- Tridentate hydrazone metal complexes derived from cephalexin and 2-hydrazinopyridine: Synthesis, characterization and antibacterial activity
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Metal(II) coordination compounds of a tridentate hydrazone ligand (HL) derived from the condensation of cephalexin antibiotic with 2-hydrazinopyridine were synthesized. The hydrazone ligand and mononuclear [ML(OAc)(H2O)] (M(II) = Mn, Co, Ni, Cu, Zn, Ag) complexes were characterized by several techniques, including elemental and thermal analysis, molar conductance and magnetic susceptibility measurements, electronic, FT-IR, EPR and 1H NMR spectral studies. The cephalexin 2-pyridinylhydrazone ligand HL behaves as a monoanionic tridentate NNO chelating agent. The biological applications of complexes have been studied on three bacteria strains (Escherichia coli, Acinetobacter baumannii and Enterococcus faecalis) by agar diffusion disc method.
- Anacona,Rincones, Maria
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Read Online
- A facile synthesis of amide derivatives of [1,2,4]triazolo[4,3-a]pyridine
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A facile synthesis for preparation of amide derivatives of [1,2,4]triazolo[4,3-a]pyridine can be achieved by the nucleophilic displacement of chloromethyl derivative with methyl amine followed by the reaction with acid analogues in the presence of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU). Reaction of 2-chloropyridine with hydrazine hydrate (99 %) gave 2-hydrazinopyridine (2). Compound 3 was obtained in good yields by treating 2-hydrazinopyridine with chloroacetyl chloride. Further 3-chloromethyl-[1,2,4]triazolo[4,3-a]pyridine (4) is obtained by treatment of compound 3 with POCl3. Nucleophilic displacement of compound 4 with methyl amine gave methyl-[1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl-amine (5). Finally protecting and deprotecting of compound 5 with Boc anhydride and HCl in dioxane gives hydrochloride salt of compound 5 i.e. (6) The reaction of hydrochloride salt of methyl-[1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl-amine with 10 different acids yields amide analogues.
- Gandikota, N. Murthy,Bolla, R. Sekhar,Viswanath, I. V. Kasi,Bethi, Sridharreddy
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Read Online
- Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[22.2]octenes Fused with Two N -Aminosuccinimide Moieties
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Efficient and reliable synthesis of substituted hydrazinylpyridines in thick-wall ACE tubes via nucleophilic substitution of a chlorine substituent in different chloropyridines is presented. Hydrazine hydrate and alkylhydrazines were used as nucleophiles and simple alcohols and diethyl ether were the only organic solvents necessary, making the process environmentally and user friendly, potentially reaching 100% atomic efficiency. In the next step, transformations of succinic anhydride moieties fused to the bicyclo[2.2.2]octene framework into succinimide moieties via nucleophilic substitution of oxygens were conducted. As nucleophiles two of the synthesized hydrazinylpyridines (2-hydrazinyl-3-nitropyridine and 2-hydrazinyl-5-nitropyridine) and also hydrazine hydrate, phenylhydrazine, and 4-nitrophenylhydrazine were used. Reactions were again carried out in ACE tubes and only simple alcohols, diethyl ether, and acetone were needed as solvents. One of the prepared bicyclo[2.2.2]octene adducts displayed water solubility thus being a promising candidate for future studies as a novel bidentate ligand for various metal cations in aqueous solutions or acting as an unprecedented halogen bond acceptor.
- Ekar, Jernej,Kranjc, Kri?tof
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p. 1112 - 1120
(2020/10/29)
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- Synthesis and study of organoselenium compound: DNA/Protein interactions, in vitro antibacterial, antioxidant, anti-inflammatory activities and anticancer activity against carcinoma cells
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New organoselenium compound was synthesized and characterized using common spectroscopic techniques. The organoselenium compound binds to Hs-DNA through hydrophobic and hydrogen binding interactions and partial intercalation in the base pairs of DNA was observed, this was also confirmed from circular dichroism (CD). The organoselenium compound was screened for potential anti-oxidant, anti-bacterial and anti-inflammatory activities using various techniques, which demonstrated better results in comparison to standards. The agarose gel electrophoresis study suggested the protective nature of organoselenium compound against supercoiled pBR322 plasmid DNA in presence of Fenton's reagent. In addition, in vitro cytotoxicity experiments against A549 and HeLa cancer cells were performed which evidenced promising anti-cancer activities with significantly low IC50 values.
- Dhavan, Pratik P.,Jadhav, Bhaskar L.,Manjare, Sudesh T.,Shelar, Divyesh S.,Singh, Pinky R.,Vaidya, Shashikant P.
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- PROCESS FOR THE SYNTHESIS OF (3-CHLORO-2-PYRIDYL)HYDRAZINE
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Described herein are novel methods of synthesizing (3-chloro-2-pyridyl)hydrazine. Compounds prepared by the methods disclosed herein are useful for preparation of certain anthranilamide compounds that are of interest as insecticides, such as, for example, the insecticides chlorantraniliprole and cyantraniliprole.
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Paragraph 0061-0063
(2021/05/29)
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- Method for industrially producing bromo-pyrazolidinic acid through micro-channel
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The invention relates to a method for industrially producing bromo-pyrazolidinic acid through a micro-channel. The method comprises the following steps: taking a 2-halogenated heterocyclic compound asa raw material; carrying out hydrazinolysis, cyclization, bromination and hydrolysis reactions in a micro-channel reactor; and carrying out acidification and filtration to obtain bromo-pyrazolidinicacid with high yield and high purity. The reaction time is greatly shortened, the safety is high, the pollution is small, pollutant emission is little, the cost is low, the post-treatment is simple, the yield of an intermediate product in each step is 80% or above, the purity of the intermediate product in each step is 90% or above, the purity of a final product is 95% or above, and the method isparticularly suitable for industrial large-scale production.
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Paragraph 0085-0087; 0094-0096; 0116-0117
(2020/08/02)
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- ASK1 inhibitor and applications thereof
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The invention relates to the technical field of medicines, specifically to a compound represented by a formula (I), a pharmaceutically acceptable salt, ester or stereoisomer thereof, a pharmaceuticalcomposition and a preparation containing the compound, the pharmaceutically acceptable salt, the ester or the isomer thereof, a method for preparing the compound, the pharmaceutically acceptable salt,the ester or the isomer thereof, and applications of the compound, the pharmaceutically acceptable salt, the ester or the isomer thereof in preparation of drugs for treating and/or preventing ASK1-mediated diseases and related diseases.
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Paragraph 0155; 0157-0159
(2020/06/17)
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- Preparation method of pyridine triazolone
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The invention discloses a preparation method of pyridine triazolone. The method comprises the following steps: 1) adding 2-chloropyridine and hydrazine hydrate into a first reaction flask, stirring, heating to 90-110 DEG C, and keeping the temperature to react for 6-8 hours to obtain a first mixed solution; 2) adding the first mixed solution into a second reaction bottle, extracting, recovering hydrazine hydrate under reduced pressure, cooling and adjusting alkali, and performing secondary extraction to obtain 2-pyridine hydrazine; 3) adding the 2-pyridylhydrazine and urea into the reaction kettle, heating to 150-160 DEG C, carrying out heat preservation reaction for 3-4 hours, cooling, adding water for dissolving, cooling, carrying out stirring reacting for 1 hour, and performing suctionfiltration, washing and drying on the reaction system to obtain a crude product; and 4) adding the crude product and DMSO into a third reaction flask, heating, stirring, filtering, cooling, carrying out heat preservation reaction for 1-2 hours, filtering, and drying to obtain pyridinetriazolone. The preparation method of pyridinetriazolone provided by the invention has the advantages that the total yield can reach 70% or above, and the purity of the obtained product can reach 99.2% or above.
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Paragraph 0014; 0019-0021
(2020/12/30)
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- Microwave-assisted synthesis of trazodone and its derivatives as new 5-HT1A ligands: Binding and docking studies
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Trazodone, a well-known antidepressant drug widely used throughout the world, works as a 5-hydroxytryptamine (5-HT2) and α1-adrenergic receptor antagonist and a serotonin reuptake inhibitor. Our research aimed to develop a new method for the synthesis of trazodone and its derivatives. In the known methods of the synthesis of trazodone and its derivatives, organic and toxic solvents are used, and the synthesis time varies from several to several dozen hours. Our research shows that trazodone and its derivatives can be successfully obtained in the presence of potassium carbonate as a reaction medium in the microwave field in a few minutes. As a result of the research work, 17 derivatives of trazodone were obtained, including compounds that exhibit the characteristics of 5-HT1A receptor ligands. Molecular modeling studies were performed to understand the differences in the activity toward 5-HT1A and 5-HT2A receptors between ligand 10a (2-(6-(4-(3-chlorophenyl)piperazin-1-yl)hexyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one) (5-HT1A Ki = 16 nM) and trazodone. The docking results indicate the lack of the binding of ligand 10a to 5-HT2AR, which is consistent with the in vitro studies. On the other hand, the docking results for the 5-HT1A receptor indicate two possible binding modes. Crystallographic studies support the hypothesis of an extended conformation.
- Jaskowska, Jolanta,Zar eba, Przemys?aw,Sliwa, Pawe?,Pindelska, Edyta,Sata?a, Grzegorz,Majka, Zbigniew
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- A family of readily synthesised phosphorescent platinum(ii) complexes based on tridentate: N^N^O -coordinating Schiff-base ligands
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The synthesis and photophysical properties of 22 platinum(ii) complexes featuring N^N^O-coordinating ligands are described. The complexes have the form Pt(N^N^O-Ln)Cl (n = 1 to 20). The tridentate ligands comprise lateral pyridine and phenolate rings, offering the metal N and O coordination respectively, linked via an imine or hydrazone unit that provides a further, central N atom for coordination. The proligands HLn, some of which have previously been reported for the coordination of 1st row transition metal ions in other contexts, are Schiff bases that are readily synthesised by condensation of salicylaldehydes either with 8-aminoquinoline (to generate imine-based ligands HL1-4) or with 2-hydrazinopyridines (to generate hydrazone-based proligands HL5-20). The Pt(ii) complexes are prepared under mild conditions upon treatment of the proligands with simple Pt(ii) salts. Metathesis of the chloride ligand by an acetylide is possible, as exemplified by the preparation of two further complexes of the form Pt(N^N^O-Ln)(-CC-Ar), where Ar = 3,5-bis(trifluoromethyl)phenyl. Nine of the complexes have been characterised in the solid state by X-ray diffraction. The imine-based complexes have intense low-energy absorption bands around 520 nm attributed to charge-transfer transitions. They display deep red phosphorescence in solution at ambient temperature, with λmax in the range 635-735 nm, quantum yields up to 4.6% and lifetimes in the microsecond range. The hydrazone complexes that feature a py-NH-NC-Ar linker display pH-dependent absorption spectra owing to the acidity of the hydrazone NH: these complexes have poor photostability in solution. In contrast, their N-methylated analogues (i.e., py-NMe-NC-Ar) show no evidence of photodecomposition. They are phosphorescent in solution at room temperature in the 600-640 nm region, the emission maximum being influenced by substituents in the phenolate ring. The results show how simply prepared tridentate Schiff base ligands-which offer the metal a combination of 5- and 6-membered chelate rings-can provide access to phosphorescent Pt(ii) complexes that have superior emissive properties to those of terpyridines, for example.
- Puttock, Emma V.,Fradgley, Jack D.,Yufit, Dmitry S.,Gareth Williams
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p. 15012 - 15028
(2019/10/22)
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- SUBSTITUTED SULFONYL HYDRAZIDES AS INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY
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The present invention relates to substituted sulfonyl hydrazides that have the ability to inhibit lysine biosynthesis via the diaminopimelate pathway in certain organisms. As a result of this activity these compounds can be used in applications where inhibition of lysine biosynthesis is useful applications of this type include the use of the compound as herbicides and/or anti- bacterial agents.
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Paragraph 0207
(2020/01/24)
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- ANNULATED GLYCOSIDASE INHIBITORS
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Compounds of formula (I) wherein A, R, W1, W2, W3, W4, W5, W6, L, Q, Rx and u have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.
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Page/Page column 105
(2019/03/12)
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- Mannich reaction of trifluoroacetaldehyde hydrazones: A useful entry to trifluoromethyl substituted heterocycles
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NH-aryl hydrazones derived from trifluoroacetaldehyde hemiacetal may be involved in efficient Mannich type reactions with formaldehydes and aromatic aldehydes. The resulting hydrazones are useful building blocks for the preparation of trifluoromethyl substituted heterocycles as shown by a straightforward preparation of 1,2-diazine derivatives under heating with β-ketoesters.
- Jia, Shuanglong,El Kaim, Laurent
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supporting information
p. 1457 - 1460
(2018/03/08)
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- Cytotoxicity of η6-areneruthenium-based molecules to glioblastoma cells and their recognition by multidrug ABC transporters
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A new series of amphiphilic η6-areneruthenium(II) compounds containing phenylazo ligands (group I: compounds 1a, 1b, 2a and 2b) and phenyloxadiazole ligands (group II: compounds 3a, 3b, 4a and 4b) were synthesized and characterized for their anti-glioblastoma activity. The effects of the amphiphilic η6-areneruthenium(II) complexes on the viability of three human glioblastoma cell lines, U251, U87MG and T98G, were evaluated. The azo-derivative ruthenium complexes (group I) showed high cytotoxicity to all cell lines, whilst most oxadiazole-derivative complexes (group II) were less cytotoxic, except for compound 4a. The cationic complexes 2a, 2b and 4b were more cytotoxic than the neutral complexes. Compounds 2a and 2b caused a significant reduction in the percentage of cells in the G0/G1 phase, with concomitant increases in the G2/M phase and fragmented DNA in the T98G cell line. The η6-areneruthenium(II) compounds were also tested in cell lines that overexpress the multidrug ABC transporters P-gp, MRP1 and ABCG2. Compounds 2b and 4a were substrates for the P-gp protein, with resistance indexes of 8.6 and 1.9, respectively. Compound 2b was also a substrate for ABCG2 and MRP1 proteins, with lower resistance indexes (1.8 and 1.6, respectively). The contribution of multidrug ABC transporters to the cytotoxicity of compound 2b in T98G cells was evidenced, since verapamil (a characteristic inhibitor of MRP1) increased the cytotoxicity of compound 2b at concentrations up to 20 μmol L?1, whilst GF120918 and Ko143 (specific inhibitors of P-gp and ABCG2, respectively) had no significant effect. In addition, we showed that compound 2b interacts with glutathione (GSH), which could explain its cellular efflux by MRP1. Our results showed that the amphiphilic η6-areneruthenium(II) complexes are promising anti-glioblastoma compounds, especially compound 2b, which was cytotoxic for all three cell lines, although it is transported by the three main multidrug ABC transporters.
- Pazinato, Jaqueline,Cruz, Otávio M.,Naidek, Karine P.,Pires, Amanda R.A.,Westphal, Eduard,Gallardo, Hugo,Baubichon-Cortay, Hélène,Rocha, Maria E.M.,Martinez, Glaucia R.,Winnischofer, Sheila M.B.,Di Pietro, Attilio,Winnischofer, Herbert
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p. 165 - 177
(2018/02/20)
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- Nickel-catalyzed direct C-H bond sulfenylation of acylhydrazines
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A Ni-catalyzed direct C-H bond sulfenylation of acylhydrazines was developed. The reaction used N-(pyridinyl)hydrazine as the bidentate-directing group, which can be smoothly removed through reductive N-N cleavage. This system can bear various important functional groups, providing an efficient route for the preparation of diverse diaryl sulfides.
- Li, Jun-Ming,Yu, Yang,Weng, Jiang,Lu, Gui
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supporting information
p. 6047 - 6056
(2018/09/06)
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- 1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA
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Two new cationic DNA intercalators, 3-phenyl-1-(6-phenylpyridin-2-yl)-1H-[1,2,4]triazolo[4,3-a]pyridin-4-ium (1a)+ and 1-phenyl-3-(6-phenylpyridin-2-yl)-3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium (1b)+, were synthesized from 2-chloropyridine and 2-chloroquinoline, respectively, in a four-step procedure. Generation of the hydrazine, followed by condensation with an aldehyde to give a hydrazone and subsequent Buchwald-Hartwig amination gave a mixture of E- and Z-configured N,N-functionalized hydrazones. Finally, oxidative cyclisation gave rise to the formation of the cationic DNA intercalators, whose molecular structures were determined by single-crystal X-ray diffraction analysis of the hexafluorophosphate and tribromide salt of (1a)+ and (1b)+, respectively. The intercalative binding of (1a)PF6 and (1b)PF6 to ctDNA was confirmed by means of UV, CD and luminescence spectroscopy, determination of the DNA melting temperature and by rheology measurements.
- Hebenbrock, Marian,Müller, Jens
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p. 885 - 893
(2018/09/06)
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- TRIAZOLONES DERIVATIVES FOR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF A VIRAL DISEASE
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The present invention relates to a compound having the general formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, tautomer, racemate, codrug, cocrystal, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameloriating or preventing a viral disease. Furthermore, specific combination therapies are disclosed.
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Page/Page column 41
(2017/04/18)
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- The Base-Promoted Annulation of 2-Hydrazinyl Pyridine and CO2 toward Triazolones
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A base-promoted annulation of 2-hydrazinyl pyridine and atmospheric pressure of CO2 has been developed in the presence of silane as reducing reagent, affording a series of triazolones in moderate to excellent yields. CO2 served as a carbonyl source in this transfomation. Moreover, benzamidrazones also worked well under this procedure. Thus, it represents a green, sustainable and straightforward pathway to access triazolone frameworks. (Figure presented.).
- Wu, Xiaopeng,Sun, Song,Wang, Bingbing,Cheng, Jiang
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supporting information
p. 3855 - 3859
(2017/11/15)
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- BICYCLIC AZAHETEROCYCLIC COMPOUNDS AS NR2B NMDA RECEPTOR ANTAGONISTS
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Disclosed are chemical entities of Formula (I): wherein R1 and Z are defined herein, as NR2B subtype selective receptor antagonists. Also disclosed are pharmaceutical compositions comprising a chemical entity of Formula (I), and methods of treating various diseases and disorders associated with NR2B antagonism, e.g., diseases and disorders of the CNS, such as depression, by administering a chemical entity of Formula (I).
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Paragraph 0276
(2016/07/05)
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- Chemoselective Synthesis of 5-Alkylamino-1H-pyrazole-4-carbaldehydes by Cesium- and Copper-Mediated Amination
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Microwave-assisted synthesis of new 5-alkylamino-pyrazole-4-carbaldehydes was performed efficiently, with yields up to 99 and short reaction times. Nucleophilic substitution of primary alkylamines with activated 5-chloro-1-(2-pyridyl)pyrazole-4-carbaldehyde was mediated by the "cesium effect". The amination of deactivated 1-aryl-5-chloropyrazole-4-carbaldehydes was also assisted by the cesium ion and catalyzed by copper(I). Hereby is described an efficient protocol for the chemoselective synthesis of new 5-alkylaminopyrazole-4-carbaldehydes from 5-chloropyrazole-4-carbaldehydes and primary alkylamines in one step to give products with good to excellent yields and short reaction times. Unexpectedly, under these reaction conditions the corresponding alkylimine formation was not observed.
- Orrego-Hernndez, Jessica,Cobo, Justo,Portilla, Jaime
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supporting information
p. 5064 - 5069
(2015/08/18)
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- A simple pincer-type chemosensor for reversible fluorescence turn-on detection of zinc ion at physiological pH range
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A new, highly selective and sensitive pincer-type chemosensor (Y) for zinc ion with turn-on fluorescence behavior in physiological pH range solution was developed. Y is based on bi-hydrazone derivatives, which contain pyridine as the fluorescent group and a hydrazone bond as recognition site. The selectivity mechanism of Y for zinc is based on the combined effects of the inhibition of excited-state intramolecular proton transfer (ESIPT) and -HC=N- isomerization, as well as chelation-enhanced fluorescence. The entire process takes less than 15 seconds. The minimum detection limit of Y for zinc reaches 1.39 × 10-8 M. Moreover, Y can conveniently detect zinc in test strip form, and it can be recycled.
- Lin, Qi,Cai, Yi,Li, Qiao,Chang, Jing,Yao, Hong,Zhang, You-Ming,Wei, Tai-Bao
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p. 4162 - 4167
(2015/05/20)
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- PROTEIN KINASE INHIBITORS (VARIANTS), USE THEREOF IN TREATING ONCOLOGICAL DISEASES AND A PHARMACEUTICAL COMPOSITION BASED THEREON
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The present invention relates to the treatment of oncological, chronic inflammatory and similar diseases with the aid of new families of chemical compounds having improved efficiency with regard to the inhibition of Abl kinase and mutant forms thereof, as well as other therapeutically significant kinases. It describes protein kinase inhibitors in the form of compounds of general formula (I) and compounds of general formula (II), or a tautomer, an individual isomer, a mixture of isomers, a pharmaceutically acceptable salt, a solvate or a hydrate thereof.
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Page/Page column
(2014/07/07)
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- Palladium catalyzed addition of arylboronic acid or indole to nitriles: Synthesis of aryl ketones
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Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.
- Das, Tuluma,Chakraborty, Amarnath,Sarkar, Amitabha
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supporting information
p. 7198 - 7202
(2015/01/09)
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- Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs
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A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.
- Nakao, Syuhei,Mabuchi, Miyuki,Shimizu, Tadashi,Itoh, Yoshihiro,Takeuchi, Yuko,Ueda, Masahiro,Mizuno, Hiroaki,Shigi, Naoko,Ohshio, Ikumi,Jinguji, Kentaro,Ueda, Yuko,Yamamoto, Masatatsu,Furukawa, Tatsuhiko,Aoki, Shunji,Tsujikawa, Kazutake,Tanaka, Akito
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supporting information
p. 1071 - 1074
(2014/03/21)
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- SUBSTITUTED HETEROAROMATIC PYRAZOLE-CONTAINING CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted heteroaromatic pyrazole-containing carboxamide and urea derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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Page/Page column 113
(2013/03/26)
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- Triazolo and imidazo dihydropyrazolopyrimidine potassium channel antagonists
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Previously disclosed C6 amido and benzimidazole dihydropyrazolopyrimidines were potent and selective blockers of IKur current. Syntheses and SAR for C6 triazolo and imidazo dihydropyrazolopyrimidines series are described. Trifluoromethylcyclohexyl N(1) triazole, compound 51, was identified as a potent and selective Kv1.5 inhibitor with an acceptable PK and liability profile.
- Finlay, Heather J.,Jiang, Ji,Caringal, Yolanda,Kover, Alexander,Conder, Mary Lee,Xing, Dezhi,Levesque, Paul,Harper, Timothy,Hsueh, Mei Mann,Atwal, Karnail,Blanar, Michael,Wexler, Ruth,Lloyd, John
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supporting information
p. 1743 - 1747
(2013/04/10)
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- Substituted Heteroaromatic Pyrazole-Containing Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
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Substituted heteroaromatic pyrazole-containing carboxamide and urea compounds as vanilloid receptor ligands, pharmaceutical compositions containing these compounds and also to a method of using these compounds for treating and/or inhibiting pain and further diseases and/or disorders.
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Paragraph 0699
(2013/03/26)
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- Substituted Cyclic Carboxamide and Urea Derivatives as Ligands of the Vanilloid Receptor
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Substituted cyclic carboxamide and urea compounds, a process for their preparation, pharmaceutical compositions containing these compounds, and the use of these compounds for the treatment and/or inhibition of pain and other conditions mediated by the vanilloid receptor 1.
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Page/Page column 34
(2012/03/10)
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- Substituted Heteroaromatic Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
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Substituted heteroaromatic carboxamide and urea compounds corresponding to formula (i) processes for the preparation thereof, pharmaceutical compositions containing these compounds and also a method of using these compounds in pharmaceutical compositions for treating or inhibiting pain and other conditions mediated at least in part via the vanilloid receptor 1.
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Page/Page column 41-42
(2012/05/20)
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- SUBSTITUTED BICYCLIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted bicyclic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.
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Page/Page column 90
(2012/05/31)
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- Substituted Bicyclic Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
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Substituted bicyclic carboxamide and urea compounds corresponding to formula (I) processes for the preparation thereof, pharmaceutical compositions containing these compounds, and a method of using these compounds for the treatment and/or inhibition of pain and other conditions mediated at least in part via the vanilloid receptor 1.
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Page/Page column 37-38
(2012/05/20)
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- Efficient synthesis of 3-substituted 1,2,4-triazolo[4,3-a]pyridine by [bis(trifluroacetoxy)iodo]benzene-catalyzed oxidative intramolecular cyclization of heterocyclic hydrazones
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A series of 1,2,4-triazolopyridines have been prepared by oxidative intramolecular cyclization of heterocyclic hydrazones with [bis(trifluroacetoxy) iodo]benzene. General applicability of this simple transformation was confirmed by synthesis of 1,2,4-triazolo[4,3-a]pyridine. The advantages of this protocol are the nontoxicity of catalyst and shorter reaction time to obtain good preparative yield.
- Padalkar, Vikas S.,Patil, Vikas S.,Phatangare, Kiran R.,Umape, Prashant G.,Sekar
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experimental part
p. 925 - 938
(2011/04/22)
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- Configurational and constitutional information storage: Multiple dynamics in systems based on pyridyl and acyl hydrazones
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The C=N group of hydrazones can undergo E/Z isomerization both photochemically and thermally, allowing the generation of a closed process that can be tuned by either of these two physical stimuli. On the other hand, hydrazine-exchange reactions enable a constitutional change in a given hydrazone. The two classes of processes: 1) configurational (physically stimulated) and 2) constitutional (chemically stimulated) give access to short-term and long-term information storage, respectively. Such transformations are reported herein for two hydrazones (bis-pyridyl hydrazone and 2-pyridinecarboxaldehyde phenylhydrazone) that undergo a closed, chemically or physically driven process, and, in addition, can be locked or unlocked at will by metal-ion coordination or removal. These features also extend to acyl hydrazones derived from 2-pyridinecarboxaldehyde. Similarly to the terpydine-like hydrazones, such acyl hydrazones can undergo both constitutional and configurational changes, as well as metal-ion coordination. All these types of hydrazones represent dynamic systems capable of acting as multiple state molecular devices, in which the presence of coordination sites furthermore allows the metal ion-controlled locking and unlocking of the interconversion of the different states.
- Chaur, Manuel N.,Collado, Daniel,Lehn, Jean-Marie
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supporting information; scheme or table
p. 248 - 258
(2011/03/21)
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- Asymmetric allylation, crotylation, and cinnamylation of N-heteroaryl hydrazones
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(Chemical Equation Presented) A new class of N-heteroaryl hydrazones has been developed as an alternative to N-acylhydrazones and 2-amlnophenol-derlved lmlnes In asymmetric allylatlon, crotylatlon, and clnnamylatlon reactions with chlral allylchlorosllanes. The hydrazones are readily and Inexpensively prepared, perform well In the allylatlon chemistry, and more Importantly, the product hydrazldes may be smoothly reduced by Pd(OH)2catalyzed hydrogenation to reveal the corresponding amine products.
- Feske, Miriam Inbar,Santanilla, Alexander Buitrago,Leighton, James L.
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supporting information; experimental part
p. 688 - 691
(2010/04/02)
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- SUBSTITUTED AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions (formula (I)).
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Page/Page column 162
(2010/11/18)
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- SUBSTITUTED PHENYLLUREAS AND PHENYLAMIDES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted phenylureas and phenylamides of formula (I), to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.
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Page/Page column 125
(2010/11/18)
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- HSP INDUCTOR
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An agent for inducing HSP, comprising a compound represented by the formula (I): ???wherein R1 is a hydrogen atom, a hydrocarbon group which may be substituted, etc.; R2 is absent, a hydrogen atom or a hydrocarbon group which maybe substituted; R3 is a heterocyclic group which may be substituted; X, Y and Z are, respectively, a hydrogen, a halogen, a nitrile, a hydrocarbon group which may be substituted, or X and Y may bind to each other to form ring A, or Y and Z may bind to each other to form ring B; bond portions indicated by a solid line and a broken line are, respectively, a single bond or a double bond, and bond portions indicated by a broken line are, respectively, a single bond or absent; ring A is a homocyclic or heterocyclic 5- to 7-membered ring which may be substituted; ring B is a homocyclic or heterocyclic 5- to 7-membered ring which may be substituted; and n is an integer of 0 or 1, or a salt thereof;
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- Catalytic amination of 2-substituted pyridines with hydrazine derivatives.
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[reaction in text] Protected pyridylhydrazine derivatives were prepared in a one-step palladium-catalyzed amination reaction using chelating phosphine ligands. 2-Pyridyl chlorides, bromides, and triflates were effective electrophiles in these reactions. Di-tert-butyl hydrazodiformate was an excellent hydrazine substrate, and the resulting products were deprotected under mild conditions. Catalytic amination provides a direct route to protected bifunctional hydrazinopyridine linkers that are suitable for metal-bioconjugate syntheses.
- Arterburn,Rao,Ramdas,Dible
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p. 1351 - 1354
(2007/10/03)
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- Synthesis of new mesomeric betaines containing a triazolopyridiniumolate system and their unexpected function as masked isocyanates
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A series of mesomeric betaines containing 1-alkylated triazolopyridiniumolate system were synthesized and their cycloaddition with dimethyl acetylenedicarboxylate were examined. An unusual ring-opening reaction occurred to give pyridone derivatives indicating that these betaines act as masked isocyanates.
- Sakai, Norio,Funabashi, Makoto,Minakata, Satoshi,Ryu, Ilhyong,Komatsu, Mitsuo
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p. 265 - 270
(2007/10/03)
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- Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2-pyridylarylhydrazone derivatives
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This work describes recent results from our research program aiming at the synthesis and pharmacological evaluation of new compounds acting as antiinflammatory, analgesic and platelet antiaggregatory. In this paper the synthesis and the pharmacological profile as analgesic, antiinflammatory and anti-platelet of new functionalized 2-pyridylarylhydrazone derivatives 5a-r are discussed. This class of N-heterocyclic derivatives represents a new series of prototype candidates with analgesic and antiinflammatory properties possessing also an important anti-aggregating activity. The pharmacological results herein disclosed suggest that the anti-inflammatory and analgesic activities of these new pyridynehydrazone derivatives observed in the carrageenan pleurisy model and acetic acid writhing test, respectively, is probably due to an interference on the arachidonic acid (AA) metabolism. The most important antiinflammatory derivative 2-(2-formylfurane)pyridylhydrazone 5p presented a 79% inhibition of pleurisy at a dose of 80.1 μmol/kg. We also described the results concerning the mechanism of action of this series of N-heterocyclic derivatives in platelet aggregation which suggest a Ca2+ participation, probably by a complexation scavenger mechanism. Compound 2-(2-formylfurane)pyridylhydrazone 5p was able to complex Ca2+ in in vitro experiments at 100 μM concentration, indicating that this series of compounds can act as Ca2+ scavenger depending on the nature of the aryl moiety present at the imine subunit.
- Todeschini, Adriane R.,De Miranda, Ana Luisa P.,Da Silva, Kelly Christine M.,Parrini, Sergio C.,Barreiro, Eliezer J.
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p. 189 - 199
(2007/10/03)
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- Design, Synthesis, and Pharmacological Activities of 2-Substituted 4-Phenylquinolines as Potential Antidepressant Drugs
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This work represents the design, synthesis, and pharmacological testing of 4-phenylquinoline derivatives as potential antidepressants.Various modifications of substituents at the 2-position of the quinoline ring were tried, and two main series of derivatives were synthesized.In the first series, an open (dialkylamino)alkyl chain is linked to the 2-position of the quinoline ring by isosteres.The second approach involved the synthesis of a novel analogue of trazodone with a 4-phenylquinoline grouping replacing the chlorophenyl group of trazodone.The potential antidepressant activity of these new compounds has been demonstrated by their antagonism to the reserpine-induced hypothermia in mice.Both length of the side chain and isosteric displacements within the side chain affect the value of the ED50 obtained.Compounds having three atoms separating the terminal nitrogen from the quinoline ring were found to be more active than those with four atoms.The 2-thia derivatives were devoid of antidepressant activity.Replacement of the open side chain at the 2-position of the quinoline ring by piperazine or substituted piperazines resulted in new compounds that are slightly more potent than imipramine.
- Alhaider, Abdulqader A.,Abbdelkader, M. Atef,Lien, Eric J.
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p. 1394 - 1398
(2007/10/02)
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