- Oxidative C-H Homocoupling of Push-Pull Benzothiazoles: An Atom-Economical Route to Highly Emissive Quadrupolar Arylamine-Functionalized 2,2′-Bibenzothiazoles with Enhanced Two-Photon Absorption
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Copper(II)-catalyzed C-H/C-H coupling of dipolar 2-H-benzothiazoles end-capped with triphenylamine moieties affords highly fluorescent 2,2′-bibenzothiazoles with quadrupolar (D-π-A-π-D) architecture displaying large two-photon absorption (TPA) cross sections (543-1252 GM) in the near-infrared region. The notably higher TPA performance as compared to quadrupolar π-systems with a widely used 2,2′-bipyridine core, along with the ease of the synthesis and chelating N^N ability, makes the title biheteroaryl platform an attractive building block for a large scope of functional dyes exploiting nonlinear optical phenomena.
- Fakis, Mihalis,Georgiou, Dimitris,Gyepes, Róbert,Hrobárik, Peter,Nociarová, Jela,Osusky, Patrik,Polyzos, Ioannis,Smolí?ek, Maro?
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supporting information
p. 5512 - 5517
(2021/07/31)
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- Design, synthesis and biological evaluation of new benzoxazolone/benzothiazolone derivatives as multi-target agents against Alzheimer's disease
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In this study, four series of compounds with benzoxazolone and benzothiazolone cores were designed, synthesized and evaluated as multifunctional agents against Alzheimer's disease (AD). Additionally, in order to shed light on the effect of the carbonyl groups of benzoxazolone/benzothiazolone, benzoxazole/benzothiazole-containing analogues were also synthesized and evaluated. Inhibition potency of all final compounds towards cholinesterase enzymes and their antioxidant activity were tested. Subsequently, the anti-inflammatory activity, cytotoxicity, apoptosis, and Aβ aggregation inhibition tests were also performed for selected compounds. The results indicated that compounds 11c, a pentanamide derivative with benzothiazolone core, and 14b, a keton derivative with benzothiazolone core, were considered as promising multi-functional agents for further investigation against AD. The reversibility, kinetic and molecular docking studies were also performed for the compounds with the highest AChE 14b (eeAChE IC50 = 0.34 μM, huAChE IC50 = 0.46 μM) and BChE 11c (eqBChE IC50 = 2.98 μM, huBChE IC50 = 2.56 μM) inhibitory activities.
- Erdogan, Merve,Kilic, Burcu,Sagkan, Rahsan Il?kc?,Aksakal, Fatma,Ercetin, Tugba,Gulcan, Hayrettin O.,Dogruer, Deniz S.
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- K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles
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We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.
- Deng, Guobo,Kuang, Daizhi,Liang, Yun,Yang, Yuan,Yu, Jiangxi,Zhang, Fuxing,Zhu, Xiaoming
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supporting information
p. 3789 - 3793
(2020/06/04)
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- Synthetic method of ammonium acetate-mediated benzothiazole compound
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The invention discloses a synthetic method of an ammonium acetate-mediated benzothiazole compound . The synthetic method comprises the steps: adding an o-haloaniline derivative, potassium sulfide, dimethyl sulfoxide, a catalyst, an additive 1 and an additive 2 into a reaction tube, carrying out a stirring reaction at the temperature of 130-150 DEG C, cooling to room temperature after the reactionis finished, and separating and purifying the product to obtain the benzothiazole compound. The invention provides the synthetic method of the benzothiazole compound by taking K2S as a sulfur source,DMSO as a carbon source and an oxidizing agent, an o-haloaniline derivative as a substrate and an ammonium acetate mediated three-component one-pot method. The method has the advantages of fewer reaction steps, mild reaction conditions, good functional group tolerance and the like.
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Paragraph 0048-0050
(2020/11/23)
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- Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase
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The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.
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Paragraph 0013; 0095
(2019/02/13)
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- A Double-Clicking Bis-Azide Fluorogenic Dye for Bioorthogonal Self-Labeling Peptide Tags
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Herein, we give the very first example for the development of a fluorogenic molecular probe that combines the two-point binding specificity of biarsenical-based dyes with the robustness of bioorthogonal click-chemistry. This proof-of-principle study reports on the synthesis and fluorogenic characterization of a new, double-quenched, bis-azide fluorogenic probe suitable for bioorthogonal two-point tagging of small peptide tags by double strain-promoted azide-alkyne cycloaddition. The presented probe exhibits remarkable increase in fluorescence intensity when reacted with bis-cyclooctynylated peptide sequences, which could also serve as possible self-labeling small peptide tag motifs. The first example of a fluorogenic molecular probe has been developed that combines the two-point binding specificity of biarsenical-based dyes with the robustness of bioorthogonal click-chemistry. The new, double-quenched, bis-azide fluorogenic probe can bind to small bis-cyclooctynylated peptide tags through a double strain-promoted click reaction (see figure; SPAAC=strain-promoted alkyne-azide cycloaddition). The probe exhibits remarkable increase in fluorescence intensity with peptide sequences that can serve as possible self-labeling small peptide tags.
- Demeter, Orsolya,Fodor, Eszter A.,Kállay, Mihály,Mez, Gábor,Németh, Krisztina,Szabó, Pál T.,Kele, Péter
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supporting information
p. 6382 - 6388
(2016/05/02)
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- Atmospheric CO2 promoted synthesis of N-containing heterocycles over B(C6F5)3 catalyst
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B(C6F5)3 combined with atmospheric CO2 was found to be highly effective for the cyclization of ortho-substituted aniline derivatives with N,N-dimethylformamide (DMF), and a series of N-containing heterocycles including benzothiazoles, benzimidazoles, quinazolinone and benzoxazole were obtained in good to excellent yields.
- Gao, Xiang,Yu, Bo,Mei, Qingqing,Yang, Zhenzhen,Zhao, Yanfei,Zhang, Hongye,Hao, Leiduan,Liu, Zhimin
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p. 8282 - 8287
(2016/10/11)
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- Enhanced treatment regimens using mTor inhibitors
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The present invention provides for methods and pharmaceutical compositions comprising inhibitors of mTorC1 and/or mTorC2. In some aspects, the invention provides for treatment regimens resulting in enhanced treatment efficacy and better tolerability.
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Page/Page column 126
(2015/11/27)
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- Ionic Liquid-Catalyzed C-S Bond Construction using CO2 as a C1 Building Block under Mild Conditions: A Metal-Free Route to Synthesis of Benzothiazoles
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The construction of the C-S bond using CO2 as a C1 feedstock can be considered as a green route for the synthesis of S-containing compounds and is of great significance. Herein, we report the acetate-based ionic liquids (ILs)-catalyzed synthesis of benzothiazoles via cyclization of 2-aminothiophenols with CO2 and hydrosilane under mild conditions (e.g., 60 °C, 0.5 MPa). It was found that the IL (e.g., 1-butyl-3-methylimidazolium acetate, [Bmim][OAc]) served as a multifunctional catalyst with activating CO2 and hydrosilane to form a formoxysilane intermediate, as well as simultaneously activating 2-aminothiophenols through a hydrogen bond, finally resulting in the production of benzothiazoles. [Bmim][OAc] showed the best performance, and a series of benzothiazoles were obtained in high yields. To the best of our knowledge, this is the first protocol for the synthesis of benzothiazoles using CO2 as a C1 building block under metal-free and mild conditions.
- Gao, Xiang,Yu, Bo,Yang, Zhenzhen,Zhao, Yanfei,Zhang, Hongye,Hao, Leiduan,Han, Buxing,Liu, Zhimin
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p. 6648 - 6652
(2015/11/23)
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- COMBINATION OF KINASE INHIBITORS AND USES THEREOF
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The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth. The present invention also provides a pharmaceutical kit effective for treating a disease condition associated with PI3 -kinase α and/or mTOR in a subject.
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Paragraph 00514
(2014/10/04)
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- COMBINATION PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
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The present invention provides for methods and pharmaceutical compositions for treating proliferative disorders. In one aspect, the method comprises administration of two cell-cycle suppressors having a synergistic effect. In another aspect, two cell-cycle suppressors having a synergistic effect are provided in a pharmaceutical composition.
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Paragraph 0498
(2014/12/09)
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- Cu-catalyzed cross-dehydrogenative coupling reactions of (benzo)thiazoles with cyclic ethers
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Copper-catalyzed cross-dehydrogenative coupling (CDC) reactions of (benzo)thiazoles with cyclic ethers were developed under mild conditions. In particular, the formation of C-C bonds via the CDC reactions between non-benzo-fused azoles and ethers are reported for the first time. In addition, the acetals, known as the masked 2-thiazolecarboxaldehydes, could be successfully obtained by this CDC reaction. The preliminary mechanism and supportive DFT calculations are discussed as well.
- Xie, Zengyang,Cai, Yuping,Hu, Hongwen,Lin, Chen,Jiang, Juli,Chen, Zhaoxu,Wang, Leyong,Pan, Yi
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supporting information
p. 4600 - 4603
(2013/09/24)
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- Structure-activity relationships of N-phenyl-N′-benzothiazol-6-ylurea synthetic derivatives: Cytokinin-like activity and adventitious rooting enhancement
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Some years ago we demonstrated the cytokinin-like activity of the synthetic N-phenyl-N′-benzothiazol-6-ylurea (PBU) and a relevant adventitious rooting adjuvant activity of symmetric urea derivatives devoid of any cytokinin- or auxin-like activity per se. Here we report the synthesis and the biological activity evaluation of nine symmetric or asymmetric ureas/thioureas, structurally related to PBU. None of them show cytokinin-like activity, while we demonstrate for the first time that PBU interacts with Arabidopsis cytokinin receptor CRE1/AHK4 in a heterologous bioassay system. Among the PBU derivatives, all the symmetric ureas/thioureas show an adventitious rooting adjuvant activity in various bioassays, confirming that this activity is strictly dependent on their chemical structure.
- Rolli, Enrico,Incerti, Matteo,Brunoni, Federica,Vicini, Paola,Ricci, Ada
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experimental part
p. 159 - 165
(2012/03/27)
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- Benzothiazoles with tunable electron-withdrawing strength and reverse polarity: A route to triphenylamine-based chromophores with enhanced two-photon absorption
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A series of dipolar and octupolar triphenylamine-derived dyes containing a benzothiazole positioned in the matched or mismatched fashion have been designed and synthesized via palladium-catalyzed Sonogashira cross-coupling reactions. Linear and nonlinear optical properties of the designed molecules were tuned by an additional electron-withdrawing group (EWG) and by changing the relative positions of the donor and acceptor substituents on the heterocyclic ring. This allowed us to examine the effect of positional isomerism and extend the structure-property relationships useful in the engineering of novel heteroaromatic-based systems with enhanced two-photon absorption (TPA). The TPA cross-sections (δTPA) in the target compounds dramatically increased with the branching of the triphenylamine core and with the strength of the auxiliary acceptor. In addition, a change from the commonly used polarity in push-pull benzothiazoles to a reverse one has been revealed as a particularly useful strategy (regioisomeric control) for enhancing TPA cross-sections and shifting the absorption and emission maxima to longer wavelengths. The maximum TPA cross-sections of the star-shaped three-branched triphenylamines are ~500-2300 GM in the near-infrared region (740-810 nm); thereby the molecular weight normalized δTPA/MW values of the best performing dyes within the series (2.0-2.4 GM?g-1?mol) are comparable to those of the most efficient TPA chromophores reported to date. The large TPA cross-sections combined with high emission quantum yields and large Stokes shifts make these compounds excellent candidates for various TPA applications, including two-photon fluorescence microscopy.
- Hrobarik, Peter,Hrobarikova, Veronika,Sigmundova, Ivica,Zahradnik, Pavol,Fakis, Mihalis,Polyzos, Ioannis,Persephonis, Peter
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experimental part
p. 8726 - 8736
(2012/01/05)
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- Non-fluorescent asymmetric cyanine dye compounds useful for quenching reporter dyes
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The invention provides asymmetric cyanine dye compounds having the general formula: including substituted forms thereof, which are non-fluorescent quencher molecules. The invention further provides reporter-quencher dye pairs, wherein the asymmetric cyanine dyes are the quenchers, polynucleotides incorporating the asymmetric cyanine dyes, and nucleic acid hybridization detection methods utilizing the dye-labeled polynucleotides.
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- Nitro-substituted non-fluorescent asymmetric cyanine dye compounds
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The invention provides an asymmetric cyanine dye compound having the structure including substituted forms thereof, wherein, at least one of R1 and R2 is linking group, X is O, S, or Se, and n ranges from 0 to 2. The invention further provides reporter-quencher dye pairs comprising the asymmetric cyanine dyes, dye-labeled polynucleotides incorporating the asymmetric cyanine dyes, and hybridization detection methods utilizing the dye-labeled polynucleotides.
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- 5- AND 6-(2-IMIDAZOLIN-2-YLAMINO) AND -(2-THIAZOLIN-2-YLAMINO)-BENZOTHIAZOLES AS ALPHA-2 ADRENERGIC LIGANDS
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This invention is directed to indole and benzothiazole compounds which are selective for cloned human alpha 2 receptors. This invention is also related to uses of these compounds for any indication where use of an alpha 2 agonist may be appropriate. Specifically, this includes use as analgesic, sedative and anaesthetic agents. In addition, this invention includes using such compounds for lowering intraocular pressure, presbyopia, treating migraine, hypertension, alcohol withdrawal, drug addiction, rheumatoid arthritis, ischemic pain, spasticity, diarrhea, nasal decongestion, urinary incontinence as well as for use as cognition enhancers and ocular vasoconstriction agents. The invention further provides a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.
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- Deamination of 2-aminothiazoles and 3-amino-1,2,4-triazines with nitric oxide in the presence of a catalytic amount of oxygen
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2-Aminothiazoles, 2-aminobenzazoles, and 3-amino-1,2,4-triazines were deaminated using nitric oxide (NO) in the presence of a catalytic amount of oxygen to afford corresponding unsubstituted heterocycles in good yields.
- Itoh, Takashi,Matsuya, Yuji,Nagata, Kazuhiro,Ohsawa, Akio
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p. 1547 - 1549
(2007/10/03)
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- Formation of ?-Anionic Complexes in Reactions between 5-Nitrothiazole, 6-Nitrobenzothiazole and Tetrabutylammonium Borohydride
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The title reactions were performed in toluene, tetrahydrofuran (THF) and dimethylsulfoxide. 1H NMR spectral data from the reaction mixtures in Me2SO and in THF indicate that each substrate affords only one respective ?-anionic complex.Kinetic data on formation of the complexes indicate that the attack of the nuclophile and stability of the complexes are affected greatly by changing the solvent.In agreement with our previous findings, in Me2SO the rate of formation of the complexes from both substrates considered is lower than that observed in less polar solvents (toluene and THF).The explanation of this trend includes comparison of charge dispersion in the transition state with respect to the initial state and the possibility of changes in the hydride ion carrier when the solvent is changed.
- Forlani, Luciano,Ferrara, Antonio,Lugli, Andrea,Todesco, Paolo E.
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p. 1703 - 1708
(2007/10/02)
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- Nitrations and Oxidations with Inorganic Nitrate Salts in Trifluoroacetic Anhydride
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Metal nitrates in trifluoroacetic anhydride nitrate many aromatic compounds in high yields at room temperature, including polymers with aromatic groups.However, this system oxidizes phenols to quinoid products.
- Crivello, J.V.
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p. 3056 - 3060
(2007/10/02)
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