- Syntheses and properties of donor - Acceptor-type 2,5-diarylthiophene and 2,5-diarylthiazole
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Equation presented. Syntheses of differently substituted 2,5-diarylthiophenes and 2,5-diarylthiazoles are carried out with the palladium-catalyzed C-H substitution reaction using AgF as an activator. Remarkably strong photoluminescence is observed in 2,5-
- Masui, Kentaro,Mori, Atsunori,Okano, Kunihiko,Takamura, Kenji,Kinoshita, Motoi,Ikeda, Tomiki
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- Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols
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A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.
- Xia, Anjie,Qi, Xueyu,Mao, Xin,Wu, Xiaoai,Yang, Xin,Zhang, Rong,Xiang, Zhiyu,Lian, Zhong,Chen, Yingchun,Yang, Shengyong
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- Bicyclic alkaloid compound, preparation method and applications thereof
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The present invention relates to a bicyclic alkaloid compound, or a tautomer, a stereoisomer, a racemate, the non-equal mixture of enantiomers, a geometric isomer, a solvate, a pharmaceutically acceptable salt or a prodrug thereof, and a pharmaceutical composition containing the compound. The invention further discloses uses of the compounds and the pharmaceutical composition thereof as drugs, especially as anti-inflammatory drugs and anti-fibrotic drugs.
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- A new face of phenalenyl-based radicals in the transition metal-free C-H arylation of heteroarenes at room temperature: Trapping the radical initiator: Via C-C σ-bond formation
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The radical-mediated transition metal-free approach for the direct C-H bond functionalization of arenes is considered as a cost effective alternative to transition metal-based catalysis. An organic ligand-based radical plays a key role by generating an aryl radical which undergoes a subsequent functionalization process. The design principle of the present study takes advantage of a relatively stable odd alternant hydrocarbon-based phenalenyl (PLY) radical. In this study, the first transition metal-free catalyzed direct C-H arylation of a variety of heteroarenes such as azoles, furan, thiophene and pyridine at room temperature has been reported using a phenalenyl-based radical without employing any photoactivation step. This protocol has been successfully applied to the gram scale synthesis of core moieties of bioactive molecules. The phenalenyl-based radical initiator has been characterized crystallographically by trapping it via the formation of a C-C σ-bond between the phenalenyl radical and solvent-based radical species.
- Ahmed, Jasimuddin,Sreejyothi,Vijaykumar, Gonela,Jose, Anex,Raj, Manthan,Mandal, Swadhin K.
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p. 7798 - 7806
(2017/10/30)
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- Photon-Quantitative 6π-Electrocyclization of a Diarylbenzo[b]thiophene in Polar Medium
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The high reactivity of 6π-electrocyclization in polar solvents has remained one of the important challenges for diarylethenes because of the emergence of a twisted intramolecular charge transfer (TICT) state at the excited state in such polar media, which usually quenches the photocyclization reaction. Herein we report on the preparation and highly efficient photocyclization of 2,3-diarylbenzo[b]thiophenes with nonsymmetric side-aryl units in a polar solvent. While the dithiazolylbenzo[b]thiophene showed a suppressed quantum yield of 6π-electrocyclization of 54% in methanol, the replacement of a thiazole unit with a thiophene ring led to a photon-quantitative 6π-cyclization reaction. The nonsymmetrical modification into the side-aryl units was considered to enhance the CH/π interactions between side-aryl units to support a photoreactive conformation in methanol. The stabilization of the photochromic reactive conformation is expected to suppress the formation of the TICT state at the excited state, leading to highly efficient photoreactivity.
- Li, Ruiji,Nakashima, Takuya,Galangau, Olivier,Iijima, Shunsuke,Kanazawa, Rui,Kawai, Tsuyoshi
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supporting information
p. 1725 - 1730
(2015/08/06)
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- NOVEL NUCLEOSIDE PHOSPHORAMIDATE COMPOUND AND USE THEREOF
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The present invention provides a novel nucleoside phosphoramidate compound, or a stereoisomer, salt, hydrate, solvate or crystal thereof for the treatment of Flaviviridae family viral infection, especially hepatitis C viral infection. The present invention also provides the pharmaceutical composition comprising a compound of the present invention, or a stereoisomer, salt, hydrate, solvate or crystal thereof and a use of the compound or the composition of the present invention in the treatment of Flaviviridae family viral infection, especially hepatitis C viral infection. The compound of the present invention has a good anti-HCV effect.
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Paragraph 0083
(2015/11/24)
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- Programmed synthesis of arylthiazoles through sequential C-H couplings
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A programmed synthesis of privileged arylthiazoles via sequential C-H couplings catalyzed by palladium or nickel catalysts has been accomplished. This versatile protocol can supply all possible arylthiazole substitution patterns (2-aryl, 4-aryl, 5-aryl, 2
- Tani, Satoshi,Uehara, Takahiro N.,Yamaguchi, Junichiro,Itami, Kenichiro
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p. 123 - 135
(2014/01/06)
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- NITROGEN-CONTAINING AROMATIC HETEROCYCLYL COMPOUND
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The present invention provides a compound having excellent regulating action on blood lipid level. The present invention provides a compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof, etc., wherein A represents a 5-membered nitrogen-containing aromatic heterocyclyl group; R1 represents COOH or the like; each R2 represents an alkyl or the like; each R3 represents an optionally substituted phenyl, an optionally substituted phenylalkyl, or the like; m represents 0, 1, 2, or 3; n represents 0 or 1; each of R4, R5, R6, and R7 represents H, an alkyl, or the like; and B represents an optionally substituted naphthyl, an optionally substituted aromatic heterocyclyl, or a group represented by the following formula (II) wherein each of B1 and B2 represents an optionally substituted phenyl or an optionally substituted aromatic heterocyclyl.
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Page/Page column 69
(2011/04/25)
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- THIAZOLE AND OXAZOLE KINASE INHIBITORS
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The present invention is concerned with substituted azole derivatives that selectively modulate, regulate, and/or inhibit signal transduction mediated by certain native and/or mutant proteine kinases implicated in a variety of human and animal diseases such as cell proliferative, metabolic, allergic, and degenerative disorders. In particular, several of these compounds are potent and selective Flt-3 inhibitors or/and syk inhibitors.
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Page/Page column 59-60
(2011/08/04)
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- Design, synthesis, and in vitro antitumor evaluation of novel diaryl ureas derivatives
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Two series of novel diaryl ureas have been designed and synthesized, with their in vitro antitumor effect screened on human non-small cell lung cancer (NSCLC) cell line A549 and human breast cancer cell line MDA-MB-231. Some target compounds demonstrated significant inhibitory activities against both cell lines. Compared to contrast drug Sorafenib, 1b, 1d, 1f, 1i were found to demonstrate more potent antitumor activities. The structures of all the newly synthesized compounds were determined by 1H, 13C NMR, MS, IR and elementary analysis.
- Sun, Min,Wu, Xiaoqing,Chen, Junqing,Cai, Jin,Cao, Meng,Ji, Min
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experimental part
p. 2299 - 2306
(2010/07/05)
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- Cobalt-catalyzed C-SMe bond activation of heteroaromatic thioethers
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Cobalt-catalyzed activation of methylthio-substituted N-heterocycles facilitates either cross-coupling reactions with aryl- or benzylzinc compounds or synthesis of the corresponding zinc compounds.
- Begouin, Jeanne-Marie,Rivard, Michael,Gosmini, Corinne
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supporting information; experimental part
p. 5972 - 5974
(2010/11/02)
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- Use of NaOH as a new activator for the palladium-catalyzed direct CH arylation of thiazole derivatives
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Sodium hydroxide is found to serve as a new activator for the palladium-catalyzed C-H arylation of thiazole derivatives with aryl bromides and aryl iodides. The reaction of benzothiazole proceeds smoothly with 4-bromoanisole to afford the corresponding coupling product in an excellent yield.
- Miyaoku, Takayuki,Mori, Atsunori
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scheme or table
p. 151 - 155
(2009/09/06)
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- ARYL AMINO ACID DERIVATIVES AS INHIBITORS FOR TREATING INFLAMMATION
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The present invention relates to a chemical genus of 3-(triaryl)-2-aminopropanol derivative inhibitors of LTA4H (leukotriene A4 hydrolase) useful for the treatment and prevention of inflammatory diseases and disorders. The compounds have general formula III: A particular embodiment is
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Page/Page column 7; 16
(2008/06/13)
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- Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate): an efficient catalyst for regioselective C-2 arylation of heterocycles
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Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate), a structurally well defined O-containing transition metal complex is reported as an efficient catalyst for regioselective direct C-2 arylation of heterocycles with aryl halides. The present protocol is applicable to a wide variety of heterocycles providing good to excellent yields of products.
- Nandurkar, Nitin S.,Bhanushali, Mayur J.,Bhor, Malhari D.,Bhanage, Bhalchandra M.
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p. 1045 - 1048
(2008/09/17)
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- Direct arylation of thiazoles on water
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Wetter is better: The direct arylation of thiazoles on water is quicker, cleaner, and higher-yielding than arylation in organic solvents. The reaction works under mild conditions for an array of aryl iodides, producing 2,5-diaryl thiazoles in excellent yields. Importantly, novel bi-heteroaryl compounds are produced without the requirement for stoichiometric organometallic coupling agents. (Figure Presented).
- Turner, Gemma L.,Morris, James A.,Greaney, Michael F.
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p. 7996 - 8000
(2008/09/17)
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- BIARYL SUBSTITUTED HETEROCYCLE INHIBITORS OF LTA4H FOR TREATING INFLAMMATION
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The present invention relates to a chemical genus of biaryl substituted heterocycle inhibitors of LTA4H (leukotriene A4 hydrolase) useful for the treatment and prevention and prophylaxis of inflammatory diseases and disorders. The compounds have general formula Ψ: An example is
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Page/Page column 78
(2008/06/13)
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- Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides
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The Pd- and Cu-mediated reaction of a large variety of π-electron sufficient heteroarenes, which include free (NH)-imidazoles, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions provides regioselectively the required 2-arylheterocycle derivatives in high yields. 2-Aryl-1-phenyl-1H-imidazoles can also be prepared by a one-pot domino HALEX and Pd- and Cu-mediated arylation reactions of 1-phenyl-1H-imidazole with activated and unactivated aryl bromides under base-free and ligandless conditions. The protocol for the synthesis of 2-arylazoles involving the use of aryl iodides has been found to be suitable for the efficient preparation of three bioactive compounds and a key intermediate in the synthesis of a heparanase inhibitor.
- Bellina, Fabio,Calandri, Chiara,Cauteruccio, Silvia,Rossi, Renzo
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p. 1970 - 1980
(2007/10/03)
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- Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions
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The first palladium- and copper-mediated C-2 arylations of thiazole, oxazole, N-methylimidazole and N-arylimidazoles, as well as of free (NH)-imidazole, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions are described. Complete selectivity has been achieved under these unprecedented conditions, which allow the use of substrates containing base-sensitive groups, such the NH groups of imidazole, benzimidazole or indole, without their prior protection. No N-arylation products were detected in the arylation of free (NH)-imidazole, -benzimidazole and -indole. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Bellina, Fabio,Cauteruccio, Silvia,Rossi, Renzo
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p. 1379 - 1382
(2007/10/03)
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- Facile synthesis of 2,5-diarylthiazoles via palladium-catalyzed tandem C-H substitutions. Design of tunable light emission and liquid crystalline characteristics
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A mild and regioselective C-H substitution reaction of thiazole by the catalysis of the palladium/copper system is found to proceed in the presence of tetrabutylammonium fluoride under mild conditions. Applying the new reaction, we synthesized various 2,5
- Mori, Atsunori,Sekiguchi, Akitoshi,Masui, Kentaro,Shimada, Tomohiro,Horie, Masaki,Osakada, Kohtaro,Kawamoto, Masuki,Ikeda, Tomiki
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p. 1700 - 1701
(2007/10/03)
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- New potent C2-symmetric malaria plasmepsin I and II inhibitors.
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A series of malaria plasmepsin (Plm) I and II inhibitors containing a C(2)-symmetric core structure have been synthesised and tested for protease inhibition activity. These compounds can be prepared using a straightforward synthesis involving a phenol nuc
- Oscarsson, Karin,Oscarson, Stefan,Vrang, Lotta,Hamelink, Elizabeth,Hallberg, Anders,Samuelsson, Bertil
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p. 1235 - 1246
(2007/10/03)
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- β1-Selective Adrenoceptor Antagonists: Examples of the 2-phenyl>imidazole Class. 2
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An attempt to develop a highly cardioselective β-adrenoceptor antagonist devoid of intrinsic sympathomimetic activity (ISA) focused on exploring structure-activity relationships around (S)--amino>-2-hydroxypropoxy>phen
- Baldwin, John J.,Christy, Marcia E.,Denny, George H.,Habecker, Charles N.,Freedman, Mark B.,et al.
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p. 1065 - 1080
(2007/10/02)
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