210223-15-7

Basic information

• Product Name: ethyl 4-phenylpyrrolo[1,2-a]quinoxaline-2-carboxylate
• Synonyms: ethyl 4-phenylpyrrolo[1,2-a]quinoxaline-2-carboxylate
• CAS NO: 210223-15-7
• Molecular Weight: 316.359
• Mol File: 210223-15-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: ethyl 4-phenylpyrrolo[1,2-a]quinoxaline-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-phenylpyrrolo[1,2-a]quinoxaline-2-carboxylate(210223-15-7)
• EPA Substance Registry System: ethyl 4-phenylpyrrolo[1,2-a]quinoxaline-2-carboxylate(210223-15-7)

Safety Data

• Hazardous Substances Data: 210223-15-7(Hazardous Substances Data)

Upstream product

• 623-47-2 propynoic acid ethyl ester 
• 70-11-1 α-bromoacetophenone 
• 4981-92-4 1-benzylbenzimidazole 
• 51-17-2 benzoimidazole 
• 100-39-0 benzyl bromide 
• 95-54-5 1,2-diamino-benzene 
• 10130-23-1 2-methyl-3-phenylquinoxaline 
• 70-23-5 ethyl Bromopyruvate 

Downstream Products

• 203513-46-6 ethyl 4-methyl-3-(4'-phenylpyrrolo[1,2-a]quinoxalin-2'-yl)-1H-pyrrole-2-carboxylate 
• 203513-50-2 2-(2-nitropropenyl)-4-phenylpyrrolo[1,2-a]quinoxaline 
• 326500-23-6 4-phenyl-2-[4-(3-trifluoromethyl-phenyl)-piperazin-1-ylmethyl]-pyrrolo[1,2-a]quinoxaline 
• 326500-22-5 2-[4-(2-methoxy-phenyl)-piperazin-1-ylmethyl]-4-phenyl-pyrrolo[1,2-a]quinoxaline 
• 326500-24-7 2-[4-(4-chloro-phenyl)-piperazin-1-ylmethyl]-4-phenyl-pyrrolo[1,2-a]quinoxaline 
• 326500-25-8 4-phenyl-2-(4-pyridin-2-yl-piperazin-1-ylmethyl)-pyrrolo[1,2-a]quinoxaline 
• 326500-21-4 4-phenyl-2-(4-phenyl-piperazin-1-ylmethyl)-pyrrolo[1,2-a]quinoxaline 
• 326500-26-9 4-phenyl-2-(4-phenyl-3,6-dihydro-2H-pyridin-1-ylmethyl)-pyrrolo[1,2-a]quinoxaline 
• 203513-49-9 4-phenylpyrrolo[1,2-a]quinoxaline-2-carboxaldehyde 
• 210223-17-9 (4-Phenyl-pyrrolo[1,2-a]quinoxalin-2-yl)-methanol 

Relevant articles and documents

Synthesis of new 2-(aminomethyl)-4-phenylpyrrolo[1,2-a]-quinoxalines and their preliminary in-vivo central dopamine antagonist activity evaluation in mice

In the search for antipsychotic agents that are not associated with extrapyramidal side effects, efforts have been focused on finding selective D4-receptor antagonists and investigating their pharmacology. Our laboratory has developed a synthesis program for new pyrroloquinoxalines with therapeutic potential. We have described the synthesis of some new pyrroloquinoxalines with substituted arylpiperazino or aryltetrahydropyrido chain at position 3 of the quinoxaline ring (2-(4-phenylpiperazin-1-ylmethyl)-4-phenylpyrrolo[1,2-a]quinoxalinium oxalate (3a), 2-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-4-phenylpyrrolo[1,2-a]quinoxal inium oxalate (3b), 2-[4-(3-trifluoromethylphenyl)piperazin-1-ylmethyl]-4-phenylpyrrolo[1,2-a]quinox alinium oxalate (3c), 2-[4-(4-chlorophenyl)piperazin-1-ylmethyl]-4-phenylpyrrolo[1,2-a]quinoxaliniumox alate (3d), 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-4-phenylpyrrolo[1,2-a]quinoxalinium oxalate (3e), and 2-(4-phenyl-1,2,3,6-tetrahydropyridin-1-ylmethyl)-4-phenylpyrrolo[1,2-a]quinoxal inium oxalate (3f)). A preliminary pharmacological study of these products was conducted using climbing behaviour induced by apomorphine (2.5 mg kg-1, s.c.) in mice. The derivatives were administered intraperitoneally 30 min before apomorphine. Haloperidol, chlorpromazine and clozapine were used as references. Among this series, 3b, 3c and 3f revealed a central dopamine antagonist activity. The most active derivative was 3b, which exhibited a profile relatively close to clozapine.

Fine tuning the outcome of 1,3-dipolar cycloaddition reactions of benzimidazolium ylides to activated alkynes

1,3-Dipolar cycloaddition reactions of benzimidazolium ylides, generated from 3-phenacylbenzimidazolium bromides, to non-symmetrical activated dipolarophiles in various reaction conditions led to complex mixtures of pyrrolo[1,2-a]benzimidazole and pyrrolo[1,2-a]quinoxaline derivatives. In order to explain all experimental results, the influence of reaction conditions on the reaction products was investigated. For the first time, 4-hydroxy-4,5-dihydropyrrolo[1,2-a]quinoxaline derivatives 6, pyrrolo[1,2-a]quinoxalinium quaternary salts 8, as well as 4-methoxy-4,5-dihydropyrrolo[1,2-a]quinoxalines 9, were separated, fully characterized and their interconversions are presented, together with a proposed reaction mechanism.

Synthesis and antituberculosis activity of new phenylpyrrolo[1,2-a] quinoxalinylpyrrole carboxylic acid derivatives

During the course of our work on the synthesis and screening of new drugs for tuberculosis, we have identified three new phenylpyrrolo[1,2-a]quinoxalinylpyrrole carboxylic acid derivatives which inhibited in-vitro Mycobacterium tuberculosis H37Rv; 97-98% inhibition at 12.5 μg mL-1.