59661-86-8

Basic information

• Product Name: 2-Phenylquinoline-4-carboxylicacidchloride
• Synonyms: 4-QUINOLINECARBONYL CHLORIDE,2-PHENYL-
• CAS NO: 59661-86-8
• Molecular Formula: C₁₆H₁₀ClNO
• Molecular Weight: 267.71
• Mol File: 59661-86-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Phenylquinoline-4-carboxylicacidchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylquinoline-4-carboxylicacidchloride(59661-86-8)
• EPA Substance Registry System: 2-Phenylquinoline-4-carboxylicacidchloride(59661-86-8)

Safety Data

• Hazardous Substances Data: 59661-86-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenylquinoline-4-carboxylic acid chloride is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
2-Phenylquinoline-4-carboxylic acid chloride is used as an intermediate in the production of agrochemicals, aiding in the creation of effective pesticides and other agricultural chemicals.
Used in Organic Chemistry Research:
2-Phenylquinoline-4-carboxylic acid chloride is used as a versatile building block and reagent in organic chemistry, enabling the synthesis of a wide range of functionalized quinoline derivatives for various applications.
Used in Biological and Medicinal Applications:
2-Phenylquinoline-4-carboxylic acid chloride is used as a starting material in research laboratories for the preparation of novel compounds with potential biological and medicinal properties.

Upstream product

• 132-60-5 cinchophen 
• 98-86-2 acetophenone 
• 91-56-5 indole-2,3-dione 
• 62-53-3 aniline 
• 42366-35-8 hydroxyimino-N-phenylacetamide 

Downstream Products

• 1752-99-4 2-phenyl-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-quinoline-4-carboxamide 
• 121331-01-9 1,2-diphenyl-4-(2-phenyl-quinoline-4-carbonyl)-pyrazolidine-3,5-dione 
• 122542-03-4 2-phenyl-quinoline-4-carboxylic acid-(4-butyl-5-oxo-1,2-diphenyl-2,5-dihydro-1H-pyrazol-3-yl ester) 
• 524-34-5 2-phenyl-quinoline-4-carboxylic acid allyl ester 
• 606-36-0 (2-phenyl-quinoline-4-carbonyl)-carbamic acid ethyl ester 
• 99670-95-8 N-(2-phenyl-quinoline-4-carbonyl)-glycine ethyl ester 
• 137117-06-7 phenyl(2-phenylquinolin-4-yl)methanone 

Relevant articles and documents

Liquid crystalline cholesterol-based ortho-palladated curcumin complexes as multifunctional biomaterials

Mononuclear ortho-palladated complexes containing 2-phenylquinoline ligand functionalized with a chiral entity and a biologically active O,O chelated ligand have been synthesized and fully characterized. The evaluation of the liquid crystalline properties

X-ray structure of an amide-appended chloromercurated derivative of 2-phenylquinoline

Reaction of the morpholine amide derivative of 2-phenyl-4-quinolinecarboxylic acid with mercury(II) acetate and lithium chloride results in chloromercuration at the ortho position on the phenyl ring; the complex was characterised by ESI mass spectrometry

Phosphorescent, Cyclometalated Cinchophen-Derived Platinum Complexes: Syntheses, Structures, and Electronic Properties

The syntheses of nine new monometallic heteroleptic platinum complexes [Pt(L1-4)(acac)], [Pt(L1)(hmacac/hfacac)], [PtCl(L1)(py)], [Pt(L1)(8-Q)], [Pt(L1)(bpy)](PF6) (where L1 = 2-phenyl-4-ethyl-quinolinecarboxylate; L2/L3 = N-functionalization o

Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.

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.

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.

Phenylquinoline transient receptor potential vanilloid 1 antagonists for the treatment of pain: Discovery of 1-(2-phenylquinoline-4-carbonyl)-N-(4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide

Reported herein is the design, synthesis, and pharmacologic characterization of a class of TRPV1 antagonists constructed on a phenylquinoline platform that evolved from Cinchophen lead. This design composes three sections: a phenylquinoline headgroup attached to an aliphatic carboxamides, which is tethered at a phenyl tail group. Optimization of this design led to the identification of 37, comprising a pyrrolidine linker and a trifluoromethyl–phenyl tail. In the TRPV1 functional assay, using cells expressed hTRPV1, 37 antagonized capsaicin-induced Ca2+ influx, with an IC50 value of 10.2 nM. In the complete mice analgesic model, 37 exhibited better antinociceptive activity than the positive control BCTC in diverse pain models. All of these results suggested that 37 could be considered as a lead candidate for the further development of antinociceptive drugs.

Combined Acylselenourea-Diselenide Structures: New Potent and Selective Antitumoral Agents as Autophagy Activators

A series of 16 new diselenide-acylselenourea conjugates have been designed following the fragment-based drug strategy. Compound in vitro cytotoxic potential was evaluated against six human cancer cell lines and two nonmalignant derived cell lines with the aim of determining their potency and selectivity. Nine derivatives exhibited GI50 values under 10 μM in at least four cancer cell lines. A clear gap situated phenyl substitution over heterocyclic moieties in terms of selectivity. Among carbocyclic compounds, derivatives 2 and 7 significantly inhibited cell growth of breast adenocarcinoma cells with GI50 values of 1.30 and 0.15 nM, respectively, with selectivity indexes 12 and 121 times higher than those obtained for doxorubicin. Preliminary mechanistic studies indicated that compounds 2 and 7 induce cell cycle arrest and autophagy-dependent cell death evidenced by the blockage of cell death with pretreatment with wortmannin or chloroquine and confirmed by the upregulation of the markers Beclin1 and LC3B in MCF-7 cells.

Decarbonylative Methylation of Aromatic Esters by a Nickel Catalyst

A Ni-catalyzed decarbonylative methylation of aromatic esters was achieved using methylaluminums as methylating agents. Dimethylaluminum chlorides uniquely worked as the methyl source. Because of the Lewis acidity of aluminum reagents, less reactive alkyl esters could also undergo the present methylation. By controlling the Lewis acidity of aluminum reagents, a chemoselective decarbonylative cross-coupling between alkyl esters and phenyl esters was successful.

Decarbonylative Diaryl Ether Synthesis by Pd and Ni Catalysis

Because diaryl ethers are present as an important motif in pharmaceuticals and natural products, extensive studies for the development of novel methods have been conducted. A conventional method for the construction of the diaryl ether moiety is the intermolecular cross-coupling reaction of aryl halides and phenols with a copper or palladium catalyst. We developed a catalytic decarbonylative etherification of aromatic esters using a palladium or nickel catalyst with our enabling diphosphine ligand to give the corresponding diaryl ethers. The present reaction can be conducted on gram scale in excellent yield. This reaction not only functions in an intramolecular setting but also allows for a cross-etherification using other phenols.