23834-14-2

Usage

Uses

Used in Pharmaceutical Applications:
7-Chloro-4-hydrazinoquinoline is used as a key intermediate in the synthesis of new Schiff base hydrazone ligands, which are important in the development of novel pharmaceutical compounds. These ligands can be used to create new drugs with potential applications in various therapeutic areas.
Used in Chemical Synthesis:
In the chemical industry, 7-Chloro-4-hydrazinoquinoline is used as a starting material for the preparation of N′-(E)-heteroaromatic-isonicotinohydrazide derivatives and heteroaromatic 7-chloro-4-quinolinylhydrazone derivatives. These derivatives have potential applications in various fields, including the development of new materials, dyes, and pigments.
Used in Research and Development:
7-Chloro-4-hydrazinoquinoline is also utilized in research and development for the exploration of its chemical properties and potential applications in various fields. This includes the study of its reactivity, stability, and the development of new synthetic routes to produce novel compounds with potential industrial and pharmaceutical applications.

Synthesis

7-chloro-4-hydrazinoquinoline is prepared byhydrazine monohydrate and 4,7-dichloroquinoline in absolute ethanol.Hydrazine monohydrate (2022 mg, 40.0 mmol) and 4,7-dichloroquinoline (800 mg, 4.00 mmol) were dissolved in absolute ethanol (50 ml). The reaction mixture was left under reflux until the reaction has gone to completion and then allowed to cool in the ice bath for crystallization to occur.(676 mg, 87%): mp: 220 – 225 ℃ (Lit.: 223 – 225 ℃); vmax/cm-1 3320 w (N-H), 3050 w (aro. C-H), 1607 m (C=N), 1448 (m, aro. C=C); δH (300 MHz; DMSO-d6) 11.09 (br. s., NH), 8.56-8.40 (2H, m, C(5)H and C(2)H), 7.97 (1H, d, J 1.9, C(8)H), 7.70 (1H, dd, J 9.0, 1.9, C(6)H), 7.10 (1H, d, J 7.2, C(3)H), 5.31 (br. s., NH); δC (75 MHz; DMSO-d6) 155.7 (Ar-C), 142.4 (C(2)H), 138.7 (Ar-C), 137.6 (Ar-C), 126.4 (C(6)H), 125.3 (C(5)H), 119.1 (C(8)H), 113.6 (Ar-C), 98.1 (C(3)H); m/z (-ES) 194 (100%, [M+H]- with 35Cl), 196 (27%, [M+H]- with 37Cl); found by +ES 194.0475, C9H9ClN3 ([M+H]+ with 35Cl), requires 194.0480, error 2.6 ppm.

InChI:InChI=1/C9H8ClN3/c10-6-1-2-7-8(13-11)3-4-12-9(7)5-6/h1-5H,11H2,(H,12,13)

Upstream product

• 86-98-6 4,7-dichloroquinoline 

Downstream Products

• 69063-03-2 4-azido-7-chloro-quinoline 
• 868662-44-6 4-[3-(4-chlorophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl]-7-chloroquinoline 
• 868662-46-8 4-[5-hydroxy-3-(4-methoxyphenyl)-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl]-7-chloroquinoline 
• 868662-48-0 4-[3-(4-biphenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl]-7-chloroquinoline 
• 868662-41-3 4-(5-hydroxy-3-phenyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl)-7-chloroquinoline 
• 868662-42-4 4-[5-hydroxy-3-(4-methylphenyl)-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl]-7-chloroquinoline 
• 868662-45-7 4-[3-(4-bromophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl]-7-chloroquinoline 
• 868662-47-9 4-[5-hydroxy-3-(4-nitrophenyl)-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl]-7-chloroquinoline 
• 868662-43-5 4-[3-(4-fluorophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl]-7-chloroquinoline 
• 934741-64-7 ethyl 1-[(7-chloroquinolin-4-yl)amino]-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate 
• 1198-40-9 4-amino-7-chloroquinoline 

Relevant academic research and scientific papers

In silico/in vitro screening and hit evaluation identified new phenothiazine anti-prion derivatives

Prion diseases or transmissible spongiform encephalopathies (TSEs) are a group of rare neurodegenerative disorders. TSEs are characterized by the accumulation of prions (PrPSc) that represent pathological isoforms of the physiological cellular prion protein PrPC. Although the conversion of PrPC to PrPSc is still not completely understood, blocking this process may lead to develop new therapies. Here, we have generated a pharmacophore model, based on anti-prion molecules reported in literature to be effective in phenotypic assay. The model was used to conduct a virtual screen of commercial compound databases that selected a small library of ten compounds. These molecules were then screened in mouse neuroblastoma cell line chronically infected with prions (ScN2a) after excluding neurotoxicity. 1 has been identified as the therapeutic hit on the basis of the following evidence: chronic treatments of ScN2a cells using 1 eliminate PrPSc loaded in both Western blotting analysis and Real-Time Quaking-Induced Conversion (RT-QuIC) assay. We also proposed the mechanism of action of 1 by which it has the ability to bind PrPC and consequentially blocks prion conversion. Herein we describe the results of these efforts.

Three-component, one-pot synthesis of anthranilamide Schiff bases bearing 4-aminoquinoline moiety as Mycobacterium tuberculosis gyrase inhibitors

An efficient three-component, one-pot protocol is described for the synthesis of biologically interesting 2-(benzylideneamino)-N-(7-chloroquinolin-4-yl)benzohydrazide derivatives from isatoic anhydride, 7-chloro-4-hydrazinylquinoline and aromatic and/or h

Antimicrobial activity and spectral, magnetic and thermal studies of some transition metal complexes of a Schiff base hydrazone containing a quinoline moiety

A series of new copper(II), cobalt(II), nickel(II), manganese(II), iron(III), and uranyl(VI) complexes of the Schiff base hydrazone 7-chloro-4-(benzylidenehydrazo) quinoline (HL) were prepared and characterized. The Schiff base behaves as a monobasic bide

Design, synthesis, and biological evaluation of novel morpholinated isatin–quinoline hybrids as potent anti-breast cancer agents

Keeping in view the emerging need for potent and safer anti-breast cancer agents as well as the pharmacological attributes of isatin, quinolone, and morpholine derivatives, novel hydrazine-linked morpholinated isatin–quinoline hybrids were designed, synthesized, and evaluated as anti-breast cancer agents. The synthesized hybrid compounds were preliminarily screened against two breast cancer cell lines (MCF-7 and MDA-MB-231). Almost all synthetics showed potent inhibitory potential against hormone-positive MCF-7 cells while being inactive against hormone-negative MDA-MB-231 cells. Potent compounds were further evaluated against the L929 (noncancerous skin fibroblast) cell line and found to be highly selective for MCF-7 cells over L929 cells. Cell cycle analysis confirmed that the most potent compound AS-4 (MCF-7: GI50 = 4.36 μM) causes mitotic arrest at the G2/M phase. Due to higher selectivity toward estrogen receptor alpha (ERα)-dependent MCF-7 cells, various binding interactions of AS-4 with ERα are also streamlined, suggesting the capability of AS-4 to completely block ERα. Overall, the study suggests that AS-4 can act as a potential lead for further development of potent and safer anti-breast cancer agents.

4-aminosalicylic acid-based hybrid compounds: Synthesis and in vitro antiplasmodial evaluation

Background: Malaria is a deadly and infectious disease responsible for millions of death worldwide, mostly in the African region. The malaria parasite has developed resistance to the currently used antimalarial drugs, and it has urged researchers to devel

In vitro and in vivo antiplasmodial activity of novel quinoline derivative compounds by molecular hybridization

Chloroquine (CQ) has been the main treatment for malaria in regions where there are no resistant strains. Molecular hybridization techniques have been used as a tool in the search for new drugs and was implemented in the present study in an attempt to pro

Design, synthesis, antimalarial activity and docking study of 7-chloro-4-(2-(substituted benzylidene)hydrazineyl)quinolines

Background: Malaria is a growing infectious disease burden due to the increasing emergence of resistant strains of Plasmodium falciparum. Because of the limited therapeutic effi-cacy of available antimalarial drugs, the development of potent antimalarial drug agents is there-fore an urgent requirement to fight against resistant malaria. Objective: The objective of this work was to develop novel quinoline-baed antimalarial agents that would be active against resistant P. falciparum malaria. Methods: Some 7-chloro-4-(2-(substituted benzylidene)hydrazineyl)quinolines were synthesized for the evaluation of their potential as possible antimalarial agents, particularly against resistant malaria. The antimalarial activity of synthesized compounds was evaluated in vitro against blood-stage parasites of P. falciparum. Further, molecular docking and drug-likeness including ADMET (Absorption, Distribution, Metabolism, Elimination and Toxicity) studies were also carried out using in silico tools. Results: Results reveal the in vitro antimalarial activity of synthesized 7-chloro-4-(2-(substituted benzylidene)hydrazineyl)quinolines against P. falciparum. The docking study investigates the an-timalarial effectiveness of synthesized quinolines as novel plasmepsin 2 inhibitors. Drug-likeness prediction exhibits acceptable drug-likeness and ADMET properties. Conclusion: Based upon our findings, it is concluded that the molecular scaffold of 7-chloro-4-(2-(substituted benzylidene)hydrazineyl)quinolines may be used as a lead structure for further modi-fications in the search of more potent antimalarial drug molecules.

Aryl quinolinyl hydrazone derivatives as anti-inflammatory agents that inhibit TLR4 activation in the macrophages

A series of aryl 7-chloroquinolinyl hydrazone derivatives (3a-u)have been synthesized in 55–76% yield using simple reaction condition. The synthesized compounds were evaluated for their anti-inflammatory activities based on their ability to inhibit pro-inflammatory cytokine secretion from the macrophages after stimulation with lipopolysaccharide (LPS). Three compounds appeared as promising anti-inflammatory agents. The mechanism of inflammatory activity of the potent compound 3e was further investigated using a series of biochemical, molecular and microscopic techniques. Further structure activity relationship (SAR)study was carried out to validate the anti-inflammatory activities of the active compounds. Our experimental data revealed that the active moiety i.e. compound 3e majorly causes inhibition of TLR4 signaling pathway and this appears to be the novel functional attribute of this compound.

Design, synthesis, anticancer, antibacterial, and antifungal evaluation of 4-aminoquinoline-1,3,5-triazine derivatives

A series of 4-aminoquinoline 1,3,5-triazine derivatives were synthesized and evaluated for anticancer activity against cancer cell lines HeLa, MCF-7, HL-60, HepG2 where these derivatives exert significant anticancer activity. The molecules found nontoxic against MCF-12A. The molecules also showed potent inhibition of EGFR-TK as compared to eroltinib in enzyme-based assay. The newly synthesized derivatives were screened for their in vitro antibacterial and antifungal activity against Bacillus subtilis, Bacillus cereus, Staphylococcus aureus, Proteus vulgaris, Escherichia coli, Pseudomonas aeruginosa and Candida albicans, Aspergillus niger, Aspergillus fumigatus using cefixime and fluconazole as standard. Antibacterial screening results suggest that compound 7c showed potent activity against S. aureus, P. aeruginosa, and P. vulgaris. In antifungal screening, compound 7b showed significant activity against A. niger, A. fumigatus and moderate activity against C. albicans.

Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives

N-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes 3a-c. Meanwhile, a similar reagent was applied to 1-[1-(4-substituted phenyl)ethylidene]-2-phenylhydrazines as substrates, which were synthesized from phenylhydrazine hydrochloride and p-substituted acetophenones, and 1,3-diarylpyrazole-4-carbaldehydes 3d-f were observed as a result. Reactions between the aldehydes 3a-f and 7-chloro-4-hydrazinylquinoline 2, obtained from reaction of 4,7-dichloroquinoline 1 and hydrazine hydrate, formed six new hydrazone compounds, namely, 4-{2-[(6-substituted-2-chloroquinolin-3-yl)methylidene]hydrazinyl}-7-chloroquinolines 4a-c and 4-(2-{[3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloroquinolines 4d-f. The chemical structures of all synthesized compounds were elucidated by the analysis of IR, 1H, 13C-NMR, and HRMS spectral data. Additionally, all of the synthesized hydrazones were evaluated in terms of cytotoxic activity against four strains of bacteria and four strains of fungus at several concentrations of substrates. As a result, three of them, 4a-c, possess the good ability as growth inhibitor of Bacillus subtilis and Aspergillus Niger at the concentration of 25 μg/mL and 50 μg/mL, respectively, while compound 4e only shows a cytotoxic activity against Aspergillus Niger at the concentration of 25 μg/mL.