- Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[22.2]octenes Fused with Two N -Aminosuccinimide Moieties
-
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
-
p. 1112 - 1120
(2020/10/29)
-
- Pyridine hydrazone derivative as well as preparation method and application thereof (by machine translation)
-
The invention relates to a pyrazine hydrazone derivative represented I, a pharmaceutically acceptable salt thereof, a pharmaceutical composition and application thereof in preparation of an influenza virus neuraminidase inhibitor. Wherein R-substituted pyridyl is selected from the group consisting of 5 - trifluoromethyl -2 - pyridyl, 3 - nitro -2 - pyridyl; Y is selected from the group consisting of: hydroxy, dihydroxyl, 3 - hydroxy -2 - C1 - C2 alkoxy, 3 - hydroxy -4 - C1 - C2 alkoxy, 3 - hydroxy -5 - C1 - C2, 3 -hydroxy -3 - C1 - C2 -6 - C1 - C2 alkoxy 4 -3 4 - hydroxy -2 - C1 - C2-4 - 5 -C1 - C2 dimethyl, Z is 4 - selected from -3: 5 - CH or N. sub. CO. (by machine translation)
- -
-
Paragraph 0087-0091; 0095-0099
(2020/11/23)
-
- PLATINUM COMPOUNDS FOR BINDING GUANINE QUADRAPLEXES
-
Compounds are described and characterized that bind guanine quadruplexes of DNA or RNA. Binding data and inhibition of growth data of five cancer cell lines are presented.
- -
-
Page/Page column 39
(2019/06/05)
-
- SUBSTITUTED SULFONYL HYDRAZIDES AS INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY
-
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.
- -
-
Paragraph 0209
(2020/01/24)
-
- Keeping it small, polar, and non-flat: diversely functionalized building blocks containing the privileged 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]- and [1,5-a]pyridine cores
-
Six sets of functionalized building blocks based on 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine as well as 5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine cores have been prepared. These compounds are non-flat, bicyclic heterocycles that are likely to find utility as privileged motifs for lead-like compound design. One set of building blocks, (5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-6-ylmethyl)amines, proved useful as a scaffold for developing compounds that stimulate glucagon-like peptide-1 (GLP-1) secretion and are novel anti-diabetes drug leads.
- Mishchuk, Alexander,Shtil, Natalia,Poberezhnyk, Mykola,Nazarenko, Konstiantyn,Savchenko, Timur,Tolmachev, Andrey,Krasavin, Mikhail
-
supporting information
p. 1056 - 1059
(2016/02/16)
-
- Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water
-
A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66-95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.
- Xia, Ran,Xie, Ming-Sheng,Niu, Hong-Ying,Qu, Gui-Rong,Guo, Hai-Ming
-
supporting information
p. 1077 - 1081
(2014/03/21)
-
- Photo-driven optical oscillators in the kHz range based on push-pull hydroxyazopyridines
-
Push-pull azophenols are valuable target molecules for stable photo-driven optical oscillators. Hydroxyazopyridinium methyl iodide salts show oscillation frequencies up to 10 kHz with no signs of fatigue upon continuous work. The Royal Society of Chemistry.
- Garcia-Amoros, Jaume,Nonell, Santi,Velasco, Dolores
-
experimental part
p. 4022 - 4024
(2011/06/25)
-
- Cyclic AMP-specific phosphodiesterase inhibitors
-
Pyrazole compounds that are potent and selective inhibitors of PDE4, as well as methods of making the same, are disclosed. Use of the compounds in the treatment of inflammatory diseases and other diseases involving elevated levels of cytokines, as well as
- -
-
-
- Azinyl and diazinyl hydrazones derived from aryl N-heteroaryl ketones: Synthesis and antiproliferative activity
-
A series of N-heteroaryl hydrazones derived from aryl N-heteroaryl or bis-N-heteroaryl methanones was prepared in search for potential novel antitumor agents. The stereochemistry of these compounds was established by means of NMR spectroscopy. Antiproliferative activity was determined in a panel of human tumor cell lines (CCRF-CEM, Burkitt's lymphoma, HeLa, ZR-75- 1, HT-29, and MEXF 276L) in vitro. Generally, the new compounds were found to be more potent (IC50 = 0.011-0.436 μM) than the ribonucleotide reductase inhibitor hydroxyurea (IC50 = 140 μM). Most of the compounds exhibited the highest activity against Burkitt's lymphoma with an IC50 of 0.011-0.035 μM. [14C]Cytidine incorporation into DNA was quantitated for selected hydrazones (Z-A, E-1, Z-3, Z-4, E-5, Z-5, E-13, E-18, Z-19, Z-24, and E-26) as a measure of the inhibition of ribonucleotide reductase in Burkitt's lymphoma cells. The E-configurated compounds were found to inhibit [14C]cytidine incorporation to a greater extent (IC50 = 0.67-5.05 μM) than the Z-isomers (IC50 = 7.20 to > 10 μM). Principal component analysis of the IC50 values obtained for inhibition of cell proliferation revealed that the cell lines tested can be grouped into three main families showing different sensitivities toward the compounds in our series [(i) CCRF-CEM, Burkitt's lymphoma, and Hela; (ii) HT-29; and (iii) MEXF 276 L].
- Easmon,Heinisch,Purstinger,Langer,Osterreicher,Grunicke,Hofmann
-
p. 4420 - 4425
(2007/10/03)
-
- Novel potassium channel openers: Synthesis and pharmacological evaluation of new N-(substituted-3-pyridyl)-N'-alkylthioureas and related compounds
-
This report describes the synthesis and pharmacological evaluation of a series of novel potassium channel openers related to the pinacidil-type compounds. Thioureas, cyanoguanidines, and pyridine N-oxides were systematically evaluated for their effects on both the inhibition of spontaneous mechanical activity in rat portal vein (in vitro) and their antihypertensive activity (in vivo), and the structure-activity relationship for this series of compounds was discussed. Good correlation between in vitro and iv antihypertensive activity was observed for these compounds. Among them, cyanoguanidines bearing a conformationally rigid unit such as a norbornyl group generally possessed potent activity in both in vitro and in vivo studies. Especially, N-(6-amino-3-pyridyl)-N'-cyano-N''-(1-methyl-2- norbornyl)guanidine (23d) was identified as a more potent potassium channel opener in vitro (EC100 = 3 x 10-8 M) than pinacidil (EC100 = 10-7 M).
- Takemoto,Eda,Okada,Sakashita,Matzno,Gohda,Ebisu,Nakamura,Fukaya,Hihara,Eiraku,Yamanouchi,Yokoyama
-
-
- Aminopyridine compounds
-
An aminopyridine compound represented by the formula: STR1 wherein n represents 0 or 1; Z represents =S, =NCN or =CHNO2 ; R1 represents --NR3 R4, --NHNR3 R4, --NHCONHR3 or --NHSO2 R3 ; R2 represents H, or substituted or unsubstituted alkyl; R3 and R4, which may be the same or different, represent H, substituted or unsubstituted alkyl, aryl, substituted or unsubstituted acyl or alkoxycarbonyl group; and R3 and R4 may form a heterocyclic ring together with a nitrogen atom to which R3 and R4 are bound, through another heteroatom or without it; an optical isomer thereof or art acid salt thereof, which is excellent in pharmacological effect and repressed in side effects as a drug for circulatory diseases.
- -
-
-
- Benzocrown Ether Hydrazones as Extractants for Alkali Metal Ions
-
Four types of benzo-15-crown-5 and benzo-18-crown-6 derivatives bearing a substituted hydrazone moiety as a proton-dissociable chromogenic group were synthesized and the solvent extraction behaviors of these compounds for alkali metal ions were evaluated spectrophotometrically.Benzo-15-crown-5 and -18-crown-6 hydrazones with 2,4-dinitro-6-(trifluoromethyl)phenyl or 2,6-dinitro-4-(trifluoromethyl)phenyl groups extracted alkali metal ions predominantly as 2:1 and 1:1 (crown ether:metal ion) complexes, respectively, from an aqueous alkaline solution into 1,2-dichloroethane and these ligands exhibited high K+-selectivity.The composition of the extracted species and the K+-selectivity depended on the polarity of the extraction solvent used.In particular, 2:2 complexes of several alkali metal ions with benzo-15-crown-5 and -18-crown-6 hydrazones bearing a 2,4-dinitro-6-(trifluoromethyl)phenyl group were readily extracted from an aqueous solution into chloroform.
- Sakamoto, Hidefumi,Goto, Hiroki,Yokoshima, Makoto,Dobashi, Makoto,Ishikawa, Junichi,et al.
-
p. 2907 - 2914
(2007/10/02)
-
- Aminopyridine compounds
-
An aminopyridine compound represented by the formula: STR1 wherein n represents 0 or 1; Z represents =S, =O, =NCN or =CHNO2 ; R1 represents --CN, --NR3 R4, --CONR3 R4, --NHNR3 R4, --NHCONHR3, --NHSO2 R3 or --SR3 ; R2 represents H, or substituted or unsubstituted alkyl; R3 and R4, which may be the same or different, represent H, substituted or unsubstituted alkyl, aryl, substituted or unsubstituted acyl or alkoxycarbonyl group; and R3 and R4 may form a heterocyclic ring together with a nitrogen atom to which R3 and R4 are bound, through another heteroatom or without it; or an acid salt thereof, which is excellent in pharmacological effect and repressed in side effects as a drug for circulatory diseases.
- -
-
-
- Synthesis and Chromogenic Properties of Some Water-Soluble 5-Nitro-2-pyridylhydrazones
-
Four new water-soluble hydrazones, α-(5-nitro-2-pyridyl)hydrazono-α-(2-quinolyl)-3-toluenesulfonic acid, α-(5-nitro-2-pyridyl)hydrazono-α-(2-thiazolyl)-3-toluenesulfonic acid, α-(2-benzothiazolyl)-α-(5-nitro-2-pyridyl)hydrazono-3-toluenesulfonic acid, and α-(2-benzimidazolyl)-α-(5-nitro-2-pyridyl)hydrazono-3-toluenesulfonic acid, were synthesized.Their proton dissociation constants were determined spectrophotometrically.The chromogenic properties of the synthesized hydrazones and their reactions with metal ions were investigated spectrophotometrically in detail.The results revealed that the synthesized hydrazones react with various metal ions including transition metal ions, especially with cadmium(II), nickel(II), and zinc(II) to form stable colored comoplexes with very large apparent molar absorptivities, so that their were found to be all very useful as highly sensitive spectrophotometric reagents.
- Ishi, Hajime,Odashima, Tsugikatsu,Kawamonzen, Yoshiaki,Katahira, Aoba-ku,Odashima, Tsugikatsu
-
p. 3398 - 3404
(2007/10/02)
-
- Photographic products and processes employing novel nondiffusible pyridylazonaphthol dye-releasing compounds
-
Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable 2-(5-nitro-2-pyridylazo)-1-naphthol dye moiety. The compound contains a ballasted carrier moiety which is capable of releasing the diffusible azo dye under alkaline conditions. The dye is transferred imagewise to an image-receiving layer where it is contacted with metal ions to form a metal-complexed azo dye transfer image of excellent stability.
- -
-
-
