- Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus
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The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.
- Ganji, Lata R.,Gandhi, Lekha,Musturi, Venkataramana,Kanyalkar, Meena A.
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p. 285 - 301
(2020/11/19)
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- Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia
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Recently, irreversible inhibitors have attracted great interest in antitumors due to their advantages of forming covalent bonds to target proteins. Herein, some benzothiazepinone compounds (BTZs) have been designed and synthesized as novel covalent GSK-3β inhibitors with high selectivity for the kinase panel. The irreversible covalent binding mode was identified by kinetics and mass spectrometry, and the main labeled residue was confirmed to be the unique Cys14 that exists only in GSK-3β. The candidate 4-3 (IC50 = 6.6 μM) showed good proliferation inhibition and apoptosis-inducing ability to leukemia cell lines, low cytotoxicity on normal cell lines, and no hERG inhibition, which hinted the potential efficacy and safety. Furthermore, 4-3 exhibited decent pharmacokinetic properties in vivo and remarkably inhibited tumor growth in the acute promyelocytic leukemia (APL) mouse model. All the results suggest that these newly irreversible BTZ compounds might be useful in the treatment of cancer such as APL.
- Zhang, Peng,Min, Zhihui,Gao, Yang,Bian, Jiang,Lin, Xin,He, Jie,Ye, Deyong,Li, Yilin,Peng, Chao,Cheng, Yunfeng,Chu, Yong
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p. 7341 - 7358
(2021/06/28)
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- Photo-Promoted Decarboxylative Alkylation of α, β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β, γ-Unsaturated Nitriles
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An efficient, catalyst/photocatalyst-free, and cost-effective methodology for the decarboxylative alkylation of α,β-unsaturated carboxylic acids to synthesize β,γ-unsaturated nitriles has been developed. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature. The methodology worked for a wide range of substrates (22 examples) with up to 83% yield. The protocol is also compatible for gram-scale synthesis.
- Pan, Chunxiang,Yang, Chunhui,Li, Kangkui,Zhang, Keyang,Zhu, Yuanbin,Wu, Shiyuan,Zhou, Yongyun,Fan, Baomin
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supporting information
p. 7188 - 7193
(2021/10/01)
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- Phenanthroline functionalized polyacrylonitrile fiber with Pd(0) nanoparticles as a highly active catalyst for the Heck reaction
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A series of polyacrylonitrile fibers (PANF) functionalized with nitrogen-containing ligands were prepared and then used to synthesize fiber-supported Pd(0) nanoparticle catalysts. The phenanthroline-functionalized PANF with immobilized Pd(0) nanoparticles (PANPhenF-Pd(0)) had the best catalytic activity for the Heck reaction under solvent-free conditions. The PANPhenF-Pd(0) efficiently stabilized the nanoparticles and they were well-dispersed with Pd(0) particle sizes of about 3 nm. The PANPhenF-Pd(0) structure was further characterized by a variety of instrumental methods. A probable mechanism based on the fiber's microenvironment is proposed for the Heck reaction catalyzed by PANPhenF-Pd(0). The PANPhenF-Pd(0) catalyst is easily recovered from the reaction system and can be used up to six times with only a slight decrease in catalytic activity and with low Pd leaching. The PANPhenF-Pd(0) catalyst also has excellent catalytic activity for gram-scale use.
- Xiao, Jian,Zhang, Haonan,Ejike, Anyaegbu Chima,Wang, Lu,Tao, Minli,Zhang, Wenqin
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- Knoevenagel-Doebner condensation promoted by chitosan as a reusable solid base catalyst
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The development of green and sustainable processes using naturally occurring biopolymers is becoming one of the suitable remedies to replace the conventional catalytic systems that generate large amount of byproducts with high risk factors. In this context, although Knoevenagel-Doebner condensation reaction has been reported with many organocatalysts including proline, no attempts were made to develop heterogeneous catalysts with environmental concerns. Considering these factors in mind, the title reaction is studied with chitosan as a heterogeneous solid base catalyst for the synthesis of α,β-unsaturated carboxylic acids through the condensation followed by decarboxylation reactions. Chitosan offers many advantages including high stability as evidenced by leaching, reusability tests, wide substrate scope and providing higher yields of the desired products with high purity. Powder X-ray diffraction (XRD), Fourier transform infrared (FT-IR), scanning electron microscope (SEM) and elemental analysis revealed that there are no major changes in the structural integrity and morphology of chitosan before and after catalysis under the optimized reaction conditions.
- Anbu, Nagaraj,Hariharan, Surendran,Dhakshinamoorthy, Amarajothi
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- Palladium(II)-Catalyzed Oxidative Decarboxylative [2 + 2 + 1] Annulation of Cinnamic Acids with Alkynes: Access to Polysubstituted Pentafulvenes
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An unprecedented palladium(II)-catalyzed oxidative decarboxylative [2 + 2 + 1] annulation of cinnamic acids with alkynes has been developed for the synthesis of polysubstituted pentafulvenes. Ag2CO3 and DMSO are essential for the reaction. This protocol features readily available starting materials, a wide substrate scope, and moderate to excellent yields. Moreover, various significant frameworks can be easily obtained from the late-stage transformations of pentafulvenes via oxidation, reduction, and Scholl-type reaction.
- Peng, Shiyong,Chen, Nuan,Zhang, Hong,He, Min,Li, Hongguang,Lang, Ming,Wang, Jian
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supporting information
p. 5589 - 5593
(2020/07/08)
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- Toward a Scalable Synthesis and Process for EMA401, Part II: Development and Scale-Up of a Pyridine- A nd Piperidine-Free Knoevenagel-Doebner Condensation
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During route scouting for EMA401 (1), an angiotensin II type 2 antagonist, we identified the synthesis of key amino acid intermediate 2 via its cinnamic acid derivative 3 as a streamlined option. In general, cinnamic acids can be synthesized from the corresponding aldehydes by a Knoevenagel-Doebner condensation in pyridine with piperidine as an organocatalyst. We aimed to replace both of these reagents and found novel conditions involving toluene as the solvent and morpholine as the organocatalyst. Scale-up of the process allowed the production of 25 kg of cinnamic acid 3 that was of the quality required for process development of the subsequent phenylalanine ammonia lyase-catalyzed step. The modified conditions were found to be widely applicable to alternative aldehydes and thus are of relevance to practitioners of chemical scale-up.
- Hardegger, Leo A.,Humair, Roger,Sidler, Eric
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p. 1756 - 1762
(2020/10/26)
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- CO2-Folded Single-Chain Nanoparticles as Recyclable, Improved Carboxylase Mimics
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Emulating the function of natural carboxylases to convert CO2 under atmospheric condition is a great challenge. Herein we report a class of CO2-folded single-chain nanoparticles (SCNPs) that can function as recyclable, function-intensified carboxylase mimics. Lewis pair polymers containing bulky Lewis acidic and basic groups as the precursor, can bind CO2 to drive an intramolecular folding into SCNPs, in which CO2 as the folded nodes can form gas-bridged bonds. Such bridging linkages highly activate CO2, which endows the SCNPs with extraordinary catalytic ability that can not only catalyze CO2-insertion of C(sp3)-H for imitating the natural enzyme's function, it can also act on non-natural carboxylation pathways for C(sp2 and sp)-H substrates. The nanocatalysts are of highly catalytic efficiency and recyclability, and can work at room temperature and near ambient CO2 condition, inspiring a new approach to sustainable C1 utilization.
- Chen, Liang,Yan, Qiang,Zeng, Rongjin
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supporting information
p. 18418 - 18422
(2020/08/21)
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- Structure-aided drug development of potential neuraminidase inhibitors against pandemic H1N1 exploring alternate binding mechanism
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Abstract: The rate of mutability of pathogenic H1N1 influenza virus is a threat. The emergence of drug resistance to the current competitive inhibitors of neuraminidase, such as oseltamivir and zanamivir, attributes to a need for an alternative approach. The design and synthesis of new analogues with alternate approach are particularly important to identify the potential neuraminidase inhibitors which may not only have better anti-influenza activity but also can withstand challenge of resistance. Five series of scaffolds, namely aurones (1a–1e), pyrimidine analogues (2a–2b), cinnamic acid analogues (3a–3k), chalcones (4a–4h) and cinnamic acid linkages (5a–5c), were designed based on virtual screening against pandemic H1N1 virus. Molecular modelling studies revealed that the designed analogues occupied 430-loop cavity of neuraminidase. Docking of sialic acid in the active site preoccupied with the docked analogues, i.e. in 430-loop cavity, resulted in displacement of sialic acid from its native pose in the catalytic cavity. The favourable analogues were synthesized and evaluated for the cytotoxicity and cytopathic effect inhibition by pandemic H1N1 virus. All the designed analogues resulting in displacement of sialic acid suggested alternate binding mechanism. Overall results indicated that aurones can be measured best among all as potential neuraminidase inhibitor against pandemic H1N1 virus. Graphical abstract: [Figure not available: see fulltext.].
- Malbari, Khushboo D.,Chintakrindi, Anand S.,Ganji, Lata R.,Gohil, Devanshi J.,Kothari, Sweta T.,Joshi, Mamata V.,Kanyalkar, Meena A.
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p. 927 - 951
(2019/02/07)
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- Pyridazinone derivative, and preparation method and medical application thereof
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The invention provides a pyridazinone derivative, and a preparation method and a medical application thereof. O-formylbenzoic acid used as a raw material reacts with dimethyl phosphite to obtain dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate, the dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate reacts with 3-cyano-4-fluorobenzaldehyde in the presence of triethylamine to prepare (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile, and the (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile is reduced by hydrazine hydrate to prepare 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid; and benzaldehyde or substituted aromatic formaldehyde or furfural used as a raw material and malonic acid undergo a Knoevenagel reaction to obtain cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid, the cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid and 1-tert-butoxycarbonylpiperazine undergo an amidation reaction, a tert-butoxycarbonyl group is removed from the obtained amidation product in the presence of trifluoroacetic acid, and the obtained product and the 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid undergo the amidation reaction to obtain a series of (E)-4-{3-[4-[(3-substituted aryl)acryloyl]piperazin-1-carbonyl]-4-fluorobenzyl}-2H-pyridazin-1-one derivatives. Results of preliminary pharmacological activity screening show that the compound represented by a general formula shown in the present invention has a certain in-vitro PARP-1 inhibition ability and a certain in-vitro tumor cell proliferation resisting activity. The structural general formula of compound is shown in the description; and in the general formula, Ar is selected from two formulas also shown in the description, and R1, R2, R3, R3, R4 and R5 can be the hydrogen atom, the fluorine atom, the chlorine atom, the bromine atom, a methyl group, a methoxy group, a tetrafluoromethyl group and a nitro group.
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Paragraph 0068-0072
(2019/10/07)
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- Substituted styrene preparation method
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The invention belongs to the technical field of synthesis of chemical and medical intermediates, and relates to a substituted styrene preparation method, in particular to a method for preparing substituted styrene by using an ionic solution. In the method, the ionic solution is used as a solvent, and the reaction catalyzing efficiency is high. The ionic solution can be repeatedly used, industrialproduction cost is saved, and environment problems caused by a traditional solvent are solved favorably.
- -
-
Paragraph 0032-0034
(2019/02/26)
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- Design, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs
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Research on thymidylate synthase inhibitors has been a hot spot for anticancer drug development. Here, based on the structures and pharmacological properties of two types of TS inhibitors, through a molecular assembly principle of drugs design, we designed and synthesized a series of 30 novel uracil derivatives as TS inhibitors. The antiproliferative ability of these compounds was evaluated against four cancer cell lines (A549, OVCAR-3, SGC-7901, and HepG2) by the MTT assay. Most of them showed excellent activities against all the tested cell lines. Furthermore, hTS assay results showed that these compounds have the unique ability to inhibit hTS activity in vitro. Notably, compound 13j exhibited the most potent activity against A549 cells (IC50 = 1.18 μM) and extremely prominent enzyme inhibition (IC50 = 0.13 μM), which was superior to the pemetrexed (PTX, IC50 = 3.29 μM and IC50 = 2.04 μM). Flow cytometric analysis showed the compound 13j could inhibit A549 cells proliferation by arresting the cell cycle in the G1/S phase, then induced the cell apoptosis. Further western blot analysis showed that compound 13j could down-regulate the cycle checkpoint proteins cyclin D1 and cyclin E to inhibit the cell cycle progression, and then induce intrinsic apoptosis by activating caspase-3, and reducing the ratio of bcl-2/bax. All of these results demonstrated that this new structure has potential drug-making properties and provides new ideas for drug development.
- Lu, Guo-qing,Li, Xin-yang,Mohamed O, Kamara,Wang, Depu,Meng, Fan-hao
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p. 282 - 296
(2019/03/27)
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- Method for preparing styrene derivative from ionic liquid
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The invention belongs to the technical field of chemical engineering and pharmaceutical intermediate synthesis and relates to a method for preparing a styrene derivative from ionic liquid. The methodhas advantages that by adoption of the ionic liquid as a solvent, high reaction catalyzing efficiency is achieved; due to reusability of the ionic liquid, industrial production cost is saved, and theenvironment problem caused by traditional solvents can be solved helpfully.
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Paragraph 0032-0034
(2019/04/06)
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- A method for the preparation of substituted styrene ion solution method
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The invention belongs to chemical and pharmaceutical intermediate synthesis technology field, relates to a process for preparing a substituted styrene ion solution method. The method takes the ionic liquid as solvent, reaction of high catalytic efficiency. The ionic liquid can be used repeatedly, save the industrialized production cost, and to facilitate the solution of the environmental problem of traditional solvent.
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Paragraph 0032; 0033; 0034
(2019/04/02)
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- Synthesis, preliminarily biological evaluation and molecular docking study of new Olaparib analogues as multifunctional PARP-1 and cholinesterase inhibitors
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A series of new Olaparib derivatives was designed and synthesized, and their inhibitory activities against poly (ADP-ribose) polymerases-1 (PARP-1) enzyme and cancer cell line MDA-MB-436 in vitro were evaluated. The results showed that compound 5l exhibited the most potent inhibitory effects on PARP-1 enzyme (16.10 ± 1.25 nM) and MDA-MB-436 cancer cell (11.62 ± 2.15 μM), which was close to that of Olaparib. As a PARP-1 inhibitor had been reported to be viable to neuroprotection, in order to search for new multitarget-directed ligands (MTDLs) for the treatment of Alzheimer’s disease (AD), the inhibitory activities of the synthesized compounds against the enzymes AChE (from electric eel) and BChE (from equine serum) were also tested. Compound 5l displayed moderate BChE inhibitory activity (9.16 ± 0.91 μM) which was stronger than neostigmine (12.01 ± 0.45 μM) and exhibited selectivity for BChE over AChE to some degree. Molecular docking studies indicated that 5l could bind simultaneously to the catalytic active of PARP-1, but it could not interact well with huBChE. For pursuit of PARP-1 and BChE dual-targeted inhibitors against AD, small and flexible non-polar groups introduced to the compound seemed to be conducive to improving its inhibitory potency on huBChE, while keeping phthalazine-1-one moiety unchanged which was mainly responsible for PARP-1 inhibitory activity. Our research gave a clue to search for new agents based on AChE and PARP-1 dual-inhibited activities to treat Alzheimer’s disease.
- Gao, Cheng-Zhi,Dong, Wei,Cui, Zhi-Wen,Yuan, Qiong,Hu, Xia-Min,Wu, Qing-Ming,Han, Xianlin,Xu, Yao,Min, Zhen-Li
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p. 150 - 162
(2018/11/30)
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- Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors
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Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. Hence, tyrosinase inhibitors are important in the fields of medicine, cosmetics and agriculture. In this study, novel N-(2-morpholinoethyl)cinnamamide derivatives bearing different substituents on phenyl ring were designed, synthesized and evaluated for their tyrosinase diphenolase inhibitory activity. The compounds were found to be better tyrosinase inhibitors (IC50s were in micro molar range) than cinnamic acid. (E)-3-(3-chlorophenyl)-N-(2-morpholinoethyl)acrylamide (B6) exhibited the highest inhibition with IC50 value of 15.2 ± 0.6 μM which was comparable to that of kojic acid. The inhibition kinetic analysis of B6 indicated that the compound was a mixed-type tyrosinase inhibitor. In silico ADME prediction indicated that B6 might show more skin penetration than kojic acid. Molecular docking analysis confirmed that the active inhibitors well accommodated in the mushroom tyrosinase active site and it was also revealed that B6 formed the most stable drug-receptor complex with the target protein. Therefore, cinnamamide B6 could be introduced as a potent tyrosinase inhibitor that might be a promising lead in cosmetics, medicine and food industry.
- Ghafari, Shahrzad,Ranjbar, Sara,Larijani, Bagher,Amini, Mohsen,Biglar, Mahmood,Mahdavi, Mohammad,Bakhshaei, Maryam,Khoshneviszadeh, Mahsima,Sakhteman, Amirhossein,Khoshneviszadeh, Mehdi
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p. 978 - 985
(2019/06/13)
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- Engineered mesoporous ionic-modified γ-Fe2O3@hydroxyapatite decorated with palladium nanoparticles and its catalytic properties in water
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A new mesoporous organic–inorganic nanocomposite was formulated and then used as stabilizer and support for the preparation of palladium nanoparticles (Pd NPs). The properties and structure of Pd NPs immobilized on prepared 1,4-diazabicyclo[2.2.2]octane (DABCO) chemically tagged on mesoporous γ-Fe2O3@hydroxyapatite (ionic modified (IM)-MHA) were investigated using various techniques. The synergistic effects of the combined properties of MHA, DABCO and Pd NPs, and catalytic activity of γ-Fe2O3@hydroxyapatite-DABCO-Pd (IM-MHA-Pd) were investigated for the Heck cross-coupling reaction in aqueous media. The appropriate surface area and pore size of mesoporous IM-MHA nanocomposite can provide a favourable hard template for immobilization of Pd NPs. The loading level of Pd in the nanocatalyst was 0.51?mmol?g?1. DABCO bonded to the MHA surface acts as a Pd NP stabilizer and can also lead to colloidal stability of the nanocomposite in aqueous solution. The results reveal that IM-MHA-Pd is highly efficient for coupling reactions of a wide range of aryl halides with olefins under green conditions. The superparamagnetic nature of the nanocomposite means that the catalyst to be easily separated from solution through magnetic decantation, and the catalytic activity of the recycled IM-MHA-Pd showed almost no appreciable loss even after six consecutive runs.
- Pashaei, Mokhtar,Mehdipour, Ebrahim,Azaroon, Maedeh
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- SOLID-SUPPORTED PALLADIUM(II) COMPLEX FOR CATALYZING MIZOROKI-HECK COUPLING REACTIONS AND A METHOD THEREOF
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A solid-supported palladium(II) complex which catalyzes the Mizoroki-Heck coupling reaction efficiently and a method of employing the solid-supported palladium(II) complex to synthesize cinnamic acid and derivatives thereof. The solid-supported palladium(II) complex is also stable and can be recycled without significantly losing catalytic activity.
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Paragraph 0137-0138
(2018/03/25)
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- METHOD FOR THE SYNTHESIS AND PRODUCTION OF ALKENYL COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing an efficient alkenyl compound conveniently and inexpensively. SOLUTION: A first compound represented by formula (1) reacts with a second compound represented by formula (3), in the presence of amino acid, in solvent containing amine, in a range of 50-200°C, to produce an alkenyl compound represented by formula (A) [where R1 is hydrogen or an optionally substituted C1-C30 alkyl group, R2 is a carboxyl group or the like, R3 and R4 are hydrogen, an optionally substituted C1-C30 alkyl group or the like]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0081; 0082
(2018/09/20)
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- An efficient and new protocol for the Heck reaction using palladium nanoparticle-engineered dibenzo-18-crown-6-ether/MCM-41 nanocomposite in water
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Palladium nanoparticle-incorporated mesoporous organosilica (MCM-41-Crown.Pd) was synthesized via the grafting of dibenzo-18-crown-6-ether moieties on the MCM-41 surface, followed by reaction of the nanocomposite with palladium acetate and then its reduction in ethanol. The cavity of the immobilized dibenzo-18-crown-6 as host material can stabilize the palladium nanoparticles effectively and prevent their aggregation and separation from the surface. The structure of the nanocomposite was characterized using various techniques. The catalytic properties of the nanocomposite in the Heck coupling reaction, one of the most useful transformations in organic synthesis, between aryl halides and olefins in water were also explored. The main advantages of the method are low cost, high yields, easy work-up and short reaction time. The nanocatalyst can be easily separated from a reaction mixture and was successfully examined for seven runs, with a slight loss of catalytic activity.
- Azaroon, Maedeh,Kiasat, Ali Reza
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- Synthesis and antibacterial evaluation of novel 11-O-carbamoyl clarithromycin ketolides
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A series of novel 11-O-carbamoyl clarithromycin ketolides were designed, synthesized and evaluated for their in vitro antibacterial activity. The results showed that the majority of the target compounds displayed improved activity compared with references against erythromycin-resistant S. pneumoniae A22072 expressing the mef gene, S. pneumoniae B1 expressing the erm gene and S. pneumoniae AB11 expressing the mef and erm genes. In particular, compounds 9, 18, 19 and 22 showed the most potent activity against erythromycin-resistant S. pneumoniae A22072 with the MIC values of 0.5?μg/mL. Furthermore, compounds 11, 18, 19, 24 and 29 were also found to exhibit favorable antibacterial activity against erythromycin-susceptible S. pyogenes with the MIC values of 0.125–1?μg/mL, and moderate activity against erythromycin-susceptible S. aureus ATCC25923 and B. subtilis ATCC9372.
- Jia, Li,Yan, Mi,Shen, Yan,Qin, Yinhui,Qiang, Shengsheng,Ma, Shutao
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supporting information
p. 3693 - 3697
(2017/07/27)
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- Synthesis and evaluation of thiochroman-4-one derivatives as potential leishmanicidal agents
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The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity.
- Vargas, Esteban,Echeverri, Fernando,Vélez, Iván D.,Robledo, Sara M.,Qui?ones, Wiston
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- Triethylamine: A potential N-base surrogate for pyridine in Knoevenagel condensation of aromatic aldehydes and malonic acid
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Cinnamic acids are intermediates with significant potential for synthesis of several industrially important chemicals. Classically, cinnamic acids are produced through Knoevenagel condensation of aromatic aldehydes and malonic acid in the presence of an organocatalyst and large amounts of carcinogenic pyridine. An alternative pyridine free reaction scheme for Knoevenagel condensation of malonic acid and aromatic aldehydes was investigated by replacing pyridine with an aliphatic tertiary amine surrogate in toluene as the reaction medium. Of the three aliphatic tertiary amines used, namely, triethyl amine (TEA), trioctyl amine (TOA) and tributyl amine (TBA), only TEA afforded cinnamic acids in comparable yields to those obtained with pyridine. Validation through a computational analysis is attempted to provide an explanation for the observed role of TEA as an aliphatic N-base instead of TBA and TOA. The use of TEA as a mild base in place of pyridine can be seen as playing the dual role of a base catalyst as well as a phase transfer agent evidenced by the in-process ATR-FITR spectroscopy. Use of the TEA-toluene system in place of pyridine can be seen as resulting in a process that affords ease of handling, separation and recycling of the solvent and the catalyst.
- Pawar, Hitesh S.,Wagh, Adhirath S.,Lali, Arvind M.
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p. 4962 - 4968
(2016/07/06)
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- Design, synthesis, and docking studies of afatinib analogs bearing cinnamamide moiety as potent EGFR inhibitors
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Two series of afatinib derivatives bearing cinnamamide moiety (10a-n and 11a-h) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, PC-3, MCF-7 and Hela). Two selected compounds (10e, 10k) were further evaluated for the inhibitory activity against EGFR and VEGFR2/KDR kinases. Seven of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 values in single-digit μM to nanomole range. Three of them are equal to more active than positive control afatinib against one or more cell lines. The most promising compound 10k showed the best activity against A549, PC-3, MCF-7 and Hela cancer cell lines and EGFR kinase, with the IC50 values of 0.07 ± 0.02 μM, 7.67 ± 0.97 μM, 4.65 ± 0.90 μM and 4.83 ± 1.28 μM, which were equal to more active than afatinib (0.05 ± 0.01 μM, 4.1 ± 2.47 μM, 5.83 ± 1.89 μM and 6.81 ± 1.77 μM), respectively. Activity of compounds 10e (IC50 9.1 nM) and 10k (IC50 3.6 nM) against EGFR kinase were equal to the reference compound afatinib (IC50 1.6 nM). Structure-activity relationships (SARs) and docking studies indicated that replacement of the aqueous solubility 4-(dimethylamino)but-2-enamide group by cinnamamide moiety didn't decrease the antitumor activity. The results suggested that methoxy substitution had a significant impact on the activity and methoxy substituted on C-4 or C-2,3,4 position was benefit for the activity.
- Tu, Yuanbiao,Ouyang, Yiqiang,Xu, Shan,Zhu, Yan,Li, Gen,Sun, Chao,Zheng, Pengwu,Zhu, Wufu
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p. 1495 - 1503
(2016/03/15)
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- Design, Synthesis and Pharmacological Evaluation of Novel Piperlongumine derivatives as Potential Antiplatelet Aggregation Candidate
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A series of novel piperlongumine derivatives (4a-i, 6a-i) were designed and synthesized. The inhibitory activities of platelet aggregation induced by ADP and AA in vitro have been evaluated by bron turbidimetry and liver microsomal incubated assay. The assay results show that compounds 4e and 6e exhibited remarkable potency to that of the positive control piplartine and aspirin.
- Wang, Yujun,Wang, Jie,Li, Jiaming,Zhang, Yanchun,Huang, Weijun,Zuo, Jian,Liu, Huicai,Xie, Di,Zhu, Panhu
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p. 833 - 840
(2016/05/19)
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- Ultrahigh performance bio-based polyimides from 4,4′-diaminostilbene
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We have developed a novel route for the synthesis of high-performance bio-polyimides (PIs) microbially-derived from photo-responsive aromatic diamine 4,4′-diaminostilbene (DAS) and its reduced counterpart 4, 4′-(ethane-1,2-diyl)dianiline (EDDA). DAS and EDDA were condensed with various commercially-available dianhydrides to obtain a series of poly(amic acid)s (PAAs) and PIs which were characterized in terms of their thermal, mechanical, and photo-functions. These bio-based PAAs showed a very high viscosity of 6.62 dL/g, and the PIs showed ultrahigh thermal resistance with Td10 values over 600 °C, which were higher than that of any bio-based plastic reported thus far. They also showed Tg values above 250 °C, and tensile strength of over 132 MPa, which is higher than that of Kapton. The PIs also showed photo-functional behavior based on stilbene-based photoreactions.
- Kumar, Amit,Tateyama, Seiji,Yasaki, Katsuaki,Ali, Mohammad Asif,Takaya, Naoki,Singh, Rajeev,Kaneko, Tatsuo
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p. 182 - 189
(2016/01/09)
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- A green chemical synthesis of coumarin-3-carboxylic and cinnamic acids using crop-derived products and waste waters as solvents
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Crop-derived products, like juices obtained from edible fruits and vegetables, and waste waters deriving from agricultural and industrial processing have been recently exploited to efficiently promote several ‘classic’ and innovative synthetic organic reactions. Such a green chemical approach prevented the use of toxic, polluting, and hazardous materials and in the mean time allowed to increase the commercial values of crop products and industrial byproducts. Coumarin-3-carboxylic and cinnamic acids represent classes of naturally occurring and semi-synthetic compounds with interesting and promising pharmacological activities. In this Letter a new and improved methodology for the Knoevenagel condensation yielding the title compounds using juices from edible fruits and vegetables (lemon, grapefruit, carrot, pomegranate, kiwi, vinegar, tomato), liqueurs (limoncello), and waste waters (buttermilk and residues of olive processing) as solvents is described. Coumarin-3-carboxylic and cinnamic acids have been synthesized in excellent yields by ultrasound irradiation from differently substituted 2-hydroxybenzaldehydes, 2-hydroxyacetophenones, and benzaldehydes, and Meldrum's acid as starting substrates. The findings described herein enforce the concept of the usefulness of products and byproducts derived from agriculture and food industry to accomplish green chemical processes.
- Fiorito, Serena,Taddeo, Vito Alessandro,Genovese, Salvatore,Epifano, Francesco
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supporting information
p. 4795 - 4798
(2016/10/05)
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- Synthesis and characterization of bifunctional lipophilic and basic mesoporous organosilica supported palladium nanoparticles as an efficient and ecofriendly nanocomposite in aqueous Heck reaction
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In the present study, a highly ordered mesoporous organosilica nanocomposite having modified pore channels with both lipophilic and basic units, SBA-R/Im-NH2, was synthesized through surfactant-templated sol-gel methodology and post modification process. The nanocomposite with ionic liquid properties was used as a potential host for supporting palladium nanoparticles. The structure and composition of the target nanocomposite, SBA-R/Im-NH2·Pd, were supported by infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), transmission electron microscopy (TEM), elemental analysis (CHNS), energy dispersive X-ray (EDX) and Brunauer-Emmett-Teller (BET) measurements. The efficiency of this porous inorganic-organic hybrid nanocomposite as a powerful catalyst in one of the most important carbon-carbon bond-forming process, the Heck coupling reaction of aryl halides with olefins, in aqueous media was also examined. This method has the advantages of high yields, cleaner reactions, simple methodology, short reaction times, easy workup, and greener conditions. In addition, the nanocatalyst can be easily separated from the reaction mixture and reused several times without significant decrease in activity and promises economic as well as environmental benefits.
- Jafari Nasab, Mina,Kiasat, Ali Reza
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p. 81614 - 81621
(2016/09/09)
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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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- Synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles from (hetero)arylacrylic acids
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A three-step method for the synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles is described. Easily accessible bis(trimethylsilyl)acetylene and acrylic acid derivatives are used as starting materials for the preparation of mono- and disubstituted 5-(trimethylsilyl)pent-1-en-4-yn-3-ones. Oxidative phthalimidoaziridination of these enynones provides the key 2-acyl-1-phthalimidoaziridines that are further utilized in the thermal expansion of the three-membered ring to furnish the target functionalizable oxazoles.
- Pankova, Alena S.,Stukalov, Alexander Yu.,Kuznetsov, Mikhail A.
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p. 1826 - 1829
(2015/04/27)
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- Base-promoted new C-C bond formation: An expedient route for the preparation of thiazolo- and imidazolo-pyridinones via Michael addition
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Base-catalyzed one-pot cyclocondensation reactions of acryloyl and cinnamoyl chlorides with β-nitroenamine derivatives have been performed under mild conditions and target 7-substituted thiazolo-[3,2-a] or imidazolo-[1,2-a]pyridin-5-one derivatives were prepared successfully in moderate to good yields. The cyclization reactions may proceed via Michael addition followed by iminoketene-amide tautomerization in view of the products formed.
- Yildirim, Muhammet,C?elikel, Derya,Evis, Naciye,Knight, David W.,Kariuki, Benson M.
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p. 5674 - 5681
(2015/03/30)
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- Design, synthesis and biological evaluation of novel sesquiterpene mustards as potential anticancer agents
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Several novel series of sesquiterpene mustards (SMs) bearing nitrogen mustard and glutathione (GSH)-reactive α-methylene-γ-butyrolactone groups were successfully prepared for the first time and showed excellent antiproliferative activities in vitro. Among them, compounds 2e and 2g displayed the highest antiproliferative properties with IC50 values ranging from 2.5 to 8.7 μM. The selectivity of these two compounds was evaluated by SRB method against human cancer and normal hepatic cells (HepG2 and L02). The induction of apoptosis and effects on the cell cycle distribution with compounds 2e and 2g were investigated by Hoechst 33,258 staining and flow cytometry, which exhibited that they could induce selective cell apoptosis and cell cycle arrest in HepG2 and L02 cells. In addition, further investigation showed that compounds 2e and 2g could obviously inhibit the proliferation of HepG2 cells by inducing significant DNA cross-linking and depleting GSH in cell media. The good cytotoxicity and selectivity of compounds 2e and 2g pointed them as promising leads for anticancer drug design.
- Xu, Yuan-Zhen,Gu, Xue-Yan,Peng, Shou-Jiao,Fang, Jian-Guo,Zhang, Ying-Mei,Huang, De-Jun,Chen, Jian-Jun,Gao, Kun
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p. 284 - 297
(2015/03/30)
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- Synthesis and characterization of two novel biological-based nano organo solid acids with urea moiety and their catalytic applications in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives under mild and green conditions
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2-Carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid as novel, mild and biological-based nano organocatalysts with urea moiety were designed, synthesized and fully characterized by FT-IR, 1H NMR, 13C NMR, mass spectrometry, elemental analysis, thermal gravimetric, derivative thermal gravimetric, X-ray diffraction patterns, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, atomic force microscopy and UV/Vis analysis. The catalytic applications of 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid were studied in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives via the condensation reaction between several aromatic aldehydes and 1-phenyl-3-methylpyrazol-5-one (synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols)), the Knoevenagel condensation of Meldrum's acid with salicylaldehyde derivatives (synthesis of coumarin-3-carboxylic acids) and the condensation of Meldrum's acid with aromatic aldehydes (synthesis of cinnamic acids) under mild and solvent-free conditions. In the presented studies, some products were formed and reported for the first time. The described nano organo solid acids have potential in industry.
- Zolfigol, Mohammad Ali,Ayazi-Nasrabadi, Roya,Baghery, Saeed
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p. 71942 - 71954
(2015/09/08)
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- Palladium nanoparticles on β-cyclodextrin functionalised graphene nanosheets: A supramolecular based heterogeneous catalyst for C-C coupling reactions under green reaction conditions
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The use of functional properties of native cyclodextrins in palladium nanoparticle-β-cyclodextrin-graphene nanosheet (Pd@CD-GNS) catalyzed carbon-carbon (C-C) coupling reactions have been investigated under green reaction conditions. The supramolecular catalyst was prepared by deposition of Pd nanoparticles (Pd NPs) on CD-GNS using ethanol as the greener solvent and in situ reducing agent. The catalyst was characterised by FTIR, XRD, RAMAN, UV-Vis spectroscopy, TEM, SAED, XPS and ICP-AES. The catalytic activity of these catalysts is investigated in C-C coupling reactions such as Suzuki-Miyaura and Heck-Mizoroki reactions of aryl bromides and aryl chlorides containing functional groups under green reaction conditions i.e. in water, under phosphine free and aerobic conditions. This catalyst afforded excellent selectivities for the products in good to excellent yields under low Pd loadings (0.2-0.05 mol%), while ensuring the recovery and reusability of the catalysts. The reused catalyst was characterized by FTIR, TEM, XPS and ICP-AES. The CD supramolecular mediators loaded on GNS act as stabilising agents for the Pd NPs. The excellent catalytic activity of this system was attributed to the presence of CDs, excellent dispersibility in water, hydrophobic nature of the GNS support for the accumulation of organic substrates in water, "Breslow effect", the presence of PTC to overcome the mass transfer limitation onto the surface of GNS and formation of ternary CD/substrate/additive complexes on the Pd-GNS surface.
- Putta, Chandrababu,Sharavath, Vittal,Sarkar, Suprabhat,Ghosh, Sutapa
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p. 6652 - 6660
(2015/03/05)
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- Alum-Cs2CO3 as a new recyclable solid base catalyst for the efficient syntheses of arylidenemalononitriles, esters and arylcinnamic acids in water
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The condensation between aromatic aldehydes and malononitrile, ethylcyanoacetate and malonic acid for the syntheses of arylidenemalononitriles, arylidenemalonic acid esters and aryl cinnamic acids in water using alum-Cs2CO3 as a solid support catalyst has been described. Alum-Cs2CO3 was found to be a highly active, stable and recyclable catalyst under reaction conditions.
- Taduri, Ashok Kumar,Devi, B. Rama
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p. 1938 - 1942
(2014/06/09)
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- Design, synthesis and evaluation of novel diaryl urea derivatives as potential antitumor agents
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A novel series of diaryl ureas containing different linker groups were designed and synthesized. Their in vitro antitumor activity against MX-1, A375, HepG2, Ketr3 and HT-29 was evaluated using the standard MTT assay. Compounds having a rigid linker group such as vinyl, ethynyl and phenyl showed significant inhibitory activity against a variety of cancer cell lines. Specifically, compound 23 with a phenyl linker group demonstrated broad-spectrum antitumor activity with IC50 values of 5.17-6.46 μM against five tested tumor cell lines. Compound 23 is more potent than reference drug sorafenib (8.27-15.2 μM), representing a promising lead for further optimization.
- Lu, Chenshu,Tang, Ke,Li, Yan,Li, Peng,Lin, Ziyun,Yin, Dali,Chen, Xiaoguang,Huang, Haihong
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p. 351 - 360
(2014/04/17)
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- Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
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A series of ninety-seven diarylpentanoid derivatives were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferone gamma (IFN-γ)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Twelve compounds (9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88 and 97) exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 ± 0.2 μM), notably compounds 88 and 97, which demonstrated the most significant NO suppression activity with IC50 values of 4.9 ± 0.3 μM and 9.6 ± 0.5 μM, respectively. A structure-activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these molecules. With the exception of the polyphenolic derivatives, low electron density in ring-A and high electron density in ring-B are important for enhancing NO inhibition. Meanwhile, pharmacophore mapping showed that hydroxyl substituents at both meta- and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives.
- Leong, Sze Wei,Mohd Faudzi, Siti Munirah,Abas, Faridah,Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Wai, Lam Kok,Abdul Bahari, Mohd Nazri,Ahmad, Syahida,Tham, Chau Ling,Shaari, Khozirah,Lajis, Nordin H.
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p. 16058 - 16081
(2015/01/08)
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- Palladium nanoparticles on noncovalently functionalized graphene-based heterogeneous catalyst for the Suzuki-Miyaura and Heck-Mizoroki reactions in water
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We describe here a methodology to synthesize a reusable heterogeneous catalyst based on palladium nanoparticles (Pd NPs) supported on noncovalently functionalized graphene using 1-pyrene carboxylic acid. This can be used efficiently for Suzuki-Miyaura and Heck-Mizoroki reactions in water up to five cycles, providing excellent yields with high selectivity of cross coupled products. It is also useful for more challenging substrates like electron-rich and electron-poor bromoarenes and chloroarenes which resulted in good isolated yields (alkenes and biphenyls) in pure water. Use of functionalized graphene in the catalyst preparation improved the dispersion of it in water medium and also acted as a stabilizing agent for the Pd NPs. The percentage of metal loading in the catalyst and its thermal stability were determined by inductively coupled plasma atomic emission spectroscopy and thermo gravimetric analysis respectively. The composite formation was confirmed by X-ray diffraction patterns, Fourier transform infrared spectroscopy and Raman spectroscopy. The surface elemental composition with oxidation state was determined by UV-visible and X-ray photoelectron spectroscopy. The size and morphology of the Pd NPs on the functionalized graphene sheets were directly observed by Transmission Electron Microscopy.
- Sharavath, Vittal,Ghosh, Sutapa
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p. 48322 - 48330
(2014/12/10)
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- Simultaneous immobilization of a matrix containing palladium and phase transfer catalyst on silica nanoparticles: Application as a recoverable catalyst for the Heck reaction in neat water
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Simultaneous covalent anchoring of a phosphonium-palladium complex/phase transfer catalyst matrix on the surface of silica nanoparticles and the application of the resulting catalyst in the Heck reaction of a variety of different haloarenes in neat aqueous media is described. This journal is the Partner Organisations 2014.
- Hajipour, Abdol R.,Azizi, Ghobad
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p. 20704 - 20708
(2014/06/09)
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- Synthesis and biological evaluation of Cu(II), Zn(II), and Ni(II) 3-(4-nitrophenyl)acrylic acid complexes with diamines as potential urease inhibitors
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Five new Cu(II), Zn(II), and Ni(II) 3-(4-nitrophenyl)acrylic acid complexes were synthesized and evaluated for inhibitory activity on jack bean urease. All five complexes were structurally determined by single crystal X-ray analysis. Compared with the positive reference acetohydroxamic acid (IC50= 13.25 μM), Cu(II) complexes 3 and 4 showed the strongest inhibitory activity against jack bean urease (IC50= 1.23 and 1.17 μM). Ni(II) and Zn(II) complexes also exhibited inhibitory activities (IC50= 10.09-13.10 μM).
- Yang, Zhong-Ming,Zhu, Hui,Sun, Juan,Qian, Shao-Song,Cai, Meng-Na,Zhu, Hai-Liang
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p. 2736 - 2746
(2014/02/14)
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- Synthesis of dendrimers terminated by DABCO ligands and applications of its palladium nanoparticles for catalyzing Suzuki-Miyaura and Mizoroki-Heck couplings
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A new kind of silica-supported third-generation dendrimers capped by 1,4-diaza-bicyclo[2.2.2]octane (DABCO) group-stabilized palladium(0) nanoparticles, and their enhanced catalytic activity in Suzuki-Miyaura and Mizoroki-Heck reactions in excellent yield under mild conditions, was reported. The resulting silica-supported dendrimer-stabilized palladium(0) nanoparticles with a particle size of 10-20 nm were prepared in situ by treatment with PdCl2 and hydrazine in ethanol at 60 °C for 24 h. The catalyst as prepared was characterized by FT-IR, X-ray diffraction, thermal analysis, elementary analysis (EA), scanning electron microscopy and transmission electron microscopy. Recycling experiments showed that the catalyst could be easily recovered by simple filtration and reused for up to five cycles without losing its activity.
- Xu, Yijing,Zhang, Zhanyi,Zheng, Jia,Du, Qinwei,Li, Yiqun
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- Fiber-palladium complex as highly active and recyclable catalyst for heck reaction in air
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A new amidoxime fibers-palladium catalyst was synthesized by the 'coordination-reduction' reaction between the amidoxime groups in fibers and Pd(II) ions. The morphology, structure and composition of the as-obtained complexes were characterized by X-ray diffraction and X-ray photoelectron spectroscopy. The results indicated that the Pd(II) ions were reduced to Pd(0) nanospheres in situ with the diameter of about 100 nm and there were coordination interactions between the Pd nanoparticles and the amidoxime fibers. The prepared catalyst demonstrated high activities for Heck coupling reaction of aryl iodine. During the reaction, the fibers serve as both the ligand and the support. In all cases, the coupling reactions proceeded efficiently without inert atmosphere. The catalyst can be easily recycled for at least eight times.
- Wu, Zhichuan,Wu, Qi,Chen, Meng,Tao, Tingxian
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p. 5783 - 5786
(2013/07/26)
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- Triton-B adsorbed on flysh: An efficient support for the base catalysed reactions under microwave irradiations
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The application of Triton-B adsorbed on flyash (a waste material of thermal plants ) has been reported for the variety of base catalysed reactions such as synthesis of cinnamic acids by Deobner reaction, synthesis of 1-(2-hydroxyphenyl)-5-phenylpent-4-ene-1, 3-diones by Baker-Venkataraman reaction and synthesis of 3-carboxycoumarins by knoevenagel reaction. This material also acts as a support for the reaction and avoids the use of any solvent in the reaction maintaining the norms of Green Chemistry.
- Goel, Vijender
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p. 1725 - 1728
(2013/06/27)
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- Synthesis of polyphenol microsphere-supported palladium complex and evaluation of its catalytic performance for Heck reaction
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Polyphenol microspheres were prepared by template polymerization of phenol in the presence of horseradish peroxidase as bio-enzyme catalyst and aqueous 1,4-dioxane as solvent. The morphology of polyphenol microspheres thus obtained was observed with a scanning electron microscope. Further, polyphenol microspheres as obtained were loaded with palladium to generate polyphenol microsphere-supported Pd complex. Resultant Pd complex catalyst supported by polyphenol microspheres was characterized by means of Fourier transformation infrared spectrometry, X-ray diffraction, X-ray photoelectron spectroscopy and scanning electron microscopy, and its thermal stability was examined. Moreover, the catalytic activity of polyphenol microsphere-supported Pd catalyst as synthesized for the Heck reactions of acrylic acid with aryl iodides was evaluated. Results indicate that the polyphenol microsphere as obtained has a diameter of about 500 nm. Polyphenol microsphere-supported Pd catalyst, as synthesized, at a dosage of 0.37 mol% Pd, possesses good catalytic activity for the Heck reactions of acrylic acid with aryl iodides in air at a low temperature of 50°C, and it also exhibits catalytic activity for bromide and activated chlorobenzene. The polyphenol microsphere-supported Pd complex has good thermal stability, and it can be readily separated and reused; the yield of the reaction of iodobenzene with acrylic acid remains at 82% after five recycle runs, showing promising potential as a catalyst for Heck reactions. Copyright
- Nie, Guangrui,Zhang, Lei,Cui, Yuanchen
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supporting information
p. 635 - 640,6
(2020/09/02)
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- Application of an air-and-moisture-stable diphenylphosphinite cellulose-supported nanopalladium catalyst for a Heck reaction
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A diphenylphosphinite cellulose-supported nanopalladium (Cell-OPPh 2-Pd0) was conveniently prepared from cellulose and chlorodiphenylphosphine in pyridine, followed by treatment of an ethanol solution of palladium chloride. The prepared catalysis was found to be air- and moisture-stable and have significant catalytic activities in Heck coupling under mild operating conditions. Various phenyl halides were coupled with alkenes in DMF under air, to afford the corresponding products in good yields. Furthermore, the catalyst can be easily recovered by simple filtration and reused for up to six cycles without losing its activity. Springer Science+Business Media B.V. 2012.
- Du, Qingwei,Li, Yiqun
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p. 1807 - 1817
(2013/02/22)
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- A PdCl2-ionic liquid brush assembly: An efficient and reusable catalyst for Mizoroki-Heck reaction in neat water
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An efficient and reusable heterogeneous catalytic assembly of PdCl 2 held in ionic liquid brushes has been synthesized and an environmentally-friendly procedure was developed for coupling aryl iodides with acrylic acid. These reactions were conducted in water under aerobic conditions with water-insoluble or even solid aryl iodides and they proceeded smoothly and cleanly without any organic co-solvent or other additives. A 0.5 mol% (based on Pd atom) dose of the catalyst was found to be sufficient for Mizoroki-Heck reaction. The catalyst is easily recovered post reaction, via simple filtration, and reused at least eight times without a noticeable loss of activity. The protocol has the advantages of excellent yield, environmental friendliness, and catalyst recyclability. Copyright
- Shi, Xianying,Han, Xiaoyan,Ma, Wenjuan,Fan, Juan,Wei, Junfa
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experimental part
p. 16 - 20
(2012/03/26)
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- Preparation of high-magnetization Fe3O4-NH 2-Pd (0) catalyst for heck reaction
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A magnetically separable Fe3O4-NH2-Pd (0) catalyst was easily synthesized by immobilizing Pd nanoparticles on the surface of magnetic Fe3O4-NH2 microspheres. It was found that the combination of Fe3O4 and triethylene tetramine (TETA) could give rise to structurally stable catalytic sites. Furthermore, the high-magnetization Fe3O4-NH 2-Pd(0) catalyst can be recovered by magnet and reused for six runs for Heck reaction without significant loss in catalytic activity.
- Ma, Mingliang,Zhang, Qiuyu,Yin, Dezhong,Dou, Jinbo,Zhang, Hepeng,Xu, Hailong
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experimental part
p. 168 - 172
(2012/03/26)
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- Convenient syntheses of pyrazolo[3,4-b]pyridin-6-ones using either microwave or ultrasound irradiation
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An efficient synthesis of 12 pyrazolo[3,4-b]pyridin-6-one derivatives was achieved using either microwave or ultrasound irradiation, resulting in yields of 40-60% and 60-95%, respectively. Under our conditions, these reactions occurred with notably reduced reaction times as compared to literature reports involving traditional heating. Furthermore, these reactions were highly regioselective and produced only one pyrazolo[3,4-b]pyridin-6-one isomer, whose identity was confirmed by NOESY spectroscopy.
- Rodrigues-Santos, Cláudio E.,Echevarria, Aurea
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body text
p. 336 - 340
(2011/02/26)
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- Sodium tetraborate-dibenzo-18-crown ether-6 complex as reagent in the synthesis of cinnamic acids from aromatic aldehydes and aliphatic carboxylic acids
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Cinnamic acids have been prepared in 74-81% yields by a new synthesis from aromatic aldehydes and aliphatic carboxylic acids in the presence of anhydrous sodium tetraborate-dibenzo-18-crown ether-6 complex as reagent, 4-dimethylaminopyridine as activating agent, pyridine as base, and N-methyl-2-pyrolidinone as solvent, at reflux (180-190°C) for 10-12 hours.
- Chiriac, Constantin I.,Tanasa, Fulga,Nechifor, Marioara
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experimental part
p. 419 - 423
(2012/01/03)
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- N-Heterocyclic carbene-Pd(II) complex derived from proline for the Mizoroki-Heck reaction in water
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N-Heterocyclic carbene-Pd(II) complex 1 derived from proline was found to be an efficient catalyst in the Mizoroki-Heck reaction of aryl bromides and iodides performed in water. The reactions can tolerate various functional groups in the substrates and all gave the corresponding coupling products in good to high yields.
- Tang, Yi-Qiang,Chu, Chun-Yan,Zhu, Lei,Qian, Bin,Shao, Li-Xiong
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experimental part
p. 9479 - 9483
(2011/12/15)
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