- DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX
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To provide a dinuclear metal complex that can be synthesized simply and easily and has a proper anticancer action.SOLUTION: The present disclosure provides a dinucleating ligand represented by the following formula (I) and a dinuclear metal complex thereof (where each X may be the same or different to represent H, Cl, OMe, or, Me, Y is H, a phenyl group, a substituted carbamoyl group or the like).SELECTED DRAWING: None
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Paragraph 0058; 0060-0061
(2021/03/19)
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- The Stronger the Better: Donor Substituents Push Catalytic Activity of Molecular Chromium Olefin Polymerization Catalysts
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The donor strength of bifunctional pyridine-cyclopentadienyl ligands was altered systematically by the introduction of donating groups in the para-position of the pyridine. In the resulting chromium complexes an almost linear correlation between donor str
- Enders, Markus,Hansen, Helge-Boj,Wadepohl, Hubert
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supporting information
p. 11084 - 11093
(2021/06/27)
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- Multiple Sulfonation of Picolyl-Based Complexes Rendering Them Highly Water-Compatible
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Multidentate ligands chosen for the complexation of hard metals frequently exhibit negative charges, which consequently elicits Coulombic compensation of the metal-ion charge. However, ligands favored by soft metal ions are neutral, which prevents the chemist from obtaining electroneutral complexes, let alone ones with a negative total charge. Here, we report on an efficient synthetic method to decorate picolyl-displaying coordination compounds with multiple sulfonate units at their periphery. We further describe rare anionic versions of three standard complexes that have only been characterized as cationic so far. Our sulfonated complexes show extensive water solubility, which confers these species with great potential for broad application in the biomedical arena.
- Salaam, Jeremy,Pilet, Guillaume,Hasserodt, Jens
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supporting information
p. 13812 - 13816
(2020/10/09)
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- Photochemical C-H Silylation and Hydroxymethylation of Pyridines and Related Structures: Synthetic Scope and Mechanisms
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Considering the synthetic relevance of heteroarenes in various areas ranging from organic synthesis to medicinal chemistry, developing practically simple methodologies to access functionalized heteroarenes is of a significant value. Described herein is an efficient approach for C-H silylation and hydroxymethylation of pyridines and related heterocycles by the combination of silanes or methanol with readily available N-methoxypyridinium ions with a low catalyst loading (2 mol %) under blue light irradiation. The synthetic importance of the developed reactions is demonstrated by the synthesis of biologically relevant compounds. Electron paramagnetic resonance spectroscopy, quantum yield measurements, and density-functional theory calculations allowed us to understand reaction mechanisms of both photocatalytic reactions.
- Rammal, Fatima,Gao, Di,Boujnah, Sondes,Hussein, Aqeel A.,Lalevée, Jacques,Gaumont, Annie-Claude,Morlet-Savary, Fabrice,Lakhdar, Sami
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p. 13710 - 13717
(2020/11/30)
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- Homogeneous Hydrogenation with a Cobalt/Tetraphosphine Catalyst: A Superior Hydride Donor for Polar Double Bonds and N-Heteroarenes
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The development of catalysts based on earth abundant metals in place of noble metals is becoming a central topic of catalysis. We herein report a cobalt/tetraphosphine complex-catalyzed homogeneous hydrogenation of polar unsaturated compounds using an air- and moisture-stable and scalable precatalyst. By activation with potassium hydroxide, this cobalt system shows both high efficiency (up to 24 000 TON and 12 000 h-1 TOF) and excellent chemoselectivities with various aldehydes, ketones, imines, and even N-heteroarenes. The preference for 1,2-reduction over 1,4-reduction makes this method an efficient way to prepare allylic alcohols and amines. Meanwhile, efficient hydrogenation of the challenging N-heteroarenes is also furnished with excellent functional group tolerance. Mechanistic studies and control experiments demonstrated that a CoIH complex functions as a strong hydride donor in the catalytic cycle. Each cobalt intermediate on the catalytic cycle was characterized, and a plausible outer-sphere mechanism was proposed. Noteworthy, external inorganic base plays multiple roles in this reaction and functions in almost every step of the catalytic cycle.
- Duan, Ya-Nan,Du, Xiaoyong,Cui, Zhikai,Zeng, Yiqun,Liu, Yufeng,Yang, Tilong,Wen, Jialin,Zhang, Xumu
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supporting information
p. 20424 - 20433
(2019/12/27)
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- Synthesis method of 2-pyridylaldehyde derivative
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The invention relates to the field of medical intermediates, in particular to a synthesis method of 2-pyridylaldehyde derivative. A synthesis path shown in the formula 1 is adopted, wherein X can be Cl or Br or CF3. Cheap starting raw materials are adopted, the use of hazardous materials which have large toxicity and are easily explosive is avoided, the cost of the product is greatly lowered, popularization and industrialized production are facilitated, and the synthesis method has the advantages of being low in cost, easy to operate, high in yield, easy to industrialize and the like. The formula 1 is shown in the description.
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Paragraph 0067-0068; 0072-0073; 0084-0086
(2018/09/28)
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- Chromatin Regulates Genome Targeting with Cisplatin
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Cisplatin derivatives can form various types of DNA lesions (DNA-Pt) and trigger pleiotropic DNA damage responses. Here, we report a strategy to visualize DNA-Pt with high resolution, taking advantage of a novel azide-containing derivative of cisplatin we named APPA, a cellular pre-extraction protocol and the labeling of DNA-Pt by means of click chemistry in cells. Our investigation revealed that pretreating cells with the histone deacetylase (HDAC) inhibitor SAHA led to detectable clusters of DNA-Pt that colocalized with the ubiquitin ligase RAD18 and the replication protein PCNA. Consistent with activation of translesion synthesis (TLS) under these conditions, SAHA and cisplatin cotreatment promoted focal accumulation of the low-fidelity polymerase Polη that also colocalized with PCNA. Remarkably, these cotreatments synergistically triggered mono-ubiquitination of PCNA and apoptosis in a RAD18-dependent manner. Our data provide evidence for a role of chromatin in regulating genome targeting with cisplatin derivatives and associated cellular responses.
- Zacharioudakis, Emmanouil,Agarwal, Poonam,Bartoli, Alexandra,Abell, Nathan,Kunalingam, Lavaniya,Bergoglio, Valérie,Xhemalce, Blerta,Miller, Kyle M.,Rodriguez, Rapha?l
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supporting information
p. 6483 - 6487
(2017/05/29)
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- VISUAL DETECTION OF PLATINATED DNA LESIONS FROM A CLICKABLE CISPLATIN PROBE USED AS DIAGNOSTIC TOOL OR TO IDENTIFY SYNERGISTIC TREATMENTS
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The present invention relates to a new compound for visualizing DNA-platinum crosslink, and its use as a research tool and in screening method for identifying candidate drug to be used in combination with platinating compounds such as cisplatin, carboplatin, and oxaliplatin. Formulae (I), (II) or (III). The project leading to this application has received funding from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program (grant agreement No [647973]).
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Page/Page column 23
(2017/07/06)
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- NOVEL MORPHOLINE DERIVATIVE OR SALT THEREOF
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There is provided a morpholine derivative represented by General Formula [1A] or a salt thereof. (In the formula, a ring A represents a ring represented by General Formula [I]; * represents a bonding position; Z2 represents CH or the like; Z1 represents CR6 or the like; R6 represents a hydrogen atom or the like; X1 represents CHR7 or the like; R7 represents a hydrogen atom or the like; X2 represents CH2 or the like; R1 and R2 are the same as or different from each other, and each of R1 and R2 represents a hydrogen atom or the like; R3, R4, and R5 are the same as or different from each other, and each of R3, R4, and R5 represents a hydrogen atom, NRaRb, or the like; and each of Ra and Rb represents a hydrogen atom, a C1-8 alkyl group which may have a substituent, or the like.)
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Paragraph 0983-0985
(2016/07/05)
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- Design of coordination interaction of Zn(II) complex with oligo-aspartate peptide to afford a high-affinity tag-probe pair
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A complementary recognition pair consisting of a genetically encodable peptide tag and a small molecular probe isa powerful tool to specifically label and manipulate a protein ofinterest under biological conditions. In this study, we report the redesign of a tag-probe pair comprising an oligo-aspartate peptide tag (such as DDDD) and a binuclear zinc complex. Isothermal-titration calorimetry screening of binding between the series of peptides and zinc complexes revealed that the binding affinity was largely influenced by subtle changes of the ligand structure of the probe. However, the binding was tolerant to differences of the tag peptide sequence. Of those tested, a pair containing a peptide tag (DDAADD) and a binuclear zinc complex possessing 4-chloropyridines (3-2Zn(II)) showed the strongest binding affinity (Ka = 3.88 × 105 M-1), which was about 10-fold larger than the conventional pair of D4-peptide tag (DDDD) and 1-2Zn(II) containing nonsubstituted pyridines (Ka = 3.73 × 104 M-1). The strong binding of this new complementary recognition pair enabled the rapid covalent labeling of a tag-fused maltose binding protein with a fluorescent zinc complex, demonstrating its potential utility in protein analysis.
- Fuchida, Hirokazu,Tabata, Shigekazu,Shindo, Naoya,Takashima, Ippei,Leng, Qiao,Hatsuyama, Yuji,Hamachi, Itaru,Ojida, Akio
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supporting information
p. 784 - 791
(2015/06/25)
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- Electrophilicity and nucleophilicity of commonly used aldehydes
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The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.
- Pratihar, Sanjay
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p. 5781 - 5788
(2014/07/22)
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- Tuning of the properties of transition-metal bispidine complexes by variation of the basicity of the aromatic donor groups
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Bispidines (3,7-diazabicyclo[3.3.1]nonanes) as very rigid and highly preorganized ligands find broad application in the field of coordination chemistry, and the redox potentials of their transition-metal complexes are of importance in oxidation reactions by high-valent iron complexes, aziridination catalyzed by copper complexes, and imaging by 64Cu positron emission tomography tracers. Here, we show that the redox potentials and stability constants of the copper(II) complexes of 15 tetradentate bispidines can be varied by substitution of the pyridine rings (variation of the redox potential over ca. 450 mV and of the complex stability over approximately 10 log units). It is also shown that these variations are predictable by the pKa values of the pyridine groups as well as by the Hammett parameters of the substituents, and the density functional theory based energy decomposition analysis also allows one to accurately predict the redox potentials and concomitant complex stability. It is shown that the main contribution emerges from the electrostatic interaction energy, and the partial charges of the pyridine donor groups therefore also correlate with the redox potentials.
- Comba, Peter,Morgen, Michael,Wadepohl, Hubert
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p. 6481 - 6501
(2013/07/19)
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- Sequence selective dual-emission detection of (i, i + 1) bis-phosphorylated peptide using diazastilbene-type Zn(ii)-Dpa chemosensor
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This paper describes a new fluorescent chemosensor for phosphorylated peptide, which comprises a rigid trans-4,4′-diazastilbene and two Zn(ii)-Dpa (2,2′-dipicolylamine) units; this chemosensor sequence-selectively binds to a (i, i + 1) bis-phosphorylated peptide and displays a dual-emission fluorescence change.
- Ishida, Yoshiyuki,Inoue, Masa-Aki,Inoue, Tomonori,Ojida, Akio,Hamachi, Itaru
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supporting information; experimental part
p. 2848 - 2850
(2009/12/01)
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- PYRIDINE DERIVATIVES SUBSTITUTED BY HETEROCYCLIC RING AND PHOSPHONOAMINO GROUP, AND ANTI-FUNGAL AGENT CONTAINING SAME
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Anti-fungal agent having excellent anti-fungal action physicochemical properties including safety and water solubility. Compound represented by formula (I), or salt thereof: wherein R1 represents hydrogen, halogen, amino, R11-NH- wherein R11 represents C1-6 alkyl, hydroxy C1-6 alkyl, C1-6 alkoxy C1-6 alkyl, or C1-6alkoxycarbonyl C1-6 alkyl, R12-(CO)-NH- wherein R12 represents C1-6 alkyl group or C1-6 alkoxy C1-6 alkyl, C1-6 alkyl, hydroxy C1-6 alkyl, cyano C1-6 alkyl, C1-6 alkoxy, or C1-6 alkoxy C1-6 alkyl or a phosphonoamino group; R2 represents hydrogen, C1-6 alkyl, amino, or a di C1-6 alkylamino group or a phosphonoamino group; one of X and Y is nitrogen while the other is nitrogen or oxygen; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, oxygen, sulfur, -CH2O-, -OCH2-, -NH-, -CH2NH-, -NHCH2-, -CH2S-, or -SCH2-; R3 represents hydrogen or halogen or C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, a 5- or 6-member heteroaryl group or a 5- or 6-member nonaromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents hydrogen or halogen; provided that either R1 or R2 represents a phosphonoamino group.
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Page/Page column 99
(2009/04/24)
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- Use of Metal Complex Compounds as Oxidation Catalysts
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The present invention relates to the use, as oxidation catalysts, of metal complex compounds having tetradentate ligands of formula (2) wherein all substitutents have the meanings as defined in Claim 1. The present invention relates also to formulations comprising such metal complex compounds, to novel metal complex compounds and to novel ligands.
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- Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
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An object of the present invention is to provide an antifungal agent which has excellent antifungal effects and is superior in terms of its physical properties, safety and metabolic stability. According to the present invention, there is disclosed a compound represented by the following formula (I), or a salt thereof: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group or a C1-6 alkoxy C1-6 alkyl group; R2 represents a hydrogen atom, a C1-6 alkyl group, an amino group or a di C1-6 alkylamino group; one of X and Y is a nitrogen atom while the other is a nitrogen atom or an oxygen atom; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom, or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, an oxygen atom, a sulfur atom, —CH2O—, —OCH2—, —NH—, —CH2NH—, —NHCH2—, —CH2S—, or —SCH2—; R3 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, a 5- or 6-member heteroaryl group, or 5- or 6-member non-aromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents a hydrogen atom or a halogen atom.
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Page/Page column 98
(2010/11/27)
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- Biological evaluation of isothiazoloquinolones containing aromatic heterocycles at the 7-position: In vitro activity of a series of potent antibacterial agents that are effective against methicillin-resistant Staphylococcus aureus
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We synthesized a diverse series of 9H-isothiazolo[5,4-b]quinoline-3,4- diones containing heteroaromatic groups at the 7-position via palladium-catalyzed cross-coupling. Many of these compounds demonstrated potent antistaphylococcal activity (MICs ≤2 μg/mL) against a multi-drug-resistant strain (ATCC 700699) and low cytotoxic activity (CC50 > 100 μM) against the human cell line Hep2 (laryngeal carcinoma).
- Wiles, Jason A.,Song, Yongsheng,Wang, Qiuping,Lucien, Edlaine,Hashimoto, Akihiro,Cheng, Jijun,Marlor, Christopher W.,Ou, Yangsi,Podos, Steven D.,Thanassi, Jane A.,Thoma, Christy L.,Deshpande, Milind,Pucci, Michael J.,Bradbury, Barton J.
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p. 1277 - 1281
(2007/10/03)
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- Simple reduction of heteroaromatic esters to alcohols using a sodium borohydride-methanol system
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Some heteroaromatic esters were reduced to the corresponding alcohols by using a sodium borohydride-methanol system. The reduction was completed within 0.15-2.0 h in refluxing THF. The alcohol products were isolated after aqueous workup in moderate to excellent yield (48-97%). Copyright Taylor & Francis, Inc.
- Boechat, Nubia,Da Costa, Jorge Carlos Santos,De Souza Mendonca, Jorge,Paes, Karla Ceodaro,Fernandes, Elisa Lopes,De Oliveira, Pedro Santos Mello,Vasconcelos, Thatyana Rocha Alves,De Souza, Marcus Vinicius Nora
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p. 3187 - 3190
(2007/10/03)
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- COMPOUNDS USEFUL AS A3 ADENOSINE RECEPTOR AGONISTS
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Compounds useful as A3 Adenosine Receptor Agonists. Adenosine analogue-type A3 receptor agonists having an N6 substituent of the formula CR20R21CYCLE where CYCLE is a specified heterocycle, e.g. a substituted pyridyl group or a substituted oxazolyl-containing bicyclic ring. 10
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Page/Page column 46
(2010/02/10)
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- Cytokine inhibitors
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Disclosed are compounds of formula (I) Where Ar1, X, Y, Q, W, R3, R4, R5, R6 and Ry are defined herein. The compounds of the invention inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. The compounds are also useful for treating diseases or conditions related to oncology and anticoagulant or fibrinolytic therapy. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.
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Page/Page column 61; 62; 64
(2010/02/08)
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- BENZAZEPINE DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE
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The present invention provides a novel benzazepine derivative represented by formula : wherein, R1 is a 5- or 6-membered aromatic ring, R2 is lower alkyl group, etc., Y is an optionally substituted imino group, ring A and ring B are independently an optionally substituted aromatic ring, W is formula -W1-X2-W2- (W1 and W2 are independently S(O)m1 (m1 is 0, 1 or 2), etc., and X2 is an optionally substituted alkylene groupetc. ), a preparation method and use thereof.
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- Synthesis of 4-[4'-(N,N-dimethylsulfamoyl)piperazin-1-YL]-pyridine derivatives as sorbitol dehydrogenase potential inhibitors
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A synthesis of various pyridines disubstituted in position 4 by a [4'- (N,N-dimethylsulfamoyl)piperazin-1-yl] group and in position 2 by different functionalities such as hydrogen, hydroxymethyl, formyl, carboxamido or cyano, is described.
- Varlet, Didier,Fourmaintraux, Eric,Depreux, Patrick,Lesieur, Daniel
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p. 797 - 804
(2007/10/03)
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- Superoxide dismutase activity of iron(II)TPEN complex and its derivatives
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Superoxide is involved in the pathogenesis of various diseases, such as inflammation, ischemia-reperfusion injury and carcinogenesis. Superoxide dismutases (SODs) catalyze the disproportionation reaction of superoxide to produce oxygen and hydrogen peroxide, and can protect living cells against the toxicity of free radicals derived from oxygen. Thus, SODs and their functional mimics have potential value as pharmaceuticals. We have previously reported that Fe(II)tetrakis-N,N,N',N'-(2-pyridylmethyl)ethylenediamine (Fe(II)TPEN) has an excellent SOD activity (IC50=0.5 μM) among many iron complexes examined (J. Biol. Chem., 264, 9243-9249 (1989)). Fe(II)TPEN can act like native SOD in living cells, and protect Escherichia coli cells from free radical toxicity caused by paraquat. In order to develop more effective SOD functional mimics, we synthesized Fe(II)TPEN derivatives with electron-donating or electron-withdrawing groups at the 4-position of all pyridines of TPEN, and measured the SOD activities and the redox potentials of these complexes. Fe(II) tetrakis-N,N,N',N'-(4-methoxy-2-pyridylmethyl)ethylenediamine (Fe(II)(4MeO)4TPEN) had the highest SOD activity (IC50=0.1 μM) among these iron-based SOD mimics. In addition, a good correlation was found between the redox potential and the SOD activity of 15 Fe(II) complexes, including iron-based SOD mimics reported in the previous paper (J. Organometal. Chem., in press). Iron-based SOD mimics may be clinically applicable, because these complexes are generally tissue-permeable and show low toxicity. Therefore our findings should be significant for the development of clinically useful SOD mimics.
- Tamura,Urano,Kikuchi,Higuchi,Hirobe,Nagano
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p. 1514 - 1518
(2007/10/03)
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- INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE
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The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras
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- Structure-activity relationship of 2-[[(2-Pyridyl)methyl]thio]-1H- benzimidazoles as anti Helicobacter pylori agents in vitro and evaluation of their in vivo efficacy
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A relationship between the structure of 21 2-[[(2-pyridyl)methyl]thio]- 1H-benzimidazoles (6) and their anti Helicobacter pylori activity expressed as minimum bactericidal concentration (MBC) values is described. Observed MBCs ranged from 256 to 1 μg/mL. The structure - activity relationship (SAR) showed that larger and more lipophilic compounds, especially compounds with such substituents in the 4-position of the pyridyl moiety, generally had lower MBC values. Four new compounds 'that were predicted to be potent by the established SAR model were synthesized and tested. One such compound, i.e., 2-[[(4-[(cyclopropylmethyl)oxy]3-methyl-2-pyridyl)methyl]thio]-1H- benzimidazole (18), was tested for in vivo efficacy in a mouse Helicobacter felis model (125 μmol/kg bid given orally for 4 days, n = 4). Unfortunately, antibacterial activity could not be clearly demonstrated in this model. Instead a potent acid secretion inhibition was observed. This finding was attributed to the methylthio compound being oxidized to the corresponding methyl sulfinyl derivative, i.e., a proton pump inhibitor, in vivo. Although the antibacterial activity had the potential of decreasing H. felis cell counts in vivo the proton pump inhibitory effect became dominant and actually promoted H. felis cell growth. Hence, we conclude that the antibacterial utility of the 2-[[(2-pyridyl)methyl]thio]1H-benzimidazoles (6) as a compound class is compromised by their propensity to become proton pump inhibitors upon metabolic oxidation in vivo.
- Kühler, Thomas C.,Swanson, Marianne,Shcherbuchin, Vladimir,Larsson, H?kan,Mellg?rd, Bj?rn,Sj?str?m, Jan-Eric
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p. 1777 - 1788
(2007/10/03)
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- AN IMPROVED METHOD FOR THE MONO-HYDROXYMETHYLATION OF PYRIDINES. A MODIFICATION OF THE MINISCI PROCEDURE
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The reaction of N-methoxy-derivatives of pyridines in methanol with ammonium persulphate gives improved yields of mono-hydroxymethylated products.In contrast to the original Minisci procedure the reaction requires only catalytic amounts of ammonium persulphate.Evidence is presented which establishes that the reaction does not proceed via an intramolecular pathway.
- Katz, R B,Mistry, J,Mitchell, M B
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p. 317 - 326
(2007/10/02)
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- 2-pyridine Derivatives: New Antiinflammatory Agents
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2-pyridine derivatives (1a-e) inhibited the dermal reverse passive Arthus reaction (RPAR) in the rat.In the same model, indomethacin was inactive, and hydrocortisone was active.Compounds 1a-d also significantly reduced exudate volume and white blood cell accumulation in the pleural RPAR.This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin.
- Haviv, Fortuna,DeNet, Robert W.,Michaels, Raymond J.,Ratajczyk, James D.,Carter, George W.,Young, Patrick R.
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p. 218 - 222
(2007/10/02)
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