181048-56-6

Basic information

• Product Name: 8-CHLORO-2-PHENYLQUINOLINE-4-CARBOXYLIC ACID
• Synonyms: ART-CHEM-BB B013654;8-CHLORO-2-PHENYLQUINOLINE-4-CARBOXYLIC ACID;8-chloro-2-phenyl-cinchoninic acid;AE-641/11229057;NSC400893;Oprea1_051222;STK255770;4-QUINOLINECARBOXYLIC ACID,8-CHLORO-2-PHENYL-
• CAS NO: 181048-56-6
• Molecular Formula: C₁₆H₁₀ClNO₂
• Molecular Weight: 283.71
• Mol File: 181048-56-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 8-CHLORO-2-PHENYLQUINOLINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 8-CHLORO-2-PHENYLQUINOLINE-4-CARBOXYLIC ACID(181048-56-6)
• EPA Substance Registry System: 8-CHLORO-2-PHENYLQUINOLINE-4-CARBOXYLIC ACID(181048-56-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 181048-56-6(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 95-51-2 o-chloroaniline 
• 7477-63-6 7-chloroisatin 
• 98-86-2 acetophenone 

Downstream Products

• 500775-82-6 8-chloro-2-phenyl-quinoline-4-carbonyl chloride 
• 181048-23-7 2-phenyl-8-chloroquinoline-4-carbonylguanidine 
• 6338-25-6 2-bromo-1-(8-chloro-2-phenyl-[4]quinolyl)-ethanol 
• 6338-21-2 2-bromo-1-(8-chloro-2-phenyl-[4]quinolyl)-ethanone 

Relevant articles and documents

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.

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.