654655-68-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Benzyl-6-bromo-2-chloroquinoline is used as an intermediate in the synthesis of (αS,βR)-Bedaquiline (B119540), a diarylquinoline derivative that acts as a potent mycobacterial inhibitor. Bedaquiline has demonstrated significant promise as a potential drug in the treatment of tuberculosis, a disease that poses a significant global health challenge. 3-benzyl-6-bromo-2-chloroquinoline's ability to inhibit mycobacterial growth makes it a valuable asset in the development of new antitubercular drugs.
In the synthesis of Bedaquiline, 3-benzyl-6-bromo-2-chloroquinoline plays a critical role, as its unique structural features allow for the formation of the desired diarylquinoline scaffold. This scaffold is essential for the biological activity of Bedaquiline, which targets the ATP synthase of mycobacteria, thereby inhibiting their energy production and growth.
Furthermore, the development of 3-benzyl-6-bromo-2-chloroquinoline as a synthetic intermediate highlights its potential for use in the creation of other diarylquinoline-based compounds with diverse applications in the pharmaceutical industry. These compounds may exhibit a range of biological activities, including antibacterial, antifungal, and anticancer properties, making 3-benzyl-6-bromo-2-chloroquinoline a versatile building block for drug discovery and development.

Upstream product

• 75-05-8 acetonitrile 
• 316146-27-7 N-(4-bromophenyl)-3-phenylpropanamide 
• 645-45-4 hydrocinnamic acid chloride 
• 106-40-1 4-bromo-aniline 
• 105479-98-9 ethyl 2-(acetoxy(phenyl)methyl)acrylate 
• 37442-45-8 ethyl 2-(hydroxy(phenyl)methyl)propenoate 
• 924658-20-8 2-[(4-bromo-phenylamino)-phenyl-methyl]-acrylic acid ethyl ester 
• 924633-09-0 3-benzyl-6-bromo-1H-quinolin-2-one 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 654655-70-6 intermediate compound 4 
• 654655-69-3 3-benzyl-6-bromo-2-methoxyquinoline 
• 1173292-03-9 3-benzyl-6-bromo-2-(1H-imidazol-1-yl)-quinoline 
• 1228594-68-0 (1S,2R)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-(6-bromo-2-chloro-quinolin-3-yl)-butan-2-ol 
• 1228594-69-1 (1R,2S)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-(6-bromo-2-chloro-quinolin-3-yl)-butan-2-ol 
• 654653-93-7 (6-bromo-2-memoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol 
• 654653-93-7 rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol 
• 843663-66-1 bedaquiline 
• 654655-80-8 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol 
• 924632-90-6 (±)-3-bromo-3-(bromo(phenyl)methyl)-2-methoxyquinoline 
• 1032468-71-5 C₃₆H₃₇BrN₄O 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF BEDAQUILINE FUMARATE

The present disclosure relates to an improved process for the preparation of bedaquiline fumarate, comprising a step of preparing bedaquiline by reaction of 3-benzyl-6-bromo-2-methoxyquinoline 5 with 3-(dimethylamino)-l-(naphthalen-l-yl)propan-l-one 4 in the presence of lithium pyrrolidide.

New 1-(2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1-phenylbutan-2-ols with antituberculosis activity

New 4-dimethylamino-2-(naphthalen-1-yl)-1-phenyl-1-(quinolin-3-yl)butan-2-ols with antituberculosis activity were synthesized. (1R*,2S*)-1-(6-Bromo-2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1-phenylbutan-2-ol hydrocitrate exhibiting high

Structural Simplification of Bedaquiline: the Discovery of 3-(4-(N,N-Dimethylaminomethyl)phenyl)quinoline-Derived Antitubercular Lead Compounds

Bedaquiline (BDQ) is a novel and highly potent last-line antituberculosis drug that was approved by the US FDA in 2013. Owing to its stereo-structural complexity, chemical synthesis and compound optimization are rather difficult and expensive. This study

A highly efficient way to recycle inactive stereoisomers of Bedaquiline into two previous intermediates via base-catalyzed Csp3Csp3 bond cleavage

Abstract Bedaquiline is a new medicine for pulmonary multi-drug resistant tuberculosis (MDR-TB), which is a pure enantiomer with two chiral centers. The current industrial preparation process requires the separation of active Bedaquiline from a mixture of four isomers. Obviously, direct dispose of the other three undesired stereoisomers will cause significant waste and increase the unnecessary cost of production. Here, we developed an efficient, facile and scalable process for recycling the inactive stereoisomers of Bedaquiline. All these inactive stereoisomers could be recycled by their conversion to two important intermediates in the Bedaquiline synthesis via a base-catalyzed Csp3Csp3 bond cleavage of a benzyl alcohol intermediate. And the precise conditions and mechanism of the base-catalyzed cleavage reaction were discussed.

NEW QUINOLINE DERIVATIVES, A METHOD FOR THE PRODUCTION AND THE USE THEREOF FOR TREATING MICROBACTERIAL INFECTIONS AND A PHARMACEUTICAL COMPOSITION BASED ON SAID DERIVATIVES

The invention relates to the new derivatives of the quinoline, their stereoisomers or mixtures in any proportion, pharmaceutically acceptable acidic or basic additive salts, including solvates that have the mycobacterial activity, to the process of their

QUINOLINE, NAPHTHALENE AND CONFORMATIONALLY CONSTRAINED QUINOLINE OR NAPHTHALENE DERIVATES AS ANTI-MYCOBACTERIAL AGENTS

The invention relates to a compound of general formula I, II, III, IV V VI, VII, VIII, IX, X or a tautomer and the stereochemically isomeric forms thereof or pharmaceutically acceptable salts thereof, a N-oxide form thereof or a pro-drug thereof. The compound is usable as a medicament for the treatment of mycobacterial disease

Trifluoroacetic acid: a more effective and efficient reagent for the synthesis of 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones and 3-arylmethyl-2-amino-quinolines from Baylis-Hillman derivatives via Claisen rearrangement

Trifluoroacetic acid has been discovered to be a highly effective and efficient reagent for the tandem Claisen rearrangement and cyclization reaction to yield 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones from compounds obtained from the SN2 r

QUINOLINE DERIVATIVES AS ANTIBACTERIAL AGENTS

Use of a compound for the manufacture of a medicament for the treatment of a bacterial infection provided that the bacterial infection is other than a Mycobacterial infection, said compound being a compound of formula (Ia) or (Ib) a pharmaceutically acceptable acid or base addition salt thereof, a stereochemically isomeric form thereof, a tautomeric form thereof or a N-oxide form thereof, wherein R1 is hydrogen, halo, haloalkyl, cyano, hydroxy, Ar, Het, alkyl, alkyloxy, alkylthio, alkyloxyalkyl, alkylthioalkyl, Ar-alkyl or di(Ar)alkyl; p is 1, 2, 3 or 4; R2 is hydrogen, hydroxy, mercapto, alkyloxy, alkyloxyalkyloxy, alkylthio, mono or di(alkyl)amino or a radical of formula ; R3 is alkyl, Ar, Ar-alkyl, Het or Het-alkyl; q is 1, 2 or 3; R4 and R5 are hydrogen, alkyl or benzyl; or R4 and R5 together and including the N to which they are attached may form a ring; R6 is hydrogen, halo, haloalkyl, hydroxy, Ar, alkyl, alkyloxy, alkylthio, alkyloxyalkyl, alkylthioalkyl, Ar-alkyl or di(Ar)alkyl ; or two vicinal R6 radicals may be taken together to form a bivalent radical of formula - CH=CH-CH=CH-; r is 1, 2, 3, 4 or 5; R7 is hydrogen, alkyl, Ar or Het; R8 is hydrogen or alkyl; R9 is oxo ; or R8 and R9 together form the radical -CH=CH-N=.

QUINOLINE DERIVATIVES AS ANTIBACTERIAL AGENTS

Use of a compound for the manufacture of a medicament for the treatment of a bacterial infection provided that the bacterial infection is other than a Mycobacterial infection, said compound being a compound of formula (Ia) or (Ib) a pharmaceutically acceptable acid or base addition salt thereof, a stereochemically isomeric form thereof, a tautomeric form thereof or a N-oxide form thereof. Several of these compounds are also claimed as such. Further the combination of the above compounds with other antibacterial agents is described

ANTIBACTERIAL QUINOLINE DERIVATIVES

The present invention relates to novel substituted quinoline derivatives according to the general Formula (Ia) or Formula (Ib): the pharmaceutically acceptable acid or base addition salts thereof, the quaternary amines thereof, the stereochemically isomer