100874-12-2

Upstream product

• 144294-89-3 4'-bromo-1H-2-phenyl-3-hydroxy-4-oxoquinoline 
• 6127-49-7 2-(4-bromophenyl)indole 
• 118-92-3 anthranilic acid 
• 586-75-4 4-chlorobenzoyl chloride 
• 18600-53-8 2-(4-bromophenyl)-4H-benzo[d][1,3]oxazine-4-one 
• 2159-40-2 2-(4-bromobenzoyl)benzoic acid 

Downstream Products

• 18600-53-8 2-(4-bromophenyl)-4H-benzo[d][1,3]oxazine-4-one 

Relevant academic research and scientific papers

Substituent effects on hydrogen bonding of aromatic amide-carboxylate

N-(p-benzoyl)-anthranilic acid (BAA) derivatives have been synthesized with different substituents (X: Br, Cl, OCH3, CH3), and their crystal structures have been analyzed in order to understand the variations in their molecular geome

The base-catalyzed oxygenation of quinoline derivatives

The base-catalyzed oxygenation of 1H-2-phenyl-3-hydroxy-4-oxoquinoline leads to cleavage products derived from either an endoperoxide or a 1,2-dioxetan intermediate. A persistent 1H-2-phenyl-3-oxy-4-oxoquinoline radical could also be detected by EPR in the reaction mixture.

A straightforward TBHP-mediated synthesis of 2-amidobenzoic acids from 2-arylindoles and their antimicrobial activity

A simple and highly efficient strategy has been developed for the synthesis of 2-amidobenzoic acids through the tert-butyl hydroperoxide (TBHP)-mediated oxygenation and sequential ring opening of 2-arylindoles in a one-pot fashion under metal-free aerobic conditions. The developed synthetic protocol is operationally simple, tolerates a wide range of functional groups, and is amenable to the gram-scale. Radical trapping experiments revealed that the reaction involves a radical pathway. The synthesized compounds (2a-s) were tested for in vitro antimicrobial activity. Among all screened compounds, 2d showed the maximum antibacterial activity against P. aerugunosa (ZOI = 17 mm, MIC = 32 μg mL-1) and compounds 2d and 2p showed the maximum (32 μg mL-1) antifungal activity against A. flavus and C. albicans.

Kinetics and mechanism of the base-catalyzed oxygenation of 1H-2-phenyl-3-hydroxy-4-oxoquinolines in DMSO/H2O

The oxygenation of 4′-substituted 1H-2-phenyl-3-hydroxy-4- oxoquinolines (PhquinH2) in a DMSO/H2O (50/50) solution leads to the cleavage products at the C2-C3 bond in about 75% yield at room temperature. The oxygenation, deduced from the product compositions, has two main pathways, one proceeding via an endoperoxide leading to CO-release, and the other through a 1,2-dioxetane intermediate without CO-loss. The reaction is specific base-catalyzed and the kinetic measurements resulted in the rate law -a...?[PhquinH2]/a...?t=kOH - [OH-] [PhquinH2] [O2]. The rate constant, activation enthalpy, and entropy at 303.16 K are as follows: kOH-=(2.42±0.03)×103mol -2L2s-1; ΔG?=73. 13±4.02 kJ mol-1; ΔH?=70.60±4. 04 kJ mol-1; ΔS?=-28±2 J mol -1 K-1. The reaction fits a Hammett linear free energy relationship for 4′-substituted substrates, and electron-releasing groups make the oxygenation reaction faster (ρ=-0.258). The EPR spectrum of the reaction mixtures showed the presence of the organic radical 1H-2-phenyl-3-oxyl-4-oxoquinoline and superoxide ion due to single electron transfer from the carbanion to dioxygen. The pathway via 1,2-dioxetane could be proved by chemiluminescence measurements.

Bio-inspired flavonol and quinolone dioxygenation by a non-heme iron catalyst modeling the action of flavonol and 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases

The mononuclear complex, FeIII(O-bs)(salen) (salenH2 = 1,6-bis(2-hydroxyphenyl)-2,5-diaza-hexa-1,5-diene; O-bsH = O-benzoylsalicylic acid) was synthesized as synthetic enzyme-depside complex, and characterized by spectroscopic methods and X-ray crystal analysis. The dioxygenation of flavonol (flaH) and 3-hydroxy-4-quinolone (quinH2) derivatives in the presence of catalytic amounts of FeIII(O-bs)(salen) results in the oxidative cleavage of the heterocyclic ring to give the corresponding O-benzoylsalicylic and anthranilic acid derivatives with concomitant release of carbon monoxide. These reactions can be regarded as biomimetic functional models with relevance to the iron-containing flavonol and the cofactor-independent 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases.

A new synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by cyanuric chloride cyclodehydration of N-benzoyl- and N-acylanthranilic acids

A new and a convenient method for the synthesis of aryl- and alkyl-2-substituted 4H-3,1-benzoxazin-4-ones by cyclodehydration of N-benzoyl- and N-acylanthranilic acid by cyanuric chloride is described.

AMIDE DERIVATIVES AND THEIR USE AS CHLORIDE CHANNEL BLOCKERS

The present invention relates to novel amide derivatives useful as chloride channel blockers. In other aspects the invention relates to the use of these compounds in a method for therapy, such as for the treatment of bone metabolic diseases, diseases resp