4930-98-7Relevant articles and documents
Tridentate hydrazone metal complexes derived from cephalexin and 2-hydrazinopyridine: Synthesis, characterization and antibacterial activity
Anacona,Rincones, Maria
, p. 169 - 175 (2015)
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.
A facile synthesis of amide derivatives of [1,2,4]triazolo[4,3-a]pyridine
Gandikota, N. Murthy,Bolla, R. Sekhar,Viswanath, I. V. Kasi,Bethi, Sridharreddy
, p. 1920 - 1924 (2017)
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.
Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[22.2]octenes Fused with Two N -Aminosuccinimide Moieties
Ekar, Jernej,Kranjc, Kri?tof
, p. 1112 - 1120 (2020/10/29)
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.
Synthesis and study of organoselenium compound: DNA/Protein interactions, in vitro antibacterial, antioxidant, anti-inflammatory activities and anticancer activity against carcinoma cells
Dhavan, Pratik P.,Jadhav, Bhaskar L.,Manjare, Sudesh T.,Shelar, Divyesh S.,Singh, Pinky R.,Vaidya, Shashikant P.
, (2021/07/25)
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.
PROCESS FOR THE SYNTHESIS OF (3-CHLORO-2-PYRIDYL)HYDRAZINE
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Paragraph 0061-0063, (2021/05/29)
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.
Method for industrially producing bromo-pyrazolidinic acid through micro-channel
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Paragraph 0085-0087; 0094-0096; 0116-0117, (2020/08/02)
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.
ASK1 inhibitor and applications thereof
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Paragraph 0155; 0157-0159, (2020/06/17)
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.
Preparation method of pyridine triazolone
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Paragraph 0014; 0019-0021, (2020/12/30)
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.
Microwave-assisted synthesis of trazodone and its derivatives as new 5-HT1A ligands: Binding and docking studies
Jaskowska, Jolanta,Zar eba, Przemys?aw,Sliwa, Pawe?,Pindelska, Edyta,Sata?a, Grzegorz,Majka, Zbigniew
, (2019/05/01)
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.
A family of readily synthesised phosphorescent platinum(ii) complexes based on tridentate: N^N^O -coordinating Schiff-base ligands
Puttock, Emma V.,Fradgley, Jack D.,Yufit, Dmitry S.,Gareth Williams
, p. 15012 - 15028 (2019/10/22)
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.
