5382-44-5

Usage

Uses

Used in Pharmaceutical Industry:
Quinoline-2-carbohydrazide is used as a building block for the development of drugs due to its wide range of biological activities, including antimicrobial, antifungal, and antiviral properties.
Used in Agrochemical Industry:
Quinoline-2-carbohydrazide is used in the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Materials Science:
Quinoline-2-carbohydrazide is used as a corrosion inhibitor, helping to protect materials from degradation and extending their lifespan.
Used in Analytical Chemistry:
Quinoline-2-carbohydrazide is used as a fluorescent probe for detecting metal ions, enabling the sensitive and selective analysis of various metal species in different samples.

InChI:InChI=1/C10H9N3O/c11-13-10(14)9-6-5-7-3-1-2-4-8(7)12-9/h1-6H,11H2,(H,13,14)

Upstream product

• 19575-07-6 quinoline-2-carboxylic acid methyl ester 
• 50342-01-3 quinolin-2-ylcarbonyl chloride 
• 1436-43-7 quinoline-2-carbonitrile 
• 93-10-7 quinoline-2-carboxylic acid 
• 4491-33-2 ethyl quinoline-2-carboxylate 
• 5470-96-2 quinoline 2-carbaldehyde 
• 91-63-4 2-methylquinoline 

Downstream Products

• 71658-29-2 N'-[(1E)-(2-hydroxyphenyl)methylidene]quinoline-2-carbohydrazide 
• 903178-41-6 N-benzyl-2-(quinolin-2-ylcarbonyl)hydrazincarbothioamide 
• 91872-12-7 C₁₇H₁₄N₄OS 
• 1125771-72-3 C₁₇H₂₀N₄OS 
• 1227872-72-1 N-(4-chlorophenyl)-2-(quinoline-2-carbonyl)hydrazinecarbothioamide 
• 1427219-40-6 C₂₀H₁₈N₄O₂S 
• 1427219-41-7 C₁₈H₁₃FN₄OS 
• 1427219-42-8 C₁₈H₁₃FN₄OS 
• 1427219-43-9 C₁₈H₁₃FN₄OS 
• 1427219-44-0 C₁₈H₁₃ClN₄OS 
• 1427219-45-1 C₁₈H₁₃ClN₄OS 
• 1427219-46-2 C₁₈H₁₃ClN₄OS 
• 1427219-47-3 C₁₈H₁₃BrN₄OS 
• 1427219-48-4 C₁₉H₁₆N₄OS 

Relevant academic research and scientific papers

Syntheses, crystal structures, and spectral characterization of two novel quinolyl substituted triazoles

Two novel quinolyl substituted triazoles, 3-(p-methoxyphenyl)-4-amino-5-(2- quinolyl)-1,2,4-triazole (5) and 3-(p-methoxyphenyl)-4-phenyl-5-(2-quinolyl)-1, 2,4-triazole (6), were successfully synthesized. The compound 5 was synthesized under solvothermal

A novel coordination mode of 4,5-diazafluorene-9-one quinaldinoylhydrazone (HL) to nickel and the crystal structure of [Ni(L)2(Py) 2](H2O)2 (Py = pyridine)

A new ligand 4,5-diazafluorene-9-one quinaldinoylhydrazone (HL) has been designed and synthesized. Ni(II) complex [Ni(L)2(Py) 2](H2O)2 has been prepared by the reaction of HL, pyridine(Py) with the NiSO4 6H2O. The crystal belongs to triclinic system, P-1 space group. The crystallographic data are: a = 10.531(2) ?, b = 11.748(2) ?, c = 10.342(2) ?, α = 115.19(3)°, β = 90.70(3)°, ￡ = 86.46(3)°. The crystal structure data indicated that the Ni(II) ion was coordinated through two oxygen and two nitrogen atoms from two HL ligands and nitrogen atoms from two pyridine molecules. Ni(II) ion is a six-coordination in the center of the octahedron. The crystal was stabilized by the intermolecular π-π stacking between the diazafluorene planes in adjacent molecules.

Application of quinoline 2-site derivative in preparation of medicine for preventing and treating agricultural plant diseases

The invention relates to the technical field of pesticide chemistry, discloses a new application of a quinoline 2-site derivative, and particularly relates to an application of the quinoline 2-site derivative in preparation of drugs for preventing and treating rape sclerotinia sclerotiorum, rhizoctonia solani, tomato botrytis cinerea, wheat fusarium graminearum and magnaporthe oryzae. The compounddisclosed by the invention is a small molecular compound which is easy to synthesize and simple in structure, and is expected to be developed into a novel agricultural bactericide.

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Design and Discovery of Novel Antifungal Quinoline Derivatives with Acylhydrazide as a Promising Pharmacophore

Inspired by natural 2-quinolinecarboxylic acid derivatives, a series of quinoline compounds containing acylhydrazine, acylhydrazone, sulfonylhydrazine, oxadiazole, thiadiazole, or triazole moieties were synthesized and evaluated for their fungicidal activity. Most of these compounds exhibited excellent fungicidal activity in vitro. Significantly, compound 2e displayed the superior in vitro antifungal activity against Sclerotinia sclerotiorum, Rhizoctonia solani, Botrytis cinerea, and Fusarium graminearum with the EC50 values of 0.39, 0.46, 0.19, and 0.18 μg/mL, respectively, and were more potent than those of carbendazim (EC50, 0.68, 0.14, >100, and 0.65 μg/mL, respectively). Moreover, compound 2e could inhibit spore germination of F. graminearum. Preliminary mechanistic studies showed that compound 2e could cause abnormal morphology of cell walls and vacuoles, loss of mitochondrion, increases in membrane permeability, and release of cellular contents. These results indicate that compound 2e displayed superior fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.

Structure based discovery of novel hexokinase 2 inhibitors

Hexokinase 2 (HK2) is over-expressed in most of human cancers and has been proved to be a promising target for cancer therapy. In this study, based on the structure of HK2, we screened over 6 millions of compounds to obtain the lead. A total of 26 (E)-N′-(2,3,4-trihydroxybenzylidene) arylhydrazide derivatives were then designed, synthesized, and evaluated for their HK2 enzyme activity and IC50 values against two cancer cell lines. Most of the 26 target compounds showed excellently in vitro activity. Among them, compound 3j showed the strongest inhibitory effects on HK2 enzyme activity with an IC50 of 0.53 ± 0.13 μM and exhibited the most potent growth inhibition against SW480 cells with an IC50 of 7.13 ± 1.12 μM, which deserves further studies.

Antiaging activity, molecular docking, and prediction of percutaneous absorption parameters of quinoline–hydrazone hybrids

The application of antiaging agents can contribute to the prevention and control of skin photoaging. In the current research, nine quinoline–hydrazone hybrids were synthesized to obtain biologically active compounds as possible antiaging agents. The compounds were tested through a comprehensive in vitro evaluation of antielastase, anticollagenase, and antihyaluronidase activities along with the determination of their potential to quench reactive oxygen species (ROS) by the ORAC method. The selected hybrids were subsequently tested on human dermal fibroblasts (HDF) to reveal possible UVB photoprotective activity. The most potent antiaging protection of all the prepared compounds was shown by the trihydroxylated quinoline–hydrazones 5 and 9, which showed the best collagenase inhibition (IC50 = 39.4 and 45.6 μM, respectively). Compound 5 also showed activity against elastase and hyaluronidase (IC50 = 164.2 and 318.8 μM, respectively). The molecular docking results suggest that the difference of inhibition between 5 and 9 is principally attributed to the hydrogen bonds interactions in the residues His218 and His228, and Zn atom in collagenase, Val216 in elastase and Tyr75 in hyaluronidase. In addition, compounds 5 and 9 were able to significantly protect human skin cells from UVB radiation in vitro. These compounds significantly decreased UVB-induced MMP-1 and ROS production and inhibited the suppression of type I procollagen synthesis in cultured HDF. The in silico dermatopharmacokinetic parameters showed promising results. Therefore, our study presented promising results for antiaging drug discovery, focusing on quinoline–hydrazone hybrids as dual inhibitors of skin aging-related enzymes, antioxidants, and inhibitors of the biological effects of UVB irradiation.

Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus

Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus.

A highly selective and sensitive turn-on probe for aluminum(III) based on quinoline Schiff's base and its cell imaging

A reversible Schiff's base fluorescence probe for Al3+, (3,5-dichloro-2- hydroxybenzylidene) quinoline-2-carbohydrazide (QC), based on quinoline derivative has been designed, synthesized and evaluated. The QC exhibited a high sensitivity and se

Pyridine methylamino dithio formic acid heteroaryl naphthenic base ester compound and preparation method and application thereof

The invention relates to a compound as shown in a general formula (I) or pharmaceutically acceptable salts or solvates thereof, and relates to a preparation method of the compound and application thereof in preparing anti-tumor drugs. Please see the general formula (I) in the description.