946-76-9

Usage

InChI:InChI=1/C9H5ClN4/c10-7-1-3-8(4-2-7)13-14-9(5-11)6-12/h1-4,13H

Upstream product

• 17333-85-6 4-chlorophenyldiazonium salt 
• 109-77-3 malononitrile 
• 13166-10-4 isopropylidenemalonodinitrile 
• 106-47-8 4-chloro-aniline 
• 922-64-5 1,1-dicyanoethylene 
• 2028-74-2 p-chlorobenzenediazonium chloride 
• 20265-96-7 p-chloroaniline hydrochloride 

Downstream Products

• 74982-78-8 2-[(4-Chloro-phenyl)-ethyl-hydrazono]-malononitrile 
• 74982-75-5 5-Amino-2-(4-chloro-phenyl)-3-thioxo-2,3-dihydro-[1,2,4]triazine-6-carbonitrile 
• 4328-22-7 O,O,O,O-tetraethyl trithiopyrophosphate 
• 1056019-65-8 N,N'-dihydroxy-2-(4-chlorphenylhydrazono)-propanediimidamide 
• 1224730-53-3 3-amino-2-p-chlorophenylhydrazono-3-phenylhydrazonopropanenitrile 

Relevant academic research and scientific papers

COMPOUNDS HAVING PSEUDOMONAS ANTI-BIOFILM PROPERTIES

The present invention relates to c-di-GMP lowering chemical compounds having anti- biofilm properties. In particular, the present invention relates to anti-biofilm compounds or salts or tautomers thereof for use in treatment and/or prevention of bacterial biofilm infection in human subjects caused by biofilm-forming bacteria of the genus Pseudomonas, in particular Pseudomonas spp. including P. aeruginosa. Methods of treating such infections in human subjects are contemplated as well. The present inventions further relates to the use of an anti-biofilm compound or a salt or tautomer thereof for dispersing biofilms in industrial water systems.

Novel heterocyclic disazo dyes containing pyrazole and phenylpyrazole. part 1: Synthesis, characterization, solvent polarity and acid-base sensitive characteristics

A series of diazotised aniline and aniline derivative compounds were reacted with solution of malononitrile in pyridine at 0–5 °C were obtained 1a-1m compounds. Then 4-arylazo-3,5-diamino-1H-pyrazole (2a-2m) derivatives were synthesized by coupling arylazo malononitrile compounds with hydrazine. Finally, the synthesized pyrazole derivative 2a-2m compounds were again diazotised. By reacting these diazotised compounds with 3-amino-5?hydroxy-1-phenylpyrazole, the new thirteen heterocyclic disazo dyes (3a-3m) were joined the dye literature and the dye industry. The structures of these newly synthesized compounds were characterized using elemental analysis and spectroscopic methods such as Fourier transform infrared spectroscopy-Attenuated total reflectance (FT-IR-ATR), 1H-Nuclear magnetic resonance (1H NMR) spectroscopy and mass spectroscopy. Then solvatochromic properties and solvent effect in dimethyl sulfoxide, dimethyl formamide, acetonitrile, acetic acid, methanol and chloroform were investigated. In addition, the effects of organic and inorganic acids and bases on the absorption spectra of the compounds and the substituent effect of the phenyl ring-bound groups were investigated.

Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents

Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.

Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate as an HIV-1 replication inhibitor

Inspired by the antiviral activity of known pyrazole-based HIV inhibitors, we screened our in-house library of pyrazole-based compounds to evaluate theirin celluloactivity against HIV-1 replication. Two hits with very similar structures appeared from single and multiple-round infection assays to be non-toxic and active in a dose-dependent manner. Chemical expansion of their series allowed an in-depth and consistent structure-activity-relationship study (SAR) to be built. Further ADME evaluation led to the selection of 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate with an advantageous pharmacokinetic profile. Finally, examination of its mode of action revealed that this compound does not belong to the three main classes of anti-HIV drugs, a feature of prime interest in the context of viral resistance.

Computer-aided molecular design of pyrazolotriazines targeting glycogen synthase kinase 3

Numerous studies have highlighted the implications of the glycogen synthase kinase 3 (GSK-3) in several processes associated with Alzheimer’s disease (AD). Therefore, GSK-3 has become a crucial therapeutic target for the treatment of this neurodegenerative disorder. Hereby, we report the design and multistep synthesis of ethyl 4-oxo-pyrazolo[4,3-d][1–3]triazine-7-carboxylates and their biological evaluation as GSK-3 inhibitors. Molecular modelling studies allow us to develop this new scaffold optimising the chemical structure. Potential binding mode determination in the enzyme and the analysis of the key features in the catalytic site are also described. Furthermore, the ability of pyrazolotriazinones to cross the blood–brain barrier (BBB) was evaluated by passive diffusion and those who showed great GSK-3 inhibition and permeation to the central nervous system (CNS) showed neuroprotective properties against tau hyperphosphorylation in a cell-based model. These new brain permeable pyrazolotriazinones may be used for key in vivo studies and may be considered as new leads for further optimisation for the treatment of AD.

Synthesis, absorption properties and biological evaluation of some novel disazo dyes derived from pyrazole derivatives

In this study, 20 novel disazo dyes containing pyrazole derivatives were synthesized by a convenient method. Diazotized aniline and some aniline derivatives were reacted with malononitrile to give 2-arylazomalononitrile derivatives 1(a-e). The synthesized 2-arylazomalononitrile derivatives were reacted with hydrazine and phenyl hydrazine to afford the corresponding 3,5-diamino-4-arylazo-1 H-pyrazole 2(a-e) and 3,5-diamino-4-arylazo-1-phenylpyrazole 3(a-e). Diazotized compounds of 2(a-e)and 3(a-e) reacted with ethylacetoacetate to give 4-arylazo-3-amino-1 H-pyrazole-5-ylazo-ethylacetoacetate 4(a-e) and 4-arylazo-3-amino-1-phenylpyrazole-5-ylazo-ethylacetoacetate 7(ae). The obtained 4(a-e) and 7(a-e) were reacted with hydrazine and phenyl hydrazine to give disazo dyes 5(a-e), 6(a-e), 8(a-e) and 9(a-e), respectively. The synthesized disazo dyes were characterized by spectroscopic techniques as well as elemental analysis. The solvatochromic behaviours of these dyes in various solvents were examined. Acid-base effects on the absorption maxima of the dyes were also reported. Antimicrobial activities of the synthesized novel disazo dyes were investigated.

An ecofriendly synthesis and DNA binding interaction study of some pyrazolo [1,5-a]pyrimidines derivatives

The DNA molecule is a target for plethora of anticancer and antiviral drugs that forms covalent and non-covalent adducts with major or minor groove of DNA. In present study we synthesized series of novel Pyrazolo [1,5-a]pyrimidine derivatives. The newly s

Efficient routes to pyrazolo[3,4-e][1,2,4]triazines and a new ring system: [1,2,4]triazino[5,6-d][1,2,3]triazines

Arylhydrazonomalononitriles 1a,b react with Phenylhydrazine to yield amidrazones 2a,b that cyclize to give 2-aryl-5-phenylhydrazono-2,5-dihydro-[1,2, 4]-triazine-6-carbonitriles 5a,b upon reaction with dimethylformamide dimethylacetal (DMFDMA). Refluxing 5a,b in glacial acetic acid resulted in the formation of the pyrazolo-1,2,4-triazines 6a,b. Compounds 6a,b were also formedupon treatment of 3-amino-4-phenylhydrazono-1-phenyl-2-pyrazolin-5-ones 7a,b with DMFDMA. Reacting these triazinyl arylhydrazononitriles 5a,b with hydroxylamine hydrochloride in ethanolic sodium acetate afforded amidrazones 8a,b that are readily cyclized in refluxing dimethylformamide into [1,2,4]triazino[1,2,3]triazines 10a,b.

Synthesis and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-ylacetonitriles

In this study, some substituted phenylhydrazono-1H-tetrazol-5-yl- acetonitriles have been synthesized (2a-o, 2a and 2k are known compounds). The synthesized compounds were characterized by spectroscopic methods [Fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR), mass spectroscopy (MS)]. In addition, antimicrobial activities of synthesized compounds were investigated against Bacillus cereus RSKK 863, Escherichia coli ATCC 3521, Pseudomonas aeruginosa ATCC 2921, and Staphylococcus aureus TP32. These compounds had antimicrobial effect against these bacteria (except for 21). Birkhaeuser Boston 2009.