6633-62-1

Usage

Uses

Used in Antiviral Applications:
NSC42124 is used as an antiviral agent for its activity against herpes simplex virus. It is being studied for its potential to inhibit viral replication and protein synthesis, making it a promising candidate for the development of new antiviral therapies.
Used in Cancer Therapy:
NSC42124 is used as an inhibitor of cancer cell growth, with research indicating its potential to be a therapeutic agent in the treatment of various types of cancer. Further studies are needed to explore its efficacy and safety profile in this application.
Used in Enhancing Antiviral Activity:
NSC42124 is used to enhance the activity of other antiviral agents, potentially improving the effectiveness of existing treatments and providing a new approach to combat viral infections.
Used in Pharmaceutical Research:
NSC42124 is used in pharmaceutical research to better understand its mechanism of action and therapeutic potential. Further studies are required to fully elucidate its safety profile and explore its applications in various medical fields.

InChI:InChI=1/C16H10ClNO2/c17-11-6-7-14-12(8-11)13(16(19)20)9-15(18-14)10-4-2-1-3-5-10/h1-9H,(H,19,20)

Upstream product

• 17630-76-1 5-chloroindole 2,3-dione 
• 98-86-2 acetophenone 
• 100-52-7 benzaldehyde 
• 106-47-8 4-chloro-aniline 
• 127-17-3 2-oxo-propionic acid 
• 65798-06-3 N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide 

Downstream Products

• 174636-77-2 6-chloro-2-phenyl-quinoline-4-carbonyl chloride 
• 1373425-27-4 C₂₂H₁₄Cl₂N₂O 
• 181048-21-5 2-phenyl-6-chloroquinoline-4-carbonylguanidine 
• 60301-56-6 6-chloro-2-phenylquinoline 

Relevant academic research and scientific papers

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.

A green synthesis of quinoline-4-carboxylic derivatives using p-toluenesulfonic acid as an efficient organocatalyst under microwave irradiation and their docking, molecular dynamics, ADME-Tox and biological evaluation

P-Toluenesulfonic acid, being an efficient, nonhazardous, and fast accessible organocatalyst, was used for the preparation of quinoline-4-carboxylic acid derivatives via a one-pot three-component reaction of aromatic benzaldehyde, substituted aniline, and pyruvic acid under microwave irradiation. After completion of the reaction, the pure products were isolated by column chromatography. Here, to achieve the desired synthesis, various catalytic and solvent conditions were applied to perform a comparison study. We are using higher yield, simple work-up process, avoiding the use of hazardous organic solvents, short reaction time and higher advantages of the present protocol in the study. Biological activities of synthesized compounds were tested against various antibacterial, antifungal, antimalarial, and antituberculosis strains. Compounds 4a and 4c (MIC 50 μg/mL) and compounds 4d and 4n (MIC 62.5 μg/mL) were found active against the Escherichia coli strain, compounds 4c and 4p (MIC 25 μg/mL) were found active against the Staphylococcus aureus strain, and compounds 4c and 4d were found active against the Plasmodium falciparum strain. Molecular docking revealed that ligands and proteins fitted exactly in the binding pocket and had significant correlation with the biological activity. We have also tested molecular dynamics and ADME-Tox parameters for the synthesized compounds.

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.

A computational study of molecular interactions and in vitro antibacterial activity of 6-substituted quinoline carboxylic acid derivatives as DNA gyrase inhibitors

Background: Quinoline nucleus is found in a vast range of biologically active compounds. The quinoline group of compounds which are anti-infective in nature are found to act by inhibiting different enzymes. DNA gyrase being one of the more common site of

Design, synthesis and biological evaluation of 2-phenylquinoline-4-carboxamide derivatives as a new class of tubulin polymerization inhibitors

A novel series of 2-phenylquinoline-4-carboxamide derivatives was synthesized, characterized and evaluated for its antiproliferative activity against five cancer cell lines, Hela, SK-OV-3, HCT116, A549 and MDA-MB-468, and a normal human fetal lung fibroblastic cell line, MRC-5. Among them, compound 7b displayed potent cytotoxic activity in vitro against SK-OV-3 and HCT116 cell lines with IC50 values of 0.5 and 0.2 μM, respectively. In general, the antiproliferative activity was correlated with the binding property of the colchicine binding site and inhibitory effect on tubulin polymerization. In addition, immunofluorescence and flow cytometry analysis revealed that selected compounds caused disruption of the mitotic spindle assembly and G2/M phase arrest of the cell cycle, which correlated with proliferation inhibitory activity. Molecular docking analysis demonstrated the interaction of 7b at the colchicine binding site of tubulin. These results indicate these compounds are promising inhibitors of tubulin polymerization for the potent treatment of cancer.

Facile synthesis of 2-phenylquinoline-4-carboxamide derivatives with variant structural features

The quinoline scaffold is an important class of heterocyclic compounds that possesses diverse chemotherapeutic activities. Thus, the 2-phenylquinoline-4- carboxamide derivatives containing a variety of moieties, such as 2-(2-furanyl)-1,3,4-oxadiazole, N-(2-methylphenyl)-4-(3-pyridinyl)-2- pyrimidinamine, 4,4′-bithiazole, purine, adamantine and resorcinol, have been designed and synthesized via Suzuki coupling, acid-base coupling and other typical reactions.

Design, synthesis and evaluation of quinoline-based small molecule inhibitor of stat3

As STAT3 has been validated as an anticancer target, its inhibitors have been shown to possess therapeutic promise for the treatment of human cancers. To identify novel and selective STAT3 inhibitors, a virtual screening based on the STAT3 SH2 domain was performed and a small molecule, 2-phenylquinoline-4- carboxylic acid (5a), with an inhibition constant Ki value of 17.53 iM to STAT3 was discovered. On this basis, the derivatives of 5a including esters, amides and dimers were synthesized. The bioactivity and inhibitory selectivity of the derivatives were assayed using human breast cancer cell lines, MDA-MB-468 and MCF-7. Among the derivatives, 5c and 9b showed the most potent inhibitory activity with a good selectivity, and also inhibited STAT3 protein level of MDA-MB-468 cells. The results demonstrated a successful application of virtual screening for lead discovery. Compound 9b might be an effective STAT3 inhibitor lead for the further development of antitumor agents.

One-pot synthesis of quinoline-4-carboxylic acid derivatives in water: Ytterbium perfluorooctanoate catalyzed Doebner reaction

Ytterbium perfluorooctanoate [Yb(PFO)3] has been proved to be an efficient catalyst for Doebner reaction of pyruvic acid, aldehydes and amines under mild conditions in water to afford quinoline-4-caboxylic acid derivatives with three component one-pot method in good yields. The process is operationally simple and environmentally benign and the catalyst has readily been recycled for several times with consistent activity. Furthermore, a plausible mechanism for this transformation is also presented.

Microwave-assisted Doebner synthesis of 2-phenylquinoline-4-carboxylic acids and their antiparasitic activities

(Chemical Equation Presented) A series of twelve substituted 2-phenylquinoline-4-carboxylic acids analogous to antimalarial and antileishmanial natural products was developed via the Doebner reaction employing microwave irradiation (MW). The products were obtained in moderate yields in 0.5-3 minutes and nine of them were evaluated in vitro against the parasites responsible for malaria, leishmaniasis and trypanosomiasis diseases (WHO, Switzerland). Four compounds exhibited activity against Trypanosoma cruzi and another two resulted active against Plasmodium falciparum and Leishmania infantum, respectively.