- Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides
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CYP24A1 (25-hydroxyvitamin D-24-hydroxylase) is a useful enzyme target for a range of medical conditions including cancer, cardiovascular and autoimmune disease, which show elevated CYP24A1 levels and corresponding reduction of calcitriol (the biologically active form of vitamin D). A series of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides have been synthesised using an efficient synthetic route and shown to be potent inhibitors of CYP24A1 (IC50 0.11–0.35?μM) compared with the standard ketoconazole. Molecular modelling using our CYP24A1 homology model showed the inhibitors to fill the hydrophobic binding site, forming key transition metal interaction between the imidazole nitrogen and the haem Fe3+ and multiple interactions with the active site amino acid residues.
- Taban, Ismail M.,Zhu, Jinge,DeLuca, Hector F.,Simons, Claire
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Read Online
- In situ generation of palladium nanoparticles: Reusable, ligand-free heck reaction in PEG-400 assisted by focused microwave irradiation
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A rapid and efficient Heck coupling reaction of aryl iodides with terminal olefins was conducted in PEG-400 at 120 °C in the presence of potassium carbonate and palladium nanoparticles formed in situ from palladium chloride under focused microwave irradiation. High to excellent product yields were achieved. The reaction medium and catalyst could be easily recycled at least five times without significant loss in reactivity. Georg Thieme Verlag Stuttgart New York.
- Du, Zhengyin,Zhou, Wanwei,Bai, Lin,Wang, Fen,Wang, Jin-Xian
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Read Online
- NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: A novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media
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The novel heterogeneous bimetallic nanoparticles of Cu-Co were synthesized based on magnetic nanoparticles, and the magnetic nanocatalyst was characterized by XRD, FE-SEM, EDX mapping, BET, TEM, HRTEM, FTIR, TGA, and VSM. This catalyst was successfully applied as a recyclable magnetically catalyst in Heck, Suzuki, and C-N cross-coupling reactions with various aryl halides (iodides, bromides, and chlorides as challengeable substrates), with olefins, phenylboronic acid, and amines, respectively. We considered the rise of synergetic effects from the different Lewis acid and Br?nsted acid sites present in the catalyst. The catalyst was synthesized with cheap, available materials and a simple synthesis method. The catalyst can be separated easily using an external magnet. It was recycled for more than ten runs without a sensible loss of its catalytic activity, and no significant leaching of the Cu and Co quantity was observed. The significant benefits of the method are high-level generality, simple operation, and there are no heavy metals and toxic solvents. This is a quick, easy, efficacious and environmentally friendly protocol, and no by-products are formed in the reaction. These features make it an appropriate practical alternative protocol. In comparison with recent works, the other advantage of this catalyst is the synthesis of a wide variety of C-C and C-N bond derivatives (more than 40 derivatives). The other significant advantage is the low temperature of the reaction and the use of the least possible amount of the catalyst (0.003 g). The efficiency was good to excellent and the catalyst selectivity has been high. We aspire that our study inspires more interest to design novel catalysts based on using low-cost metal ions (such as cobalt and copper) in the cross-coupling reactions. This journal is
- Alavi G., Seyyedeh Ameneh,Nasseri, Mohammad Ali,Kazemnejadi, Milad,Allahresani, Ali,Hussainzadeh, Mahdi
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p. 7741 - 7757
(2021/05/13)
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- Aminomethylpyridinequinones as new ligands for PEPPSI-type complexes
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A set of six new catalysts possessing quinone moieties in a pyridine ligand was synthesized and fully characterized by standard analytical techniques, including X-Ray crystallography. The results obtained in Suzuki and Mizoroki–Heck cross-coupling reactions catalyzed by quinone-based compounds were comparable to these obtained in the presence of the original PEPPSI complex designed by Organ. DFT calculations allow to see the structural and electronic factors to describe their similarity. On the other hand, steric maps and NCI plots were the tools to have a more global view of the systems studied, leaving the sphere of reactivity around the metal.
- Gajda, Roman,Poater, Albert,Brotons-Rufes, Artur,Planer, Sebastian,Wo?niak, Krzysztof,Grela, Karol,Kajetanowicz, Anna
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p. 138 - 156
(2021/03/22)
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- Synthesis of Pd@graphene oxide framework nanocatalyst with enhanced activity in Heck-Mizoroki cross-coupling reaction
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A new method was developed for producing a catalyst involving a Pd nanoparticle (NP) embedded in a graphene oxide framework (Pd@GOF) with ordered macro- and mesoporous structures. First, 5,5′-diamino-2,2′-bipyridine was selected as cross-linking for covalent modification of GO nanosheets to prepare a three-dimensional (3D) framework with interlayer spaces in which well-dispersed and ultra-small Pd NPs in situ grew and embedded the framework. The synthesized nanopores 3D Pd@GOF can act as nanoreactors to help the reaction substrates thoroughly come into contact with the surface of Pd NPs, thereby exhibiting high activity toward the Heck reaction, rarely reported concerning Pd NPs supported on one-side functionalized graphene. The Pd@GOF catalyst can be used 10 times without any significant loss in the catalytic activity, confirming the long-term stability of this catalyst. Therefore, the covalently assembled GOF was proposed as a universal platform for hosting noble metal NPs to construct the desired metal@GOF nanocatalyst with improved activity and stability that can be used in a broad range of practical applications.
- Shekarizadeh, Arezoo,Azadi, Roya
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- Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts
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Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.
- Filimonov, Victor D.,Krasnokutskaya, Elena A.,Kassanova, Assia Zh.,Fedorova, Valentina A.,Stankevich, Ksenia S.,Naumov, Nikolay G.,Bondarev, Alexander A.,Kataeva, Veronika A.
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supporting information
p. 665 - 674
(2018/09/14)
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- Hedgehog pathway inhibitors of the acylthiourea and acylguanidine class show antitumor activity on colon cancer in vitro and in vivo
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Small series of acylguanidine and acylthiourea derivatives were synthesized in gram-scale and assayed for their ability to modulate the Hh signalling pathway. In vitro studies showed a low micromolar inhibitory activity toward tumor cell lines, while the oral administration revealed an excellent ADME profile in vivo. Compound 5 emerged as the most active and safe inhibitor of colon cancer cells both in vitro and in a xenograft mouse model. Based on these data, 5 could be prioritized to further development with the perspective of clinical studies.
- Vesci, Loredana,Milazzo, Ferdinando Maria,Stasi, Maria Antonietta,Pace, Silvia,Manera, Francesco,Tallarico, Carlo,Cini, Elena,Petricci, Elena,Manetti, Fabrizio,De Santis, Rita,Giannini, Giuseppe
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p. 368 - 379
(2018/08/17)
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- Chemoselective and Sequential Palladium-Catalyzed Couplings for the Generation of Stilbene Libraries via Immobilized Substrates
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A versatile palladium-catalyzed tandem synthetic sequence to afford E-stilbenes libraries has been developed. Excellent regio- and stereocontrol have been achieved by means of the sequence of Hiyama and Heck cross-couplings. Undesirable homocoupling bypro
- Traficante, Carla I.,Fagundez, Catherine,Serra, Gloria L.,Mata, Ernesto G.,Delpiccolo, Carina M. L.
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supporting information
p. 225 - 229
(2016/06/01)
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- A highly active nickel-fibre complex as a catalyst for the Heck reaction
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A new amidoxime fibre-nickel catalyst (AOFs-Ni(0)) was synthesised by a coordination and reduction reaction. The X-ray diffraction patterns indicated that the Ni(II) ions were reduced to Ni(0). The scanning electron microscope image showed that the Ni(0) particles which were reduced in situ had a diameter of about 300 nm. This catalyst demonstrated high activity in the Heck coupling reaction of aryl iodine and conjugated alkenes without the protection of an inert atmosphere.
- Wu, Zhi-Chuan,Yang, Quan,Chen, Meng,Liu, Li,Tao, Ting-Xian
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p. 164 - 166
(2016/04/20)
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- Efficiency of [2 + 2] photodimerization of various stilbene derivatives within the DNA duplex scaffold
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A DNA duplex was used as a scaffold to evaluate the intrinsic reactivity of [2 + 2] photodimerization between stilbene derivatives; the duplex pre-organizes the substrates avoiding the need for an association step. Unmodified stilbenes were first introduc
- Doi, Tetsuya,Kashida, Hiromu,Asanuma, Hiroyuki
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supporting information
p. 4430 - 4437
(2015/04/14)
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- Palladium nanoparticles supported on triazine functionalised mesoporous covalent organic polymers as efficient catalysts for Mizoroki-Heck cross coupling reaction
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A novel class of mesoporous covalent organic polymer (MCOP) was synthesised by the nucleophilic substitution of cyanuric chloride with 4,4′- dihydroxybiphenyl. The MCOP was fully characterized using powder X-ray diffraction analysis, Fourier transform infrared spectroscopy, 13C-solid state NMR spectroscopy, field emission scanning electron microscopy and thermogravimetric analysis. These nitrogen rich materials act as good supports for palladium nanoparticles (Pd NPs) and exhibit excellent catalytic activity towards Mizoroki-Heck cross coupling between aryl bromides and alkenes. Hot filtration tests demonstrate that the presence of the triazine rings on the polymers is beneficial for enhancing the stability of Pd NPs. The polymers are also cheap, easy to synthesise and can be recycled up to five times with only a minor loss of activity. the Partner Organisations 2014.
- Puthiaraj, Pillaiyar,Pitchumani, Kasi
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p. 4223 - 4233
(2014/10/15)
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- Time-dependent stereoselective Heck reaction using mesoporous Pd/TiO 2 nanoparticles catalyst under sunlight
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Pd(0)-doped mesoporous TiO2 nanoparticles (Pd/TiO2) have been synthesized using an EISA method. The catalytic activity of Pd/TiO2 nanoparticles (NPs) is significantly enhanced under solar light irradiation for the Heck reaction. The Heck coupling product gives a considerable amount of Z-isomer, due to photochemical isomerization of the initially formed E-isomer, providing a facility for the time-dependent selectivity of E/Z-isomers under sunlight at ambient conditions. The Royal Society of Chemistry.
- Soni, Saurabh S.,Kotadia, Deepali A.
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p. 510 - 515
(2014/02/14)
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- Pd doped SiO2 nanoparticles: An efficient recyclable catalyst for Suzuki, Heck and Sonogashira reactions
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Palladium doped silica (Pd/SiO2) mesoporous material was synthesized via the sol-gel route using the P123 triblock copolymer as a structure directing agent. Pd/SiO2 was efficiently used as a catalyst for Suzuki, Heck and Sonogashira reactions under microwave irradiation. The catalyst exhibited high activity for all the coupling reactions and can be recycled nine times without a significant loss in its catalytic activity. This journal is the Partner Organisations 2014.
- Kotadia, Deepali A.,Patel, Urmila H.,Gandhi, Sahaj,Soni, Saurabh S.
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p. 32826 - 32833
(2014/08/18)
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- Small-molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): Synthesis and biological evaluation
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The synthesis of imidazole styrylbenzamide, tert-butyl styrylimidazole, and tert-butyl styrylsulfonate derivatives is described. Evaluation of binding affinity and inhibitory activity against CYP24A1 identified the imidazole styrylbenzamides as potent inhibitors of CYP24A1, having selectivity with respect to CYP27B1 comparable with or greater than that of the standard ketoconazole. Further evaluation of the 3,5-dimethoxy and 3,4,5-trimethoxy derivatives in chronic lymphocytic leukemia cells revealed that co-treatment of 1α,25-dihydroxyvitamin D3plus inhibitor coordinately upregulated GADD45α and CDKN1A. Docking experiments on the inhibitors in the CYP24A1 enzyme active site suggest the compounds reach the active site through the vitamin D access tunnel and are exposed to multiple hydrophobic residues. The imidazole styrylbenzamides are optimally positioned to allow interaction of the imidazole with the heme, and, in the case of the methoxy derivatives, a hydrogen bond between the 3-methoxy group and Gln82 stabilizes the molecule in a favorable active conformation.
- Ferla, Salvatore,Aboraia, Ahmed S.,Brancale, Andrea,Pepper, Christopher J.,Zhu, Jinge,Ochalek, Justin T.,Deluca, Hector F.,Simons, Claire
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p. 7702 - 7715
(2015/01/08)
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- Copper(ii) oxide on aluminosilicate mediated Heck coupling of styrene with aryl halides in water
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CuO/aluminosilicate has been found to be an efficient catalyst for the aqueous Heck coupling of styrene with aryl halides under ligand free conditions. The catalyst (CuO/aluminosilicate) was prepared from CuCl2· 6H2O, aluminium nitrate and tetraethyl orthosilicate (TEOS) and characterized by XRD, HR-TEM, SEM-EDX and XPS. The reaction conditions were optimized with different solvents, bases, catalyst amounts and temperatures using sytrene and 4-chlorobenzonitrile as a model system. The scope of the reaction was subsequently extended to include various substituted aryl halides. Regioselectivity, heterogeneity and reusability were performed.
- Babu, S. Ganesh,Neelakandeswari,Dharmaraj,Jackson, S. David,Karvembu
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p. 7774 - 7781
(2013/06/27)
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- Palladium nanoparticles, stabilized by lignin, as catalyst for cross-coupling reactions in water
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Palladium nanoparticles of a definite shape (spherical) and dimension (8-14 and 16-20 nm) were prepared employing two water soluble lignin samples as both reducing and stabilizing agent in definitely green experimental conditions, namely aqueous solution, aerobic conditions, moderate temperature, short times. The above nanoparticles were employed as catalyst for a series of carbon-carbon coupling reactions carried out in water at mild conditions. Heck and Suzuki reactions were performed for several substrates, by changing the nature of halogen, the substituents at the aromatic ring, the bases employed and the temperature. Product yields were satisfactory and selectivities very good. Other two cross-coupling reactions, namely Sonogashira and Stille, were also tested: iodine derivatives showed always the best reactivity, while chlorine derivatives did not react.
- Coccia, Francesca,Tonucci, Lucia,D'Alessandro, Nicola,D'Ambrosio, Primiano,Bressan, Mario
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- Heck-type reaction of aryldiazonium silica sulfates
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Aryldiazonium silica sulfates were employed as new and efficient reagents for Heck-type arylation reactions with styrene and methyl acrylate. The reactions were carried out in an organic solvent, in the presence of Pd(OAc)2 as precatalyst without use of base and free ligand. The trans isomers of desired products, methyl cinnamates and stilbenes, were obtained with full conversion. Use of a catalytic amount of Pd(OAc)2 produced the corresponding products in short reaction times and excellent yields. Springer-Verlag 2011.
- Pirisedigh, Azadeh,Zarei, Amin,Seyedjamali, Hojjat,Khazdooz, Leila,Hajipour, Abdol R.
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experimental part
p. 791 - 795
(2012/09/05)
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- Solvent- and light-controlled unidirectional transit of a nonsymmetric molecular axle through a nonsymmetric molecular wheel
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The development of a pseudorotaxane motif capable of performing unidirectional threading and dethreading processes under control of external stimuli is particularly important for the construction of processive linear motors based on rotaxanes and, at leas
- Arduini, Arturo,Bussolati, Rocco,Credi, Alberto,Monaco, Simone,Secchi, Andrea,Silvi, Serena,Venturi, Margherita
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p. 16203 - 16213
(2013/02/23)
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- Double-threaded dimer and supramolecular oligomer formed by stilbene modified cyclodextrin: Effect of acyl migration and photostimuli
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We observed changing supramolecular structures of stilbene-α- cyclodextrin (StiO-α-CD) by photoirradiation and migration. Stilbene derivatives show photoinduced isomerization under irradiation with λ =340 nm to give 2-cis-StiO-α-CD and with λ =254 nm to give 2-trans-StiO-α-CD. Photoisomerization of StiO-α-CD shows the photostationary state during 30 min. 2D NMR and diffusion coefficient studies revealed that 2-trans-StiO-α-CD forms a double-threaded dimer but 2-cis-StiO-α-CD changes to a supramolecular oligomer by photoirradiation. We found that the mutual migration of a stilbene group (StiO) on α-CD occurs under neutral conditions. The StiO group of α-CD (StiO-α-CD) moves between the C2 and C3 positions on the secondary hydroxyl group of StiO-α-CD (the wider rim of α-CD) to give 3-trans-StiO-α-CD. 3-trans-StiO-α-CD forms a supramolecular oligomer, whereas 3-cis-StiO-α-CD changes to a double-threaded dimer, indicating that 3-StiO-α-CDs gives the opposite results in the supramolecular structures of 2-StiO-α-CDs. The thermal isomerization (migration) is very slow. It takes about 300 h to reach the equilibrium state. Moreover, the migration rate constant (ktrans3→2) of the trans-StiO group from the C3 position to the C2 position of α-CD is faster than k trans2→3 from the C2 position to the C3 position of α-CD. On the other hand, kcis2→3 of the cis-StiO group from the C2 position to the C3 position of α-CD is faster than kcis3→2 from the C3 position to the C2 position, meaning kcis2→3 > kcis3→2, which is the opposite result for k trans3→2 > ktrans2→3. The formation of a stable double-threaded dimer would suppress the migration of the StiO group of StiO-α-CDs in aqueous solutions.
- Kanaya, Akira,Takashima, Yoshinori,Harada, Akira
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experimental part
p. 492 - 499
(2011/04/15)
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- Photoresponsive formation of pseudo[2]rotaxane with cyclodextrin derivatives
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The two isomers of 6-stilbene-amide-α-CD (6-StiNH-α-CD) exhibit different inclusion behaviors upon complexation with an alkyl chain bearing pyridinium end caps. Photoisomerization of the stilbene moiety of the CD derivative affects threading due to comple
- Wang, Zhibin,Takashima, Yoshinori,Yamaguchi, Hiroyasu,Harada, Akira
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supporting information; experimental part
p. 4356 - 4359
(2011/10/18)
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- Alpha-helical mimetics
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Benzoyl urea derivatives that are alpha helical peptides mimetics that mimic BH3-only proteins, compositions containing them, their conjugation to cell-targeting-moieties, and their use in the regulation of cell death are disclosed. The benzoyl urea derivatives are capable of binding to and neutralizing pro-survival Bcl-2 proteins. Use of benzoyl urea derivatives in the treatment and/or prophylaxis of diseases or conditions associated with deregulation of cell death are also described.
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Page/Page column 90
(2011/05/18)
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- Unusually stable, versatile, and pure arenediazonium tosylates: Their preparation, structures, and synthetic applicability
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(Graph Presented) A new, simple, and effective method for the diazotization of a wide range of arylamines has been developed by using a polymer-supported diazotization agent in the presence of p-toluenesulfonic acid. Various pure arenediazonium tosylates with unusual stabilities can be easily prepared by this method. As a result, these salts are useful and versatile substrates for subsequent transformations, such as halogenation and Heck-type reactions. The unusual stabilities of arenediazonium tosylates are also preliminarily discussed with their X-ray structures.
- Filimonov, Victor D.,Trusova, Marina,Postnikov, Pavel,Krasnokutskaya, Elena A.,Lee, Young Min,Hwang, Ho Yun,Kim, Hyunuk,Chi, Ki-Whan
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supporting information; experimental part
p. 3961 - 3964
(2009/05/30)
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- Switching between supramolecular dimer and nonthreaded supramolecular self-assembly of stilbene amide-α-cyclodextrin by photoirradiation
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3-trans-Stilbene amide-α-cyclodextrin (3-trans-Sti-α-CD) formed a double-threaded dimer in aqueous solutions. In contrast, the photoisomerization of the stilbene moiety in 3-Sti-α-CD from trans to cis leads to the structural changes from the double-threaded dimer to nonthreaded supramolecular assemblies in aqueous solutions. The structures of these supramolecular complexes have been found to be controllable by photoirradiation. Copyright
- Yamauchi, Kazuhiro,Takashima, Yoshinori,Hashidzume, Akihito,Yamaguchi, Hiroyasu,Harada, Akira
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p. 5024 - 5025
(2008/09/20)
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- Relative rotational motion between α-cyclodextrin derivatives and a stiff axle molecule
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(Figure Presented) Novel [2]rotaxanes bearing α-cyclodextrin (α-CD) derivatives and a diphenylacetylene axis molecule with trinitrobenzene as a bulky stopper have been prepared to investigate the relative rotary movement of a ring relative to an axis molecule and that of an axis molecule in a ring by NMR techniques. [2]Rotaxanes 2 and 3 were composed of α-CD derivatives (2: 6-phenyl-amide-α-CD; 3: 6-stilbene-amide- α-CD). The protons of α-CDs in rotaxanes were thoroughly assigned by the two-dimensional NMR techniques (TOCSY, COSY, ROESY, HMQC, and HMBC). The protons of α-CD in rotaxane 1 did not show splitting, whereas the resonance peak shifts and splitting for the corresponding protons of α-CD derivatives in rotaxanes 2 and 3 were observed by the shielding and deshielding effects from a diphenylacetylene axis molecule. The splitting of resonance peaks was closely related to the rotary movements of α-CDs and an axis molecule. We supposed that α-CD in rotaxane 1 rotates freely around a diphenylacetylene axis molecule, and vice versa, whereas the rotary movement of α-CD derivatives and the axis molecules of rotaxanes 2 and 3 were restricted by the steric repulsion between the substituent group of α-CD and the stopper group of an axis molecule. To estimate the relative rotary movement of CDs and an axis molecule in rotaxanes, the rotational correlation time (τc) of rotaxanes was measured by 13C NMR. The results indicate that the corresponding rotary movement of the modified α-CD and the axis molecules in rotaxanes 2 and 3 depends on the size of the substituent group.
- Nishimura, Dai,Oshikiri, Tomoya,Takashima, Yoshinori,Hashidzume, Akihito,Yamaguchi, Hiroyasu,Harada, Akira
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p. 2496 - 2502
(2008/09/19)
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- Palladium-iminodiacetic acid immobilized on pH-responsive polymeric microspheres: Efficient quasi-homogeneous catalyst for Suzuki and Heck reactions in aqueous solution
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The pH-responsive core-shell microspheres of poly(styrene-co-methylacrylic acid) (PS-co-PMAA) containing a polystyrene (PS) core and a poly(methylacrylic acid) (PMAA) shell are synthesized by one-stage soap-free copolymerization and the catalyst system palladium-iminodiacetic acid (IDA-Pd) is immobilized on the outer shell-layer of the core-shell microspheres to form the quasi-homogeneous and easily accessible catalyst PS-co-PMAA-IDA-Pd. This quasi-homogeneous PS-co-PMAA-IDA-Pd catalyst is highly dispersed in the reaction medium just like a homogeneous one and can be separated like a heterogeneous catalyst by adjusting the pH of the reaction medium. Suzuki reactions employing the quasi-homogeneous PS-co-PMAA-IDA-Pd catalyst are efficiently performed in water as the sole solvent under mild conditions such as room temperature. The PS-co-PMAA-IDA-Pd catalyst is also used in Heck reactions of a wide range of aryl halides with styrene and proves to be efficient in aqueous solution. The PS-co-PMAA-IDA-Pd catalyst has a low leaching loss and can be reused at least 4 times without loss of activity.
- Zhang, Jianzheng,Zhang, Wangqing,Wang, Yao,Zhang, Minchao
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experimental part
p. 2065 - 2076
(2009/08/07)
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- ALPHA-HELICAL MIMETICS
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Benzoyl urea derivatives that are alpha helical peptide mimetics that mimic BH3-only proteins, compositions containing them, their conjugation to cell-targeting moieties, and their use in the regulation of cell death are disclosed. The benzoyl urea derivatives are capable of binding to and neutralising pro-survival Bcl-2 proteins. Use of the benzoyl urea derivatives in the treatment and/or prophylaxis of diseases or conditions associated with deregulation of cell death are also disclosed.
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Page/Page column 182
(2010/02/15)
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- Silica-supported poly-γ-aminopropylsiloxane palladium (Pd 2+)-transition metal (Cu2+) complex: A new catalyst system for Heck reaction
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A new silica-supported poly-γ-aminopropysiloxane transition metal (Cu2+) and palladium (Pd2+) catalyst has been prepared from organic silica via immobilization on fumed silica, followed by treatment with Cu(OAc)2 and PdCl2 in ethanol. The catalyst is efficient for Heck arylation of aryl iodides with alkene. The effects of reaction temperature and Pd2+ content on catalytic properties have also been studied. Pd2+ has been found to improve the catalytic performance, reducing the reaction temperature (70°C) and the induction period. It provides an economic way to synthesize unsymmetrical trans-stilbenes.
- Zhao, Shao Fen,Zhou, Ren Xian,Zheng, Xiao Ming
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p. 2215 - 2217
(2007/10/03)
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- N,N-dimethyl-β-alanine as an inexpensive and efficient ligand for palladium-catalyzed Heck reaction
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N,N-Dimethyl-β-alanine was found to be a more powerful phosphine-free ligand than the previously reported ligand, N,N-dimethylglycine, in the Pd-catalyzed Heck reaction for a variety of aryl bromides, aryl iodides, and activated aryl chlorides with a practical turnover number of 103. Both kinetic and theoretical studies suggested that N,N-dimethyl-β-alanine led to faster oxidative addition of an aryl halide to Pd than N,N-dimethylglycine.
- Cui, Xin,Li, Zhe,Tao, Chuan-Zhou,Xu, Yu,Li, Juan,Liu, Lei,Guo, Qing-Xiang
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p. 2467 - 2470
(2007/10/03)
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- 5′-Tethered Stilbene Derivatives as Fidelity- and Affinity-Enhancing Modulators of DNA Duplex Stability
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A series of 5′-linked stilbene-DNA conjugates with different substituents in the distal aromatic ring of the stilbene was prepared, and the effect of the modifications on duplex stability was determined via UV-melting curves. A trimethoxystilbene derivative as a 5′-substituent increases duplex melting points by up to 12.2 °C per modification. With this alkoxystilbene substituent, terminal mismatches in DNA duplexes lower the melting point by up to 23.4 °C over the perfectly matched control, whereas terminal mismatches in unmodified DNA cause melting point depressions of no more than 6.1 °C. An aminomethylstilbene substituent linked to an oligopyrrolamide minor groove binder increases the melting point of an all-A/T decamer by up to 32.7 °C, thus shifting the melting point into a range typical for duplexes with statistical G/C-content. An affinity- and selectivity-enhancing effect was also observed when the trimethoxystilbene cap was employed on a small DNA microarray. The phosphoramidite of the trimethoxystilbene can be readily employed in automatic DNA synthesis, facilitating the generation of DNA chips with improved fidelity. Copyright
- Dogan, Zeynep,Paulini, Ralph,Stuetz, Jan A. Rojas,Narayanan, Sukunath,Richert, Clemens
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p. 4762 - 4763
(2007/10/03)
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- Organic silica ligated to palladium (0) complex: A highly active and stereoselective catalyst for Heck reaction
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Organic silica ligated to palladium(0) complex has been prepared from poly-γ-cyanopropyl triethoxysilane and fumed silica, followed by treatment with palladium chloride in ethanol and then the reduction with KBH4 in ethanol. This catalyst is highly active and stereoselective for Heck reaction at 90°C or 1O0°C.
- Zhao,Zhou,Yang,Zheng
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p. 2274 - 2276
(2007/10/03)
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- Fe(III)-catalyzed cross-coupling between functionalized arylmagnesium compounds and alkenyl halides
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Functionalized arylmagnesium reagents bearing an ester, cyano, nonaflate or trialkylsilyloxy group undergo fast cross-coupling reactions with alkenyl iodides or bromides in the presence of catalytic amounts of Fe(acac)3 (5 mol%) at-20 °C within
- Dohle,Kopp,Cahiez,Knochel
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p. 1901 - 1904
(2007/10/03)
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- HECK REACTIONS IN SOLID PHASE SYNTHESIS
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Heck reactions of polymer bound aryl iodide (1) or styrene (2) with olefins or aryl halides generally gave good yields of products of high purity.The methodology developed can be applied as a convenient procedure for generating 1,2-disubstituted olefins i
- Yu, Kuo-Long,Deshpande, Milind S.,Vyas, Dolatrai M.
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p. 8919 - 8922
(2007/10/02)
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- 4-halogenostilbene derivatives and processes for their preparation
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Novel compounds of the formula STR1 and processes for their preparation are described. X represents bromine or iodine and R1, R2 and R3 have the meaning indicated in the patent claim. The compounds (I) are valuable intermediates for the preparation of fluorescent brighteners of the divinylstilbene type.
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- Retinobenzoic acids. 3. Structure-activity relationships of retinoidal azobenzene-4-carboxylic acids and stilbene-4-carboxylic acids
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Alkyl-substituted azobenzene-4-carboxylic acids are potent differentiation inducers of human promyelocytic leukemia cell line HL-60 to mature granulocytes. Their structure-activity relationships are very similar to those of other retinoidal benzoic acids which are generally represented by 4 and named retinobenzoic acids. The structure-activity relationships of azobenzenecarboxylic acids can also be applied to the known retinoid TTNPB (3). Thus, (E)-4-[2-(3,4-diisopropylphenyl)-1-propenyl]benzoic acid (St30 (28)), and (E)-4-[2-(3-tert-butylphenyl)ethenyl]benzoic acid (St40) (29)), the acyclic alkyl analogues of TTNPB, are nearly as active as retinoic acid. Among the oxidatively derived compounds (Az90, Ep series and Ox series) of azobenzene- or stilbenecarboxylic acids, Az90 (71) and Ep80 (61) have strong activities. However, all the bishydroxylated derivatives of TTNPB are inactive, while a diketo analogue Ox580 (69) has only weak potency. The activities of conformationally restricted compounds of TTNPB offer some information on the stereochemistry of the active form of these retinoidal compounds.
- Kagechika,Himi,Namikawa,Kawachi,Hashimoto,Shudo
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p. 1098 - 1108
(2007/10/02)
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