- BORON-CONTAINING CYCLIC EMISSIVE COMPOUNDS AND COLOR CONVERSION FILM CONTAINING THE SAME
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The present disclosure relates to novel photoluminescent complexes comprising a BODIPY moiety covalently bonded to a blue light absorbing moiety, a color conversion film comprising the photoluminescent complex, and a back-light unit using the same.
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Page/Page column 93; 94
(2020/10/21)
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- Synthesis, Characterization, and Evaluation of Near-IR Boron Dipyrromethene Bioconjugates for Labeling of Adenocarcinomas by Selectively Targeting the Epidermal Growth Factor Receptor
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A series of five boron dipyrromethene (BODIPY) bioconjugates containing an epidermal growth factor receptor (EGFR)-targeted pegylated LARLLT peptide and/or a glucose or biotin ethylene diamine group were synthesized, and the binding capability of the new conjugates to the extracellular domain of EGFR was investigated using molecular modeling, surface plasmon resonance, fluorescence microscopy, competitive binding assays, and animal studies. The BODIPY conjugates with a LARLLT peptide were found to bind specifically to EGFR, whereas those lacking the peptide bound weakly and nonspecifically. All BODIPY conjugates showed low cytotoxicity (IC50 > 94 μM) in HT-29 cells, both in the dark and upon light activation (1.5 J/cm2). Studies of nude mice bearing subcutaneous human HT-29 xenografts revealed that only BODIPY conjugates bearing the LARLLT peptide showed tumor localization 24 h after intravenous administration. The results of our studies demonstrate that BODIPY bioconjugates bearing the EGFR-targeting peptide 3PEG-LARLLT show promise as near-IR fluorescent imaging agents for colon cancers overexpressing EGFR.
- Kaufman, Nichole E. M.,Meng, Qianli,Griffin, Kaitlin E.,Singh, Sitanshu S.,Dahal, Achyut,Zhou, Zehua,Fronczek, Frank R.,Mathis, J. Michael,Jois, Seetharama D.,Vicente, M. Gra?a H.
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p. 3323 - 3335
(2019/04/26)
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- HEPATITIS C VIRUS INHIBITORS AND USES THEREOF IN PREPARATION OF DRUGS
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A series of hepatitis C virus (HCV) inhibitors and compositions and applications thereof in the preparation of drugs for treating chronic HCV infection. Especially, a series of compounds that are used as NS5A inhibitors, and compositions and uses thereof in the preparations of drugs.
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Paragraph 0357; 0360
(2017/12/17)
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- Benzoporphyrins: Selective Co-sensitization in Dye-Sensitized Solar Cells
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A novel class of dyes, namely benzoporphyrins, was synthesized and implemented into dye-sensitized solar cells. They feature complementary absorptions compared to N719, which renders them promising candidates for co-sensitization in DSSCs. Notably, metallated benzoporphyrins reveal a TiO2-nanoparticle attachment that is size and aggregation dependent. Therefore, unproductive energy-transfer events between the selectively attached dyes can be prevented. In light of the latter, an efficiency improvement of 39 % has been achieved upon selective adsorption of benzoporphyrins and N719 onto different layers of TiO2 photoelectrode.
- Lodermeyer, Fabian,Costa, Rubén D.,Malig, Jenny,Jux, Norbert,Guldi, Dirk M.
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supporting information
p. 7851 - 7855
(2016/06/09)
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- TAMBJAMINES AND B-RING FUNCTIONALIZED PRODIGININES
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Embodiments of tambjamines and B-ring functionalized prodiginines are disclosed. Methods of synthesizing and using the disclosed compounds are also disclosed. Some embodiments of the disclosed compounds have antimalarial activity. Certain embodiments of t
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Page/Page column 18; 19; 29
(2016/11/17)
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- Electrochemistry of nonplanar copper(II) tetrabutano- and tetrabenzotetraarylporphyrins in nonaqueous media
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Two series of copper tetraarylporphyrins containing β,β′-fused tetrabutano or tetrabenzo groups were synthesized and characterized as to their electrochemistry and spectroelectrochemistry in nonaqueous media. The examined compounds are represented as butano-(TpYPP)CuII and benzo-(TpYPP)CuII, where TpYPP is the porphyrin dianion and Y is a CH3, H or Cl substituent on the para-position of the four meso-phenyl rings of the compound. Each neutral porphyrin in the two series is ESR active and shows a typical d9 Cu(ii) signal in frozen CH2Cl2 solution. Each Cu(ii) porphyrin also undergoes two reversible one-electron reductions and two reversible one-electron oxidations in DMF or CH2Cl2 containing 0.1 M tetra-n-butylammonium perchlorate to give a π-anion radical and dianion upon reduction and a π-cation radical and dication upon oxidation. A third one-electron oxidation is also observed for butano-(TpYPP)Cu (Y = CH3 and H) and benzo-(TPP)Cu in PhCN and this process is assigned to the CuII/CuIII transition. The reversible half-wave potential for the first oxidation of each compound in both series is shifted negatively by about 500 mV as compared to E1/2 values for oxidation of the related copper tetraarylporphyrin without the four fused benzo or butano rings while smaller positive shifts of 60 and 300 mV are seen for reduction of the tetrabenzotetraarylporphyrins and tetrabutaotetraarylporphyrins, respectively, as compared to the same redox reactions of the related tetraarylporphyrins. The electrochemically measured HOMO-LUMO gap averages 1.76 ± 0.05 V for benzo-(TpYPP)CuII, 2.04 ± 0.06 V for butano-(TpYPP)CuII and 2.33 ± 0.03 for (TpYPP)Cu in CH2Cl2.
- Ye, Lina,Ou, Zhongping,Fang, Yuanyuan,Xue, Songlin,Song, Yang,Wang, Liping,Wang, Mengli,Kadish, Karl M.
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p. 77088 - 77096
(2015/09/28)
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- Synthesis and Structure-Activity Relationships of Tambjamines and B-Ring Functionalized Prodiginines as Potent Antimalarials
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Synthesis and antimalarial activity of 94 novel bipyrrole tambjamines (TAs) and a library of B-ring functionalized tripyrrole prodiginines (PGs) against a panel of Plasmodium falciparum strains are described. The activity and structure-activity relationsh
- Kancharla, Papireddy,Kelly, Jane Xu,Reynolds, Kevin A.
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p. 7286 - 7309
(2015/10/05)
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- OXYGEN SENSORS
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Oxygen sensing luminescent dyes, polymers and sensors comprising these sensors and methods of using these sensors and systems are provided.
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-
Paragraph 0111
(2014/09/30)
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- FUSED PYRROLE DERIVATES AS ESTROGEN RECEPTOR LIGANDS
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The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein Z, A, B, D,E, G, M1, M2, M3, M4, M5, M6, p, q, r, R3, R4, R5 and R6 are as defined in the specification. The invention also provides the use of such co
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Page/Page column 51-51
(2012/10/18)
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- Manganese(III) complexes of bis(hydroxyphenyl)dipyrromethenes are potent orally active peroxynitrite scavengers
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We report a new series of biscyclohexano-fused Mn(III) complexes of bis(hydroxyphenyl)dipyrromethenes, 4a-c, as potent and orally active peroxynitrite scavengers. Complexes 4a-c are shown to reduce peroxynitrite through a two-electron mechanism, thereby forming the corresponding Mn(V)O species, which were characterized by UV, NMR, and LC-MS methods. Mn(III) complex 4b and its strained BODIPY analogue 9b were analyzed by X-ray crystallography. Finally, complex 4a is shown to be an orally active and potent analgesic in a model carrageenan-induced hyperalgesia known to be driven by the overproduction of peroxynitrite.
- Rausaria, Smita,Kamadulski, Andrew,Rath, Nigam P.,Bryant, Leesa,Chen, Zhoumou,Salvemini, Daniela,Neumann, William L.
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supporting information; experimental part
p. 4200 - 4203
(2011/06/21)
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- Retooling manganese(III) porphyrin-based peroxynitrite decomposition catalysts for selectivity and oral activity: A potential new strategy for treating chronic pain
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Redox-active metalloporphyrins represent the most well-characterized class of catalysts capable of attenuating oxidative stress in vivo through the direct interception and decomposition of superoxide and peroxynitrite. While many interesting pharmacologic
- Rausaria, Smita,Ghaffari, Mahsa M.E.,Kamadulski, Andrew,Rodgers, Kenny,Bryant, Leesa,Chen, Zhoumou,Doyle, Tim,Shaw, Michael J.,Salvemini, Daniela,Neumann, William L.
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supporting information; experimental part
p. 8658 - 8669
(2012/02/16)
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- Synthesis and evaluation of the antiproliferative activity of novel isoindolo[2,1-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives
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A novel series of isoindolo[2,1-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives was synthesized and evaluated in vitro against various human cancer cell lines for antiproliferative activity. These new compounds displayed activity against leukemia a
- Desplat, Vanessa,Moreau, Stephane,Belisle-Fabre, Solene,Thiolat, Denis,Uranga, Juliette,Lucas, Romain,Moor, Laure De,Massip, Stephane,Jarry, Christian,Mossalayi, Djavad M.,Sonnet, Pascal,Deleris, Gerard,Guillon, Jean
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scheme or table
p. 657 - 667
(2012/04/04)
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- Tunable phosphorescent NIR oxygen indicators based on mixed benzo-and naphthoporphyrin complexes
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A series of π-extended phosphorescent palladium(II) and platinum(II) porphyrin complexes were synthesized, in which additional benzene rings are fused radially onto at least one of the four peripheral benzo groups. The photophysical properties of the metalloporphyrins palladium(II)-meso-tetra-(4- fluorophenyl)mononaphthotribenzoporphyrin (Pd1NF), cispalladium(II)-meso-tetra- (4-fluorophenyl)dibenzodinaphthoporphyrin (Pd2NF), and palladium(II)-meso-tetra- (4-fluorophenyl)monobenzotrinaphthoporphyrin (Pd3NF) and the corresponding platinum(II) compounds (Pt1NF, cis-Pt2NF, Pt3NF) were investigated. The compounds under investigation absorb intensively in the near-infrared region (628-691 nm) and emit at room temperature at 815-882 nm. Phosphorescence quantum yields of the platinum(II) porphyrins range from 25 to 53% with luminescence decay times of 21 to 44 μs in deoxygenated toluene solutions at room temperature. The corresponding palladium(II) complexes exhibit quantum yields in the range of 7 to 18% with lifetimes of 106 to 206 μs. Density functional theory (DFT) calculations revealed nonplanar geometries for all complexes and corroborate the absorption characteristics. The subsequent π extension of the porphyrin system leads to near-infrared absorbing oxygen indicators with tailor-made luminescence properties as well as tunable oxygen sensitivity.
- Niedermair, Fabian,Borisov, Sergey M.,Zenkl, Gunter,Hofmann, Oliver T.,Weber, Hansjoerg,Saf, Robert,Klimant, Ingo
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scheme or table
p. 9333 - 9342
(2011/01/09)
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- Highly efficient, near-infrared electrophosphorescence from a Pt-metalloporphyrin complex
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(Graph Presented) Red-shifting beyond red: The nonplanar porphyrin complex [Pt(tpbp)] (tpbp = tetraphenyltetrabenzoporphyrin) has been used as a phosphorescent dopant in highly efficient electrophosphorescent devices that emit in the near-infrared region
- Borek, Carsten,Hanson, Kenneth,Djurovich, Peter I.,Thompson, Mark E.,Aznavour, Kristen,Bau, Robert,Sun, Yiru,Forrest, Stephen R.,Brooks, Jason,Michalski, Lech,Brown, Julie
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p. 1109 - 1112
(2008/03/14)
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- Pyrrole and pyrazole DAAO inhibitors
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Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: wherein R1 and R2 are independently selected from hydrogen, halo, nitro, alkyl, acyl, alkylaryl, and XYR5; or R1 and R2, taken together, form a 5, 6, 7 or 8-membered substituted or unsubstituted carbocyclic or heterocyclic group; X and Y are independently selected from O, S, NH, and (CR6R7)n; R3 is hydrogen, alkyl or M+; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc ion or a mixture thereof; Z is N or CR4; R4 is from selected from hydrogen, halo, nitro, alkyl, alkylaryl, and XYR5; R5 is selected from aryl, substituted aryl, heteroaryl and substituted heteroaryl; R6 and R7 are independently selected from hydrogen and alkyl; n is an integer from 1 to 6; at least one of R1, R2 and R4 is other than hydrogen; and at least one of X and Y is (CR6R7)n. D-serine or cycloserine may be coadministered along with the compound of formula I.
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Page/Page column 63
(2008/06/13)
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- Novel Versatile Synthesis of Substituted Tetrabenzoporphyrins
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A novel general synthetic route to tetraaryltetrabenzoporphyrins (Ar 4TBP) with various peripheral functional groups is developed. The procedure includes (i) Barton-Zard condensation of 1-nitro- or 1-phenylsulfonylcyclohexenes with isocyanoacet
- Finikova, Olga S.,Cheprakov, Andrei V.,Beletskaya, Irina P.,Carroll, Patrick J.,Vinogradov, Sergei A.
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p. 522 - 535
(2007/10/03)
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- Partial reduction of annulated heterocycles as a general route to medium rings containing oxygen and nitrogen.
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The preparation of annulated furans and pyrroles is described as part of a general strategy for the synthesis of medium ring heterocycles. After Birch reduction, the corresponding dihydro compounds were oxidatively cleaved to produce medium ring ethers an
- Donohoe,Raoof,Linney,Helliwell
-
p. 861 - 864
(2007/10/03)
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- The Preparation of Pyrrole-2-carboxylates from Vinyl Sulfones
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The reaction of the anion of ethyl isocyanoacetate with suitably substituted vinyl p-tolyl sulfones gives fair to good yields of pyrrole-2-carboxylates substituted in the 3-, 4- or 3- and 4-positions.From the reaction of 1-phenyl-1-tolylsulfonylethene with ethyl isocyanoacetate, two diastereoisomers of ethyl 4,6-diphenyl-4,6-bis(p-tolylsulfonyl)-3,4,5,6-tetrahydro-2H-azepine-2-carboxylate (4) were also isolated.
- Arnold, Dennis P.,Burgess-Dean, Leon,Hubbard, Jason,Rahman, M. Abdur
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p. 969 - 974
(2007/10/02)
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- Nonionic superbase-promoted synthesis of oxazoles and pyrroles: Facile synthesis of porphyrins and α-C-acyl amino acid esters
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The reaction of acyl chlorides or acid anhydrides with isocyanoacetates in the presence of the superior strong nonionic base P(MeNCH2CH2)3N (1) gave oxazoles in 98-99% yield. Treatment of the oxazoles with HCl-MeOH gave α-
- Tang,Verkade
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p. 7793 - 7802
(2007/10/02)
-
- Porphyrins with Exocyclic Rings. 2. Synthesis of Geochemically Significant Tetrahydrobenzoporphyrins from 4,5,6,7-Tetrahydro-2H-isoindoles
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Benzo- and tetrahydrobenzoporphyrins are widespread constituents of oil shales and petroleum.Although the origins of these materials are not known, a case is made for divinylchlorophyll a, a widespread pigment in marine algae, being the precursor to many of these geoporphyrins.Total syntheses of four tetrahydrobenzoporphyrins related to etioporphyrin III are described.Tetrahydroisoindoles were prepared by condensation of isocyanoacetates with 1-nitrocyclohexene in the presence of DBU or by reaction of aminomalonates with 2-formylcyclohexanone.Condensation of 3-unsubstituted 4,5,6,7-tetrahydro-2H-isoindoles 23c and 23d with (acetoxymethyl)pyrroles in the presence of Montmorillonite clay gave dipyrrylmethanes 28a and 36a in excellent yield.Hydrogenolysis of the benzyl esters and subsequent acid-catalyzed condensation with pyrrole aldehydes 37a and /or 37b gave a series of a,c-biladiene dihydrobromides.Copper(II) mediated cyclization of the a,c-biladienes 32, 33, 35, and 38, followed by demetallation with 15percent sulfuric acid-trifluoroacetic acid, gave four isomeric tetrahydrobenzoporphyrins 10-13 in unusually high yield.This work provides a general route for the synthesis of these important porphyrin molecular fossils.
- May, Donald A.,Lash, Timothy D.
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p. 4820 - 4828
(2007/10/02)
-
- Synthesis of Pyrroles via Ethyl N-(3-Oxo-1-alkenyl)glycinates
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The reaction of ethyl glycinate hydrochloride (1) with 1,3-dicarbonyl compounds 2a-g in presence of triethylamine leads to the formation of ethyl N-(3-oxo-1-alkenyl)glycinates 3a-g.These compounds are easily converted to the pyrroles 4a-g by base-catalyze
- Hombrecher, Hermann K.,Horter, Gaby
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p. 389 - 391
(2007/10/02)
-
- Porphyrin synthesis from nitrocompounds
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A new porphyrin synthesis starting from nitroalkenes or their equivalents is described. For example, octaethylporphyrin, coproporphyrin, porphyrin-1,2,3,4,5,6,7,8 octapropionic acid, and 2,7,12,17 tetraarylporphyrin are prepared in good yield from readily available materials such as 1-nitropropane, nitroethane, nitromethane, and aldehydes.
- Ono, Noboru,Kawamura, Hisayuki,Bougauchi, Masahiro,Maruyama, Kazuhiro
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p. 7483 - 7496
(2007/10/02)
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- Synthesis of Octaalkyl- and Octaarylporphyrins from Nitroalkenes
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Symmetrically substituted octaalkyl- and octaarylporphyrins are readily prepared by the reduction of 2-ethoxycarbonyl-3,4-dialkyl (or diaryl)pyrroles with LiAlH4 followed by treatment with acetic acid and oxidizing agents.
- Ono, Noboru,Maruyama, Kazuhiro
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p. 1511 - 1514
(2007/10/02)
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