopentene switches with axial chirality

Three new photochemically reversible but thermally stable dithienylcyclopentene switches with axial chirality were synthesized and characterized. All the compounds exhibited photochemically reversible isomerization with thermal stability between its open form and closed form in both organic solvent and liquid crystal host. Their photoresponsive behaviors in organic solvents were characterized by 1H NMR, UV-vis, and CD spectra. These chiral molecular switches were found not only to be able to act as a chiral dopant and induce a helical superstructure in an achiral liquid crystal host but also to be able to reversibly and dynamically tune the transmittance and reflection of the resulting chiral phase upon light irradiation. The helical twisting powers, transmittance, and reflection spectra of photoswitchable cholesteric LCs were measured. Dopant 1 exhibited an unusually high helical twisting power, which is significantly larger than those of the known chiral diarylethenes reported as chiral dopants so far.

Solid-phase combinatorial synthesis of ester-type banana-shaped molecules by sequential palladium-catalyzed carbonylation

16 five-ring ester-type Br-substituted banana-shaped molecules were synthesized in a combinatorial manner using palladium-catalyzed carbonylative esterification on a polymer-support and their mesophase behavior was investigated. The Royal Society of Chemistry 2009.