- Synthesis of benzyl thioether derivatives via N-heterocyclic carbene palladium(II)-catalyzed cross coupling of benzylammonium salts with thiophenols
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A new route to benzyl thioether derivatives has been developed via the N-heterocyclic carbene palladium(II)-catalyzed cross coupling of benzylammonium salts with thiophenols. Under the optimal conditions, different benzylammonium salts could be well toler
- Wang, Tao,Guo, Jiarui,Xu, Yongli,Wang, Xiaobo,Wang, Yan,Feng, Dandan,Liu, Lantao
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- USP30 INHIBITORS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of USP30, and the treatment of USP30-mediated disorders.
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Paragraph 00753; 00755-00756
(2021/03/19)
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- Enhancement of Benzothiazoles as Pteridine Reductase-1 Inhibitors for the Treatment of Trypanosomatidic Infections
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2-Amino-benzo[d]thiazole was identified as a new scaffold for the development of improved pteridine reductase-1 (PTR1) inhibitors and anti-trypanosomatidic agents. Molecular docking and crystallography guided the design and synthesis of 42 new benzothiazoles. The compounds were assessed for Trypanosoma brucei and Leishmania major PTR1 inhibition and in vitro activity against T. brucei and amastigote Leishmania infantum. We identified several 2-amino-benzo[d]thiazoles with improved enzymatic activity (TbPTR1 IC50 = 0.35 μM; LmPTR1 IC50 = 1.9 μM) and low μM antiparasitic activity against T. brucei. The ten most active compounds against TbPTR1 were able to potentiate the antiparasitic activity of methotrexate when evaluated in combination against T. brucei, with a potentiating index between 1.2 and 2.7. The compound library was profiled for early ADME toxicity, and 2-amino-N-benzylbenzo[d]thiazole-6-carboxamide (4c) was finally identified as a novel potent, safe, and selective anti-trypanocydal agent (EC50 = 7.0 μM). Formulation of 4c with hydroxypropyl-β-cyclodextrin yielded good oral bioavailability, encouraging progression to in vivo studies.
- Linciano, Pasquale,Pozzi, Cecilia,Iacono, Lucia Dello,Di Pisa, Flavio,Landi, Giacomo,Bonucci, Alessio,Gul, Sheraz,Kuzikov, Maria,Ellinger, Bernhard,Witt, Gesa,Santarem, Nuno,Baptista, Catarina,Franco, Caio,Moraes, Carolina B.,Müller, Wolfgang,Wittig, Ulrike,Luciani, Rosaria,Sesenna, Antony,Quotadamo, Antonio,Ferrari, Stefania,P?hner, Ina,Cordeiro-Da-Silva, Anabela,Mangani, Stefano,Costantino, Luca,Costi, Maria Paola
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p. 3989 - 4012
(2019/05/06)
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- Nano cobalt ferrite catalyzed coupling reaction of nitroarene and alkyl halide: An odorless and ligand-free rout to unsymmetrical thioether synthesis
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This study describes an odorless protocol for the synthesis of unsymmetrical sulfides via cobalt ferrite (CoFe2O4) catalyzed cross-coupling reaction of nitroarenes with alkyl halides in the presence of thiourea as sulfur source under
- Moghaddam, Firouz Matloubi,Pourkaveh, Raheleh
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- Synthesis of sulfonimide-based branched arylsulfonyl chlorides
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A four-step synthesis of two branched arylsulfonyl chlorides bearing a sulfonimide branching point is described. The protocol consists of the nucleophilic substitution of a nitro group or a halogen in the corresponding nitro aromatic compounds with benzyl mercaptide and reduction of the remaining nitro group to the amino group. The latter was persulfonylated with 4-toluene sulfonyl chloride and, finally, the benzylsulfide group was converted into a sulfonyl chloride moiety.
- Rozhkov, Vladimir V.,Kolotylo, Mykola V.,Onys'Ko, Petro P.,Lukin, Oleg
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p. 308 - 309
(2016/01/12)
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- Novel heterogeneous catalyst systems based on Pd(0) nanoparticles onto amine functionalized silica-cellulose substrates [Pd(0)-EDA/SCs]: Synthesis, characterization and catalytic activity toward C-C and C-S coupling reactions in water under limiting basic conditions
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Novel heterogeneous catalyst systems based on the immobilization of Pd(0) nanoparticles onto ethylene diamine functionalized silica-cellulose substrates [Pd(0)-EDA/SCs] are reported with a view to introduce new synthetic routes under base-free conditions. The base functionalized organic/inorganic hybrid provides specific basic sites for the reactions to occur under base-free or less basic conditions, and that too with excellent yields. Moreover, the basic nitrogen sites present on the substrate can effectively stabilize and enhance the activity of Pd(0) nanoparticles by preventing their agglomeration and controlling their size. All the catalysts were characterized by TGA and FTIR analysis and the most active catalyst, [Pd(0)-EDA/SC-2] was further characterized by SEM, TEM, HRTEM, EDX, CHN and XRD studies. Additionally, it is shown that the Pd(0)-EDA/SCs exhibits excellent activity under limiting basic conditions for the C-C and C-S coupling reactions employing water as the "Green solvent". Furthermore, the novel catalyst could be recovered in a facile manner from the reaction mixture and could be reused up to five times without significant loss of catalytic activity.
- Bhardwaj, Madhvi,Sahi, Seema,Mahajan, Hitesh,Paul, Satya,Clark, James. H.
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- Metal acetylacetonates covalently anchored onto amine functionalized silica/starch composite for the one-pot thioetherification and synthesis of 2H-indazoles
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This paper reports a series of novel metal acetylacetonates covalently anchored onto amine functionalized silica/starch composite, prepared by the Schiff condensation of metal acetylacetonates [Co(acac)2, Cu(acac)2, Pd(acac)2, Ru(acac)3, Mn(acac)3, Co(acac)3] with organically modified 3-aminopropyl silica/starch composite. Different metal acetylacetonates have been chosen with a view to select the most active heterogeneous catalyst. Among various catalysts, covalently anchored Cu(acac)2 onto amine functionalized silica/starch composite [ASS-Cu(acac)2] was found to be the most active and recyclable catalyst for the one-pot thioetherification and one-pot three component synthesis of 2H-indazoles via consecutive C-N and N-N bond formations. All the catalysts were characterized by FTIR, TGA and AAS analysis and the most active catalyst, [ASS-Cu(acac)2] was further characterized by SEM and TEM. The catalyst could be recovered by simple filtration and reused with almost consistent activity for four consecutive runs.
- Sodhi, Ravinderpal Kour,Changotra, Avtar,Paul, Satya
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p. 1819 - 1831
(2015/02/19)
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- The effect of nitrogen atoms in the enantioselective oxidation of aryl or heteroaryl benzyl sulfides
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Some aminophenyl benzyl sulfides or benzyl pyridyl sulfides were asymmetrically oxidized with tert-butyl hydroperoxide in the presence of a complex between titanium i-propoxide and (S, S)-hydrobenzoin, an oxidation system that works particularly well with
- Capozzi, Maria Annunziata M.,Fracchiolla, Giuseppe,Cardellicchio, Cosimo
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p. 646 - 650
(2014/01/06)
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- One-pot thioetherification of aryl halides with thiourea and benzyl bromide in water catalyzed by Cu-grafted furfural imine-functionalized mesoporous SBA-15
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Surface functionalization of SBA-15 followed by its reaction with Cu(OAc)2 has been carried out to develop a new Cu-grafted functionalized mesoporous material, which catalyzes one-pot three component coupling of different aryl halides with thiourea and benzyl bromide in aqueous medium to produce aryl thioethers in very good yields (80-88%).
- Mondal, John,Modak, Arindam,Dutta, Arghya,Basu, Sohini,Jha,Bhattacharyya, Dibyendu,Bhaumik, Asim
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supporting information; experimental part
p. 8000 - 8002
(2012/09/08)
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- A highly efficient palladium-catalyzed one-pot synthesis of unsymmetrical aryl alkyl thioethers under mild conditions in water
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A palladium-catalyzed, one-pot synthesis of unsymmetrical aryl alkyl thioethers involving aryl halides (aryl bromides and chlorides), thiourea and alkyl bromides has been realized under mild conditions (room temperature to 50 °C) in water with polyoxyethanyl α-tocopheryl sebacate (PTS) as amphiphile. The PTS/water could be recycled in up to eight runs without an obvious change in its activity. Copyright
- Wang, Liang,Zhou, Wei-You,Chen, Sheng-Chun,He, Ming-Yang,Chen, Qun
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supporting information; experimental part
p. 839 - 845
(2012/05/20)
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- Carbon-sulfur coupling reactions catalyzed by Pd-NHC complex
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The cross-coupling reaction of aryl halides with aliphatic or aromatic thiols catalyzed by (SIPr)Pd(Py)Clis reported. This Pd-N-heterocyclic carbene (NHC) complex shows good to excellent activities toward various deactivated electron-rich aryl halides and even with unactivated aryl chlorides in C-S coupling reactions. The reactions proceeded in good yields, broad scope, and high tolerance of functional groups. The Pd-NHC complex is stable and easily to synthesize, so it is an excellent candidate to replace Pd-organophosphanes commonly used in C-S coupling catalysis. Georg Thieme Verlag Stuttgart - New York.
- Shi, Yanhui,Cai, Zhengyuan,Guan, Pei,Pang, Guangsheng
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supporting information; experimental part
p. 2090 - 2096
(2011/10/09)
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- Efficient reduction of nitroarenes over nickel-iron mixed oxide catalyst prepared from a nickel-iron hydrotalcite precursor
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Nickel-iron mixed oxide prepared from a nickel-iron hydrotalcite precursor was found to be a highly efficient catalyst for the chemoselective reduction of nitroarenes under mild reaction conditions.
- Shi, Qixun,Lu, Rongwen,Lu, Lianhai,Fu, Xinmei,Zhao, Defeng
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p. 1877 - 1881
(2008/09/17)
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- A facile one-pot preparation of alkyl aminoaryl sulfides for the synthesis of GW7647 as an agonist of peroxisome proliferator-activated receptor α
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We have developed two simple and high yielding one-pot syntheses of alkyl aminoaryl sulfides containing a series of four-steps: in situ protection of the free amine by reaction with a Grignard reagent, halogen-lithium exchange, sulfur insertion, and a substitution reaction with various electrophiles. Through this protocol, we have successfully synthesized tert-butyl-2-[4-(2-aminoethyl) phenylsulfanyl]-2-methylpropanoate, a key intermediate for the synthesis of GW7647 and GW9578 (ureido-TiBAs), in 92% yield. Furthermore, we were able to improve the overall yield of, GW7647 to 66%, 3 times the yield previously reported.
- Ham, Jungyeob,Cho, Sung Jin,Ko, Jaeyoung,Chin, Jungwook,Kang, Heonjoong
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p. 5781 - 5784
(2007/10/03)
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- Synthesis and in vitro antifungal activity of 4-substituted phenylguanidinium salts
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A series of 4-substituted phenylguanidinium derivatives was synthesized and its antimicrobial activity was evaluated in vitro against eight potentially pathogenic strains of fungi.
- Braunerova, Gabriela,Buchta, Vladimir,Silva, Luis,Kunes, Jiri,Palat Jr., Karel
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p. 443 - 450
(2007/10/03)
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- BENZAZEPINE DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE
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The present invention provides a novel benzazepine derivative represented by formula : wherein, R1 is a 5- or 6-membered aromatic ring, R2 is lower alkyl group, etc., Y is an optionally substituted imino group, ring A and ring B are independently an optionally substituted aromatic ring, W is formula -W1-X2-W2- (W1 and W2 are independently S(O)m1 (m1 is 0, 1 or 2), etc., and X2 is an optionally substituted alkylene groupetc. ), a preparation method and use thereof.
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- Efflux pump inhibitors
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Compounds are described which have efflux pump inhibitor activity. Also described are methods of using such efflux pump inhibitor compounds and pharmaceutical compositions which include such compounds.
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