cas 7560-50-1, 4-Formylcinnamic acid methyl ester

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Pd salen complex@CPGO as a convenient, effective heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions
A Pd(II) Schiff base complex supported on graphene oxide nanosheets (Pd(II) salen@CPGO) has been synthesized and characterized by FT-IR, ICP-AES, XRD, SEM/EDX and TEM. The synthesized nanocatalyst has been found to be an efficient heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki coupling reactions. Pd(II) salen@CPGO could be separated and recovered easily from the reaction mixture and recycled several times without a discernible decrease in its catalytic activity. The construction of a solid sheet-supported Pd catalyst would be expected to be a promising system to perform heterogeneous catalytic reactions.
Ghabdian, Mahdieh,Nasseri, Mohammad Ali,Allahresani, Ali,Motavallizadehkakhky, Alireza
p. 1713 - 1728
(2018/05/25)

Palladium(II) complexes of (t-butyl salicylidene) diphenyl disulfide diamine: synthesis, structure, spectral characterization and catalytic properties
The hexadentate N2S2O2 donor ligand N,N’-bis(3,5-tert-butylsalicylidene) diphenyl disulfide-2,2’-diamine was synthesised by the condensation of 2-aminophenyl disulfide and 3,5-di-tert-butyl-2-hydroxybenzaldehyde and its mo
Bhowon, Minu G.,Jhaumeer Laulloo, Sabina,Hosten, Eric C.,Elaheebacus, Sumayya,Dowlut, Mounisha R.
p. 537 - 545
(2021/08/03)

Curcumin histone deacetylase inhibitor and preparation method and medical application thereof
The invention relates to the fields of medicinal chemistry and biology, in particular to a curcumin histone deacetylase inhibitor. The invention also discloses a preparation method of the inhibitor and an application of the inhibitor in exerting anti-tumor activity by inhibiting histone deacetylase.
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Paragraph 0038-0041

(2021/07/24)

HISTONE DEACETYLASE 6 INHIBITORS AND METHOD FOR TREATING NEUROPATHIC PAIN
Disclosed herein are hydroxamic acid compounds. Also disclosed is a method of using the hydroxamic acid compounds for treating a condition associated with histone deacetylase 6.
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Paragraph 0068; 0082-0083

(2021/01/29)

Triazine-hyperbranched polymer-modified magnetic nanoparticles-supported nano-cobalt for C–C cross-coupling reactions
Design of hyperbranched polymers (HBPs) and crafting them in catalytic systems especially in organic chemistry are a relatively unexplored domain. This paper reports the utilization of triazine-hyperbranched polymer (THBP)-coated magnetic chitosan nanoparticles (MCs) as stabilizing matrix for cobalt nanoparticles. Cobalt nanoparticles were fabricated by coordination cobalt(II) ions with amine-terminated triazine polymer and then reduced into Co(0) using sodium borohydride in aqueous medium. The Co(0)-THBP@MCs were fully characterized by FT-IR, SEM–EDX, TEM, and TGA analyses. The presence of metallic cobalt was determined by ICP and XRD techniques. This novel hyperbranched polyaromatic polymer-encapsulated cobalt nanoparticles showed high catalytic activity in Mizoroki–Heck and Suzuki–Miyaura cross-coupling reactions. Heck and Suzuki reactions were carried out using 0.35 and 0.4?mol% of cobalt nanoparticles in which the turnover number (TON) values were calculated as 271 and 225, respectively. In addition, the produced heterogeneous catalyst could be recovered and reused without considerable loss of activity. Oxygen stability and high reusability over 7 runs with trace leaching of the cobalt into the reaction media as well as moisture stability of the immobilized cobalt nanoparticles are their considerable worthwhile advantages.
Hajipour, Abdol R.,Sadeghi, Shaghayegh
p. 3219 - 3233
(2021/08/06)

Synthesis and structural characterization of a palladium complex as an anticancer agent, and a highly efficient and reusable catalyst for the Heck coupling reaction under ultrasound irradiation: A convenient sustainable green protocol
The complex [Pd(paOH)2].2Cl (1) was synthesized by the self-assembly method with palladium chloride and pyridine-2-carbaldehyde-oxime (paOH) in aqueous acetonitrile solution under ambient conditions. Complex 1 was fully characterized by FT-IR, UV–vis and NMR spectroscopic techniques, as well as elemental analysis. The single crystal X-ray structure of complex 1 indicates that the Pd(II) ion is bonded to four nitrogen atoms from two pyridine-2-carbaldehyde-oxime ligands. The molecular geometry of the Pd(II) ion in complex 1 is distorted square-planar with a trans geometry and with two free chloride ions. Using an MTT assay, the anticancer activities of the palladium complex 1 were studied with respect to human breast cancer (MCF-7) and hepatocellular carcinoma (HePG-2) cell lines. The data obtained show that complex 1 displays strong activity towards the viability and the growth of the cancer cell lines MCF-7 and HepG2. Additionally, complex 1 exhibits excellent catalytic activity for the Heck cross-coupling reaction with water as the solvent under ultrasound irradiation. Ultrasound irradiation not only enhanced the rate and the yield of the reaction, but also promoted the in situ generation of a well-dispersed zero-valent Pd-colloidal species as the active catalyst from complex 1. Finally, the luminescence spectrum of complex 1 is discussed.
El-bendary, Mohamed M.,Saleh, Tamer S.,Al-Bogami, Abdullah S.
(2020/12/02)

Development and pre-clinical testing of a novel hypoxia-activated KDAC inhibitor
Tumor hypoxia is associated with therapy resistance and poor patient prognosis. Hypoxia-activated prodrugs, designed to selectively target hypoxic cells while sparing normal tissue, represent a promising treatment strategy. We report the pre-clinical efficacy of 1-methyl-2-nitroimidazole panobinostat (NI-Pano, CH-03), a novel bioreductive version of the clinically used lysine deacetylase inhibitor, panobinostat. NI-Pano was stable in normoxic (21% O2) conditions and underwent NADPH-CYP-mediated enzymatic bioreduction to release panobinostat in hypoxia (2). Treatment of cells grown in both 2D and 3D with NI-Pano increased acetylation of histone H3 at lysine 9, induced apoptosis, and decreased clonogenic survival. Importantly, NI-Pano exhibited growth delay effects as a single agent in tumor xenografts. Pharmacokinetic analysis confirmed the presence of sub-micromolar concentrations of panobinostat in hypoxic mouse xenografts, but not in circulating plasma or kidneys. Together, our pre-clinical results provide a strong mechanistic rationale for the clinical development of NI-Pano for selective targeting of hypoxic tumors.
Skwarska, Anna,Calder, Ewen D.D.,Sneddon, Deborah,Bolland, Hannah,Odyniec, Maria L.,Mistry, Ishna N.,Martin, Jennifer,Folkes, Lisa K.,Conway, Stuart J.,Hammond, Ester M.
p. 1258 - 13,1270
(2021/09/16)

Coordination from Heteroscorpionate Ligand Towards Pd(II) via Pd???Hδ?C(sp3) Interaction: Structural and Catalytic Studies
The coordination ability of the heteroscorpionate ligand 2,2-bis(3,5-dimethylpyrazol-1-yl)-1-p-tolylethanol (1) towards palladium (II) dihalides was evaluated. The structures of the respective palladium complexes (2 and 3) were elucidated in solution by NMR spectroscopy, and their molecular structures were established by single crystal X-ray diffraction analyses. Both studies revealed the existence of Pd???Hδ?C(sp3) anagostic interactions. The molecular structure of complexes 2 and 3 displays coordination of ligand 1 to palladium in a κ3-NNH tridentate fashion via two nitrogen atoms and one δ-anagostic H???Pd interaction. The metal center exhibits a square pyramidal geometry. The distances of anagostic Hδ???Pd interactions ranged from 2.566 to 2.576 ?. The δ-anagostic H???Pd interactions in complexes 2 and 3 were also identified by Bader's quantum theory of atoms in molecules (QTAIM) and non-covalent interaction (NCI) analysis. The catalytic efficiencies of complexes 2 and 3 in the Suzuki-Miyaura cross-coupling reactions were evaluated and the results showed that palladium (II) dibromide complex is the most efficient of the series. Complex 3 was also evaluated in Mizoroki-Heck cross-coupling reactions.
Castillo-Moreno, Miguel ángel,Cruz-Borbolla, Julián,González-Montiel, Simplicio,Ignacio Sandoval-Chávez, César,Manuel Vásquez-Pérez, José,Mendoza-Espinosa, Daniel,Salazar-Pereda, Verónica
supporting information
p. 2661 - 2668
(2021/07/06)

A Bis (BICAAC) Palladium(II) Complex: Synthesis and Implementation as Catalyst in Heck-Mizoroki and Suzuki-Miyaura Cross Coupling Reactions
Carbenes are one of the most appealing, well-explored, and exciting ligands in modern chemistry due to their tunable stereoelectronic properties and a wide area of applications. A palladium complex (BICAAC)2PdCl2 with a recently discovered cyclic (alkyl)(amino)carbene having bicyclo[2.2.2] octane skeleton (BICAAC) was synthesized and characterized. The enhanced σ-donating and π-accepting ability of this carbene lend a hand to form a robust Pd-carbene bond, which allowed us to probe its reactivity as a precatalyst in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions with low catalyst loading in open-air conditions. The diverse range of substrates was explored for both the cross-coupling reactions. To get a better understanding of the catalytic reactions, several analytical techniques such as field-emission scanning electron microscopy, high-resolution transmission electron microscopy, and powder X-ray diffraction were employed in a conclusive manner.
Chakrabortty, Soumyadeep,Kaur, Mandeep,Adhikari, Manu,Manar, Krishna K.,Singh, Sanjay
supporting information
p. 6209 - 6217
(2021/05/06)

Synthesis and characterization of a new bis-NHC palladium complex and its catalytic activity in the Mizoroki–Heck reaction
A new bis-N-heterocyclic carbene palladium complex, (C13H9N2F2)2PdCl2, is synthesized by a three-step reaction and characterized by 1H NMR and 13C NMR spectroscopy as well as by X-ray crystallography. This new bis-N-heterocyclic carbene palladium complex has excellent stability and is capable of efficiently catalyzing the Mizoroki–Heck coupling reaction of aryl halides with acrylates.
Cui, Jin,Feng, Can,Liu, Cheng-Xin,Wang, Yu-Fang,Zhang, Ming-Jie
p. 684 - 688
(2020/05/22)

Pd/Cu-free Heck and Sonogashira coupling reactions applying cobalt nanoparticles supported on multifunctional porous organic hybrid
A new heterogeneous cobalt catalyst has been synthesized by immobilizing Co species onto a nitrogen-rich porous organic polymer (Co@imine-POP). The heterogeneous catalyst synthesized was efficient in Heck and Sonogashira cross-coupling reactions in green media under mild reaction conditions without inert air and phase transfer agents. This phosphine-, copper-, and palladium-free catalyst was stable under the reaction conditions and could be reused for at least eight successive runs without a discernible decrease in its catalytic activity.
Hajipour, Abdol R.,Khorsandi, Zahra
(2020/02/11)

Palladium-Based Catalysts Supported by Unsymmetrical XYC–1 Type Pincer Ligands: C5 Arylation of Imidazoles and Synthesis of Octinoxate Utilizing the Mizoroki–Heck Reaction
A series of new unsymmetrical (XYC–1 type) palladacycles (C1–C4) were designed and synthesized with simple anchoring ligands L1–4H (L1H = 2-((2-(4-methoxybenzylidene)-1-phenylhydrazinyl)methyl)pyridine, L2H = N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono)methyl)aniline, L3H = N,N-diethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono)methyl) aniline and L4H = 4-(4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono) methyl)phenyl)morpholine H = dissociable proton). Molecular structure of catalysts (C1–C4) were further established by single X-ray crystallographic studies. The catalytic performance of palladacycles (C1–C4) was explored with the direct Csp2–H arylation of imidazoles with aryl halide derivatives. These palladacycles were also applied for investigating of Mizoroki–Heck reactions with aryl halides and acrylate derivatives. During catalytic cycle in situ generated Pd(0) nanoparticles were characterized by XPS, SEM and TEM analysis and possible reaction pathways were proposed. The catalyst was employed as a pre-catalyst for the gram-scale synthesis of octinoxate, which is utilized as a UV-B sunscreen agent.
Maji, Ankur,Singh, Ovender,Singh, Sain,Mohanty, Aurobinda,Maji, Pradip K.,Ghosh, Kaushik
p. 1596 - 1611
(2020/04/29)

Threonine stabilizer-controlled well-dispersed small palladium nanoparticles on modified magnetic nanocatalyst for Heck cross-coupling process in water
We report the synthesis of magnetically separable Fe3O4@Silica-Threonine-Pd0 magnetic nanoparticles with a core–shell structure. After synthesis of Fe3O4@Silica, threonine as an efficient stabilizer/ligand was bonded to the surface of Fe3O4@Silica. Then, palladium nanoparticles were generated on the threonine-modified catalyst. The threonine stabilizer helps to generate palladium nanoparticles of small size (less than 4?nm) with high dispersity and uniformity. Magnetically separable Fe3O4@Silica-Threonine-Pd0 nanocatalyst was fully characterized using various techniques. This nanocatalyst efficiently catalysed the Heck cross-coupling reaction of a variety of substrates in water medium as a green, safe and inexpensive solvent at 80°C. The Fe3O4@Silica-Threonine-Pd0 catalyst was used for at least eight successful consecutive runs with palladium leaching of only 0.05%.
Sarvi, Iraj,Gholizadeh, Mostafa,Izadyar, Mohammad
(2018/11/23)

Evaluation of α-hydroxycinnamic acids as pyruvate carboxylase inhibitors
Through a structure-based drug design project (SBDD), potent small molecule inhibitors of pyruvate carboxylase (PC) have been discovered. A series of α-keto acids (7) and α-hydroxycinnamic acids (8) were prepared and evaluated for inhibition of PC in two assays. The two most potent inhibitors were 3,3′-(1,4-phenylene)bis[2-hydroxy-2-propenoic acid] (8u) and 2-hydroxy-3-(quinoline-2-yl)propenoic acid (8v) with IC50 values of 3.0 ± 1.0 μM and 4.3 ± 1.5 μM respectively. Compound 8v is a competitive inhibitor with respect to pyruvate (Ki = 0.74 μM) and a mixed-type inhibitor with respect to ATP, indicating that it targets the unique carboxyltransferase (CT) domain of PC. Furthermore, compound 8v does not significantly inhibit human carbonic anhydrase II, matrix metalloproteinase-2, malate dehydrogenase or lactate dehydrogenase.
Burkett, Daniel J.,Wyatt, Brittney N.,Mews, Mallory,Bautista, Anson,Engel, Ryan,Dockendorff, Chris,Donaldson, William A.,St. Maurice, Martin
p. 4041 - 4047
(2019/08/26)

Bis-quinoline-2-carboxylic acid Copper Salt as an Efficient Catalyst for Synthesis of Aryl Olefins by Heck Reaction
Abstract: A bis-quinoline-2-carboxylic acid copper salt as a single crystal was prepared and characterized by X-ray single crystal analysis. The crystal as a catalyst was applied to the Mizoroki–Heck coupling reaction between arylboronic acids and α-olefins. A series of diarylethenes and aryl olefins were synthesized with good to excellent yields at room temperature. The catalytic system exhibited good functional group tolerance and low pollution. Graphic Abstract: A bis-quinoline-2-carboxylic acid copper salt as a single crystal was prepared and characterized by X-ray single crystal analysis. The crystal as a catalyst was applied to the Mizoroki–Heck coupling reaction between arylboronic acids and α-olefins[InlineMediaObject not available: see fulltext.].
Zuo, Minghui,Li, Zhuofei,Fu, Wanyong,Guo, Rui,Hou, Chuanfu,Guo, Weihao,Sun, Zhizhong,Chu, Wenyi
p. 3217 - 3223
(2019/07/17)

Homoleptic cis- and trans-palladium(II) bis(guanidinato) complexes derived from N-aryl-N′,N″-di(pyridin-2-yl)- and N-aryl-N′,N″-bis(6-methylpyridin-2-yl)guanidines: Catalysts for Heck-Mizoroki coupling reactions
N-Aryl-N′,N″-di(pyridin-2-yl)- and N-aryl-N′,N″-bis(6-methylpyridin-2-yl)guanidines (1–4 and 5–7) were isolated in 75%–81% yields. Reactions of Pd(OAc)2 with guanidines 2–7 carried out separately in toluene at 60 °C for 3 h afforded 8–13 respectively in 69%–80% yields. Compounds 1–13 were characterized by elemental analyses, HR-MS, IR and NMR (1H and 13C) spectroscopy. Molecular structures of guanidines 1, 4, 5 and 6 and those of 8–13 were determined by single crystal X-ray diffraction. The Pd(II) atom in 8–10 revealed trans geometry while that in 11–13 revealed cis geometry. DFT calculations were carried out on model compounds 9a (trans) and its hypothetical cis isomer, 9b and 12a (cis) and its hypothetical trans isomer 12b which indicated a very small energy difference between the 9a/9b pair (1.28 kcal/mol) whereas a large energy difference was observed between the 12a/12b pair (26.38 kcal/mol) in CH2Cl2. The catalytic utility of 9 in Heck-Mizoroki coupling reactions involving styrene and methyl acrylate and aryl bromides/aryl chlorides in the presence of NaOAc and excess of tetrabutylammonium bromide (TBAB) at 120 °C was explored. Both activated and de-activated aryl bromides and aryl chlorides were coupled with styrene and in addition, the aryl chlorides were coupled with methyl acrylate in the presence of 9 to afford the respective coupling products in 68% ? >99% yields. Neat reaction carried out with 9 and TBAB under the optimized condition released the colloidal Pd black as verified by EDAX, PXRD and SEM techniques thereby implying the heterogeneous nature of catalysis.
Mishra, Vishwesh,Thomas, Jisha Mary,Chinnappan, Sivasankar,Thirupathi, Natesan
p. 1 - 17
(2019/05/06)

PdII Immobilized on Ferromagnetic Multi-Walled Carbon Nanotubes Functionalized by Aminated 2-Chloroethylphosphonic Acid with S -Methylisothiourea (FMMWCNTs@CPA@SMTU@PdII NPs) Applied as a Highly Efficient and Recyclable Nanostructured Catalyst for Suzuki-Miyaura and Mizoroki-Heck Cross-Coupling Reactions in Solvent-Free Conditions
The new ferromagnetic nanostructured FMMWCNTs@CPA@SMTU@PdII NPs (IV) as an eco-friendly heterogeneous nanocatalyst with a particle size of ～20-30 nm reported earlier by our group has been found to be very effective for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions at ambient temperature. The procedure has been applied for a wide range of aryl halides, arylboronic acids, and alkenes. The magnetic separation by an external magnetic field, mild reaction conditions, and catalyst reusability up to four times without significant decrease in catalytic activity (reduced catalytic activity from 11 to 18 % in the fifth, sixth, and seventh cycles) made the present method sustainable and economically viable for C-C cross-coupling reactions.
Ghasemzadeh, Maryam Sadat,Akhlaghinia, Batool
p. 674 - 692
(2019/07/12)

Structurally Diverse Histone Deacetylase Photoreactive Probes: Design, Synthesis, and Photolabeling Studies in Live Cells and Tissue
Histone deacetylase (HDAC) activity is modulated in vivo by post-translational modifications and formation of multiprotein complexes. Novel chemical tools to study how these factors affect engagement of HDAC isoforms by HDAC inhibitors (HDACi) in cells and tissues are needed. In this study, a synthetic strategy to access chemically diverse photoreactive probes (PRPs) was developed and used to prepare seven novel HDAC PRPs 9–15. The class I HDAC isoform engagement by PRPs was determined in biochemical assays and photolabeling experiments in live SET-2, HepG2, HuH7, and HEK293T cell lines and in mouse liver tissue. Unlike the HDAC protein abundance and biochemical activity against recombinant HDACs, the chemotype of the PRPs and the type of cells were key in defining the engagement of HDAC isoforms in live cells. Our findings suggest that engagement of HDAC isoforms by HDACi in vivo may be substantially modulated in a cell- and tissue-type-dependent manner.
Aboukhatwa, Shaimaa M.,Hanigan, Thomas W.,Taha, Taha Y.,Neerasa, Jayaprakash,Ranjan, Rajeev,El-Bastawissy, Eman E.,Elkersh, Mohamed A.,El-Moselhy, Tarek F.,Frasor, Jonna,Mahmud, Nadim,McLachlan, Alan,Petukhov, Pavel A.
supporting information
p. 1096 - 1107
(2019/04/17)

Templating effect of carbon nanoforms on highly cross-linked imidazolium network: Catalytic activity of the resulting hybrids with Pd nanoparticles
Two different carbon nanoforms (CNFs), namely multi-walled carbon nanotubes (MWCNTs) and carbon nanohorns (CNHs), have been chosen as support for the direct polymerization of a bis-vinylimidazolium salt. Transmission electron microscopy analyses revealed a templating effect of the CNFs on the growth of the polymeric network, which perfectly covers their whole surfaces creating a cylindrical or spherical coating for MWCNTs and CNHs, respectively. Subsequently, the CNFs-polyimidazolium have been used as stabilizers for Pd nanoparticles (Pd NPs), and the obtained materials have been characterized by means of analytical and spectroscopic techniques and then employed as easily recoverable and recyclable catalysts for Suzuki and Heck reactions. Quantitative conversions have been obtained in almost all the explored reactions, even employing low loading of catalyst (down to 0.007 mol%). Suzuki reactions were carried out in pure water under aerobic conditions. Both materials showed excellent activity and recyclability for the investigated C-C coupling reactions, with the CNHs-based material resulting slightly more active than the MWCNTs-based one due to a higher superficial exposure of Pd NPs.
Campisciano, Vincenzo,Calabrese, Carla,Liotta, Leonarda Francesca,La Parola, Valeria,Spinella, Alberto,Aprile, Carmela,Gruttadauria, Michelangelo,Giacalone, Francesco
(2019/05/10)

SBA-15/POSS-Imidazolium Hybrid as Catalytic Nanoreactor: the role of the Support in the Stabilization of Palladium Species for C?C Cross Coupling Reactions.
Supported imidazolium modified polyhedral oligomeric silsesquioxanes (POSS) on SBA-15 have been used as platform for Pd(II) species. The so-obtained material was firstly characterized by means of TGA, solid state NMR, TEM, XPS, SAXS, porosimetry and ICP-OES and it was successfully tested as pre-catalyst in C?C cross couplings, namely Suzuki-Miyaura and Heck reactions. In both cases, the solid proved to be highly efficient and easily recoverable from the reaction mixture. The recyclability was verified for up to seven cycles without showing any activity decrease. Interestingly, only Pd(II) was detected in the reused catalyst in the Heck reaction. Therefore, the versatility of the material was investigated by using various aryl halides. Our palladium nanocomposite was able to promote both Suzuki and Heck reactions down to 0.0007 mol% showing outstanding turnover frequency (TOF) values of 114,286 and 32,381 h?1, respectively. Comparison with the palladium catalyst on SiO2-POSS-imidazolium support showed interesting differences in terms of stabilization of Pd species and recyclability. The excellent outcome of the reactions could be ascribed to the textural properties of the SBA-15 support and the presence of the imidazolium-POSS nanocage within the pores of SBA-15, that worked as a sort of nanoreactor. (Figure presented.).
Calabrese, Carla,Campisciano, Vincenzo,Siragusa, Fabiana,Liotta, Leonarda F.,Aprile, Carmela,Gruttadauria, Michelangelo,Giacalone, Francesco
p. 3758 - 3767
(2019/05/15)

An efficient class of bis-NHC salts: Applications in Pd-catalyzed reactions under mild reaction conditions
This study describes an efficient class of bis-N-heterocyclic carbene (bis-NHC) salts that can be easily made from commercially available and inexpensive starting materials. The application of these salts to Pd-catalyzed reactions is described. The palladium (Pd) catalyst generated in situ was highly effective under mild reaction conditions.
Chiu, Chien-Cheng,Chiu, Hui-Tzu,Lee, Dong-Sheng,Lu, Ta-Jung
p. 26407 - 26415
(2018/08/04)

Postsynthetic modification of single Pd sites into uncoordinated polypyridine groups of a MOF as the highly efficient catalyst for Heck and Suzuki reactions
A novel holmium(iii) metal-organic framework (Ho-MOF), namely, [Ho(2-TriPP-COO)3] (2) has been hydrothermally obtained using 4′-(4-carboxyphenyl)-2,2′:6′,2′′-terpyridine (2-TriPP-COOH) and Ho(NO3)3·5H2O, and it is structurally characterized by single-crystal XRD, powder XRD as well as elemental analysis. The postsynthetic modification of Ho-MOF is based on the utilization of a strong coordination effect between Pd2+ ions and free polypyridine groups in the skeleton of Ho-MOF, which play a critical role to access the highly efficient Pd-HoMOF catalyst. Also, Pd-HoMOF exhibits very high activity in Heck and Suzuki-Miyaura cross-coupling reactions. Moreover, the MOF catalyst displays good thermal stability (up to 400 °C), and it can be recovered and reused for five reaction cycles. The bridging between the MOF structure and homogeneous molecular Pd catalyst represents a good example in designing highly efficient catalysts for various fine chemical transformations.
Dong, Dapeng,Li, Zhenghua,Liu, Dedi,Yu, Naisen,Zhao, Haiyan,Chen, Huiying,Liu, Jia,Liu, Dongping
p. 9317 - 9323
(2018/06/08)

Pd nanoparticles immobilized on magnetic chitosan as a novel reusable catalyst for green Heck and Suzuki cross-coupling reaction: In water at room temperature
A novel type of magnetically responsive chitosan nanocomposite was successfully synthesized as a green and high powerful palladium-based heterogeneous catalyst and its efficiency in Heck and Suzuki cross-coupling was evaluated. This catalyst promote a large library of functional substrates of these reactions under mild and sustainable conditions (water or ethanol as solvent, at room temperature, in significantly short reaction time (20?minutes)) and stand as recyclable, metal scavenging catalytic systems.
Hajipour, Abdol R.,Sadeghi, Ali R.,Khorsandi, Zahra
(2018/03/01)

Syntheses, characterization, solution behavior and catalytic activity of trans-[(guanidine)2PdX2] (X?=?Cl and OC(O)R; R?=?Me, Ph and tBu) in Heck–Mizoroki coupling reactions involving chloroarenes/methyl acrylate
Trans-[{(ArNH)2C[dbnd]NAr}2PdX2] (Ar = 2,5-Me2C6H3; X = Cl (1) and OC(O)R; R = Me (2), Ph (3), and tBu (4)) were isolated in high yields and characterized by elemental analysis, IR, and NMR (1H and 13C) spectroscopy. The molecular structures of the aforementioned complexes were determined by single crystal X-ray diffraction which revealed trans syn anti-anti (1·CHCl3), trans anti anti-syn (2·CHCl3 and 3·C7H8) and trans anti anti-anti (4) stereochemistry in solid state. Complexes 2·CHCl3, 3·C7H8 and 4 contain a pair of R11(8) rings stabilized by an intramolecular N–H?O hydrogen bond between the guanidine ligand and the carboxylate moiety. The influence of shape and size of the anion upon the stereochemistry of the complexes in the solid state and in solution are discussed. VT 1H NMR spectroscopic studies carried out on samples of 1 and 3 revealed the presence of a mixture of two rotamers in solution which arise due to the restricted [dbnd]C–N(H)Ar single bond rotation of the guanidine ligand in both complexes. Complexes 1–4 were shown to be active catalysts even when used in 0.001 mol% in Heck–Mizoroki coupling reactions involving chlorobenzene and methyl acrylate. The scope of 1 in Heck–Mizoroki coupling reactions involving methyl acrylate and nine distinct chloroarenes were explored at 0.01 mol% which afforded the coupling products in 81?96% yields.
Elumalai, Palani,Ujjval, Rishabh,Nethaji, Munirathinam,Thirupathi, Natesan
p. 313 - 322
(2018/06/20)

Monodentate phosphorus-coordinated palladium(II) complexes as new catalyst for Mizoroki-Heck reaction of aryl halides with electron-deficient olefins
Four novel palladium(II) complexes coordinated by phosphorus atoms from both 3,5-disubstituted-1H-1,2,4-diazaphospholes in monodentate fashion were developed as efficient catalyst for the Mizoroki-Heck reaction of aryl halides with electron-deficient olefins. The coupling reaction of aryl halide bearig different functional groups with olefin derivatives took place and the corresponding products were isolated in good to excellent yields under optimal conditions. The procedure exhibits good functional group tolerance and wide substrate scope. This Mizoroki-Heck reaction was further achieved using Pd(OAc)2 and 3,5-di-isopropyl-1H-1,2,4-diazaphospholes as combined catalyst, which provide the convenient and alternative method in organic synthesis
Zhao, Fang,Xin, Li,Zhang, Yingying,Jia, Xuefeng
supporting information
p. 493 - 496
(2017/09/06)

Kryptofix 5 as an inexpensive and efficient ligand for the palladium-catalyzed Mizoroki-Heck reaction
A novel complex of PdCl2 with a multidentate cryptand ligand, Kryptofix 5, has been prepared and characterized by various techniques including 1H- and 13C NMR spectroscopy, Fourier transform infrared (FT-IR), Raman, ultraviolet and visible (UV-VIS) spectroscopy, inductively coupled plasma (ICP), CHN elemental and energy dispersive X-ray analysis (EDX). This heat- and air-stable complex was utilized as a highly active catalyst for the Mizoroki-Heck reaction of aryl halides with various olefins. Interestingly, it was found that aryl bromides as well as aryl iodides were efficiently cross-coupled with terminal alkenes at 130?°C in 10?min. Furthermore, the least reactive aryl chlorides reacted with styrene to obtain the desired products in acceptable yields.
Movassagh, Barahman,Ranjbari, Shabnam
(2018/01/27)

Synthesis, crystal structures, and application of two new pincer type palladium(II)-Schiff base complexes in C-C cross-coupling reactions
Two new pincer type Pd(II)-Schiff base complexes of the general formula [PdL1(PPh3)] 1 and [PdL2(PPh3)] 2, (where L1 = 2-(2,3-Dihydroxybenzylideneamino)phenolate and L2 = 2-(2,3-dihydroxybenzylidene)hydrazinecarbothioamidate) were synthesised by the reaction of the palladium acetate with the corresponding ligand in methanol as yellow crystalline solids in high yields. Both complexes were fully characterized by FT-IR, 1H NMR, 13C NMR, 31P NMR, elemental analysis and single crystal X-ray diffraction studies. The crystal structures confirmed the tridentate nature of the pincer type Schiff base ligands and the distorted square planar geometry around the metal centre in both cases. The triphenylphosphine acted as an auxiliary ligand and occupied the fourth coordination site at palladium. The complexes were found to be efficient homogenous catalysts for a series of Suzuki-Miyaura, Heck-Mizoroki and Sonogashira reactions at a low catalyst loading (0.08 mol%), and without the use of any additives. All organic products were fully characterized by 1H and 13C NMR studies.
Agrahari, Bhumika,Layek, Samaresh,Anuradha,Ganguly, Rakesh,Pathak, Devendra D.
p. 345 - 354
(2017/12/01)

Self-assembled Pd nanoparticle-containing ionic liquid: Efficient and reusable catalyst for the Heck reaction in water
A self-assembled Pd nanoparticle-containing ionic liquid as metal–organic polymer was successfully prepared. The structure of the catalyst was characterized using Fourier transform infrared and 1H NMR spectroscopies, scanning electron microscopy and elemental analysis. The catalyst was effectively employed in the palladium-catalyzed Heck reaction in water as a green solvent. Moreover, due to its stability the catalyst can be recovered simply and effectively and reused nine times without much loss of activity.
Zong, Yingxiao,Wang, Junke,An, Pengli,Yue, Guoren,Pan, Yi,Wang, Xicun
p. 2389 - 2396
(2017/09/30)

Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst
Chitosan (CS) is a porous, self-standing, nanofibrillar microsphere that can be used as a metal carrier. Amino groups on CS enable to modulate cobalt coordination using a safe organic ligand (methyl salicylate). This catalyst efficiently promotes Heck cross-coupling of a large library of functional substrates under mild and sustainable conditions (polyethylene glycol as solvent at 80 °C in a short time (1 h)). The cobalt complex was also used as a heterogeneous, efficient, inexpensive, and green catalyst for Sonogashira cross-coupling reactions. The reactions of various aryl halides and phenylacetylene provided the corresponding products in moderate to good yields. More importantly, this phosphine, copper, and palladium-free catalyst was stable under the reaction conditions and could be easily reused using an external magnet for at least five successive runs without a discernible decrease in its catalytic activity.
Hajipour, Abdol R.,Rezaei, Fatemeh,Khorsandi, Zahra
supporting information
p. 1353 - 1361
(2017/08/18)

Synthesis and characterization of a new Pd(II)-Schiff base complex [Pd(APD)2]: An efficient and recyclable catalyst for Heck-Mizoroki and Suzuki-Miyaura reactions
The synthesis of a new Schiff base ligand “4-((Z)-((Z)-3-hydroxy-1,3-diphenylallylidene)amino) -1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (APD)” and its palladium complex [Pd(APD)2] is described. The ligand and complex are characterized by FTIR, FESEM, EDX, Elemental analyses and Mass spectrometry. The structure of the ligand is also confirmed by single crystal X-ray determination and 1H NMR data. The complex is insoluble in almost all common organic solvents. It has been used as an efficient catalyst in a series of Heck-Mizoroki and Suzuki-Miyaura coupling reactions giving good TON and TOF. The ease of synthesis, air-stability and recyclability are some of the important characteristics of the synthesized catalyst.
Layek, Samaresh,Anuradha,Agrahari, Bhumika,Pathak, Devendra D.
p. 105 - 112
(2017/06/19)

HISTONE DEACETYLASE 6 INHIBITORS AND USE THEREOF
Disclosed is hydroxamic acid compounds of Formula (I) set forth herein. Also disclosed are a pharmaceutical composition containing such a compound and a method of using the compound for treating a condition associated with histone deacetylase 6.
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Page/Page column 12-13

(2017/12/18)

Hg(II) and Pd(II) complexes with a new selenoether bridged biscarbene ligand: Efficient mono- and bis-arylation of methyl acrylate with a pincer biscarbene Pd(II) precatalyst
Two equivalents of 1-benzyl-3-bromoethylbenzimidazolium bromide couple with Na2Se to produce the first selenoether bridged bis-benzimidazolium salt (LH2)Br2. The nitrate (LH2)(NO3)2 and tetrafluoroborate (LH2)(BF4)2 salts were also synthesized from (LH2)Br2. The reaction of Hg(OAc)2 with (LH2)Br2 gave the first pseudo pincer carbene mercury complex, [Hg(L-κ2C)][HgBr4] (C1). Different complexes of Pd(ii) with selenoether bridged carbene were obtained using (LH2)Br2 and (LH2)(NO3)2. Syntheses of these complexes were dependent on the counter anion and the temperature. Thus, the pincer type ionic complex [PdBr(L-κ3CSeC)]Br (C2) was isolated at 80 °C and the pseudo pincer type neutral complex cis-[PdBr2(L-κ2C)] (C3) was isolated at room temperature from (LH2)Br2 and Pd(OAc)2 in DMSO. The nitrate precursor (LH2)(NO3)2 on palladation with Pd(OAc)2 afforded [Pd(L-κ4CBzCSeC)]NO3 (C4) showing an unprecedented intramolecular metallation at the ortho position of the benzyl wingtip of the benzimidazole moiety. The ligand salts and metal complexes have been characterized using HRMS, heteronuclear NMR and IR spectroscopy. Single crystal X-ray structures of the ligand salts (LH2)Br2 and (LH2)(BF4)2 and complexes C1-C4 have also been elucidated. Complex C2 showed good activity for C-C coupling in the mono-Heck reaction of methyl acrylate and arylbromides. Interestingly, the less common bis-arylation was also observed with deactivated arylbromides as the result of double-Heck coupling.
Rishu,Prashanth, Billa,Bawari, Deependra,Mandal, Ushnish,Verma, Aditya,Choudhury, Angshuman Roy,Singh, Sanjay
supporting information
p. 6291 - 6302
(2017/07/10)

NOVEL SALTS AND POLYMORPHIC FORMS OF PANOBINOSTAT
The present invention provides novel crystalline polymorphic form of DL-lactate salt of Panobinostat of Formula-I. This invention also provides process for preparation of crystalline forms of Panobinostat DL-lactate. Further, the present invention relates to a novel pharmaceutically acceptable salts and solid forms of Panobinostat.
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Page/Page column 11

(2018/04/12)

Efficient nickel(II) naringenin-oxime complex catalyzed Mizoroki-Heck cross-coupling reaction in the presence of hydrazine hydrate
A novel nickel(ii) naringenin-oxime complex was designed, synthesized and characterized. Therein, the nickel(ii) naringenin oxime complex as an efficient catalyst was used in Mizoroki-Heck coupling reactions of aryl halides containing electron-rich and electron-deficient substituents with styrene, methyl acrylate and divinylbenzene (DVB), respectively. The reaction proceeded efficiently under alkaline conditions in the presence of 0.30 mol% of the Ni(ii) naringenin oxime complexand N2H4·H2O as the reductant in EtOH at 80 °C, and 32 alkene products were afforded in moderate to excellent yields, containing four new olefins. The new catalytic system not only provided an inexpensive and efficient process with greener conditions, but also broadened the reaction scope.
Song, Jin-Yi,Liu, Yang,Zhao, Hong-Yan,Han, Hua-Tao,Li, Zhuo-Fei,Guo, Wei-Hao,Chu, Wen-Yi,Sun, Zhi-Zhong
p. 12288 - 12292
(2017/10/16)

Palladium nanoparticles immobilized on a magnetic chitosan-anchored Schiff base: Applications in Suzuki-Miyaura and Heck-Mizoroki coupling reactions
A palladium nanocatalyst Fe3O4@CS-SB-Pd has been synthesized and characterized by FT-IR, XRD, XPS, FESEM, EDX, TEM, TGA, and ICP-AES analysis. The nanocatalyst has been found to be an efficient and magnetically separable heterogeneous catalyst for Suzuki-Miyaura and Heck-Mizoroki coupling reactions at a low concentration (0.02 mol% of Pd). The nanocatalyst afforded arylated products with high TON (4950) and TOF (9900 h-1) in the Suzuki-Miyaura coupling reactions. However, for the Heck-Mizoroki coupling reaction, the values of TON and TOF were found to be 4900 and 7350 h-1, respectively. The nanocatalyst could be easily recovered from the reaction mixture by using an external magnet and recycled up to five times without significant decrease in its catalytic activity. All isolated products were obtained as white to off-white crystalline solids and brown oils and fully characterized by 1H and 13C NMR spectroscopy.
Anuradha,Kumari, Shweta,Layek, Samaresh,Pathak, Devendra D.
p. 5595 - 5604
(2017/07/11)

Flexible, dicationic imidazolium salts for in situ application in palladium-catalysed Mizoroki–Heck coupling of acrylates under aerobic conditions
The synthesis, characterization and in situ catalytic performance of new unsymmetric N,N′-disubstituted imidazolium-based dicationic salts in Mizoroki–Heck coupling of acrylates with aryl bromides under aerobic conditions are described. A series of flexible dicationic salts with varying steric and electronic properties were synthesized in good to excellent yields. All the salts were well characterized using spectroscopic techniques. X-ray diffraction analysis of two salts with the same dicationic backbone and different counter anions shows that the ligand adopts two different conformations which are influenced by the nature of the anion. Thus, the ligand is capable of changing its conformation according to the change in environment due to its flexible nature. All the synthesized imidazolium salts were found to be active in in situ palladium-catalysed Mizoroki–Heck coupling under aerobic conditions. Amongst the salts, the hydroxyl-functionalized imidazolium salt, incorporating the features of both bidentate chelating O,O ligand and carbene, shows the maximum catalytic activity. A variety of aryl and heteroaryl methyl and ethyl cinnamates were synthesized using these imidazolium salts as preligands. In addition, NMR studies confirm in situ generation of normal N-heterocyclic carbenes from the C-2 position of imidazol-2-ylidene ring. The mercury poisoning test was also performed to ascertain the nature of catalytically active palladium species. Aerobic conditions, low catalytic loading (0.5?mol%), shorter reaction times, broad functional group tolerance and good to excellent isolated yields are some of the significant features of the novel catalytic systems described here. Copyright
Milton, Marilyn Daisy,Garg, Parul
p. 759 - 766
(2016/09/04)

Regioselective Heck reaction catalyzed by Pd nanoparticles immobilized on DNA-modified MWCNTs
This is the first report of regioselective Heck reaction of aryl iodides with 2,3-dihydrofuran using heterogonous nanocatalyst. Herein, palladium nanoparticles is immobilized on DNA-modified multi walled carbon nanotubes and characterized by FT-IR spectroscopy, UV-vis spectroscopy, field emission scanning electron microscopy, X-ray diffraction, transmission electron microscopy, inductively coupled plasma and elemental analysis. DNA as a well-defined structure and biodegradable natural polymer generate the palladium catalyst which showed high activity in common and regioselective Heck reaction in excellent yields and good selectivity under ligand-free and mild reaction conditions. Moreover, the catalyst could be recovered and reused at least nine times without any considerable loss of its catalytic activity.
Hajipour, Abdol R.,Khorsandi, Zahra,Farrokhpour, Hossein
p. 59124 - 59130
(2016/07/06)

Imidazolyl-Functionalized Ordered Mesoporous Polymer from Nanocasting as an Effective Support for Highly Dispersed Palladium Nanoparticles in the Heck Reaction
New imidazolyl-functionalized ordered mesoporous cross-linked polymers were prepared by the copolymerization of the ionic liquid 3-benzyl-1-vinyl-1H-imidazolium bromide with divinylbenzene as the cross-linker and azobisisobutyronitrile as the radical initiator in the presence of O-silylated SBA-15 as the hard template. The materials were characterized by N2 adsorption–desorption analysis, TEM, thermogravimetric analysis, elemental analysis, and FTIR spectroscopy. The material, which benefits from the use of entrapped ionic liquid in the prepared polymer matrix in combination with its ordered mesoporous structure, is an excellent environment for the stabilization of highly dispersed Pd nanoparticles to result in a recyclable catalyst system with a significant activity in the Heck coupling reaction of aryl halides. The presence of well-distributed imidazolium functionalities in the polymeric framework might be responsible for the relatively uniform and nearly atomic scale distribution of Pd nanoparticles throughout the mesoporous structure and the prevention of Pd agglomeration during the reaction, which results in high durability, high stability, and good recycling characteristics of the catalyst. Although our catalyst system operates in a homogeneous pathway, it is also very stable and recyclable.
Karimi, Babak,Marefat, Mohammad Reza,Hasannia, Maliheh,Akhavan, Pari Fadavi,Mansouri, Fariborz,Artelli, Zahra,Mohammadi, Fariba,Vali, Hojatollah
p. 2508 - 2515
(2016/08/25)

Recyclable glucose-derived palladium(0) nanoparticles as in situ-formed catalysts for cross-coupling reactions in aqueous media
In situ-generated, glucose-derived palladium(0) nanoparticles were shown to be convenient and effective catalysts for aqueous Mizoroki-Heck, Sonogashira and Suzuki-Miyaura cross-coupling reactions. The addition of only 4-10 mol% glucose to the reaction mixture lead to a significant increase in yield of the desired products in comparison to processes that omitted the renewable sugar. Interestingly, the Mizoroki-Heck reaction was observed to proceed in good yield even as the reaction reached acidic pH levels. Extensive analysis of the size and morphology of the in situ-formed palladium nanoparticles using advanced analytical techniques showed that the zero valent metal was surrounded by hydrophilic hydroxyl groups. The increased aqueous phase affinity afforded by these groups allowed for facile recycling of the catalyst.
Camp, Jason E.,Dunsford, Jay J.,Dacosta, Oliver S. G.,Blundell, Rebecca K.,Adams, James,Britton, Joshua,Smith, Robert J.,Bousfield, Thomas W.,Fay, Michael W.
p. 16115 - 16121
(2016/02/20)

Phosphanamine-functionalized magnetic nanoparticles (PAFMNP): An efficient magnetic recyclable ligand for the Pd-catalyzed Heck reaction of chloroarenes
A phosphanamine-functionalized trimethoxysilyl compound (DPPPA) was synthesized and reacted with magnetic nanoparticles in order to synthesise a novel magnetic reusable phosphanamine ligand (PAFMNP) for application in transition metal-catalyzed coupling reactions. The Pd complex of PAFMNP (Pd-PAFMNP) was found to be an efficient heterogeneous catalyst for the Heck reaction of aryl chlorides. Only 1.0 mol% of catalyst was needed to accomplish the Heck reaction of the aryl chlorides. The catalyst was reusable at least 5 times without a significant decrease in its catalytic activity.
Panahi, Farhad,Zarnaghash, Narges,Khalafi-Nezhad, Ali
p. 1250 - 1255
(2016/02/19)

Synthesis and crystal structures of a series of (μ-thiophenolato)(μ-pyrazolato-N,N′) double bridged dipalladium(II) complexes and their application in Mizoroki-Heck reaction as highly efficient catalysts
Three new binucleating S-protected ligand precursors, 2-(N,N-dimethylthiocarbamato)-5-methylisophthalaldehyde di-2′-hydroxy 5′-methylanil (1b), 2-(N,N-dimethylthiocarbamato)-5-tert-butylisophthalaldehyde di-2′-hydroxyanil (2a) and 2-(N,N-dimethylthiocarbamato)-5-tert-butylisophthalaldehyde di-2′-hydroxy 5′-methylanil (2b), have been synthesized. The reaction of these ligand precursors with PdCl2 in the presence of pyrazole under Pd-mediated S-C cleavage yielded a series of binuclear palladium(II) complexes of general formula [LPd2(pz)], where pz is the exogenous bridging pyrazolyl ligand and L3- represents a series of pentadentate thiophenol-based bridging ligands originated from their corresponding ligand precursors. All the compounds were characterized by elemental analysis, IR, 1H NMR and UV-Vis spectroscopies. The binuclear μ-thiophenolato-μ-pyrazolato palladium(II) complexes have also been characterized by single crystal X-ray diffraction analysis. Crystal structure analyses of the complexes show that two PdII centers are located in distorted square-planar environments, arranged in binuclear units with PdPd distance of 3.57 ?. The catalytic activity of these new binuclear palladium complexes was studied in Mizoroki-Heck C-C coupling reaction of methyl- and n-butyl acrylate with various types of aryl iodides and bromides. All reactions were completed for very short times with very excellent yield. Reactions were stereoselective and only trans isomers were obtained in each case.
Khadir, Narjes,Tavakoli, Ghazal,Assoud, Abdeljalil,Bagherzadeh, Mojtaba,Boghaei, Davar M.
p. 107 - 117
(2015/11/18)

A novel bisoxazoline/Pd composite microsphere: A highly active catalyst for Heck reactions
A novel bisoxazoline/Pd microsphere catalyst was successfully prepared. The structure of the solid catalyst was characterized by SEM, TGA and FT-IR. The catalyst exhibits excellent activity for the Heck reaction. Moreover, the catalyst shows outstanding stability and reusability, can be recovered simply and effectively and reused six times without any activity decrease.
Wang, Junke,Zong, Yingxiao,Yue, Guoren,Hu, Yulai,Wang, Xicun
p. 76285 - 76290
(2015/09/28)

Pd(II) complexes of Schiff bases and their application as catalysts in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions
Schiff bases of 2-(phenylthio)aniline, (C6H5)SC6H4N=CR (R=(o-CH3)(C6H5), (o-OCH3)(C6H5) or (o-CF3)(C6H5)), and their palladium complexes (PdLCl2) were synthesized. The compounds were characterized using 1H NMR and 13C NMR spectroscopy and micro analysis. Also, electrochemical properties of the ligands and Pd(II) complexes were investigated in dimethylformamide-LiClO4 solution with cyclic and square wave voltammetry techniques. The Pd(II) complexes showed both reversible and quasi-reversible processes in the -1.5 to 0.3V potential range. The synthesized Pd(II) complexes were evaluated as catalysts in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions.
Kele, Mustafa,Kele, Hülya,Emir, Duygu Melis
p. 543 - 548
(2015/08/04)

NOVEL COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
The present invention relates to novel compounds having histone deacetylase 6 (HDAC6) inhibitory activity, isomers thereof, or pharmaceutically acceptable salts thereof, the use thereof for the preparation of therapeutic medicaments, pharmaceutical compositions comprising the same, a method of treating disease using the composition, and methods for preparing the novel compounds. The novel compounds according to the present invention have histone deacetylase 6 (HDAC6) inhibitory activity, and are effective for the prevention or treatment of HDAC6-associated diseases, including cancer, inflammatory diseases, autoimmune diseases, neurological diseases and neurodegenerative disorders.
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Paragraph 701; 702

(2015/10/05)

Silica-acetylacetone-supported palladium nanoparticles as an efficient and reusable catalyst in the Heck-Mizoroki C-C cross-coupling reaction
The preparation of palladium nanoparticles supported on acetylacetone-modified silica gel and their catalytic application for Heck olefination of aryl halides were investigated. The catalyst was characterized using X-ray diffraction, X-ray photoelectron spectroscopy, and transmission and scanning electron microscopies. The supported palladium nanoparticles are demonstrated to be a highly active and reusable catalyst for the Heck reaction. Several reaction parameters, including type and amount of solvent and base, were evaluated. The heterogeneity of the catalytic system was investigated with results indicating that there is a slight palladium leaching into the reaction solution under the applied reaction conditions. Despite this metal leaching, the catalyst can be reused nine times without significant loss of catalytic activity.
Hajipour, Abdolreza,Shirdashtzade, Zohre,Azizi, Ghobad
p. 143 - 146
(2015/03/30)

Optimization of a Novel Binding Motif to (E)-3-(3,5-Difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenyl)acrylic Acid (AZD9496), a Potent and Orally Bioavailable Selective Estrogen Receptor Downregulator and Antagonist
The discovery of an orally bioavailable selective estrogen receptor downregulator (SERD) with equivalent potency and preclinical pharmacology to the intramuscular SERD fulvestrant is described. A directed screen identified the 1-aryl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole motif as a novel, druglike ER ligand. Aided by crystal structures of novel ligands bound to an ER construct, medicinal chemistry iterations led to (E)-3-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenyl)acrylic acid (30b, AZD9496), a clinical candidate with high oral bioavailability across preclinical species that is currently being evaluated in phase I clinical trials for the treatment of advanced estrogen receptor (ER) positive breast cancer.
De Savi, Chris,Bradbury, Robert H.,Rabow, Alfred A.,Norman, Richard A.,De Almeida, Camila,Andrews, David M.,Ballard, Peter,Buttar, David,Callis, Rowena J.,Currie, Gordon S.,Curwen, Jon O.,Davies, Chris D.,Donald, Craig S.,Feron, Lyman J. L.,Gingell, Helen,Glossop, Steven C.,Hayter, Barry R.,Hussain, Syeed,Karoutchi, Galith,Lamont, Scott G.,MacFaul, Philip,Moss, Thomas A.,Pearson, Stuart E.,Tonge, Michael,Walker, Graeme E.,Weir, Hazel M.,Wilson, Zena
p. 8128 - 8140
(2015/11/09)

Development and evaluation of ST-1829 based on 5-benzylidene-2-phenylthiazolones as promising agent for anti-leukotriene therapy
Different inflammatory diseases and allergic reactions are mediated by leukotrienes, which arise from the oxygenation of arachidonic acid catalyzed by 5-lipoxygenase (5-LO). One promising approach for an effective anti-leukotriene therapy is the inhibition of this key enzyme. This study presents the synthesis and development of a potent and direct 5-LO inhibitor based on the well characterized 5-benzylidene-2-phenylthiazolone C06, whose further pharmacological investigation was precluded due to its low solubility. Through optimization of C06, evaluation of structure-activity relationships including profound assessment of the thiazolone core and consideration of the solubility, the 5-benzyl-2-phenyl-4-hydroxythiazoles represented by 46 (ST-1829, 5-(4-chlorobenzyl)-2-p-tolylthiazol-4-ol) were developed. Compound 46 showed an improved 5-LO inhibitory activity in cell-based (ICinf50/inf values 0.141/4M) and cell-free assays (ICinf50/inf values 0.03 1/4M) as well as a prominent enhanced solubility. Furthermore, it kept its promising inhibitory potency in the presence of blood serum, excluding excessive binding to serum proteins. These facts combined with the non-cytotoxic profile mark a major step towards an effective anti-inflammatory therapy.
Lill, Andreas P.,R?dl, Carmen B.,Steinhilber, Dieter,Stark, Holger,Hofmann, Bettina
supporting information
p. 503 - 523
(2014/12/11)

Iminophosphine palladium(II) complexes: Synthesis, characterization, and application in Heck cross-coupling reaction of aryl bromides
Palladium(II) complexes containing phosphorus and nitrogen donor atoms (iminophosphine), dichlorido{N-[2-(diphenylphosphino)benzylidene]-2- trifluoromethylaniline}palladium(II) 1, dichlorido{N-[2-(diphenylphosphino) benzylidene]-3-trifluoromethylaniline}palladium(II) 2, dichlorido{N-[2- (diphenylphosphino)benzylidene]-2-methylaniline}palladium(II) 3, dichlorido{N-[2-(diphenylphosphino)benzylidene]-3-methylaniline}palladium(II) 4 have been successfully synthesized and fully characterized by FT-IR and NMR (1H, 31P, 19F, and 13C) spectroscopy techniques. These complexes were first step tested in the reaction of bromobenzene and styrene to determine the optimal coupling reaction conditions and then successfully applied as catalysts for Heck cross-coupling reactions of activated and deactivated aryl bromides with styrene derivatives and several acrylates. Copyright
Yilmaz, Mustafa Kemal,Guezel, Bilgehan
p. 529 - 536
(2014/07/07)

CHEMICAL COMPOUNDS
The invention concerns compounds of Formula (I) or pharmaceutically-acceptable salts thereof, wherein R1 to R5 have any of the meanings defined hereinbefore in the description: processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of cell proliferative disorders.
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Paragraph 0450-0452

(2014/12/09)

Synthesis, structural characterization and catalytic activity of benzimidazole-functionalized Pd(II) N-heterocyclic carbene complexes
Two Pd(II)-NHC complexes bearing benzimidazole and pyridine groups have been successfully prepared and fully characterized by NMR and X-ray diffraction analysis. The structure of palladium complexes are a typical square-planar with palladium surrounded by two pairs of trans-arranged benzimidazole and carbene ligands. The Pd-NHC complexes have been proved to be a highly efficient catalyst for the Mizoroki-Heck coupling reaction of aryl halides with various substituted acrylates under mild conditions in excellent yields. Copyright
Diao, Yalin,Hao, Rong,Kou, Junfeng,Teng, Mingyu,Huang, Guoli,Chen, Yegao
p. 546 - 551
(2013/09/23)