4779-54-8

Usage

Uses

Used in Pharmaceutical Industry:
2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID HYDRAZIDE is used as an intermediate in the production of pharmaceuticals for its potential role in drug development. Its anti-inflammatory and anti-tumor properties make it a candidate for the creation of medications targeting various diseases and conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID HYDRAZIDE is utilized as a key component in the synthesis of complex organic molecules, taking advantage of its reactive nature to form a variety of compounds.
Used in Medicinal Chemistry Research:
2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID HYDRAZIDE is employed as a subject of study in medicinal chemistry research, where its biological activities and potential applications in drug development are explored and expanded upon.
Used in Industrial and Agricultural Applications:
Due to its anti-fungal and anti-bacterial activities, 2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID HYDRAZIDE is used in various industrial and agricultural applications, such as in the development of fungicides and bactericides, contributing to the control of microbial growth and the preservation of materials and crops.

InChI:InChI=1/C16H13N3O/c17-19-16(20)13-10-15(11-6-2-1-3-7-11)18-14-9-5-4-8-12(13)14/h1-10H,17H2,(H,19,20)

Upstream product

• 4546-48-9 methyl 2-phenylquinoline-4-carboxylate 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 132-60-5 cinchophen 
• 4420-46-6 ethyl 2-phenylquinoline-4-carboxylate 
• 98-86-2 acetophenone 

Downstream Products

• 16219-60-6 NCI-130847 
• 55542-52-4 2-phenyl-quinoline-4-carboxylic acid-(3-nitro-benzylidenehydrazide) 
• 5445-69-2 2-phenyl-quinoline-4-carboxylic acid-{4-[bis-(2-chloro-ethyl)-amino]-benzylidenehydrazide} 
• 83185-22-2 2-Phenyl-quinoline-4-carboxylic acid [1-[5-(2-hydroxy-adamantan-2-yl)-thiophen-2-yl]-meth-(E)-ylidene]-hydrazide 
• 313241-28-0 4-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylquinoline 

Relevant academic research and scientific papers

Design, synthesis, and antibacterial evaluation of new quinoline-1,3,4-oxadiazole and quinoline-1,2,4-triazole hybrids as potential inhibitors of DNA gyrase and topoisomerase IV

DNA gyrase and topoisomerase IV (topo IV) inhibitors are among the most interesting antibacterial drug classes without antibacterial pipeline representative. Twenty-four new quinoline-1,3,4-oxadiazole and quinoline-1,2,4-triazole hybrids were developed and tested against DNA gyrase and topoisomerase IV from Escherichia coli and Staphylococcus aureus. The most potent compounds 4c, 4e, 4f, and 5e displayed an IC50 of 34, 26, 32, and 90 nM against E. coli DNA gyrase, respectively (novobiocin, IC50 = 170 nM). The activities of 4c, 4e, 4f, and 5e on DNA gyrase from S. aureus were weaker than those on E. coli gyrase. Compound 4e showed IC50 values (0.47 μM and 0.92 μM) against E. coli topo IV and S. aureus topo IV, respectively in comparison to novobiocin (IC50 = 11, 27 μM, respectively). Antibacterial activity against Gram-positive and Gram-negative bacterial strains has been studied. Some compounds have demonstrated superior antibacterial activity to ciprofloxacin against some of the bacterial strain studied. The most active compounds in this study showed no cytotoxic effect with cell viability>86%. Finally, a molecular docking analysis was performed to investigate the binding mode and interactions of the most active compounds to the active site of DNA gyrase and topoisomerase IV (topo IV) enzymes.

Design and synthesis of novel quinoline/chalcone/1,2,4-triazole hybrids as potent antiproliferative agent targeting EGFR and BRAFV600E kinases

New quinoline / chalcone hybrids containing 1,2,4-triazole moiety have been designed, synthesized and their structures elucidated and confirmed by various spectroscopic techniques. The designed compounds showed moderate to good activity on different NCI 60 cell lines in a single-dose assay with a growth inhibition rate ranging from 50% to 94%. Compounds 7b, 7d, 9b, and 9d were the most active compounds in most cancer cell lines with a growth inhibition percent between 77% and 94%. Newly synthesized hybrids were evaluated for their anti-proliferative activity against a panel of four human cancer cell lines. Compounds 7a, 7b, 9a, 9b, and 9d showed promising antiproliferative activities. These compounds were further tested for their inhibitory potency against EGFR and BRAFV600E kinases with erlotinib as a reference drug. The molecular docking study of compounds 7a, 7b, 9a, 9b, and 9d revealed nice fitting into the active site of EGFR and BRAFV600E kinases. Compounds 7b, 9b, and 9d displayed the highest binding affinities and similar binding pattern to those of erlotinib.

The remarkable selectivity of the 2-arylquinoline-based acyl hydrazones toward copper salts: Exploration of their catalytic applications in the copper catalysed: N -arylation of indole derivatives and C1-alkynylation of tetrahydroisoquinolines via the A

Ligands promoting copper-catalysed coupling reactions have received increasing attention because of their ability to enhance the catalytic activity of copper, making these reactions applicable in different fields such as drugs, pharmaceutically interestin

New quinoline/1,2,4-triazole hybrids as dual inhibitors of COX-2/5-LOX and inflammatory cytokines: Design, synthesis, and docking study

A novel series of 19 quinoline/1,2,4-triazole hybrid 6a-i and 7a-j was synthesized and evaluated in vitro as dual COX-2/5-LOX inhibitors. Compounds 6e, 6i, and 7e displayed the highest potency and selectivity for inhibiting COX-2 activity (IC50 = 7.25, 8.13, and 8.48 nM, respectively; selectivity index (COX-1/COX-2) = 44.89, 30.30, and 33.47, respectively) in comparison to celecoxib (COX-2 IC50 = 42.60 nM; selectivity index (SI) = 8.05). The anti-inflammatory activity of the newly synthesized compounds was further examined in vivo using a carrageenan induced paw edema assay. Interestingly, the in vitro findings of the COX inhibitory assay were consistent with the in vivo assay. Moreover, 6e, 6i, and 7e showed a substantial reduction in serum concentrations of PGE2, TNF-α, IL-6. Molecular docking analysis of compounds 6e, 6f, 6i, 7e, and 7f revealed high binding affinities toward COX-2 compared to COX-1, which was matched with the experimental results. In addition, these compounds exhibited different binding orientations into the active site of COX-2, which were dependent on the type of substitutions on N4 of the triazole ring. Among the tested derivatives, compounds 6e, 6i and 7e which showed high selectivity to COX-2, exhibited hydrogen bonding interactions with key amino acids in COX-2 such as Arg120, Arg513, and/or Glu524. In addition, the tested compounds also showed multiple hydrogen bonds with the Arg101, Val110, Arg138 or His130 in 5-LOX. These findings show, taken together, that those derivatives are good leads to potential anti-inflammatory agents with lowest gastric damage.

SMALL MOLECULE ENTEROVIRUS INHIBITORS AND USES THEREOF

This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quinoline (or similar) structure which function as antagonists of androgen receptor activity, and their use as therapeutics for the treatment of cancer (e.g., castration-resistant prostate cancer) and other conditions characterized with androgen receptor activity and/or androgen receptor expression.

NO-releasing STAT3 inhibitors suppress BRAF-mutant melanoma growth

Constitutive activation of STAT3 can play a vital role in the development of melanoma. STAT3-targeted therapeutics are reported to show efficacy in melanomas harboring the BRAFV600E mutant and also in vemurafenib-resistant melanomas. We designed and synthesized a series of substituted nitric oxide (NO)-releasing quinolone-1,2,4-triazole/oxime hybrids, hypothesizing that the introduction of a STAT3 binding scaffold would augment their cytotoxicity. All the hybrids tested showed a comparable level of in vitro NO production. 7b and 7c exhibited direct binding to the STAT3-SH domain with IC50 of ～ 0.5 μM. Also, they abrogated STAT3 tyrosine phosphorylation in several cancer cell lines, including the A375 melanoma cell line that carries the BRAFV600E mutation. At the same time, they did not affect the phosphorylation of upstream kinases or other STAT isoforms. 7c inhibited STAT3 nuclear translocation in mouse embryonic fibroblast while 7b and 7c inhibited STAT3 DNA-binding activity in the A375 cell line. Their anti-proliferating activity is attributed to their ability to trigger the production of reactive oxygen species and induce G1 cell cycle arrest in the A375 cell line. Interestingly, 7b and 7c showed robust cell growth suppression and apoptosis induction in two pairs of BRAF inhibitor-na?ve (-S) and resistant (-R) melanoma cell lines containing a BRAF V600E mutation. Surprisingly, MEL1617-R cells that are known to be more resistance to MEK inhibition by GSK1120212 than MEL1617-S cells exhibit a similar response to 7b and 7c.

Synthesis and Anticonvulsant Potential of Some New 4-[5-substituted-[1,3,4] oxadiazole-2-yl]-2-phenylquinolines

A new series of 4-[5-substituted-[1, 3, 4] oxadiazole-2-yl]-2-phenylquinolines was synthesized and evaluated for their anticonvulsant potential using minimal electroshock and subcutaneous pentylenetetrazole animal model methods. The structures of compounds were elucidated by elemental analysis (C, H, N) and spectral data (infrared,1H nuclear magnetic resonance, and Mass). Locomotor behavior of compounds was evaluated by actophotometer, and toxicology study was also performed to evaluate their significance as required anticonvulsant compounds.

New quinoline/chalcone hybrids as anti-cancer agents: Design, synthesis, and evaluations of cytotoxicity and PI3K inhibitory activity

A series of quinoline-chalcone hybrids was designed as potential anti-cancer agents, synthesized and evaluated. Different cytotoxic assays revealed that compounds experienced promising activity. Compounds 9i and 9j were the most potent against all the cell lines tested with IC50 = 1.91–5.29 μM against A549 and K-562 cells. Mechanistically, 9i and 9j induced G2/M cell cycle arrest and apoptosis in both A549 and K562 cells. Moreover, all PI3K isoforms were inhibited non selectively with IC50s of 52–473 nM when tested against the two mentioned compounds with 9i being most potent against PI3K-γ (IC50 = 52 nM). Docking of 9i and 9j showed a possible formation of H-bonding with essential valine residues in the active site of PI3K-γ isoform. Meanwhile, Western blotting analysis revealed that 9i and 9j inhibited the phosphorylation of PI3K, Akt, mTOR, as well as GSK-3β in both A549 and K562 cells, suggesting the correlation of blocking PI3K/Akt/mTOR pathway with the above antitumor activities. Together, our findings support the antitumor potential of quinoline-chalcone derivatives for NSCLC and CML by inhibiting the PI3K/Akt/mTOR pathway.

Discovery of Quinoline Analogues as Potent Antivirals against Enterovirus D68 (EV-D68)

Enterovirus D68 (EV-D68) is an atypical nonpolio enterovirus that mainly infects the respiratory system of humans, leading to moderate-to-severe respiratory diseases. In rare cases, EV-D68 can spread to the central nervous system and cause paralysis in infected patients, especially young children and immunocompromised individuals. There is currently no approved vaccine or antiviral available for the prevention and treatment of EV-D68. In this study, we aimed to improve the antiviral potency and selectivity of a previously reported EV-D68 inhibitor, dibucaine, through structure-activity relationship studies. In total, 60 compounds were synthesized and tested against EV-D68 using the viral cytopathic effect assay. Three compounds 10a, 12a, and 12c were identified to have significantly improved potency (EC50 180) compared with dibucaine against five different strains of EV-D68 viruses. These compounds also showed potent antiviral activity in neuronal cells, such as A172 and SH-SY5Y cells, suggesting they might be further developed for the treatment of both respiratory infection as well as neuronal infection.

Convergent synthesis and cytotoxicity of novel trifluoromethyl-substituted (1H-pyrazol-1-yl)(quinolin-4-yl) methanones

A convergent synthesis of a series of 16 new polysubstituted (5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl)(quinolin-4-yl)methanones, starting from isatin and alky(aryl/heteroaryl) ketones, is described. The diheteroaryl methanones were achieved at yields of up to 95% by a [3?+?2] cyclocondensation reaction involving 4-alkyl(aryl/heteroaryl)-4-methoxy-1,1,1-trifluorobut-3-en-2-ones (by two-step reaction) and 2-alkyl(aryl/heteroaryl)-4-carbohydrazides (by three-step reaction). Subsequently, representative dehydrated heterocyclic derivatives were obtained from the respective 5-hydroxy-2-pyrazoline moieties by classical dehydration reactions, which resulted in the corresponding (5-(trifluoromethyl)-1H-pyrazol-1-yl)(quinolin-4-yl)methanones (three examples) at yields of 69–82%. The subsequent cytotoxicity evaluation showed that compounds with aromatic groups at the 2-position of the quinoline and a methyl moiety at the 3-position of the pyrazole have significant cytotoxicity in human leukocytes at high concentrations (200?μM).