- ADMET Polymers Containing Precisely Spaced Pendant Boronic Acids and Esters
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Precise aryl boronic ester- and acid-containing polymers have been synthesized via acyclic diene metathesis. High-molecular weight phenyl boronic acid polymers were synthesized. Cross-linked phenyl boronic acid polymers were also synthesized and demonstrate a unique crystallization behavior not usually seen in cross-linked polymers. (Graph Presented).
- Simocko, Chester,Young, Thomas C.,Wagener, Kenneth B.
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Read Online
- A Revised Modular Approach to (–)-trans-Δ8-THC and Derivatives Through Late-Stage Suzuki–Miyaura Cross-Coupling Reactions
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A revised modular approach to various synthetic (–)-trans-Δ8-THC derivatives through late-stage Suzuki–Miyaura cross-coupling reactions is disclosed. Ten derivatives were synthesized allowing both sp2- and sp3-hybridized cross-coupling partners with minimal β-hydride elimination. Importantly, we demonstrate that a para-bromo-substituted THC scaffold for Suzuki–Miyaura cross-coupling reactions has been initially reported incorrectly in recent literature.
- Bloemendal, Victor R. L. J.,Sondag, Daan,Elferink, Hidde,Boltje, Thomas J.,van Hest, Jan. C. M.,Rutjes, Floris P. J. T.
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Read Online
- Metal-free OLED triplet emitters by side-stepping Kasha's rule
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Keeping it light: Most organic fluorophores do not show useful emission from the triplet excited state. A new class of materials is presented for organic light-emitting diodes that exhibit phosphorescence under electrical excitation, even at room temperat
- Chaudhuri, Debangshu,Sigmund, Eva,Meyer, Annemarie,Roeck, Lisa,Klemm, Philippe,Lautenschlager, Sebastian,Schmid, Agnes,Yost, Shane R.,Vanvoorhis, Troy,Bange, Sebastian,Hoeger, Sigurd,Lupton, John M.
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Read Online
- Acylative desymmetrization of cyclic meso-1,3-diols by chiral DMAP derivatives
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An efficient enantioselective acylative desymmetrization of cyclic meso-1,3-diols was developed by using a chiral DMAP derivative 1e having a 1,1¤-binaphthyl unit. The reactions required only 0.5mol% of the catalyst and showed good to excellent enantioselectivity. With this transformation, 5a, a key building block for the synthesis of natural products, was easily obtained in almost enantiomerically pure form after a single recrystallization. Control experiments revealed that tert-alcohol units on the catalyst were responsible for both the catalytic activity and enantioselectivity.
- Mandai, Hiroki,Hironaka, Tsubasa,Mitsudo, Koichi,Suga, Seiji
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supporting information
p. 471 - 474
(2021/03/15)
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- Total synthesis of decarboxyaltenusin
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The total synthesis of decarboxyaltenusin (5'-methoxy-6-methyl-[1,1'-biphenyl]-3,3',4-triol), a toxin produced by various mold fungi, has been achieved in seven steps in a yield of 31% starting from 4-methylcatechol and 1-bromo-3,5-dimethoxybenzene, where
- Warmuth, Lucas,Wei?, Aaron,Reinhardt, Marco,Meschkov, Anna,Schepers, Ute,Podlech, Joachim
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supporting information
p. 224 - 228
(2021/02/26)
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- Columnar Propeller-Like 1,3,5-Triphenylbenzenes: Probing the Effect of Chlorine on the Suzuki Cross-Coupling and Liquid Crystalline Properties
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Suzuki cross-couplings either between chlorinated N-methyliminodiacetic acid (MIDA)-protected aryl boronates and 1,3,5-tribromobenzene or between chlorinated aryl bromides and phenyltrisboronic species to star-shaped 1,3,5-triphenylbenzenes with different substitution patterns and chloro substituents at the outer phenyl rings were studied. The chlorinated precursors required for the respective reaction were synthesized and characterized. Depending on the used coupling reaction target triphenylbenzenes were isolated in yields between 42 % and 88 %. Their mesomorphic properties were influenced by the substitution pattern and number of peripheral chlorine atoms. Triphenylbenzene with 3,5-alkoxy substitution and H in para-position self-assembled into either columnar hexagonal (Colh) mesophases or a soft crystal. While threefold chloro substitution in meta-position of the outer phenyl rings led to stable room temperature Colho phases, triphenylbenzenes with threefold para-chloro or 3,5-dichloro substitution were non-mesomorphic. Based on X-ray diffraction data a helical packing model for the observed phases similar to that of related alkoxy-substituted triphenylbenzenes was proposed.
- Grunwald, Marco André,W?hrle, Tobias,Forschner, Robert,Baro, Angelika,Laschat, Sabine
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supporting information
p. 2190 - 2198
(2020/03/03)
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- CONJUGATED CHEMICAL INDUCERS OF DEGRADATION AND METHODS OF USE
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The subject matter described herein is directed to antibody-CIDE conjugates (Ab-CIDEs), to pharmaceutical compositions containing them, and to their use in treating diseases and conditions where targeted protein degradation is beneficial.
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Page/Page column 442; 461-462
(2020/05/28)
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- Kolbe-Schmitt type reaction under ambient conditions mediated by an organic base
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The combined use of an organic base for resorcinols realized a Kolbe-Schmitt type reaction under ambient conditions. When resorcinols (3-hydroxyphenol derivatives) were treated with DBU under a carbon dioxide atmosphere, nucleophilic addition to carbon dioxide proceeded to afford the corresponding salicylic acid derivatives in high yields.
- Sadamitsu, Yuta,Okumura, Akira,Saito, Kodai,Yamada, Tohru
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supporting information
p. 9837 - 9840
(2019/08/20)
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- Lone pair-π: Vs. σ-hole-π interactions in bromine head-containing oxacalix[2]arene[2]triazines
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Two new bromine head-containing oxacalix[2]arene[2]triazines were designed and synthesized. Owing to the bromine head and complementary V-shaped cavity, the solid state structure of oxacalix[2]arene[2]triazine having N,N-dipropylamino substituents showed
- Naseer, Muhammad Moazzam,Bauzá, Antonio,Alnasr, Hazem,Jurkschat, Klaus,Frontera, Antonio
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p. 3251 - 3257
(2018/06/18)
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- Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid
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We demonstrate the versatile use of the cyclopropylmethyl group to protect phenols through the total synthesis of two benzofuran-based natural products, that is, anigopreissin A and the resveratrol–piceatannol hybrid. This protecting group is a good alter
- Kumar, Arvind,Saleeb, Michael,Werz, Dominik,Elofsson, Mikael
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p. 953 - 956
(2018/11/23)
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- o-xylylene bis(triethyl ammonium tribromide) as a mild and recyclable reagent for rapid and regioselective bromination of anilines and phenols
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Background: o-Xylylene bis(triethyl ammonium tribromide) (OXBTEATB) as a recyclable and high bromine containing di-(tribromide) reagent has been employed for the bromination of various organic substrates such as phenol and aniline or its derivatives. This catalyst can be recovered and reused several times. Methods: Aryl bromides shown in Table 1, were easily produced from bromination of aromatic compounds by OXBTEATB. This high-yield process lets the reagents to be recycled and reused. Results: As shown in Table 1, substituted anilines, phenols and β-naphthol were found to be the most reactive and immediately converted to the corresponding mono-brominated products by OXBTEATB. Conclusion: OXBTEATB can be considered a solidified bromine. This novel reagent has variable solubility in different polar protic and aprotic solvents but insoluble in non-polar aprotic solvent. Subsequently, OXBTEATB can be recognized as a more useful brominating and regioselective catalyst than the liquid bromine.
- Hemati, Roya,Shahvelayati, Ashraf S.,Yadollahzadeh, Khadijeh
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p. 682 - 687
(2018/07/14)
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- Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N -Sulfonyl Aldimines
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A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis-ortho-functionalized arene.
- Shikora, Jonathan M.,Chemler, Sherry R.
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supporting information
p. 2133 - 2137
(2018/04/30)
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- Second Generation Grp94-Selective Inhibitors Provide Opportunities for the Inhibition of Metastatic Cancer
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Glucose regulated protein 94 (Grp94) is the endoplasmic reticulum (ER) resident isoform of the 90 kDa heat shock protein (Hsp90) family and its inhibition represents a promising therapeutic target for the treatment of many diseases. Modification of the first generation cis-amide bioisostere imidazole to alter the angle between the resorcinol ring and the benzyl side chain via cis-amide replacements produced compounds with improved Grp94 affinity and selectivity. Structure–activity relationship studies led to the discovery of compound 30, which exhibits 540 nm affinity and 73-fold selectivity towards Grp94. Grp94 is responsible for the maturation and trafficking of proteins associated with cell signaling and motility, including select integrins. The Grp94-selective inhibitor 30 was shown to exhibit potent anti-migratory effects against multiple aggressive and metastatic cancers.
- Crowley, Vincent M.,Huard, Dustin J. E.,Lieberman, Raquel L.,Blagg, Brian S. J.
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supporting information
p. 15775 - 15782
(2017/11/14)
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- HYDROXY FORMAMIDE DERIVATIVES AND THEIR USE
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Disclosed are compounds having the formula: wherein R1, R2 and R3 are as defined herein, and methods of making and using the same, including use as inhibitors of BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.
- -
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Paragraph 0513; 0514
(2016/12/16)
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- POCOP-Type Pincer Complexes of Nickel: Synthesis, Characterization, and Ligand Exchange Reactivities of New Cationic Acetonitrile Adducts
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This report describes the synthesis, characterization, and ligand exchange studies of a family of cationic acetonitrile adducts of nickel featuring resorcinol-based, pincer-type POCOP ligands. The compounds [(R-POCOPR′)Ni(NCMe)][OSO2CF3] (R-POCOPR′ = 2,6-(R′2PO)2(RnC6H3-n); R′ = i-Pr: R = H (1), p-Me (2), p-OMe (3), p-CO2Me (4), p-Br (5), m,m-t-Bu2 (6), m-OMe (7), m-CO2Me (8); R′ = t-Bu: R = H (9), p-CO2Me (10)) were prepared in 80-93% yields by reacting the corresponding charge-neutral bromo derivatives with Ag(OSO2CF3) in acetonitrile. The impact of the R- and R′-substituents on electronics and structures of 1-10 have been probed by NMR, UV-vis, and IR spectra, X-ray crystallography, and cyclic voltammetry measurements. The observed ν(C≡N) values were found to increase with the increasing electron-withdrawing nature of R, i.e., in the order 7 2C-substituted cations showed the highest oxidation potentials. Moreover, all cationic adducts showed greater oxidation potentials compared with their corresponding charge-neutral bromo precursors. Equilibrium studies conducted with selected [(R-POCOPR′)Ni(NCMe)][OSO2CF3] and (R-POCOPR′)NiBr (R′ = i-Pr) have confirmed facile MeCN/Br exchange between these derivatives and show that the cationic adducts are stabilized with MeO-POCOP, whereas the charge-neutral bromo species are stabilized with MeO2C-POCOP. The potential implications of these findings for the catalytic reactivities of the title cationic complexes have been discussed. (Chemical Equation Presented).
- Lapointe, Sbastien,Vabre, Boris,Zargarian, Davit
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p. 3520 - 3531
(2015/08/06)
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- Iron-mediated C-H coupling of arenes and unactivated terminal alkenes directed by sulfur
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A sulfur-directed Fe(iii)-mediated ortho C-H coupling of arenes with unactivated terminal alkenes gives products of regioselective alkene chloroarylation. The novel mechanism involves redox-activation of the arene partner and alkene addition to the result
- Cavanagh, Craig W.,Aukland, Miles H.,Hennessy, Alan,Procter, David J.
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supporting information
p. 9272 - 9275
(2015/06/02)
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- HYDROXY FORMAMIDE DERIVATIVES AND THEIR USE
-
Disclosed are compounds having the formula (I): wherein R1, R2 and R3 are as defined herein, and methods of making and using the same, including use as inhibitors of BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.
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Page/Page column 102
(2015/07/23)
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- Protein and enzyme gated supramolecular disassembly
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An amphiphilic nanoassembly was designed to respond to the concurrent presence of a protein and an enzyme. We present herein a system, where in the presence of these two stimuli supramolecular disassembly and molecular release occur. This molecular releas
- Guo, Jing,Zhuang, Jiaming,Wang, Feng,Raghupathi, Krishna R.,Thayumanavan
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supporting information
p. 2220 - 2223
(2014/03/21)
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- PYRROLOTRIAZINONE DERIVATIVES AS PI3K INHIBITORS
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New pyrrolotriazinone derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Phosphoinositide 3-Kinases (PI3Ks).
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Page/Page column 105
(2014/05/07)
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- POLYCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
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The present disclosure provides compounds, or pharmaceutically acceptable salts thereof, for inhibiting the growth of a microbe; treating a mammal having a microbial infection, malaria, mucositis, an ophthalmic infection, an otic infection, a cancer, or a Mycobacterium infection; killing or inhibiting the growth of a Plasmodium species; inhibiting the growth of a Mycobacterium species; modulating an immune response in a mammal; or antagonizing unfractionated heparin, low molecular weight heparin, or a heparin/low molecular weight heparin derivative.
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Page/Page column 186; 187; 194
(2014/07/07)
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- SHIP1 MODULATORS AND METHODS RELATED THERETO
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Compounds of formula (I): [Formula should be inserted here]; where [Formula should be inserted here], n, R1, R4a, R4b, R5, R7 and R8 are defined herein, or pharmaceutically acceptable salts thereof, are described herein. The disclosed compounds have activity as SHIP1 modulators, and thus may be used to treat any of a variety of diseases, disorders or conditions that would benefit from SHIP1 modulation. Compositions comprising a compound of formula (I) in combination with a pharmaceutically acceptable carrier or diluent are also disclosed, as are methods of SHIP1 modulation by administration of such compounds to an animal in need thereof.
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Page/Page column 149
(2014/07/23)
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- A triple bond side-chained 2D-conjugated benzodithiophene based photovoltaic polymer
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A series of triple bond side-chained benzodithiophene copolymers, derived from 4,8-bis(1-ethynyl-3,5-bis(octyloxy)phenyl)-benzo[1,2-b:4,5-b′]dithiophene, were synthesized by Stille coupling reactions. Several electron acceptors are introduced into the pol
- Wen, Shuguang,Yun, Xiao,Chen, Weichao,Liu, Qian,Zhu, Dangqiang,Gu, Chuantao,Sun, Mingliang,Yang, Renqiang
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p. 58426 - 58431
(2015/02/19)
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- NOVEL LUMINESCENT LANTHANIDE CHELATES WITH ENHANCED EXCITATION PROPERTIES
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The present application discloses a luminescent lanthanide chelate comprising one or more chromophoric moieties of the formula (I) or of the formula (III) wherein R1, R2 and R2* each independently are selected from carbon-containing substituents forming a C—O bond with the neighbouring oxygen atom, R3 and R4 each represent a bond between the chromophoric moiety and other moieties of the chelate, and Ln3+ is a lanthanide ion, as well as the corresponding luminescence lanthanide chelating ligand. The application also discloses a detectable molecule comprising a biospecific binding reactant (such as an antibody) conjugated to the luminescent lanthanide chelate as well as a method of carrying out a biospecific binding assay, the use of such a detectable molecule in a specific bioaffinity based binding assay utilizing time-resolved fluorometric determination of a specific luminescence, and a solid support material conjugated with the luminescent lanthanide chelate.
- -
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Paragraph 0118
(2013/07/25)
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- Role of amphiphilicity in the design of synthetic mimics of antimicrobial peptides with gram-negative activity
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Two new series of aryl SMAMPs (synthetic mimics of antimicrobial peptides) with facially amphiphilic (FA) and disrupted amphiphilic (DA) topologies were designed and synthesized to directly assess the role of amphiphilicity on their antimicrobial activity
- Thaker, Hitesh D.,Cankaya, Alper,Scott, Richard W.,Tew, Gregory N.
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supporting information
p. 481 - 485
(2013/07/04)
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- CYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
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The present invention provides compounds, or pharmaceutically acceptable salts thereof, for inhibiting the growth of a microbe; treating a mammal having a microbial infection, mucositis, an ophthalmic infection, an otic infection, a cancer, or a Mycobacterium infection; inhibiting the growth of a Mycobacterium species; modulating an immune response in a mammal; or antagonizing unfractionated heparin, low molecular weight heparin, or a heparin/low molecular weight heparin derivative.
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Page/Page column 98; 99
(2013/07/05)
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- Pyrrole-fused azacoronene family: The influence of replacement with dialkoxybenzenes on the optical and electronic properties in neutral and oxidized states
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A novel pyrrole-fused azacoronene family was synthesized via oxidative cyclodehydrogenation of the corresponding hexaarylbenzenes as the key step, and the crystal structures of tetraazacoronene 3b and triazacoronene 4a were elucidated. The photophysical p
- Takase, Masayoshi,Narita, Tomoyuki,Fujita, Wataru,Asano, Motoko S.,Nishinaga, Tohru,Benten, Hiroaki,Yoza, Kenji,Muellen, Klaus
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supporting information
p. 8031 - 8040
(2013/07/19)
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- Synthetic mimics of antimicrobial peptides with immunomodulatory responses
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A new series of aryl-based synthetic mimics of antimicrobial peptides (SMAMPs) with antimicrobial activity and selectivity have been developed via systematic tuning of the aromatic groups and charge. The addition of a pendant aromatic group improved the a
- Thaker, Hitesh D.,Som, Abhigyan,Ayaz, Furkan,Lui, Dahui,Pan, Wenxi,Scott, Richard W.,Anguita, Juan,Tew, Gregory N.
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experimental part
p. 11088 - 11091
(2012/08/28)
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- New ruthenium metathesis catalysts with chelating indenylidene ligands: Synthesis, characterization and reactivity
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Six new ruthenium complexes bearing a bidentate (κ2O,C)- isopropoxy-indenylidene and PPh3 or PCy3 ligands have been synthesized and characterized by 1H, 13C NMR spectroscopy and X-ray crystallography.
- Kabro, Anzhelika,Ghattas, Ghazi,Roisnel, Thierry,Fischmeister, Cedric,Bruneau, Christian
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supporting information; experimental part
p. 3695 - 3700
(2012/05/07)
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- SHIP1 MODULATORS AND METHODS RELATED THERETO
-
Compounds of structure (I): including stereoisomers and pharmaceutically acceptable salts thereof, wherein X, R1, R2, R3, R4, R5, R6 and R7 are as defined herein. Such compounds have activity as SHIP1 modulators, and thus may be used to treat any of a variety of diseases, disorders or conditions that would benefit from SHIP1 modulation. Compositions comprising a compound of structure (I) in combination with a pharmaceutically acceptable carrier or diluent are also disclosed, as are methods of SHIP1 modulation by administration of such compounds to an animal in need thereof.
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Page/Page column 26-27
(2011/06/24)
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- Donor-acceptor-donor-based π-conjugated oligomers for nonlinear optics and near-IR emission
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A family of multi-heterocycle donor-acceptor-donor (DAD) telechelic conjugated oligomers designed for two-photon absorption (2PA) and emission in the near-infrared (near-IR) were prepared, and the relationship between their spectral, structural, and elect
- Ellinger, Stefan,Graham, Kenneth R.,Shi, Pengjie,Farley, Richard T.,Steckler, Timothy T.,Brookins, Robert N.,Taranekar, Prasad,Mei, Jianguo,Padilha, Lazaro A.,Ensley, Trenton R.,Hu, Honghua,Webster, Scott,Hagan, David J.,Van Stryland, Eric W.,Schanze, Kirk S.,Reynolds, John R.
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scheme or table
p. 3805 - 3817
(2012/04/04)
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- Synthesis of a doubly strapped light-harvesting porphyrin bearing energy donor molecules hanging on to the straps: An attempt toward macroscopic control over molecular conformation that affects the efficiency of fluorescence resonance energy transfer
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We report here the synthesis of a light-harvesting molecule 1, in which 5,5'-diphenyl-2,2'-bithiophene units (energy donors) and a doubly strapped porphyrin (energy acceptor) are three-dimensionally connected through four alkyl chains to form a "universal
- Ogi, Soichiro,Sugiyasu, Kazunori,Takeuchi, Masayuki
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supporting information; experimental part
p. 40 - 48
(2011/03/22)
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- Molecular design of small organic molecules based on structural information for a conformationally constrained peptide that binds to G-CSF receptor
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Based on structural information for a peptide (P8-2KAQ) that binds to granulocyte-colony stimulating factor receptor (G-CSFR), small ligands with a biaryl scaffold were designed and their binding affinities were evaluated.
- El-Haggar, Radwan,Kamikawa, Ken,Machi, Kazuya,Ye, Zhengmao,Ishino, Yuko,Tsumuraya, Takeshi,Fujii, Ikuo
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supporting information; experimental part
p. 1169 - 1172
(2010/06/15)
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- Total synthesis of berkelic acid
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A productive total synthesis of both enantiomers of berkelic acid (1) is outlined that takes the structure revision of this bioactive fungal metabolite previously proposed by our group into account. The successful route relies on a fully optimized triple-deprotection/1,4-addition/spiroacetalization cascade reaction sequence, which delivers the tetracyclic core 32 of the target as a single isomer in excellent yield. The required cyclization precursor 31 is assembled from the polysubstituted benzaldehyde derivative 20 and methyl ketone 25 by an aldol condensation, in which the acetyl residue in 20 transforms from a passive protecting group into an active participant. Access to fragment 25 takes advantage of the Collum-Godenschwager variant of the ester enolate Claisen rearrangement, which clearly surpasses the classical Ireland-Claisen procedure in terms of diastereoselectivity. Although it is possible to elaborate 32 into the target without any additional manipulations of protecting groups, a short detour consisting in the conversion of the phenolic -OH into the corresponding TBS-ether is beneficial. It tempers the sensitivity of the compound toward oxidation and hence improves the efficiency and reliability of the final stages. Orthogonal ester groups for the benzoate and the aliphatic carboxylate terminus of the side chain secure an efficient liberation of free berkelic acid in the final step of the route. Queue up: Three deprotection and three bond-forming reactions, all of which are effected just by a trace of HCl, zip an easily attained enone to the polycyclic core of berkelic acid in diastereomerically pure form and essentially quantitative yield. This cascade process paves the way to a concise and effective total synthesis of this alleged metalloproteinase-3 inhibitor and cytotoxic metabolite derived from an extremophilic fungus.
- Snaddon, Thomas N.,Buchgraber, Philipp,Schulthoff, Saskia,Wirtz, Conny,Mynott, Richard,Fuerstner, Alois
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supporting information; experimental part
p. 12133 - 12140
(2011/02/25)
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- Disassembly of dendritic micellar containers due to protein binding
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Disassembling a supramolecular assembly and releasing the contents of the assembly in response to a stimulus are important goals of supramolecular chemistry. When proteins are used as the stimulus, the biological relevance of the supramolecular event dram
- Azagarsamy, Malar A.,Yesilyurt, Volkan,Thayumanavan
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supporting information; scheme or table
p. 4550 - 4551
(2010/06/13)
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- LEUKOTRIENE B4 INHIBITORS
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Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, COPD
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Page/Page column 46
(2010/10/03)
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- Synthesis of (-)-berkelic acid
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An extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6-dihydroxybenzoic acid is the key step in the synthesis of (-)-berkelic acid confirming Fuerstner's reassignment of the stereochemistry at C18 and C1
- Wu, Xiaoxing,Zhou, Jingye,Snider, Barry B.
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supporting information; experimental part
p. 1283 - 1286
(2009/06/30)
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- Novel CYP17 inhibitors: Synthesis, biological evaluation, structure-activity relationships and modelling of methoxy- and hydroxy-substituted methyleneimidazolyl biphenyls
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Recently, the steroidal CYP17 inhibitor Abiraterone entered phase II clinical trial for the treatment of androgen-dependent prostate cancer. As 17α-hydroxylase-17,20-lyase (CYP17) catalyzes the last step in androgen biosynthesis, inhibition of this target should affect not only testicular but also adrenal androgen formation. Therefore CYP17 inhibitors should be advantageous over existing therapies, for example with GnRH analogues. However, steroidal drugs are known for side effects which are due to affinities for steroid receptors. Therefore we decided to synthesize non-steroidal compounds mimicking the natural CYP17 substrates pregnenolone and progesterone. The synthesis and biological evaluation of a series of 15 novel and highly active non-steroidal CYP17 inhibitors are reported. The compounds were prepared via Suzuki-cross-coupling, Grignard reaction and CDI-assisted SNt-reaction with imidazole and their inhibitory activity was examined with recombinant human CYP17 expressed in Escherichia coli. Promising compounds were further tested for their selectivity against the hepatic enzyme CYP3A4 and the glucocorticoid-forming enzyme CYP11B1. All compounds turned out to be potent CYP17 inhibitors. The most active compounds 7 and 8 were much more active than Ketoconazole showing activity comparable to Abiraterone (IC50 values of 90 and 52 nM vs. 72 nM). Most compounds also showed higher selectivities than Ketoconazole, but turned out to be less selective than Abiraterone. Docking studies using our CYP17 protein model were performed with selected compounds to study the interactions between the inhibitors and the amino acid residues of the active site.
- Hille, Ulrike E.,Hu, Qingzhong,Vock, Carsten,Negri, Matthias,Bartels, Marc,Mueller-Vieira, Ursula,Lauterbach, Thomas,Hartmann, Rolf W.
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experimental part
p. 2765 - 2775
(2009/10/09)
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- Truxene-based columnar liquid crystals: Self-assembled structures and electro-active properties
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Columnar liquid-crystalline (LC) truxene derivatives containing branched flexible alkyl chains have been designed and synthesized. The dicyanomethylene and dithiafulvene substituents have been introduced into the π-conjugated truxene framework to tune the
- Isoda, Kyosuke,Yasuda, Takuma,Kato, Takashi
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supporting information; experimental part
p. 1619 - 1625
(2010/07/03)
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- Enzyme-triggered disassembly of dendrimer-based amphiphilic nanocontainers
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(Figure Presented) We demonstrate a new enzyme-induced disassembly of amphiphilic nanocontainers based on dendrimers. Disassembly and the ensuing release of noncovalently bound guest molecules are of great interest because of their implications in areas s
- Azagarsamy, Malar A.,Sokkalingam, Punidha,Thayumanavan
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supporting information; scheme or table
p. 14184 - 14185
(2010/02/15)
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- Site-specific installation and study of electroactive units in every layer of dendrons
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(Graph Presented) Whereas encapsulation of functional groups at the core of dendrimers is well-understood, very little is known about their intermediate layers or even the periphery. Here we report on a systematic investigation of every layer of dendrimer
- Azagarsamy, Malar A.,Krishnamoorthy, Kothandam,Sivanandan, Kulandaivelu,Thayumanavan
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scheme or table
p. 9475 - 9485
(2010/03/04)
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- Liquid crystalline behavior of tetraaryl derivatives of benzo[c]cinnoline, tetraazapyrene, phenanthrene, and pyrene: The effect of heteroatom and substitution pattern on phase stability
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A series of closely related tetrasubstituted derivatives of benzo[c]cinnoline (1), tetraazapyrene (2), phenanthrene (3), and pyrene (4) were investigated for their mesogenic properties using thermal, optical, spectroscopic, and powder XRD analyses. Only three 3,4-dioctyloxyphenyl derivatives exhibited mesogenic properties. Substitution of N for CH (3 → 1 and 4 → 2 pairs) and also increase of the core element size (1 → 2 and 3 → 4 pairs) significantly increases the mesophase stability. The findings and observed trends were rationalized by analysis of conformational properties which included calculation of the planarization energy, and modeling of aliphatic chain density and fill fractions. MO calculations showed that the tetraaza derivative 2c is significantly electron deficient and suitable for electron conductive materials. The Royal Society of Chemistry.
- Sienkowska, Monika J.,Farrar, John M.,Zhang, Fan,Kusuma, Sharat,Heiney, Paul A.,Kaszynski, Piotr
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p. 1399 - 1411
(2008/02/07)
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- Synthesis of 5-substituted resorcinol derivatives via cross-coupling reactions
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Suzuki and Stille cross-coupling reactions were utilized in the synthesis of 5-substituted 1,3-dimethoxybenzerie and 5-substituted resorcinol derivatives. The substituted resorcinol derivatives were obtained in only three steps from inexpensive reagents. 1,3-Dimethoxybenzoic acid and 1-chloro-3,5-dimethoxybenzene were transformed into 1-iodo-, 1-bromo-, 1-trimethyltin-3,5-dimethoxybenzene and 3,5-dimethoxyphenyl boronic acid. 5-Allyl-1,3-dimethoxybenzene and 3,5-dimethoxybiphenyl derivatives were obtained via cross coupling reactions under mild conditions. HI, BBr3 and AlI3 were used to demethylate these dimethoxybenzenes into their resorcinol derivatives.
- Dol, Georg C.,Kamer, Paul C. J.,Van Leeuwen, Piet W. N. M.
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p. 359 - 364
(2007/10/03)
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