- Novel functionalized indigo derivatives for organic electronics
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A series of nine novel indigo derivatives, including diiodoindigo, octahalogenated indigoids and compounds with extended π-conjugated system, were synthesized, characterized and investigated as semiconductor materials in organic field-effect transistors (OFETs). Among them, 6,6′-diiodoindigo demonstrated the ambipolar behavior with balanced p-type and n-type mobilities. The complete substitution of hydrogens at the indigo core with halogen atoms led to low electron mobilities in OFETs. An extension of the conjugated system through the introduction of small aromatic substituents (thiophene and phenyl) resulted in predominant p-type behavior. Fusion of aromatic rings resulted in z-shaped dibenzoindigo, which showed poor charge transport properties due to the non-optimal arrangement of molecules along each other in the crystal lattice. The acquired data fulfilled the previously reported model based on the relationship between the chemical nature of substituents and their positions at the indigo core, optoelectronic properties of materials and their performance in OFETs. The results of this study will be useful for rational design of a new generation of the indigo-based semiconductors for biocompatible organic electronics.
- Klimovich, Irina V.,Zhilenkov, Alexander V.,Кuznetsova, Lidiya I.,Frolova, Lubov A.,Yamilova, Olga R.,Troyanov, Sergey I.,Lyssenko, Konstantin A.,Troshin, Pavel A.
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- SULFINYLPHENYL OR SULFONIMIDOYLPHENYL BENZAZEPINES
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This invention relates to novel sulfinylphenyl or sulfonimidoylphenyl benzazepine compounds of the formula (I) wherein X and R1 to R6 are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are TLR agonists and may therefore be useful as medicaments for the treatment of diseases such as cancer, autoimmune diseases, inflammation, sepsis, allergy, asthma, graft rejection, graft-versus-host disease, immunodeficiencies, and infectious diseases.
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- BENZAZEPINE SULFONAMIDE COMPOUNDS
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This invention relates to novel benzazepine sulfonamide compounds of the formula (I), wherein R4 or R5 is -SO2-NR7R8 and R1 to R8 and Y are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are TLR agonists and may therefore be useful as medicaments for the treatment of diseases such as cancer, autoimmune diseases, inflammation, sepsis, allergy, asthma, graft rejection, graft-versus-host disease, immunodeficiencies, and infectious diseases.
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- Reexamination of the bromination of 2-nitrobenzaldehyde with NBS or NaBr-NaIO4 in sulfuric acid
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Two literature procedures for selective bromination of 2-nitrobenzaldehyde using N-bromosuccinimide (NBS) or NaBr-NaIO4 in sulfuric acid were examined. In contrast to the reports that 4-bromo-2-nitrobenzaldehyde is formed as a single product in good yield, reactions using NBS gave a number of isomeric mono- and dibrominated products identified by spectroscopical methods and by sodium borohydride reduction to the corresponding benzyl alcohol, and reactions using NaBr-NaIO4 did not furnish any product. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Cummings, Matthew M.,Soederberg, Bjoern C. G.
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supporting information
p. 954 - 958
(2014/03/21)
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- SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS
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Provided are compositions and methods useful for modulation of signaling through the Toll-like receptors TLR7 and/or TLR8. The compositions and methods have use in treating or preventing disease, including cancer, autoimmune disease, fibrotic disease, cardiovascular disease, infectious disease, inflammatory disorder, graft rejection, or graft-versus-host disease.
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Page/Page column 57-58
(2012/07/28)
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- SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS
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Provided are compositions and methods useful for modulation of signaling through the Toll- like receptors TLR7 and/or TLR8. The compositions and methods have use in treating or preventing disease, including cancer, autoimmune disease, infectious disease, inflammatory disorder, graft rejection, and graft-verses-host disease.
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- SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS
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Provided are compositions and methods useful for modulation of signaling through the Toll-like receptors TLR7 and/or TLR8. The compositions and methods have use in treating or preventing disease, including cancer, autoimmune disease, infectious disease, inflammatory disorder, graft rejection, and graft-verses-host disease.
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- A simple, safe and efficient synthesis of Tyrian purple (6,6'-Dibromoindigo)
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6,6'-Dibromoindigo is a major component of the historic pigment Tyrian purple, arguably the most famous dye of antiquity. Over the last century, chemists have been interested in developing practical syntheses of the compound We describe herein a new, reasonably simple and efficient synthesis of Tyrian purple which opens the way to the production of large quantities of the dye with minimal hazards and at low cost.
- Wolk, Joel L.,Frimer, Aryeh A.
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experimental part
p. 5561 - 5580
(2010/12/20)
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- METHODS OF SYNTHESIS OF BENZAZEPINE DERIVATIVES
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The disclosure describes method of synthesis of substituted benzazepine derivatives. Preferred methods according to the disclosure allow for large-scale preparation of benzazepine compounds having low levels of metal impurities. In some embodiments, preferred methods according to the disclosure also allow for the preparation of benzazepine derivatives without the use of chromatographic purification methods and in better yield than previously used methods for preparing such compounds. The methods disclosed herein find utility in synthetic organic chemistry as well as medicinal chemistry.
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Page/Page column 25-26
(2010/06/11)
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- QUINAZOLINES FOR PDK1 INHIBITION
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The invention provides novel quinazoline compounds that are inhibitors of PDK1. Also provided are pharmaceutical compositions including the compounds, and methods of treating proliferative diseases, such as cancers, with the compounds or compositions.
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- 8-SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS
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Provided are compositions and methods useful for modulation of signaling through the Toll-like receptors TLR7 and/or TLR8. The compositions and methods have use in the treatment of autoimmunity, inflammation allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer and immunodeficiency.
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Page/Page column 35; 3/3
(2010/11/26)
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- Bromination of deactivated aromatics: A simple and efficient method
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(Chemical Equation Presented) Highly deactivated aromatic compounds were smoothly monobrominated by treatment with N-bromosuccinimide (NBS) in concentrated H2SO4 medium affording the corresponding bromo derivatives in good yields. Mild reaction conditions and simple workup provides a practical and commercially viable route for the synthesis of bromo compounds of deactivated aromatics.
- Rajesh,Somasundaram,Saiganesh,Balasubramanian
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p. 5867 - 5869
(2008/02/09)
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- Synthesis and biological evaluation of conformationally constrained analogs of the antitumor agents XK469 and SH80. Part 5
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Conformational restriction of bioactive molecules offers the possibility of generating structures of increased potency. To this end, a synthesis has been achieved of (R,S)-2-[(8-chlorobenzofurano[2,3-b]quinolinyl)oxy]propionic acid (12a), a highly rigidified, polycyclic analog of 2-{4-[(7-chloro-2-quinoxalinyl) oxy]phenoxy}propionic acid (2a, XK469). Efforts to effect the same synthesis of the corresponding 8-bromo-derivative led to a mixture of intermediate, 8-chloro (9a), and 8-bromo-2-hydroxybenzofurano[2,3-b]quinoline (9b), generated by halogen-exchange, via an aromatic SRN1(ARN1) reaction of precursor, 8b, with pyridine hydrochloride. The presumption that conformational restriction of 1b-12a might enhance the antitumor potency of the latter has not been sustained. In fact, 12a proved to be significantly less active than 1b. However, it is apparent that virtually all of the spatial and steric properties of 12a, necessary for improved activity, including the disposition of the 2-oxypropionic acid side chain remain to be identified.
- Hazeldine, Stuart T.,Polin, Lisa,Kushner, Juiwanna,White, Kathryn,Corbett, Thomas H.,Horwitz, Jerome P.
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p. 2462 - 2467
(2007/10/03)
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- Synthetic studies on perophoramidine and the communesins: Construction of the vicinal quaternary stereocenters
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An efficient synthetic strategy for installation of the two vicinal quaternary carbon centers of the communesins is reported. Key steps include the O-allylation/Claisen rearrangement of spirolactone systems, which are formed by tandem intramolecular Heck cyclization/carbonylation. Substituent and solvent effects on the stereochemical outcome of the Claisen rearrangements have been examined. The stereochemical assignment of the allyl spirolactone previously reported as 17 has now been revised to 31, which has the communesin relative configuration at the quaternary carbons. Key C-allyl spirolactone 59 bearing functional handles required for the communesin core has been constructed with a 9.8:1 diastereomer ratio.
- Seo, Jae Hong,Artman III, Gerald D.,Weinreb, Steven M.
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p. 8891 - 8900
(2007/10/03)
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- Quinazoline derivatives
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A compound of the formula (I) or a pharmaceutically acceptable salt thereof, a hydrate thereof, a solvate thereof, an optically active compound thereof, a racemate thereof or a diastereomer mixture thereof has a superior tyrosine-specific protein kinase inhibitory activity and is useful as a pharmaceutical agent, particularly as an agent for the prophylaxis or treatment of various cancers, psoriasis or diseases caused by arteriosclerosis, and the like.
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Page/Page column 30-31
(2010/02/07)
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- NOVEL FUSED TRIAZOLONES AND THE USES THEREOF
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This invention relates to novel compounds having the structural diagram (I) and to their pharmaceutical compositions and to their methods of use. These novel compounds provide a treatment or prophylaxis of cancer.
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- CYCLIC COMPOUNDS AND USES THEREOF
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Compounds of general formula (1) or salts thereof, exhibiting preventive and therapeutic effects against HIV infectious diseases wherein R1 is an optionally substituted five- or six-membered ring group; X1 is a free valency or the like; W is a divalent group represented by, e. g., general formula (2) (wherein A and B are each an optionally substituted five-to seven-membered ring; E1 and E4 are each optionally substituted carbon or the like; E2 and E3 are each oxygen or the like; and a and b are each a single bond or a double bond); X2 is a divalent group constituting a straight chain moiety; Z1 is a divalent cyclic group or the like; Z2 is a free valency or the like; and R2 is optionally substituted amino or the like.
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- An improved synthetic procedure for 6,6′-dibromoindigo (Tyrian purple)
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Tyrian purple was the most precious dye of antiquity. We describe a simple synthetic procedure that yields the actual dye, 6,6′-dibromoindigo 1, in considerably improved overall yield and of analytical purity, also being amenable to scale-up.
- Imming,Imhof,Zentgraf
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p. 3721 - 3727
(2007/10/03)
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- Benzo-1,6-naphthyridine Synthesis via Intramolecular Diels-Alder Reactions of Aryl Oxazoles: Synthetic Approach to 2-Bromoleptoclinidinone
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A new route for the synthesis of benzo-1,6-naphthyridines is described.The method involves the intramolecular Diels-Alder cycloaddition of aryl oxazoles with substituted acrylamides to give pyridines and was developed as a route to the antileukemic aromatic alkaloid 2-bromoleptoclinidinone.
- Jung, Michael E.,Dansereau, Susan M.K.
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p. 767 - 778
(2007/10/02)
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- Regioselective Bromine/Lithium Exchange in 2,5-Dibromo-1-nitrobenzene. - A Simple Synthesis of 4-Bromo-2-nitrobenzaldehyde and 6,6'-Dibromoindigo
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The reaction of phenyllithium with 2,5-dibromo-1-nitrobenzene (1) in tetrahydrofuran at -105 deg C leads to the lithium derivative 2 with high regioselectivity.By reaction with dimethylformamide 2 is converted into 4-bromo-2-nitrobenzaldehyde (3) in 92percent yield.The isomeric aldehyde 4 is not formed.With the same reaction sequence 2,4-dibromo-1-nitrobenzene (5) can be transformed into 5-bromo-2-nitrobenzaldehyde (6).From aldehyde 3 and nitromethane Tyrian purple (7) is easily accessible. - Keywords: Dibromonitrobenzenes; Bromine-lithium exchange; Formylation, regioselective; Indigo, 6,6'-dibromo-; Tyrian purple
- Voss, Gundula,Gerlach, Hans
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p. 1199 - 1202
(2007/10/02)
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