- An effective biocompatible fluorescent probe for bisulfite detection in aqueous solution, living cells, and mice
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Sulfur dioxide, an air pollutant, is easily hydrated to sulfites and bisulfites and extremely harmful to human health. On the other hand, endogenous sulfur dioxide is the fourth gasotransmitter. In view of the above, it is worth developing an effective method for the detection of these compounds. In this paper, a novel colorimetric fluorescent probe (Hcy-Mo), based on hemi-cyanine, for bisulfites is reported. Hcy-Mo shows excellent selectivity for bisulfites over various other species including cysteine, glutathione, CN-, and HS-, and undergoes 1,4-addition reactions at the C-4 atom of the ethylene group. The reaction can be completed in 30 s in a PBS buffer solution and displays high sensitivity (limit of detection is 80 nM) for bisulfites. Test paper experiments show that the probe can be used for bisulfite detection in aqueous solutions. In addition, Hcy-Mo exhibits excellent cell permeability and low cytotoxicity for the successful detection of bisulfites in living MDA-MB-231 cells and in living mice, implying that this probe would be of great benefit to biological researchers for investigating the detailed biological and pharmacological functions of bisulfites in biological systems. This journal is
- Cui, Guiling,Hu, Yuefu,Huang, Wencai,Qi, Qingrong,Yang, Li,Zhou, Ruqiao
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- Design, synthesis and biological assessment of new thiazolylhydrazine derivatives as selective and reversible hMAO-A inhibitors
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In the recent works, it was shown that numerous thiazolylhydrazine derivatives display hMAO inhibitory activity in the range of micromolar concentration. Hence, in the present study a new series of new thiazole-hydrazines (3a-3n) were designed, synthesized, characterized and screened for their hMAO-A and hMAO-B inhibitory activity by an in vitro flurometric method. The enzyme inhibition assay revealed that most of the synthesized compounds have selective inhibition potency against hMAO-A. The compounds 3f and 3h showed promising hMAO-A inhibition with an IC50 values of 0.012 μM and 0.011 μM and significant selectivity indexes of 1214 and 1601 towards hMAO-A, respectively. The mechanism of hMAO-A inhibition of compounds 3f and 3h was investigated by Lineweaver-Burk graphics and reversible-competitive inhibition of hMAO-A was determined. Cytotoxicity and genotoxicity studies were carried out and the compound 3h was found as non-cytotoxic and non-genotoxic. Theoretical calculation of ADME properties suggested that synthesized compounds may have a good pharmacokinetic profile. The docking study of compound 3f and 3h revealed that there is a strong interaction between the active sites of hMAO-A and analyzed compound.
- Can, Nafiz ?ncü,Osmaniye, Derya,Levent, Serkan,Sa?l?k, Begüm Nurpelin,Korkut, Bü?ra,Atl?, ?zlem,?zkay, Yusuf,Kaplanc?kl?, Zafer As?m
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- Preparation and characterization of cobalt-containing P,N-ligands and an unusual palladium complex ion pair: their applications in amination reactions
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Several cobalt-containing P,N-ligands, alkyne-bridged dicobalt phosphines [(μ-PPh2CH2PPh2)Co2(CO)4(μ,η-Me2NCH2C{triple bond, long}CPR2)] (4a: R=tBu; 4b: R=P
- Hsiao, You-Chen,Chiang, Wen-Yuan,Weng, Chia-Ming,Hong, Fung-E.
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- Synthesis of dihydropyrazole sulphonamide derivatives that act as anti-cancer agents through COX-2 inhibition
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COX-2 has long been exploited in the treatment of inflammation and relief of pain; however, research increasingly suggests COX-2 inhibitors might possess potential benefits to thwart tumour processes. In the present study, we designed a series of novel COX-2 inhibitors based on analysis of known inhibitors combined with an in silico scaffold modification strategy. A docking simulation combined with a primary screen in vitro were performed to filter for the lead compound, which was then substituted, synthesized and evaluated by a variety of bioassays. Derivative 4d was identified as a potent COX-2 enzyme inhibitor and exerted an anticancer effect through COX-2 inhibition. Further investigation confirmed that 4d could induce A549 cell apoptosis and arrest the cell cycle at the G2/M phase. Moreover, treatment with 4d reduced A549 cell adhesive ability and COX-2 expression. The morphological variation of treated cells was also visualized by confocal microscopy. Overall, the biological profile of 4d suggests that this compound may be developed as a potential anticancer agent.
- Qiu, Han-Yue,Wang, Peng-Fei,Li, Zhen,Ma, Jun-Ting,Wang, Xiao-Ming,Yang, Yong-Hua,Zhu, Hai-Liang
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- Design, synthesis, and bioactivity investigation of novel benzimidazole derivatives as potent urease inhibitors
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Herein, we synthesized a series of novel benzimidazole derivatives 5a–k and screened their bioactivity as potent urease inhibitors. The structure of the 5a–k was elucidated using spectroscopic technics (1H-NMR, 13C-NMR, MS), elementa
- Abdel-Jalil, Raid,Al-Saadi, Abdullah Mohammed,Amanlou, Massoud,Amini, Mohsen,Saeedian Moghadam, Ebrahim,Talebi, Meysam
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supporting information
(2021/12/10)
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- Design and synthesis of methoxyphenyl- and coumarin-based chalcone derivatives as anti-inflammatory agents by inhibition of NO production and down-regulation of NF-κB in LPS-induced RAW264.7 macrophage cells
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Exaggerated inflammatory responses may cause serious and debilitating diseases such as acute lung injury and rheumatoid arthritis. Two series of chalcone derivatives were prepared as anti-inflammatory agents. Methoxylated phenyl-based chalcones 2a-l and c
- Emam, Soha H.,Sonousi, Amr,Osman, Eman O.,Hwang, Dukhyun,Kim, Gun-Do,Hassan, Rasha A.
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- Design and synthesis of novel furan, furo[2,3-d]pyrimidine and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives as potential VEGFR-2 inhibitors
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Novel furan 6a-c, furo[2,3-d]pyrimidine 7a-f, 9, 10a-f, 12a,b, 14a-d and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine 8a-f derivatives were designed based on their structural similarity to a previously described oxazole VEGFR-2 back pocket binding fragment. The designed compounds were synthesized and screened for their in vitro VEGFR-2 inhibitory activity where they exhibited good to moderate nanomolar inhibition with improved ligand efficiencies. 8b and 10c (IC50 = 38.72 ± 1.7 and 41.40 ± 1.8 nM, respectively) were equipotent to sorafenib and 6a, 6c, 7f, 8a, 8c, 10b, 10f, 12b, 14c and 14d showed good activity (IC50 = 43.31–98.31 nM). The furotriazolopyrimidines 8a-c and furopyrimidine derivative 10c were further evaluated for their in vitro antiproliferative activity against human umbilical vein endothelial cells (HUVECs) where 8b showed higher potency than sorafenib and resulted in cell cycle arrest at G2/M phase whereas 8c revealed good antiproliferative activity with cell cycle arrest at G1 phase. Moreover, 8a-c and 10c showed significant inhibitory effects on the invasion and migration of HUVECs. Molecular docking study was conducted to gain insight about the potential binding mode. The furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives 8b and 8c represent interesting starting point for antiangiogenic compounds based on their activity and favorable drug likeness profiles.
- Abd El-Mageed, Menna M.A.,Eissa, Amal A.M.,Farag, Awatef El-Said,Osman, Essam Eldin A.
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- Pyridoxine-resveratrol hybrids as novel inhibitors of MAO-B with antioxidant and neuroprotective activities for the treatment of Parkinson's disease
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A series of pyridoxine-resveratrol hybrids were designed and synthesized as monoamine oxidase B inhibitors for the treatment of Parkinson's disease. Most of them exhibited potent inhibitory activities on MAO-B with high selectivity. Specifically, compounds 12a, 12g and 12l showed the most excellent inhibition to hMAO-B with the IC50 values of 0.01 μM, 0.01 μM and 0.02 μM, respectively. Further reversibility study demonstrated that 12a and 12l were reversible and 12g was irreversible MAO-B inhibitors. Molecular docking studies of MAO revealed the binding mode and high selectivity of these compounds with MAO-B. In addition, these three representative compounds also exhibited low cytotoxicity and excellent neuroprotective effect in the test on H2O2-induced PC-12 cell injury. Moreover, 12a, 12g and 12l showed good antioxidant activities and high blood-brain barrier permeability. Overall, all of these results highlighted 12a, 12g and 12l were potential and excellent MAO-B inhibitors for PD treatment.
- Cao, Zhongcheng,Deng, Yong,Li, Wei,Shi, Yichun,Song, Qing,Yang, Xia,Zhang, Li
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- Design, synthesis, characterization and fluorescence property evaluation of dehydroacetic acid-based chalcones
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Abstract: In this study, we decided to synthesize some new chalcone-type dyes derived from dehydroacetic acid (DHA) by the condensation of 4-amino-substituted benzaldehyde with DHA under the base-catalyzed condition and investigate their ability for rearrangement in acidic condition. For this purpose, initially we prepared the 4-aminobenzaldehyde derivatives via nucleophilic aromatic substitution reaction of 4-fluorobenzaldehyde with variety of amines in the presence of K2CO3 as base in DMF. The Knoevenagel condensation of DHA with 4-aminobenzaldehyde derivatives results in the desired compounds. In continuation, Fries rearrangement applied on DHA-chalcone compounds results in characterization of new pyranilidene-type derivatives. The optical responses of new dyes containing UV–Vis absorption and fluorescence spectroscopy were measured in dichloromethane (ET = 40?kcal/mol). Pyranilidene derivatives show low λmax values in comparison with chalcones, and molecule with strong dipole, in polar solvents, shows the bathochromic shift due to more stabilization of excited state in compared with ground state of molecule. Large stocks shifts were obtained for synthesized compounds. Graphic abstract: [Figure not available: see fulltext.].
- Teimuri-Mofrad, Reza,Rahimpour, Keshvar,Gholizadeh, Mohammad
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p. 1103 - 1109
(2019/12/30)
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- Design and Synthesis of some new 2,4,6-trisubstituted quinazoline EGFR inhibitors as targeted anticancer agents
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The present study describes the synthesis of 6-bromo-2-(pyridin-3-yl)-4-substituted quinazolines starting from 4-chloro derivative VI via the reaction with either phenolic compounds to obtain VIIa-f, IXa-d, 2-amino-6-(un)substituted benzothiazole to produce VIIIa-c or hydrazine hydrate to give X. Reaction of the hydrazino functionality of X with appropriate acid anhydride, acid chloride or aldehyde affords XIa-c, XIIa-c and XIVa-i, respectively. The target compounds were screened for their efficacy as EGFR inhibitors compared to gefitinib. Compounds eliciting superior EGFR inhibitory activity were further screened for their in vitro cytotoxicity against two human cancer cell lines namely: MCF7 (breast) and A549 (lung), in addition to normal fibroblast cell WI38 relative to gefitinib as a reference. Furthermore, compounds that showed potent inhibitory activity on wild-type EGFR were screened against mutant EGFR and assayed for their cytotoxicity against mutant EGFR-expressing cell lines PC9 and HCC827. The unsubstituted benzothiazol-2-amine VIIa showing superior EGFR inhibition (IC50 = 0.096 μM) and anticancer activity against MCF-7 cell line (IC50 = 2.49 μM) was subjected to cell cycle analysis and apoptotic assay. Moreover, a molecular docking study was performed to investigate the interaction of some representive compounds with the active site of EGFR- TK.
- Abbass, Safinaz E. S.,Allam, Heba Abdelrasheed,Aly, Enayat E.,El Kerdawy, Ahmed M.,Farouk, Ahmed K. B. A. W.,Rashwan, Essam
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- Multifunctional quinoxaline-hydrazone derivatives with acetylcholinesterase and monoamine oxidases inhibitory activities as potential agents against Alzheimer’s disease
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Multitarget molecules are considered as an effective way for the treatment of AD, instead of the classic one-drug-one-target strategy because of the multifactorial nature of AD. A variety of studies indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted quinoxaline-hydrazone derivatives were synthesized, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity and MAOA/B inhibitory activity. Based on the experimental results, compound 5l exhibited good inhibitory potency on both AchE (IC50 = 0.028 ± 0.001 μM) and monoamine oxidase B (IC50 = 0.046 ± 0.002 μM). Molecular modeling studies showed that 5l could bind to the active site of AChE and MAO-B. Taken together, these results suggested that compound 5l might be a potential multifunctional agent for the treatment of AD.
- Ilgin, Sinem,Karaduman, Abdullah Burak,Levent, Serkan,Osmaniye, Derya,?avu?o?lu, Betül Kaya,?evik, Ulviye Acar,?zkay, Yusuf,Kaplancikli, Zafer As?m,Karaburun, Ahmet ?a?r?,Sa?lik, Begüm Nurpelin,Turan, Gülhan
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p. 1000 - 1011
(2020/04/29)
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- METHOD FOR THE SYNTHESIS OF CYCLIC DEPSIPEPTIDES
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The present invention relates to a method for the synthesis of cyclic depsipeptides, in particular emodepside, from the open form.
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Page/Page column 54-55
(2019/05/30)
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- Novel 1,4-dihydropyrano[2,3-c]pyrazole derivatives: Synthesis, characterization, biological evaluation and in silico study
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In the present study, a series of novel and biologically potent 6-amino-1-(2,4-dinitrophenyl)-4-phenyl-1,4-dihydropyrano [2,3-c]pyrazole-5-carbonitrile derivatives (5a-5u) have been synthesized through multicomponent reaction between various substituted a
- Vasava, Mahesh S.,Bhoi, Manoj N.,Rathwa, Sanjay K.,Shetty, Shilpa S.,Patel, Rikin D.,Rajani, Dhanji P.,Rajani, Smita D.,Patel, Alpesh,Pandya, Himanshu A.,Patel, Hitesh D.
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p. 383 - 402
(2019/01/21)
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- Application of hydrazino and hydrazido linkers to connect benzenesulfonamides with hydrophilic/phobic tails for targeting the middle region of human carbonic anhydrases active site: Selective inhibitors of hCA IX
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Herein we report the design and synthesis of three different sets of novel benzenesulfonamides (5a-e, 7a-e and 10a-d) incorporating hydrophilic/hydrophobic tails by hydrazido or hydrazino linkers. The newly synthesized benzenesulfonamides were examined in vitro for their inhibitory activity towards four human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IX and XII using a stopped-flow CO2 hydrase assay. All these isoforms were inhibited by the sulfonamides (5a-e, 7a-e and 10a-d) with variable degrees in the following KI ranges: 76.8–357.4 nM for hCA I, 8.2–94.6 nM for hCA II, 2.0–46.3 nM for hCA XI, and 8.3–88.3 nM for hCA XII. The sulfonamide 7d exhibited potent anti-proliferative activity against breast MCF-7 cancer cell line under both normoxic and hypoxic conditions with IC50 values equal 3.32 ± 0.06 and 8.53 ± 0.32 μM, respectively, which are comparable to the reference drug doxorubicin (IC50 = 2.36 ± 0.04 and 8.39 ± 0.25 μM, respectively). Furthermore, 7d was screened for cell cycle disturbance and apoptosis induction in MCF-7 cells. It was found to persuade cell cycle arrest at G2-M stage as well as to alter the Sub-G1 phase, also, 7d resulted in a significant increase in the percent of annexinV-FITC positive apoptotic cells from 1.03 to 18.54%. Molecular docking study was carried out for 7d within the hCA IX and hCA XII active sites to rationalize the obtained inhibition results.
- Allam, Heba Abdelrasheed,Fahim, Samar H.,F.Abo-Ashour, Mahmoud,Nocentini, Alessio,Elbakry, Mohamed E.,Abdelrahman, Mohamed A.,Eldehna, Wagdy M.,Ibrahim, Hany S.,Supuran, Claudiu T.
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p. 547 - 556
(2019/07/04)
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- A two-aromatic substituted propylene ketone compound and its preparation method and application (by machine translation)
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The present invention discloses a two-aromatic substituted propylene ketone compound and its preparation method and application, its structural formula such as formula (I) as shown: Wherein A is B is hydrogen, methyl or ethyl; C is a substituted benzene ring, pyridine and furan heterocyclic, 2 - pyridyl, 3 - pyridyl, 4 - pyridyl, 5 - 1 H - indolyl, 4 - (N, N - dimethylamino) phenyl, 4 - (N - pyrrolyl) phenyl, 4 - [1 - (N - methyl piperazinyl)] phenyl or 4 - (1 - morpholinyl) phenyl. The compounds of the invention has a novel structure, to inhibit the cells MCL active effect, high safety, the preparation cost is low and the like, can be used as a MCL very promising drug. (by machine translation)
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Paragraph 0152; 0153; 0154; 0155; 0156; 0159; 0160
(2019/05/28)
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- A lysosome-targeting and polarity-specific fluorescent probe for cancer diagnosis
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A lysosome-targeting and polarity-specific fluorescent probe CPM has been rationally designed for cancer diagnosis and imaging. We have successfully shown that lysosome polarity may serve as an ubiquitious marker for cancer detection. The potential of CPM for cancer diagnosis has also been demonstrated at the levels of live cells, organs, whole animal, and clinical patient tissue samples.
- Fan, Li,Wang, Xiaodong,Ge, Jinyin,Li, Feng,Wang, Xiao,Wang, Juanjuan,Shuang, Shaomin,Dong, Chuan
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supporting information
p. 4703 - 4706
(2019/05/02)
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- Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines
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Herein, we describe a new catalytic approach to accessing aromatic amines from an abundant feedstock, namely phenols. The most reliable catalytic method for converting phenols to aromatic amines uses an activating group, such as a trifluoromethane sulfonyl group. However, this activating group is eliminated as a leaving group during the amination process, resulting in significant waste. Our nickel-catalyzed decarboxylation reaction of aryl carbamates forms aromatic amines with carbon dioxide as the only byproduct. As this amination proceeds in the absence of free amines, a range of functionalities, including a formyl group, are compatible. A bisphosphine ligand immobilized on a polystyrene support (PS-DPPBz) is key to the success of this reaction, generating a catalytic species that is significantly more active than simple nonsupported variants.
- Nishizawa, Akihiro,Takahira, Tsuyoshi,Yasui, Kosuke,Fujimoto, Hayato,Iwai, Tomohiro,Sawamura, Masaya,Chatani, Naoto,Tobisu, Mamoru
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supporting information
p. 7261 - 7265
(2019/05/16)
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- A group of diphosphine-thiosemicarbazone complexes of palladium: Efficient precursors for catalytic C–C and C–N coupling reactions
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Reaction of 4-R-benzaldehyde thiosemicarbazone (denoted in general as HL-R; where H stands for the dissociable acidic proton and R (R = OCH3, CH3, H, Cl and NO2) for the substituent) with [Pd(dppe)(EtOH)2]2+, generated in situ via interaction of [Pd(dppe)Cl2] (dppe = 1,2-bis(diphenylphosphino)ethane) with AgNO3 in hot ethanol, in the presence of triethylamine affords a group of orange complexes of the type [Pd(dppe)(L-R)]NO3. Structures of [Pd(dppe)Cl2] and [Pd(dppe)(L-OCH3)]NO3 have been determined by X-ray crystallography. In the [Pd(dppe)(L-R)]NO3 complexes, the thiosemicarbazone ligands are coordinated to the metal center as monoanionic bidentate N,S-donors forming five-membered chelate rings. The [Pd(dppe)(L-R)]NO3 complexes show intense absorptions in the visible and ultraviolet regions, which have been analyzed by TDDFT calculations. All the [Pd(dppe)(L-R)]NO3 complexes are found to efficiently catalyze Suzuki-type C–C and Buchwald-type C–N coupling reactions.
- Thapa, Kiran,Paul, Piyali,Bhattacharya, Samaresh
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p. 232 - 239
(2018/11/06)
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- Functionalised bicyclic tetramates derived from cysteine as antibacterial agents
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Routes to bicyclic tetramates derived from cysteine permitting ready incorporation of functionality at two different points around the periphery of a heterocyclic skeleton are reported. This has enabled the identification of systems active against Gram-positive bacteria, some of which show gyrase and RNA polymerase inhibitory activity. In particular, tetramates substituted with glycosyl side chains, chosen to impart polarity and aqueous solubility, show high antibacterial activity coupled with modest gyrase/polymerase activity in two cases. An analysis of physicochemical properties indicates that the antibacterially active tetramates generally occupy physicochemical space with MW of 300-600, clog D7.4 of -2.5 to 4 and rel. PSA of 11-22%. This work demonstrates that biologically active 3D libraries are readily available by manipulation of a tetramate skeleton.
- Panduwawala, Tharindi D.,Iqbal, Sarosh,Thompson, Amber L.,Genov, Miroslav,Pretsch, Alexander,Pretsch, Dagmar,Liu, Shuang,Ebright, Richard H.,Howells, Alison,Maxwell, Anthony,Moloney, Mark G.
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supporting information
p. 5615 - 5632
(2019/06/13)
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- Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes
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Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here, we report that a stable organic semiconductor material, mesoporous graphitic carbon nitride (mpg-CN), can act as a visible-light photoredox catalyst to orchestrate oxidative and reductive interfacial electron transfers to two different substrates in a two- or three-component system for direct twofold carbon–hydrogen functionalization of arenes and heteroarenes. The mpg-CN catalyst tolerates reactive radicals and strong nucleophiles, is straightforwardly recoverable by simple centrifugation of reaction mixtures, and is reusable for at least four catalytic transformations with conserved activity.
- Ghosh, Indrajit,Khamrai, Jagadish,Savateev, Aleksandr,Shlapakov, Nikita,Antonietti, Markus,K?nig, Burkhard
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p. 360 - 366
(2019/08/15)
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- A new kind of near-infrared fluorescent probe synthesis and to Fe2 + Detecting activity evaluation
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Near-infrared fluorescence probe, it has the following structural formula I. The experiment proves, the fluorescence probe directed against the Fe2 + It has very good selectivity and specificity, can quantitatively detect the Fe in aqueous solu
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Paragraph 0010-0011
(2019/07/04)
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- Quantum yield improvement of red-light-emitting firefly luciferin analogues for in vivo bioluminescence imaging
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The dimethylamino group of AkaLumine ((4S)-2-[(1E,3E)-4-[4-(dimethylamino)phenyl]-1,3-butadien-1-yl]-4,5-dihydro-4-thiazolecarboxylic acid), a red-light-emitting firefly luciferin analogue, was replaced by cyclic amino groups (1-pyrrolidinyl, 1-piperidino, 1-azepanyl, and 4-morpholino) to give AkaLumine analogues exhibiting desirable bioluminescence with emission maxima in the red region (656–667 nm). In particular, a bioluminescence reaction of 1-pyrrolidinyl analogue with a recombinant Photinus pyralis luciferase showed a higher quantum yield than that with AkaLumine, giving an improved bioluminescence intensity. The 1-pyrrolidinyl analogue also showed the strongest luminescence in whole-body luciferase-expressing mice among the analogues, indicating that a quantum yield improvement of a luciferin analogue is effective to increase bioluminescence imaging intensity.
- Kiyama, Masahiro,Iwano, Satoshi,Otsuka, Satoshi,Lu, Shijia W.,Obata, Rika,Miyawaki, Atsushi,Hirano, Takashi,Maki, Shojiro A.
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p. 652 - 660
(2018/01/04)
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- Biological evaluation and in silico molecular docking study of a new series of thiazol-2-yl-hydrazone conglomerates
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A new series of hybridized thiazol-2-yl-hydrazone derivatives having diverse substituents were designed, synthesized, and screened for their anti-inflammatory property by a carrageenan-induced paw edema method. The compounds 11a, 11b, 11c, 11d, 11e, 11g, 11m and 11p revealed significant inhibition when compared to Diclofenac sodium. Subsequently, two highly potent compounds (11d and 11e) were evaluated for their cytotoxic effect on the tumor cell line. The binding interactions of thiazol-2-yl-hydrazones with the cyclooxygenase-2 (COX-2) protein (PDB: 3LN1) displayed effective interactions with Arg-120, Tyr-385 and Tyr-355 amino acids, the main criteria of the COX-2 inhibitor. In addition, all the compounds showed moderate to good in vitro antibacterial activity. Most active benzyloxy derivatives were also tested to understand the radical scavenging efficacy by the 2,2-diphenyl-1-picrylhydrazyl method. Graphical Abstract: [Figure not available: see fulltext.].
- Bhat, Mahima,Gurubasavaraja Swamy,Poojary, Boja,Revanasiddappa,Vijay Kumar,Kumar, Vasantha
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p. 2779 - 2805
(2018/02/19)
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- Synthesis and anticandidal activity of new imidazole-chalcones
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In the present work, 15 new 1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-substituedphenyl)prop-2-en-1-one derivatives (3a–3o) were synthesized to evaluate their antifungal activity. Structures of newly synthesized imidazole derivatives (3a–3o) were characterized by IR,1H-NMR,13C-NMR, and LCMSMS spectroscopic methods. The anticandidal activity of compounds (3a–3o) against C. albicans (ATCC 24433), C. krusei (ATCC 6258), C. parapsilosis (ATCC 22019), and C. glabrata (ATCC 90030) was elucidated according to the EUCAST definitive (EDef 7.1) method. Consistent with the activity studies, 3a–3d were found to be more potent derivatives with their MIC50 values (0.78 μg/mL–3.125 μg/mL) against Candida strains. Compound 3c indicated similar antifungal activity to ketoconazole against all Candida species and was evaluated as the most active derivative in the series. Effects of the most potent derivatives 3a–3d on ergosterol biosynthesis were observed by LC-MS-MS method, which is based on quantification of the ergosterol level in C. krusei. Moreover, these compounds were subjected to a cytotoxicity test for the preliminary toxicological profiles and were found as non-cytotoxic. Furthermore, docking studies for the most active derivative 3c were performed to evaluate its binding modes on lanosterol 14-α-demethylase. In addition to in vitro tests, docking studies also revealed that Compound 3c is a potential ergosterol biosynthesis inhibitor.
- Osmaniye, Derya,Avu?o Glu, Bet l Kaya,Sa gl?k, Beg m Nurpelin,Levent, Serkan,Acar evik, Ulviye,Atl?, Zlem,Zkay, Yusuf,Kaplanc?kl?, Zafer As?m
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- Buchwald-Hartwig amination reaction of aryl halides using heterogeneous catalyst based on Pd nanoparticles decorated on chitosan functionalized graphene oxide
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In this work, graphene oxide was functionalized with chitosan (GO-Chit) followed by a simple approach for immobilization of palladium nanoparticles onto a chitosan grafted graphene oxide surface. The Pd-nanocomposite (GO-Chit-Pd) was characterized using Transmission Electron Microscopy (TEM), Fourier transforms infrared spectroscopy (FT-IR), and X-ray diffraction (XRD) measurements. The catalytic activity of the prepared heterogeneous graphene oxide functionalized chitosan-palladium (GO-Chit-Pd) was investigated in term of C-N coupling reaction (Buchwald-Hartwig amination reaction of aryl halides) yielding products of N-arylamines. The easy purification, convenient operation, and environmental friendliness, combined with a high yield, render this method viable for use in both laboratory research and larger industrial scales. Studying the reusability of the catalyst in this work showed that it could be reused for five times without obvious loss in catalytic activity.
- Sarvestani, Mosayeb,Azadi, Roya
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- 2-PHENYLIMIDAZO[4,5-B]PYRIDIN-7-AMINE DERIVATES USEFUL AS INHIBITORS OF MAMMALIAN TYROSINE KINASE ROR1 ACTIVITY
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Compound of formula (I′) or (I′′) or a pharmaceutically acceptable salt thereof. The compound is an inhibitor of mammalian kinase enzyme activity, including ROR1 tyrosine kinase activity and may be used in the treatment of disorders associated with such activity.
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Page/Page column 86; 87
(2018/03/26)
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- NH3?H2O: The Simplest Nitrogen-Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water
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Aqueous ammonia (NH3?H2O) has been shown to serve as the simplest nitrogen-containing ligand to effectively promote copper-catalyzed selective alcohol oxidation under air in water. A series of alcohols with varying electronic and steric properties were selectively oxidized to aldehydes with up to 95 % yield. Notably, by increasing the amount of aqueous ammonia in neat water, the exclusive formation of aryl nitriles was also accomplished with good-to-excellent yields. Additionally, the catalytic system exhibits a high level of functional group tolerance with ?OH, ?NO2, esters, and heteroaryl groups all being amenable to the reaction conditions. This one-pot and green oxidation protocol provides an important synthetic route for the selective preparation of either aldehydes or nitriles from commercially available alcohols.
- Zhang, Guofu,Ma, Danting,Zhao, Yiyong,Zhang, Guihua,Mei, Guangyao,Lyu, Jinghui,Ding, Chengrong,Shan, Shang
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p. 885 - 889
(2018/12/10)
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- Structure-based design, synthesis and crystallization of 2-arylquinazolines as lipid pocket ligands of p38α MAPK
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In protein kinase research, identifying and addressing small molecule binding sites other than the highly conserved ATP-pocket are of intense interest because this line of investigation extends our understanding of kinase function beyond the catalytic phosphotransfer. Such alternative binding sites may be involved in altering the activation state through subtle conformational changes, control cellular enzyme localization, or in mediating and disrupting protein-protein interactions. Small organic molecules that target these less conserved regions might serve as tools for chemical biology research and to probe alternative strategies in targeting protein kinases in disease settings. Here, we present the structure-based design and synthesis of a focused library of 2-arylquinazoline derivatives to target the lipophilic C-terminal binding pocket in p38α MAPK, for which a clear biological function has yet to be identified. The interactions of the ligands with p38α MAPK was analyzed by SPR measurements and validated by protein X-ray crystallography.
- Bührmann, Mike,Wiedemann, Bianca M.,Müller, Matthias P.,Hardick, Julia,Ecke, Maria,Rauh, Daniel
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- Design, Synthesis, and Structure–Activity Relationship Analysis of Thiazolo[3,2-a]pyrimidine Derivatives with Anti-inflammatory Activity in Acute Lung Injury
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Acute lung injury (ALI) has a high lethality rate, and interleukin-6 (IL-6) and tumor necrosis factor-α (TNF-α) contribute most to tissue deterioration in cases of ALI. In this study, we designed and synthesized a new series of thiazolo[3,2-a]pyrimidine derivatives based on a previously identified lead compound, and we evaluated their anti-inflammatory activities. Structure–activity relationship studies led to the discovery of two highly potent inhibitors. The two promising compounds were found to inhibit lipopolysaccharide (LPS)-induced IL-6 and TNF-α release in a dose-dependent manner in mouse primary peritoneal macrophages (MPMs). Furthermore, administration of these compounds resulted in lung histopathological improvements and attenuated LPS-induced ALI in vivo. Taken together, these data indicate that these novel thiazolo[3,2-a]pyrimidine derivatives could be developed as candidate drugs for the treatment of ALI.
- Chen, Lingfeng,Jin, Yiyi,Fu, Weitao,Xiao, Siyang,Feng, Chen,Fang, Bo,Gu, Yugui,Li, Chenglong,Zhao, Yunjie,Liu, Zhiguo,Liang, Guang
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supporting information
p. 1022 - 1032
(2017/07/11)
-
- A kind of the benzene is joint nitrogen heterocyclic chalcone derivatives and its preparation method and application
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The invention discloses a phenyl-nitrogen alkadienone derivative as well as a preparation method and application thereof, and belongs to the field of medicinal chemistry. Nitrogen-containing heterocycle and a chalcone parent nucleus skeleton are spliced to simply, efficiently and environment friendly synthesize a 12 phenyl-nitrogen alkadienone derivative. The phenyl-nitrogen alkadienone derivative has a general structural formula shown as follows: (see the specification), wherein R1 is a halogen element or trimethoxy; R2 is N-methyl piperazine, morpholine, imidazole, nafoxidine and piperidine. X is a halogen element or H. An in-vitro anticancer activity test of the compound proves that the derivative has an effect of inhibiting a human neuroblastoma cell line (SK-N-SH), can be used as a candidate or lead compound to be further developed and is used for preparing a drug for resisting human neuroblastoma.
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Paragraph 0020-0021
(2017/09/26)
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- Novel 6-phenylnicotinohydrazide derivatives: Design, synthesis and biological evaluation as a novel class of antitubercular and antimicrobial agents
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In our ongoing efforts to develop potent antitubercular agents based on the 6-phenylnicotinohydrazide, herein we report the design, synthesis and biological evaluation of three sets of 6-phenylnicotinohydrazide derivatives 8a-g, 12 and 16a, b. The designed compounds were synthesized and in vitro evaluated for their antitubercular activity. In addition, their antifungal and antibacterial activities were evaluated as well. The nicotinohydrazide class displayed different levels of antimicrobial activity and possessed a distinctive pattern of selectivity against the tested microorganisms. However, the 2,6-dichlorobenzylidene counterpart 8b emerged as the most active one in this study, with superior antimycobacterial activity (minimum inhibitory concentration (MIC)=3.90 μg/mL) and potent broad-spectrum antimicrobial activities with MIC range of 0.24-1.95 μg/mL. The structure-activity relationship for such nicotinohydrazides has been established. Further, the cytotoxicity of the most active antitubercular compounds 8b, d and g were tested against the normal breast cells WI-38; none of them displayed significant cytotoxic effect, thereby providing a good therapeutic index.
- Soliman, Dalia Hussein,Eldehna, Wagdy Mohamed,Ghabbour, Hazem Ahmed,Kabil, Maha Mamdouh,Abdel-Aziz, Marwa Mostafa,Abdel-Aziz, Hatem Abdel-Kader
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p. 1883 - 1893
(2017/11/20)
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- Development and in Vitro Evaluation of a Microbicide Gel Formulation for a Novel Non-Nucleoside Reverse Transcriptase Inhibitor Belonging to the N-Dihydroalkyloxybenzyloxopyrimidines (N-DABOs) Family
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Preventing HIV transmission by the use of a vaginal microbicide is a topic of considerable interest in the fight against AIDS. Both a potent anti-HIV agent and an efficient formulation are required to develop a successful microbicide. In this regard, molecules able to inhibit the HIV replication before the integration of the viral DNA into the genetic material of the host cells, such as entry inhibitors or reverse transcriptase inhibitors (RTIs), are ideal candidates for prevention purpose. Among RTIs, S- and N-dihydroalkyloxybenzyloxopyrimidines (S-DABOs and N-DABOs) are interesting compounds active at nanomolar concentration against wild type of RT and with a very interesting activity against RT mutations. Herein, novel N-DABOs were synthesized and tested as anti-HIV agents. Furthermore, their mode of binding was studied by molecular modeling. At the same time, a vaginal microbicide gel formulation was developed and tested for one of the most promising candidates.
- Tintori, Cristina,Brai, Annalaura,Dasso Lang, Maria Chiara,Deodato, Davide,Greco, Antonia Michela,Bizzarri, Bruno Mattia,Cascone, Lorena,Casian, Alexandru,Zamperini, Claudio,Dreassi, Elena,Crespan, Emmanuele,Maga, Giovanni,Vanham, Guido,Ceresola, Elisa,Canducci, Filippo,Ari?n, Kevin K.,Botta, Maurizio
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p. 2747 - 2759
(2016/04/10)
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- Nucleophilicity Parameters of Stabilized Iodonium Ylides for Characterizing Their Synthetic Potential
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Kinetics and mechanisms of the reactions of the β-dicarbonyl-substituted iodonium ylides 1(a-d) with several π-conjugated carbenium and iminium ions have been investigated. All reactions proceed with rate-determining attack of the electrophile at the nucleophilic carbon center of the ylides to give iodonium ions, which rapidly expel iodobenzene and undergo different subsequent reactions. The second-order rate constants k2 for the reactions of the iodonium ylides with benzhydrylium ions correlate linearly with the electrophilicity parameters E of the benzhydrylium ions and thus follow the linear free energy relationship log k(20 °C) = sN(N + E) (eq 1), where electrophiles are characterized by one parameter (E), while nucleophiles are characterized by two parameters: the nucleophilicity N and the susceptibility sN. The nucleophilicity parameters 4 + at the carbanionic center of Meldrum's acid or dimedone, respectively, reduces the nucleophilicity by approximately 10 orders of magnitude. The iodonium ylides 1(a-d) thus have nucleophilicities similar to those of pyrroles, indoles, and silylated enol ethers and, therefore, should be suitable substrates in iminium-activated reactions. Good agreement of the measured rate constant for the cyclopropanation of the imidazolidinone-derived iminium ion 10a with the iodonium ylide 1a with the rate constant calculated by eq 1 suggests a stepwise mechanism in which the initial nucleophilic attack of the iodonium ylide at the iminium ion is rate-determining. The reaction of cinnamaldehyde with iodonium ylide 1a catalyzed by (5S)-5-benzyl-2,2,3-trimethyl-imidazolidin-4-one (11a, MacMillan's first-generation catalyst) gives the corresponding cyclopropane with an enantiomeric ratio of 70/30 and, thus, provides proof of principle that iodonium ylides are suitable substrates for iminium-activated cyclopropanations.
- Chelli, Saloua,Troshin, Konstantin,Mayer, Peter,Lakhdar, Sami,Ofial, Armin R.,Mayr, Herbert
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supporting information
p. 10304 - 10313
(2016/09/03)
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- Dihydropyrazoles containing morpholine: Design, synthesis and bioassay testing as potent antimicrobial agents
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A series of dihydropyrazole derivatives containing morpholine was designed and synthesized as antimicrobial agents. All of the synthesized compounds were characterized by 1H-NMR and MS. Afterwards they were evaluated for in vitro antibacterial activity against four bacteria strains. Along with S. aureus TyrRS inhibition and cytotoxicity examination, some compounds proved to be of low toxicity and potent, especially against Gram-positive bacteria strains. Compound 4s exhibited the potential to be new a antibacterial drug with strong broad-spectrum antimicrobial activity and enzyme inhibitory activity. Docking simulation was performed to position compound 4s into the S. aureus TyrRS structure active site to investigate the probable binding mode. A 3D-QSAR model was also established to explain how structural alterations affect the activity and guide further study.
- Wang, Peng-Fei,Qiu, Han-Yue,Ma, Jun-Ting,Yan, Xiao-Qiang,Gong, Hai-Bin,Wang, Zhong-Chang,Zhu, Hai-Liang
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p. 24997 - 25005
(2015/03/30)
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- Design, synthesis, 3D pharmacophore, QSAR, and docking studies of carboxylic acid derivatives as Histone Deacetylase inhibitors and cytotoxic agents
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In this study, five series of (E)-6-(4-substituted phenyl)-4-oxohex-5-enoic acids IIb-f (E), (E)-3-(4-(substituted)-phenyl)acrylic acids IIIa-g (E), 4-(4-(substituted)phenylamino)-4-oxobutanoic acids VIa,b,e, 5-(4-(substituted)phenylamino)-5-oxopentanoic acids VIIa,f and 2-[(4-(substituted)phenyl) carbamoyl]benzoic acids VIIIa,e were designed and synthesized. Selected compounds were screened in vitro for their cytotoxic effect on 60 human NCI tumor cell lines. Compound IIf (E) displayed significant inhibitory activity against NCI Non-Small Cell Lung A549/ATCC Cancer cell line (68% inhibition) and NCI-H460 Cancer cell line (66% inhibition). Moreover, the final compounds were evaluated in vitro for their cytotoxic activity on HepG2 Cancer cell line in which histone deacetylase (HDAC) is overexpressed. Compounds IIc (E), IIf (E), IIIb (E), and IIIg (E) exhibited the highest cytotoxic activity against HepG2 human cancer cell lines with IC50ranging from 2.27 to 10.71 μM. In addition, selected compounds were tested on histone deacetylase isoforms (HDAC1-11). Molecular docking simulation was also carried out for HDLP enzyme to investigate their HDAC binding affinity. In addition, generation of 3D-pharmacophore model and quantitative structure activity relationship (QSAR) models were combined to explore the structural requirements controlling the observed cytotoxic properties.
- Abdel-Atty, Mona M.,Farag, Nahla A.,Kassab, Shaymaa E.,Serya, Rabah A.T.,Abouzid, Khaled A.M.
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- Synthesis of 2-aryl-1,1-bis(silyl)alkenes containing alkyl(aryl)amine groups
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4-Alkyl-(aryl)aminobenzaldehydes have been generated via the nucleophilic aromatic substitution reaction of 4-fluorobenzaldehyde with appropriated amines and N-heterocycles using hexadecyltrimethylammonium bromide as catalyst and converted to 1,1-bis(silyl)-1-alkene derivatives via the Peterson olefination reaction. The reaction of (HMe2Si)3CLi with these aromatic aldehydes led to new 2-aryl-1,1-bis(silyl)alkenes.
- Safa, Kazem Dindar,Nadimi, Sanaz,Alyari, Maryam
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p. 498 - 501
(2014/11/08)
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- Formation of dispersed palladium-nickel bimetallic nanoparticles in microemulsions: Synthesis, characterization, and their use as efficient heterogeneous recyclable catalysts for the amination reactions of aryl chlorides under mild conditions
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A simple method for preparing spherical palladium-nickel bimetallic nanoparticles with a molar ratio of 1.0 (Pd0.5-Ni0.5 B-NPs) has been adopted using a water-in-oil microemulsion system of water/aerosol-OT/ isooctane at room temperature. The morphology, size, structure, and elemental composition of these particles as the superior catalyst were characterized by field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), energy dispersive analysis using X-rays (EDAX), and X-ray fluorescence (XRF) analyses. The effects of the reaction parameters on the Buchwald-Hartwig amination reaction yield in the presence of these NPs as catalyst have been screened and the results are evaluated by using chlorobenzene and morpholine as a model reaction. Initially, differences in the catalytic properties of some synthesized NPs have been compared. In this context, Pd-Ni B-NPs with the molar ratio of 1 : 1 (Pd/Ni = 1) showed the highest catalytic activity for this reaction. The Pd0.5-Ni0.5 B-NPs are stable and the leaching of catalyst in solution is very low. Therefore, they has been employed as efficient catalysts in the C-N coupling reaction. Finally, a mechanism for an amination reaction on the Pd/Ni catalyst surface was proposed.
- Heshmatpour, Felora,Abazari, Reza
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p. 55815 - 55826
(2015/02/05)
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- 2,6-Bis(diphenylphosphino)pyridine: A simple ligand showing high performance in palladium-catalyzed CN coupling reactions
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The use of commercially available 2,6-bis(diphenylphosphino)pyridine as a ligand in conjunction with K2CO3, DMAc and TBAB is an effective method for the palladium-catalyzed CN coupling of a variety of aryl halides with anilines, N-heterocyclic aromatic amines, and a cyclic secondary amine. The reactions proceed in good to excellent yield (up to 98%) while the loading of Pd(OAc)2 was as low as 0.025 mol %.
- Nadri, Shirin,Rafiee, Ezzat,Jamali, Sirous,Joshaghani, Mohammad
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p. 4098 - 4101
(2014/07/22)
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- Synthesis, structure and chemical transformations of 4-aminobenzaldehyde
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A possibility of nucleophilic substitution of the fluorine atom in 4-fluorobenzaldehyde with amines (morpholine, piperidine or cytisine) under convection heating and microwave irradiation was shown. Reactions of 4-morpholinyl- and 4-piperidinylbenzaldehyd
- Nurkenov,Fazylov,Arinova,Turdybekov,Turdybekov,Talipov,Ibragimov
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p. 1864 - 1868
(2014/01/06)
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- Design, synthesis, and evaluation of inhibitors of pyruvate phosphate dikinase
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Pyruvate phosphate dikinase (PPDK) catalyzes the phosphorylation reaction of pyruvate that forms phosphoenolpyruvate (PEP) via two partial reactions: PPDK + ATP + Pi → PPDK-P + AMP + PPi and PPDK-P + pyruvate → PEP + PPDK. Based on i
- Wu, Chun,Dunaway-Mariano, Debra,Mariano, Patrick S.
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p. 1910 - 1922
(2013/04/10)
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- TREATMENT OF DISEASES BY EPIGENETIC REGULATION
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The present disclosure provides non-naturally occurring polyphenol compounds that inhibit the bromodomain and extra terminal domain (BET) proteins. The disclosed compositions and methods can be used for treatment and prevention of cancer, including NUT midline carcinoma, Burkitt's Lymphoma, Acute Myelogenous Leukemia, and Multiple Myeloma; autoimmune or inflammatory diseases or conditions, and sepsis.
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- Design of substituted imidazolidinylpiperidinylbenzoic acids as chemokine receptor 5 antagonists: Potent inhibitors of R5 HIV-1 replication
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The redesign of the previously reported thiophene-3-yl-methyl urea series, as a result of potential cardiotoxicity, was successfully accomplished, resulting in the identification of a novel potent series of CCR5 antagonists containing the imidazolidinylpiperidinyl scaffold. The main redesign criteria were to reduce the number of rotatable bonds and to maintain an acceptable lipophilicity to mitigate hERG inhibition. The structure-activity relationship (SAR) that was developed was used to identify compounds with the best pharmacological profile to inhibit HIV-1. As a result, five advanced compounds, 6d, 6e, 6i, 6h, and 6k, were further evaluated for receptor selectivity, antiviral activity against CCR5 using (R5) HIV-1 clinical isolates, and in vitro and in vivo safety. On the basis of these results, 6d and 6h were selected for further development.
- Skerlj, Renato,Bridger, Gary,Zhou, Yuanxi,Bourque, Elyse,McEachern, Ernest,Metz, Markus,Harwig, Curtis,Li, Tong-Shuang,Yang, Wen,Bogucki, David,Zhu, Yongbao,Langille, Jonathan,Veale, Duane,Ba, Tuya,Bey, Michael,Baird, Ian,Kaller, Alan,Krumpak, Maria,Leitch, David,Satori, Michael,Vocadlo, Krystyna,Guay, Danielle,Nan, Susan,Yee, Helen,Crawford, Jason,Chen, Gang,Wilson, Trevor,Carpenter, Bryon,Gauthier, David,MacFarland, Ron,Mosi, Renee,Bodart, Veronique,Wong, Rebecca,Fricker, Simon,Schols, Dominique
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supporting information
p. 8049 - 8065
(2013/11/06)
-
- Synthesis, analgesic and anti-inflammatory activities of some novel pyrazolines derivatives
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In search for a new analgesic and anti-inflammatory agent with improved potency, we designed and synthesized a series of 3,2-(4,5-dihydro-5-(4- morphilinophenyl)-1H-pyarazol-3-yl)phenols 6(a-g) and its N-phenylpyrazol-1- carbothioamide 7(a-g) by Claisan-Schmidt condensation followed by the reaction of hydrazine hydrate. All the synthesized compounds were assayed for their in vivo analgesic and anti-inflammatory activities. All the compounds synthesized showed the potential to demonstrate analgesic and anti-inflammatory activity, of particular interest compounds 6a, 6b, 6g, 7a, 7d and 7g were found comparable to Diclofenac.
- Joshi, Ratnadeep S.,Mandhane, Priyanka G.,Diwakar, Santosh D.,Dabhade, Sanjay K.,Gill, Charansingh H.
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experimental part
p. 3721 - 3725
(2010/09/05)
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- Buchwald-Hartwig C-N cross coupling reactions catalyzed by a pseudo-pincer Pd(II) compound
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The reaction of the imino compound [C6H4-1-(OH)-3-(CH{double bond, long}NC6H2-2,4,6-Me3)] (1) with [Pd(COD)Cl2] affords in good yields the cyclometalated product {A figure is presented} (2), both species being unequivocally identified by single crystal X-ray structure analysis. Careful analysis of both structures in the solid state reveals the presence of important hydrogen bond interactions, leading in the case of the Pd(II) derivative to the formation of a pseudo-pincer/non-covalent pincer compound {A figure is presented} (2). The catalytic activity of this species was examined in Buchwald-Hartwig C-N cross coupling of morpholine with a series of p-substituted bromo-benzenes.
- Avila-Sorrosa, Alcives,Estudiante-Negrete, Fabiola,Hernández-Ortega, Simón,Toscano, Rubén A.,Morales-Morales, David
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experimental part
p. 1262 - 1268
(2010/07/05)
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- Preparation of a cobalt-containing P,N-bidentate ligand ligated palladium complex: Its applications in amination and Suzuki cross-coupling reactions
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A cobalt-containing P,N-ligand, alkyne-bridged dicobalt phosphine [(μ-PPh2CH2PPh2)Co2(CO)4(μ,η-Me2NCH2C{triple bond, long}CP(Cy)2)] (4c), was prepared from the reaction of Me2NCH2C{triple bond, long}CPR2 (2c) with a dppm-bridged dicobalt complex [Co2(CO)6(μ-P,P-PPh2CH2PPh2)] (3). Further reaction of 4c with Pd(COD)Cl2 gave a 4c-chelated palladium dichloride complex (μ-PPh2CH2PPh2)Co2(CO)4(μ,η-Cy2PC{triple bond, long}CCH2NMe2)PdCl2 (5c). Compound 5c was characterized by spectroscopic methods and crystal structure of 5c was determined by single-crystal X-ray diffraction techniques. It shows that 4c is an authentic cobalt-containing P,N-bidentate ligand. Amination and Suzuki reactions employing either a 4c/palladium salt system or an isolated 5c as the catalytic precursor led to satisfactory results.
- Chiang, Wen-Yuan,Hong, Fung-E
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experimental part
p. 1473 - 1481
(2009/09/05)
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- PHARMACEUTICAL COMPOSITION COMPRISING PYRAZOLONE DERIVATIVE
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The present invention relates to pharmaceutical compositions containing a compound represented by formula (I), or a pharmaceutically acceptable prodrug or salt thereof, or a hydrate or solvate thereof as an active ingredient, (wherein, R1, R2, R3, and R4 are the same as R1, R2, R3, and R4 in the description of the present invention).
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Page/Page column 165
(2010/11/30)
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- Evaluation of aromatic amination catalyzed by palladium on carbon: A practical synthesis of triarylamines
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A heterogeneous palladium on carbon (Pd/C)-catalyzed coupling between amines and aromatic halides including aromatic chlorides has been achieved using sodium tert-butoxide (NaO-t-Bu) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) as a ligand in cyclopentyl methyl ether (CPME). The use of potassium tert-butoxide (KO-t-Bu) in place of NaO-t-Bu brought about the benzyne-mediated aromatic amination even without Pd/C and dppf, giving a mixture of regioisomers when 4-substituted bromobenzenes were employed as the substrate. The combination of Pd/C, dppf, NaO-t-Bu could be utilized for the syntheses of a broad range of triarylamines by replacing CPME with mesitylene which can provide a higher reaction temperature. The Pd/C could be quantitatively recovered and reused until at least the fourth cycle without any loss in catalytic activity. The quite low leaching of palladium (1.1%) was demonstrated by an inductively coupled plasma-atomic emission spectrometric analysis.
- Monguchi, Yasunari,Kitamoto, Katsunori,Ikawa, Takashi,Maegawa, Tomohiro,Sajiki, Hironao
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supporting information; experimental part
p. 2767 - 2777
(2009/12/08)
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- COMPOUNDS FOR THE PREVENTION AND TREATMENT OF CARDIOVASCULAR DISEASES
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The present disclosure relates to compounds, which are useful for regulating the expression of apolipoprotein A-I (ApoA-I), and their use for treatment and prevention of cardiovascular disease and related disease states, including cholesterol- or lipid-related disorders, such as, for example, atherosclerosis.
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Page/Page column 40
(2008/12/07)
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- Arylsulfonamido-substituted hydroxamic acid derivatives
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α-Amino hydroxamic acid derivative of formula (I), in which R is C2–C7-alkyl, which is mono-, di- or trisubstituted by halogen, nitro, lower acyloxy, trifluoromethoxy, cyano, C3–C5-cycloalkyl or unsubstituted or substituted C3–C4-heteroaryl comprising one or two heteroatoms selected from the group consisting of O, S and N; or C3–C7-alkenyl or C3–C7-alkynyl, which in each case is unsubstituted or mono-, di- or trisubstituted by halogen, nitro, lower acyloxy, trifluoromethoxy, cyano, C3–C5-cycloalkyl or unsubstituted or substituted C3–C6-heteroaryl comprising one or two heteroatoms selected from the group consisting of O, S and N; and the other symbols are as defined in claim 1, are described. These compounds are MMP and in particular MMP2 inhibitors and can be used for treatment of MMP dependent diseases, in particular inflammation conditions, rheumatoid arthritis, osteoarthritis, tumors (tumor growth, metastasis, progression or invasi n) and pulmonary disorders (e.g. emphysema, COPD).
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Page/Page column 46
(2008/06/13)
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