- Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes
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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.
- Webster, Stacey,O'Rourke, Kerry M.,Fletcher, Conor,Pimlott, Sally L.,Sutherland, Andrew,Lee, Ai-Lan
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supporting information
p. 937 - 943
(2017/12/26)
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- Effect of isouronium/guanidinium substitution on the efficacy of a series of novel anti-cancer agents
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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.
- Previtali, Viola,Trujillo, Cristina,Amet, Rebecca,Zisterer, Daniela M.,Rozas, Isabel
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supporting information
p. 735 - 743
(2018/05/04)
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- Synthesis and spectroscopic properties of photochromic dithienylethene-functionalized subphthalocyanine conjugate
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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.
- Shi, Maohu,Chen, Jingzhi,Shen, Zhen
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p. 1082 - 1089
(2016/12/14)
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- Polymerizable liquid crystal compound
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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
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Paragraph 0133; 0134
(2019/04/02)
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- Synthesis, structure, and SAR of tetrahydropyran-based LpxC inhibitors
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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.
- Murphy-Benenato, Kerry E.,Olivier, Nelson,Choy, Allison,Ross, Philip L.,Miller, Matthew D.,Thresher, Jason,Gao, Ning,Hale, Michael R.
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supporting information
p. A1213 - A1218
(2015/04/27)
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- Solvent-free NaHSO4-SiO2-catalyzed efficient tetrahydropyranylation of alcohols and phenols
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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.
- Kinfe, Henok H.,Mebrahtu, Fanuel M.,Moshapo, Paseka T.
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p. 1237 - 1242
(2013/04/10)
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- NOVEL ARYLALKENE DERIVATIVES AND USE THEREOF AS SELECTIVE ESTROGEN RECEPTOR MODULATORS
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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.
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Paragraph 0197; 0315
(2013/07/19)
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- Simple and efficient method for tetrahydropyranylation of alcohols and phenols by using silica supported sodium hydrogen sulphate as a catalyst
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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.
- Ravi Kumar,Satyanarayana,Srinivasa Reddy
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experimental part
p. 3876 - 3878
(2012/09/21)
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- Synthesis and characterization of light-driven dithienylcyclopentene switches with axial chirality
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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.
- Li, Yannian,Urbas, Augustine,Li, Quan
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experimental part
p. 7148 - 7156
(2011/10/31)
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- Solid-phase combinatorial synthesis of ester-type banana-shaped molecules by sequential palladium-catalyzed carbonylation
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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.
- Yoshida, Masahito,Doi, Takayuki,Kang, Sungmin,Watanabe, Junji,Takahashi, Takashi
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supporting information; experimental part
p. 2756 - 2758
(2009/12/03)
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- ASCORBATE, VITAMIN K3 AND HYDROXYTOLANS IN THE TREATMENT OF CANCER
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The combination of compounds of the hydroxytolan family with ascorbate plus naphthoquinone (Vitamin K3; VK3), or a quinone or semiquinone analogue of VK3, kill tumor cells, inhibit tumor growth and development, and treat cancer in subjects in need thereof.
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Page/Page column 20
(2009/01/23)
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- Liquid crystal dimers derived from naturally occurring chiral moieties: synthesis and characterization
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Naturally occurring cholesterol and α-chloroalkanoyl units derived from natural α-amino acids (l-valine, l-leucine, and l-isoleucine) have been utilized to prepare three different series of nonsymmetric liquid crystal dimers. Tolane (diphenylacetylene), w
- Yelamaggad, Channabasaveshwar V.,Shanker, Govindaswamy
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p. 3760 - 3771
(2008/09/20)
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- Synthesis and mesomorphic properties of rigid-core ionic liquid crystals
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Ionic liquid crystals combine the unique solvent properties of ionic liquids with self-organization found for liquid crystals. We report a detailed analysis of the structure-property relationship of a series of new imidazolium-based liquid crystals with an extended aromatic core. Investigated parameters include length and nature of the tails, the length of the rigid core, the lateral substitution pattern, and the nature of the counterion. Depending on the molecular structure, two mesophases were observed: a bilayered SmA 2 phase and the more common monolayered SmA phase, both strongly interdigitated. Most materials show mesophases stable to high temperatures. For some cases, crystallization could be suppressed, and room-temperature liquid crystalline phases were obtained. The mesomorphic properties of several mixtures of ionic liquid crystals were investigated. Many mixtures showed full miscibility and ideal mixing behavior; however, in some instances we observed, surprisingly, complete demixing of the component SmA phases. The ionic liquid crystals and mixtures presented have potential applications, due to their low melting temperatures, wide temperature ranges, and stability with extra ion-doping.
- Kouwer, Paul H. J.,Swager, Timothy M.
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p. 14042 - 14052
(2008/09/17)
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- Convenient syntheses of m- and p-ethynylphenols
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m-lodophenol (4a) was found to couple with 2-methylbut-3-yn-2-ol (5) in the presence of PdCl2-CuI-Ph3P-in triethylamine to afford 3-(3-hydroxy-3-methylbut-1-ynyl)phenol(6a), which was conveniently converted into m-ethynylphenol (7a). Under the same conditions, p-iodophenol did not couple with 5. However, p-iodo-1-[(tetrahydro-2H-pyran-2-yl)oxy]benzene (4b) did react with 5 to afford 1-[(tetrahydro-2H-pyran-2-yl)oxy]-4-[2-hydroxy-2-methyl- 4-but-3-ynyl]benzene (6b), which was similarly converted into 1-[(tetrahydro-2H-pyran-2-yl)oxy]-4-ethynylbenzene (7b) with loss of acetone. Removal of the tetrahydropyranyl protecting group from 7b furnished p-ethynylphenol (8).
- Lai, Guo-Qiao,Liu, Shi-Ling,Xu, Jin-Feng,Shen, Yong-Jia
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p. 203 - 204
(2007/10/03)
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- Methods for treating subjects infected with a herpes virus or neisseria gonorrheae
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The present invention provides a method of inhibiting the formation of infectious herpes virus particles, particularly infectious herpes simplex virus (HSV) particles, in a host cell. The method involves administering an effective amount of a hydroxylated
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- POLYMERIZABLE COMPOSITION SHOWING LIQUID-CRYSTAL PHASE AND OPTICALLY ANISOTROPIC OBJECT MADE WITH THE SAME
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An object of the present invention is to provide a polymerizable liquid crystal composition incorporating a polymerizable liquid crystal compound which displays a low nematic phase temperature, displays excellent compatibility with other polymerizable liquid crystal compounds, and furthermore yields a product following polymerization, of good transparency and high mechanical strength. A polymerizable composition is provided which displays a liquid crystal phase, and moreover incorporates a liquid crystal backbone with two or more ring structures and a compound with a partial structure represented by the general formulaP-S-A-D-E- [wherein P1 represents a polymerizable functional group; S1 represents -(CH2)w-, - O(CH2)w-, -(CH2)wO-, -(CH2)wC(=O)O-, -(CH2)wOC(=O)-, -C(=O)O(CH2)w- or - OC(=O)(CH2)w- (w: 1 to 20); A1 and E1 each represent a hydrocarbon ring or a hetero ring, although E1 is a ring incorporated within the liquid crystal backbone; and D1 represents - C(=O)-O-(CH2)m-O-, -O(CH2)m-O-C(=O)-, -O-C(=O)-(CH2)m-O-, or -O(CH2)m-C(=O)-O- (m: 1 to 15)].
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- High birefringence phenylacetylene liquid crystals with low viscosity
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We have synthesized new high Δ n 3-ring phenylacetylene(3PA) liquid crystals which have substituent groups with core center phenyl ring and investigated the effects of substitution on physical properties. Nematic range and viscosity were improved remarkab
- Sekine, Chizu,Fujisawa, Koichi,Iwakura, Kazunori,Minai, Masayoshi
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p. 711 - 718
(2007/10/03)
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- A novel calamitic liquid crystalline oligomer composed of three non- identical mesogenic entities: Synthesis and characterization
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The synthesis and evaluation of the mesomorphic properties of the first trimesogen consisting of three non-identical calamitic mesogenic entities have been described.
- Yelamaggad,Hiremath,Shankar Rao,Krishna Prasad
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- New chiral tolane series with antiferroelectric properties
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A new series of chiral tolane with aliphatic end chains ranging from heptyloxy to dodecyloxy has been synthesized and characterized. The mesomorphic properties have been analyzed by optical microscopy on pure compounds and mixtures, D.S.C, electro-optical
- Cluzeau,Nguyen,Destrade,Isaert,Barois,Babeau
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- Synthesis of Some Substituted Dimethyl and Diethyl 4-(Phenylethynyl)-2,6-pyridinedicarboxylates
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Substituted dimethyl and diethyl 4-(phenylethynyl)-2,6-pyridinedicarboxylates were prepared by coupling reactions between dialkyl 4-halo-2,6-pyridinedicarboxylates and terminal arylacetylenes in the presence of an organopalladium catalyst and copper(I) iodide in a suitable solvent system.The terminal acetylenes needed in this work were synthesized from the corresponding aryl halides using either (trimethylsilyl)acetylene or 2-methyl-3-butyn-2-ol followed by deprotection of the triple bond, depending on the nature of the compound in question.
- Takalo, Harri,Kankare, Jouko,Haenninen, Elina
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p. 448 - 454
(2007/10/02)
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