- Green synthesis of biphenyl carboxylic acids via Suzuki–Miyaura cross-coupling catalyzed by a water-soluble fullerene-supported PdCl2 nanocatalyst
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A green synthesis of variously substituted biphenyl carboxylic acids was achieved through Suzuki–Miyaura cross-coupling of a bromobenzoic acid with an aryl boronic acid using a water-soluble fullerene-supported PdCl2 nanocatalyst (C60-TEGs/ PdCl2). Yields of more than 90% were obtained at room temperature in 4 h using 0.05 mol% catalyst and 2 equiv. K2CO3.
- Liu, Wanyun,Zhou, Xiuming,Huo, Ping,Li, Jingbo,Mei, Guangquan
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- 1,5-disubstituted tetrazole compounds, and preparation method and application thereof
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The invention discloses 1,5-disubstituted tetrazole compounds, and a preparation method and an application thereof. The 1,5-disubstituted tetrazole compounds have good antitumor activity. The invention also provides a use of the 1,5-disubstituted tetrazol
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- NOVEL SELECTIVE 11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1
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The present invention relates to novel selective 11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors and the use thereof to prevent age-induced skin structure and function defects.
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Page/Page column 21-22; 30
(2017/02/09)
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- New telmisartan-derived PPARγ agonists: Impact of the 3D-binding mode on the pharmacological profile
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In previous studies, the 4′-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid was identified as pharmacophoric core for PPARγ activation. In this structure-activity relationship study the C2-alkyl chain was elongated and the 2-COOH group was changed to a carbamide/carbonitrile or shifted to the 3- or 4-position. Furthermore, the benzo[d]imidazole was exchanged by 2,3-dihydrobenzo[d]thiazole or 1H-indole. C2-propyl derivatives showed the profile of partial agonists, while elongation of the C2-chain to that of an n-heptyl group or a 4-COOH shift changed the pharmacological profile to that of a potent full agonist. This finding can be explained by binding to the LBD in different ligand conformations. Two anchoring points (Tyr473 and Arg288) exist in the LBD, which have to be contacted to achieve receptor activation. In a crystal violet chemosensitivity assay using COS-7?cells and LNCaP cells expressing PPARγ only the carbamide derivatives influenced the cell growth, independently on the presence of the PPARγ. Therefore, receptor mediated cytotoxicity can be excluded.
- Obermoser, Victoria,Urban, Margarethe E.,Murgueitio, Manuela S.,Wolber, Gerhard,Kintscher, Ulrich,Gust, Ronald
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supporting information
p. 138 - 152
(2016/08/30)
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- Melamine and melamine-formaldehyde polymers as ligands for palladium and application to Suzuki-Miyaura cross-coupling reactions in sustainable solvents
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The Suzuki-Miyaura cross-coupling reaction is a foundation stone of modern organic synthesis, as evidenced by its widespread use in the preparation of pharmaceuticals, agrochemicals, polymers, and other functional materials. With the prevalence of this venerable reaction in industrial synthesis, it is prudent to ensure its application adheres to the tenets of green chemistry. The introduction of cross-coupling catalysts that are active in sustainable solvents is therefore an important endeavor. In this report, a melamine-palladium complex is introduced as a versatile catalyst for the Suzuki-Miyaura cross-coupling reaction. This catalyst is soluble and active in both water and the renewable organic solvent ethyl lactate. The melamine-palladium catalyst can also be cross-linked by reaction with formaldehyde to generate an insoluble polymeric catalyst that can be recovered after the cross-coupling. The melamine-palladium system is inexpensive, easy to handle, bench-stable, and effective in catalysis in the presence of a variety of impurities (high cross-coupling yields were obtained in reactions run in unfiltered river water to illustrate this final point). Additionally, investigations reported herein revealed an intriguing relationship between catalytic efficiency and the base employed in the cross-coupling reaction. Implications for the mechanism of transmetalation in aqueous Suzuki-Miyaura cross-coupling reaction are discussed.
- Edwards, Grant A.,Trafford, Mitchell A.,Hamilton, Alaina E.,Buxton, Audrey M.,Bardeaux, Matthew C.,Chalker, Justin M.
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p. 2094 - 2104
(2014/04/03)
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- A highly efficient catalyst of a nitrogen-based ligand for the Suzuki coupling reaction at room temperature under air in neat water
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Glycine, as a kind of commercially available and inexpensive ligand, is used to prepare an air-stable and water-soluble catalyst for the Suzuki-Miyaura reaction in our study. In the presence of 0.1% [PdCl2(NH 2CH2COOH)2] as the catalyst, extremely excellent catalytic activity towards the Suzuki-Miyaura coupling of aryl halides containing the carboxyl group with various aryl boronic acids is observed at room temperature under air in neat water. the Partner Organisations 2014.
- Liu, Shiwen,Lv, Meiyun,Xiao, Daoan,Li, Xiaogang,Zhou, Xiuling,Guo, Mengping
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supporting information
p. 4511 - 4516
(2014/06/23)
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- Suzuki-miyaura cross-coupling under solvent-free conditions
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A solvent-free reaction protocol for Suzuki-Miyaura cross-couplings was developed. (Hetero)aryl bromides and chlorides are coupled with pinacol arylboronates in high yields. The reaction is catalyzed by conventional bis(triphenylphosphine)palladium(II) chloride [(PPh3) 2PdCl2] and/or palladium(II) acetate/SPhos [Pd(OAc) 2/SPhos] under air. Copyright
- Asachenko, Andrey F.,Sorochkina, Kristina R.,Dzhevakov, Pavel B.,Topchiy, Maxim A.,Nechaev, Mikhail S.
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p. 3553 - 3557
(2014/01/06)
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- Synthesis and functionalization of cyclic sulfonimidamides: A novel chiral heterocyclic carboxylic acid bioisostere
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An efficient synthesis of aryl substituted cyclic sulfonimidamides designed as chiral nonplanar heterocyclic carboxylic acid bioisosteres is described. The cyclic sulfonimidamide ring system could be prepared in two steps from a trifluoroacetyl protected sulfinamide and methyl ester protected amino acids. By varying the amino acid, a range of different C-3 substituted sulfonimidamides could be prepared. The compounds could be further derivatized in the aryl ring using standard cross-coupling reactions to yield highly substituted cyclic sulfonimidamides in excellent yields. The physicochemical properties of the final compounds were examined and compared to those of the corresponding carboxylic acid and tetrazole derivatives. The unique nonplanar shape in combination with the relatively strong acidity (pKa 5-6) and the ease of modifying the chemical structure to fine-tune the physicochemical properties suggest that this heterocycle can be a valuable addition to the range of available carboxylic acid isosteres.
- Pemberton, Nils,Graden, Henrik,Evertsson, Emma,Bratt, Emma,Lepistoe, Matti,Johannesson, Petra,Svensson, Per H.
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supporting information; experimental part
p. 574 - 578
(2012/08/29)
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- Suzuki-Miyaura coupling reactions in aqueous microdroplets with catalytically active fluorous interfaces
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Using microfluidic techniques and a novel fluorous-tagged palladium catalyst, we generated droplet reactors with catalytically active walls and used these compartments for small molecule synthesis.
- Theberge, Ashleigh B.,Whyte, Graeme,Frenzel, Max,Fidalgo, Luis M.,Wootton, Robert C. R.,Huck, Wilhelm T. S.
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supporting information; experimental part
p. 6225 - 6227
(2010/02/16)
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- Correlation of anti-HIV activity with anion spacing in a series of cosalane analogues with extended polycarboxylate pharmacophores
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Cosalane and its synthetic derivatives inhibit the binding of gp120 to CD4 as well as the fusion of the viral envelope with the cell membrane. The binding of the cosalanes to CD4 is proposed to involve ionic interactions of the negatively charged carboxylates of the ligands with positively charged arginine and lysine amino acid side chains of the protein. To investigate the effect of anion spacing on anti-HIV activity in the cosalane system, a series of cosalane tetracarboxylates was synthesized in which the two proximal and two distal carboxylates are separated by 6-12 atoms. Maximum activity was observed when the proximal and distal carboxylates are separated by 8 atoms. In a series of cosalane amino acid derivatives containing glutamic acid, glycine, aspartic acid, β-alanine, leucine, and phenylalanine residues, maximum activity was displayed by the di(glutamic acid) analogue. A hypothetical model has been devised for the binding of the cosalane di(glutamic acid) conjugate to CD4. In general, the compounds in this series are more potent against HIV-1RF in CEM-SS cells than they are vs HIV-1IIIB in MT-4 cells, and they are least potent vs HIV-2ROD in MT-4 cells.
- Santhosh,Paul,De Clercq,Pannecouque,Witvrouw,Loftus,Turpin,Buckheit, Jr.,Cushman
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p. 703 - 714
(2007/10/03)
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- Identification of optimal anion spacing for anti-HIV activity in a series of cosalane tetracarboxylates
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The binding of the anti-HIV agent cosalane to CD4 is thought to involve ionic interactions of negatively charged carboxylates of the ligand with positively charged residues on the surface of the protein. An investigation of the optimal anion distances for anti-HIV activity in a series of cosalane tetracarboxylate analogues has been completed, and maximal activity results when the two proximal and the two distal carboxylates are separated by eight atoms. (C) 2000 Elsevier Science Ltd.
- Paul, Gitendra C.,De Clercq, Erik,Pannecouque, Christophe,Witvrouw, Myriam,Loftus, Tracy L.,Turpin, Jim A.,Buckheit Jr., Robert W.,Cushman, Mark
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p. 2149 - 2152
(2007/10/03)
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- Heterocyclic derivatives in the treatment of Ischaemia and related diseases
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Compounds of the formula: STR1 wherein A, R1, R2, R3 and m are defined as in the specification or a pharmaceutically acceptable acid addition salt or N-oxide thereof, are calcium and sodium channel antagonists useful for treating mammals having a variety of disease states, such as stroke, epilepsy, hypertension, angina, migraine, arrhythmia, thrombosis, embolism, and also for treatment of spinal injuries.
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