63277-57-6

Basic information

• Product Name: Ethyl 8-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate
• Synonyms: ethyl 8-bromo-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carboxylate;Ethyl 8-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate;8-bromo-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carboxylic acid ethyl ester;ETHYL 8-BROMO-3,4-DIHYDRO-1H-PYRIDO[4,3-B]INDOLE-2(5H)-CARBOXYLATE
• CAS NO: 63277-57-6
• Molecular Formula: C₁₄H₁₅BrN₂O₂
• Molecular Weight: 323.1851
• Mol File: 63277-57-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl 8-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 8-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate(63277-57-6)
• EPA Substance Registry System: Ethyl 8-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate(63277-57-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 63277-57-6(Hazardous Substances Data)

Upstream product

• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 29976-53-2 N-ethoxycarbonyl-4-piperidone 
• 106-40-1 4-bromo-aniline 
• 41931-18-4 (4-bromophenyl)hydrazine hydrochloride salt 
• 589-21-9 (4-bromophenyl)hydrazine 

Downstream Products

• 73931-16-5 8-Bromo-5-phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester 
• 1566528-21-9 C₂₃H₂₄BrFN₂O₃ 
• 1566527-97-6 8-bromo-5-(3-(4-fluorophenoxy)propyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 
• 497261-38-8 8-bromo-2,3,4,5-tetrahydro-1H-pyrido-[4,3-b]indole 

Relevant articles and documents

Enantioselective synthesis of cis-hexahydro-γ-carboline derivatives via Ir-catalyzed asymmetric hydrogenation

A novel synthetic route was developed for the construction of a chiral cis-hexahydro-γ-carboline derivative through Ir/ZhaoPhos-catalyzed asymmetric hydrogenation of corresponding tetrahydro-γ-carboline with high yields (up to 99% yield), excellent diastereoselectivities (up to >99 : 1 dr) and enantioselectivities (up to 99% ee), and high substrate-to-catalyst ratios (up to 5000).

Novel Carboline Derivatives as Potent Antifungal Lead Compounds: Design, Synthesis, and Biological Evaluation

A series of novel antifungal carboline derivatives was designed and synthesized, which showed broad-spectrum antifungal activity. Particularly, compound C38 showed comparable in vitro antifungal activity to fluconazole without toxicity to human embryonic lung cells. It also exhibited good fungicidal activity against both fluconazole-sensitive and -resistant Candida albicans cells and had potent inhibition activity against Candida albicans biofilm formation and hyphal growth. Moreover, C38 showed good synergistic antifungal activity in combination with fluconazole (FLC) against FLC-resistant Candida species. Preliminary mechanism studies revealed that C38 might act by inhibiting the synthesis of fungal cell wall.

Design and synthesis of antifungal benzoheterocyclic derivatives by scaffold hopping

The incidence of invasive fungal infections and associated mortality is increasing dramatically. Although azoles are first-line antifungal agents, cross-resistance and hepatic toxicity are their two major limitations. The discovery of novel non-azole lead compounds will be helpful to overcome these problems. On the basis of our previously reported benzopyran non-azole CYP51 inhibitor, scaffold hopping was used to design structurally diverse new compounds and expand the structure-activity relationships of the lead structure. Five kinds of scaffolds, namely benzimidazole, benzoxazole, benzothiazole, quinazolin-4-one and carboline, were chosen for synthesis. In vitro antifungal activity data and results from molecular docking revealed that the scaffold was important for the antifungal activity. Several compounds showed potent activity against both standard and clinically resistant fungal pathogens, suggesting that they can serve as a good starting point for the discovery of novel antifungal agents.