525593-33-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
3-bromo-5-nitro-1H-indole is utilized as a key building block for the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and functional groups contribute to the development of new compounds with therapeutic and pesticidal properties, respectively.
Used in Medicinal Chemistry and Drug Discovery:
3-bromo-5-nitro-1H-indole is employed as a precursor in the preparation of diverse compounds with potential biological activities. Its exploration in medicinal chemistry and drug discovery is driven by its potential antimicrobial and antitumor properties, which could lead to the development of new treatments for infectious diseases and cancer.
Used in Antimicrobial Applications:
In the field of antimicrobial research, 3-bromo-5-nitro-1H-indole is used as a compound with potential antimicrobial properties. Its ability to inhibit the growth of various microorganisms makes it a candidate for further study and development as a new antimicrobial agent.
Used in Antitumor Applications:
3-bromo-5-nitro-1H-indole is also used in antitumor research, where it is studied for its potential to inhibit tumor growth and proliferation. Its application in this field could contribute to the discovery of novel antitumor agents for the treatment of various types of cancer.

Upstream product

• 6146-52-7 5-nitroindole 
• 685-87-0 Diethyl 2-bromomalonate 

Downstream Products

• 14182-35-5 5-nitro-3-phenyl-1H-indole 3ha 
• 1436867-82-1 8-bromo-6-isobutyl-1-(4-methylphenyl)-6H-isoxazolo[4,3-e]indole 
• 1436867-81-0 8-bromo-6-butyl-1-(4-methylphenyl)-6H-isoxazolo[4,3-e]indole 
• 1436867-80-9 8-bromo-1-(4-methylphenyl)-6-propyl-6H-isoxazolo[4,3-e]indole 
• 1436867-79-6 8-bromo-6-ethyl-1-(4-methylphenyl)-6H-isoxazolo[4,3-e]indole 
• 1436867-77-4 8-bromo-6-butyl-1-(4-chlorophenyl)-6H-isoxazolo[4,3-e]indole 
• 1436867-76-3 8-bromo-1-(4-chlorophenyl)-6-propyl-6H-isoxazolo[4,3-e]indole 
• 1436867-75-2 8-bromo-1-(4-chlorophenyl)-6-ethyl-6H-isoxazolo[4,3-e]indole 

Relevant academic research and scientific papers

Visible-Light Photocatalytic Double C-H Functionalization of Indoles: A Synergistic Experimental and Computational Study

Herein is disclosed a novel visible-light photocatalytic double C-H functionalization of indoles. The reaction affords 2,3-difunctionalized indoles in up to 84% yield, but the reaction rate depends strongly on electronic substituent effects. Mechanistic DFT studies and control experiments suggest that the secondary functionalization occurs through an independent photocatalytic oxidation of bromide ions formed during the reaction to generate molecular bromine capable of electrophilic C-3 bromination.

Predicting the Substrate Scope of the Flavin-Dependent Halogenase BrvH

The recently described flavin-dependent halogenase BrvH is able to catalyse both the bromination and chlorination of indole, but shows significantly higher bromination activity. BrvH was annotated as a tryptophan halogenase, but does not accept tryptophan as a substrate. Its native substrate remains unknown. A predictive model with the data available for BrvH was analysed. A training set of compounds tested in vitro was docked into the active site of a complete protein model based on the X-ray structure of BrvH. The atoms not resolved experimentally were modelled by using molecular mechanics force fields to obtain this protein model. Furthermore, docking poses for the substrates and known non-substrates have been calculated. Parameters like distance, partial charge and hybridization state were analysed to derive rules for predicting activity. With this model for activity of the BrvH, a virtual screening suggested several structures for potential substrates. Some of the compounds preselected in this way were tested in vitro, and several could be verified as convertible substrates. Based on information on halogenated natural products, a new dataset was created to specifically search for natural products as substrates/products, and virtual screening in this database yielded further hits.

Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study

A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.

INDOLE (SULFOMYL) N-HYDROXY BENZAMIDE DERIVATIVES AS SELECTIVE HDAC INHIBITORS

The present invention provides the sulfonyl hydroxamic acid compounds of general formulae (I) useful as HDAC inhibitors and process for preparation of these indole based sulfonyl hydroxamic acid derivatives. wherein ring A and B is aryl or heteroaryl or c

PhI(OAc)2/NaX-mediated halogenation providing access to valuable synthons 3-haloindole derivatives

This paper describes a mild phenyliodine diacetate mediated method for selective chlorination, bromination, and iodination of indole C-H bonds using sodium halide as a source for analogous halogenations. The combination of NaX and phenyliodine diacetate provides an invincible system for halogenation of indoles. This protocol was compatible with a wide array of indole substrates and provides straight forward access to potential halogenated arenes.

A quick, mild and efficient bromination using a CFBSA/KBr system

Bromination is a fundamental transformation in organic chemistry and brominated compounds as building blocks are of paramount importance in organic synthesis. In our study, we have developed an efficient method of bromination by using a CFBSA/KBr system at room temperature in a short reaction time. Notably, this approach has been proven to be applicable to a range of substrates including 1,3-diketones and β-keto esters, phenols, aromatic amines and heteroarenes with good to excellent yields.

RORC2 INHIBITORS AND METHODS OF USE THEREOF

The present invention provides compounds, pharmaceutical compositions, methods of inhibiting RORγ activity and/or reducing the amount of IL-17 in a subject, and methods of treating various medical disorders using such compounds and pharmaceutical compositions.

Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin

Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions.

Synthesis and biological evaluation of novel isoxazolo[4,3-e]indoles as antibacterial agents

The synthesis of a new series of 8-bromo-6-alkyl-1-aryl-6H-isoxazolo[4,3-e] indole derivatives is described. All the newly synthesized compounds were screened for their antibacterial activity against Escherichia coli HB101, Staphylococcus aureus pathogens (methicillin resistant S. aureus and methicillin susceptible S. aureus), Pseudomonas aeruginosa, and Bacillus subtilis; also MIC values of these compounds were determined.

Synthesis and biological activities of isogranulatimide analogues

The synthesis of new isogranulatimide analogues, their inhibitory activities toward the Checkpoint 1 kinase (Chk1), and their in vitro cytotoxicities toward four tumor cell lines (one murine L1210 leukemia, and three human cell lines: DU145 prostate carci