265111-01-1

Usage

Uses

Used in Organic Synthesis:
1-(5-Bromo-1-Tosyl-1H-Indol-3-Yl)Ethanone is used as an intermediate in organic synthesis for the production of various indole derivatives. Its unique structure allows for the creation of a wide range of compounds with potential applications in different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-(5-Bromo-1-Tosyl-1H-Indol-3-Yl)Ethanone is used as a key compound in the development of new drugs. Its potential biological activities make it a promising candidate for the treatment of various medical conditions. Researchers can utilize 1-(5-Bromo-1-Tosyl-1H-Indol-3-Yl)Ethanone to design and synthesize novel therapeutic agents with improved efficacy and selectivity.
Used in Chemical Research:
1-(5-Bromo-1-Tosyl-1H-Indol-3-Yl)Ethanone is also used in chemical research to study the properties and reactivity of indole derivatives. Understanding the behavior of 1-(5-Bromo-1-Tosyl-1H-Indol-3-Yl)Ethanone can provide valuable insights into the development of new synthetic methods and the creation of novel chemical entities with diverse applications.

Upstream product

• 96546-77-9 N-tosyl-5-bromoindole 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 19620-90-7 1-(5-bromo-1H-indol-3-yl)ethan-1-one 
• 10075-50-0 5-bromo-1H-indole 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 158991-80-1 5-bromo-N-(1-p-toluenesulphonylindole)-3-carboxaldehyde 

Downstream Products

• 265111-03-3 N-toluenesulfonyl-5-bromo-3-(2-bromoacetyl)indole 
• 341998-57-0 (E)-1-(5-bromo-1-tosyl-1H-indol-3-yl)-3-(dimethylamino)prop-2-en-1-one 
• 213473-00-8 Meridianin C 
• 1311395-22-8 4-(5-bromo-1H-indol-3-yl)-5-(4-acetylphenyl)pyrimidin-2-amine 
• 1311395-26-2 4-[2-amino-4-(5-bromo-1H-indol-3-yl)pyrimidin-5-yl]benzamide 
• 1311395-30-8 4-(5-bromo-1H-indol-3-yl)-5-(4-trifluoromethylphenyl)pyrimidin-2-amine 
• 1311395-34-2 4-(5-bromo-1H-indol-3-yl)-5-(3-methoxyphenyl)pyrimidin-2-amine 
• 290333-07-2 (E)-1-(5-bromo-1-tosyl-1H-indol-3-yl)-3-(dimethylamino)prop-2-en-1-one 

Relevant academic research and scientific papers

A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study

Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.

Discovery of Potent and Brain-Penetrant Tau Tubulin Kinase 1 (TTBK1) Inhibitors that Lower Tau Phosphorylation in Vivo

Structural analysis of the known NIK inhibitor 3 bound to the kinase domain of TTBK1 led to the design and synthesis of a novel class of azaindazole TTBK1 inhibitors exemplified by 8 (cell IC50: 571 nM). Systematic optimization of this series of analogs l

Second-Generation Meridianin Analogues Inhibit the Formation of Mycobacterium smegmatis Biofilms and Sensitize Polymyxin-Resistant Gram-Negative Bacteria to Colistin

Drug-resistant bacteria are rapidly becoming a significant problem across the globe. One element that factors into this crisis is the role played by bacterial biofilms in the recalcitrance of some infections to the effects of conventional antibiotics. Bacteria within a biofilm are highly tolerant of both antibiotic treatment and host immune responses. Biofilms are implicated in many chronic infections, including tuberculosis, in which they can act as bacterial reservoirs, requiring an arduous antibiotic regimen to eradicate the infection. A separate, compounding problem is that antibiotics once seen as last-resort drugs, such as the polymyxin colistin, are now seeing more frequent usage as resistance to front-line drugs in Gram-negative bacteria becomes more prevalent. The increased use of such antibiotics inevitably leads to an increased frequency of resistance. Drugs that inhibit biofilms and/or act as adjuvants to overcome resistance to existing antibiotics will potentially be an important component of future approaches to antibacterial treatment. We have previously demonstrated that analogues of the meridianin natural product family possess adjuvant and antibiofilm activities. In this study, we explore structural variation of the lead molecule from previous studies, and identify compounds showing both improved biofilm inhibition potency and synergy with colistin.

Synthesis, antimicrobial and cytotoxic activities, and molecular docking studies of N-arylsulfonylindoles containing an aminoguanidine, a semicarbazide, and a thiosemicarbazide moiety

Thirty-six N-arylsulfonyl-3-substituted indoles were designed and synthesized by combining the N-arylsulfonylindoles with aminoguanidine, semicarbazide, and thiosemicarbazide, respectively. Their antibacterial activities were screened, and cytotoxic activities were evaluated. The results showed that aminoguanidines (6) exhibited much better antibacterial activity than semicarbazides (7) and thiosemicarbazides (8). Most compounds in series 6 showed potent inhibitory activity against the tested bacterial strains, including multidrug-resistant strains, with MIC values in the range of 1.08–23.46 μM. The cytotoxic activity of the compounds 6c, 6d, 6h, 6j, 6k and 6l was assessed in two human cancer cell lines A590 and SGC7901, and one human normal cell line HEK 293T. The results indicated that compounds selected exhibited excellent activity against the tested cancer cells with IC50 values in the range of 1.51–15.12 μM suggesting the potential of them as new antibacterial and anticancer agents. What's more, the results of resistance study revealed that resistance of the tested bacteria toward 6d is not easily developed. Molecular docking studies revealed that the aminoguanidine and arylsulfonylindole moieties played a significant role in binding the target site of E. coli FabH-CoA receptor.

Discovery of novel indoleaminopyrimidine NIK inhibitors based on molecular docking-based support vector regression (SVR) model

A set of NF-κB-inducing kinase (NIK) inhibitors was used to develop a molecular docking-based QSAR model by using nonlinear regression method. The accuracy of the QSAR model was remarkably improved by integrating the docking scores and key interaction pro

Optimization, Structure-Activity Relationship, and Mode of Action of Nortopsentin Analogues Containing Thiazole and Oxazole Moieties

Plant diseases seriously endanger plant health, and it is very difficult to control them. A series of nortopsentin analogues were designed, synthesized, and evaluated for their antiviral activities and fungicidal activities. Most of these compounds displayed higher antiviral activities than ribavirin. Compounds 1d, 1e, and 12a, with excellent antiviral activities, emerged as novel antiviral lead compounds, among which 1e was selected for further antiviral mechanism research. The mechanism research results indicated that these compounds may play an antiviral role by aggregating viral particles to prevent their movement in plants. Further fungicidal activity tests revealed that nortopsentin analogues displayed broad-spectrum fungicidal activities. Compounds 2p and 2f displayed higher antifungal activities against Alternaria solani than the commercial fungicides carbendazim and chlorothalonil. Current research has laid a foundation for the application of nortopsentin analogues in plant protection.

Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria

In the last 30 years, development of new classes of antibiotics has slowed, increasing the necessity for new options to treat multidrug resistant bacterial infections. Development of antibiotic adjuvants that increase the effectiveness of currently available antibiotics is a promising alternative approach to classical antibiotic development. Reports of the ability of the natural product meridianin D to modulate bacterial behavior have been rare. Herein, we describe the ability of meridianin D to inhibit biofilm formation of methicillin-resistant Staphylococcus aureus (MRSA) and to increase the potency of colistin against colistin-resistant and sensitive Gram-negative bacteria. Analogues were identified that are capable of inhibiting and dispersing MRSA biofilms and lowering the colistin MIC to below the CLSI breakpoint against Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli.

Meridianin derivatives as potent Dyrk1A inhibitors and neuroprotective agents

Meridianins are a group of marine-derived indole alkaloids which are reported to possess kinase inhibitory activities. In the present Letter, we report synthesis of N1-substituted and C-ring modified meridianin derivatives and their evaluation as Dyrk1A inhibitors and neuroprotective agents. Among the library of 52 compounds screened, morpholinoyl linked derivative 26b and 2-nitro-4-trifluoromethyl phenyl sulfonyl derivative 29v displayed potent inhibition of Dyrk1A with IC50 values of 0.5 and 0.53 μM, respectively. The derivative 26b also inhibited Dyrk2 and Dyrk3 with IC50 values of 1.4 and 2.2 μM, respectively showing 2.2 and 4.4 fold selectivity for Dyrk1A with respect to Dyrk2 and Dyrk3. The compound 26b was not cytotoxic to human neuroblastoma SH-SY5Y cells (IC50 >100 μM) and it displayed significant neuroprotection against glutamate-induced neurotoxicity in these cells at 10 μM. Molecular modelling studies of compound 26b led to identification of key interactions in the binding site of Dyrk1A and the possible reasons for observed Dyrk1A selectivity over Dyrk2.

Gold(I)-catalyzed dearomative rautenstrauch rearrangement: Enantioselective access to cyclopenta[ b ]indoles

A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These studies show vast differenc

Pim kinase inhibitory and antiproliferative activity of a novel series of meridianin C derivatives

A novel series of meridianin C derivatives substituted at C-5 position were prepared. These derivatives were tested for their kinase inhibitory potencies against all three family members of the pim kinases (Pim-1, Pim-2 and Pim-3). In addition, their anti