99655-68-2

Usage

Uses

Used in Organic Synthesis:
3-Bromo-1-(phenylsulfonyl)-1H-indole is used as a building block in organic synthesis for the creation of various organic compounds. Its unique structure, which includes both a brominated indole and a phenylsulfonyl group, allows for the development of a wide range of chemical entities with diverse properties and potential applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-Bromo-1-(phenylsulfonyl)-1H-indole is utilized as a key intermediate in the synthesis of pharmaceuticals. Its presence in the molecular structure can contribute to the compound's pharmacological properties, making it a valuable component in the development of new drugs.
Used in Pharmaceutical Industry:
3-Bromo-1-(phenylsulfonyl)-1H-indole is used in the pharmaceutical industry as a precursor for the development of new drugs. Its potential biological activity and the possibility of it being investigated for pharmacological properties make it a promising candidate for further research and development into potential therapeutic agents.
Used in Laboratory Research:
3-BROMO-1-(PHENYLSULFONYL)-1H-INDOLE is also used in laboratory research for studying its chemical properties and potential reactivity with other molecules. Understanding its behavior in various chemical reactions can provide insights into its utility in the synthesis of complex organic molecules and its potential applications in different fields.

InChI:InChI=1/C14H10BrNO2S/c15-13-10-16(14-9-5-4-8-12(13)14)19(17,18)11-6-2-1-3-7-11/h1-10H

Upstream product

• 1484-27-1 3-bromoindole 
• 98-09-9 benzenesulfonyl chloride 
• 40899-71-6 1-benzenesulfonylindole 
• 145887-97-4 3-bromo-2-phenylsulfinyl-1-phenylsulfonylindole 
• 120-72-9 indole 
• 145887-95-2 3-bromo-1-phenylsulfonyl-2-phenylthioindole 
• 278593-17-2 1-(phenylsulfonyl)-1H-indole-3-carboxylic acid 

Downstream Products

• 80360-17-4 1-(phenylsulfonyl)-3-(trimethylsilyl)indole 
• 144660-56-0 3-bromo-1-(phenylsulfonyl)indol-2-yl 3-carboxy-4-pyridyl ketone 
• 102210-80-0 1-(benzenesulfonyl)-3-(β,β-dimethylacrylyl)indole 
• 102210-76-4 3-methyl-1-[1-(phenylsulfonyl)-1H-indol-2-yl]but-2-en-1-one 
• 155440-55-4 1-(benzenesulfonyl)-1'-(tert-butyldimethylsilyl)-3,3'-biindole 
• 83400-76-4 1,2-dihydro-1-(phenylsulfonyl)-3H-indol-3-one 
• 145662-43-7 2,3-Dibromo-1-(phenylsulfonyl)indole 
• 99532-45-3 3-acetyl-1-benzenesulfonylindole 
• 99532-49-7 1-[1-(benzenesulfonyl)-1H-indol-3-yl]propan-1-one 
• 188820-86-2 1-(1-Benzenesulfonyl-1H-indol-3-yl)-isoquinoline 
• 145662-44-8 3-bromo-2-iodo-1-(phenylsulfonyl)-1H-indole 
• 883141-48-8 3-(2-methylphenyl)-1-(phenylsulfonyl)-1H-indole 
• 129271-98-3 1-(phenylsulfonyl)-1H-indol-3-ylboronic acid 
• 17771-42-5 3-(3-methyl-2-butenyl)indole 

Relevant academic research and scientific papers

Rationally designed N-phenylsulfonylindoles as a tool for the analysis of the non-basic 5-HT6R ligands binding mode

Among all of the monoaminergic receptors, the 5-HT6R has the highest number of non-basic ligands (approximately 5% of compounds stored in 25th version of ChEMBL database have the strongest basic pKa below 5, calculated using the Instant JChem c

Rational Design of Original Fused-Cycle Selective Inhibitors of Tryptophan 2,3-Dioxygenase

Tryptophan 2,3-dioxygenase (TDO2) is a heme-containing enzyme constitutively expressed at high concentrations in the liver and responsible for l-tryptophan (l-Trp) homeostasis. Expression of TDO2 in cancer cells results in the inhibition of immune-mediated tumor rejection due to an enhancement of l-Trp catabolism via the kynurenine pathway. In the study herein, we disclose a new 6-(1H-indol-3-yl)-benzotriazole scaffold of TDO2 inhibitors developed through rational design, starting from existing inhibitors. Rigidification of the initial scaffold led to the synthesis of stable compounds displaying a nanomolar cellular potency and a better understanding of the structural modulations that can be accommodated inside the active site of hTDO2.

Synthesis and DNA binding of 6-(alkylamino)indolo[1,2-b][2,7]naphthyridine-5,12-quinones

We describe the synthesis of eight novel putative mono– and bis–DNA intercalators from a common precursor, 6-bromoindolo[1,2-b][2,7]naphthyridine-5,12-dione. Of these new indoloquinones, our data indicate that two are most likely DNA mono–intercalators, but weaker than ethidium bromide, and two others are DNA bis–intercalators. Our indoloquinones are inactive against mammalian topoisomerase II.

Discovery of a potent protein kinase D inhibitor: insights in the binding mode of pyrazolo[3,4-d]pyrimidine analogues

In this study, we set out to rationally optimize PKD inhibitors based on the pyrazolo[3,4-d]pyrimidine scaffold. The lead compound for this study was 1-NM-PP1, which was previously found by us and others to inhibit PKD. In our screening we identified one compound (3-IN-PP1) displaying a 10-fold increase in potency over 1-NM-PP1, opening new possibilities for specific protein kinase inhibitors for kinases that show sensitivity towards pyrazolo[3,4-d]pyrimidine derived compounds. Interestingly the observed SAR was not in complete agreement with the commonly observed binding mode where the pyrazolo[3,4-d]pyrimidine compounds are bound in a similar fashion as PKD's natural ligand ATP. Therefore we suggest an alternate binding mode where the compounds are flipped 180 degrees. This possible alternate binding mode for pyrazolo[3,4-d]pyrimidine based compounds could pave the way for a new class of specific protein kinase inhibitors for kinases sensitive towards pyrazolo[3,4-d]pyrmidines.

A Palladium(II)-Catalyzed C-H Activation Cascade Sequence for Polyheterocycle Formation

Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)-catalyzed C-H activation strategy for the construction of such systems has been developed. Starting from simple 1,3-dienyl-substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step. Don't overdo it: A palladium(II)-catalyzed C-H activation cascade sequence for the synthesis of polyheterocycles is reported. Aromatization of the initially formed dihydro species occurred with a quinone oxidant. In some cases the use of one equivalent of the oxidant enabled isolation of the dihydro species as a single isomer (see scheme; X=NMe, O, S).

FUNCTIONALISED AND SUBSTITUTED INDOLES AS ANTI-CANCER AGENTS

The present invention relates to anti-tropomyosin compounds, processes for their preparation, and methods for treating or preventing a proliferative disease, preferably cancer, using compounds of the invention.

Decarboxylative halogenation of indolecarboxylic acids using hypervalent iodine(III) reagent and its application to the synthesis of polybromoindoles

Hypervalent iodine mediated decarboxylative halogenation of indoledicarboxylic acid derivatives was studied. The treatment of 1-methylindole-2,3-dicarboxylic acid with phenyliodine diacetate (PIDA) in the presence of lithium bromide gave 1-methyl-3,3-brom

Synthesis of a pentalene centered polycyclic fused system

A novel pentalene-centered polycyclic 24π-electron system, IB1, was synthesized via a Pd-catalyzed homocoupling reaction. The geometry structure was studied by X-ray diffraction and theoretical method. The HOMO level of IB1 was studied by electrochemical

The synthesis of 2- and 3-aryl indoles and 1,3,4,5-tetrahydropyrano[4,3-b]indoles and their antibacterial and antifungal activity

A series of 2- and 3-aryl substituted indoles and two 1,3,4,5-tetrahydropyrano[4,3-b]indoles were synthesized from indole and 5-methoxyindole. The 2-aryl indoles were synthesized from the 1-(phenylsulfonyl)indole derivatives using magnesiation followed by iodination. The 2-iodinated compounds were then subjected to Suzuki-Miyaura reactions. In addition, the 3-aryl indoles were made from the corresponding 3-bromoindoles using Suzuki-Miyaura reactions. The 1,3,4,5-tetrahydropyrano[4,3-b]indoles were also synthesized from 1-(phenylsulfonyl)indole by magnesiation followed by treatment with allylbromide. The product was then converted into [2-allyl-1-(phenylsulfonyl)-1H-indol-3-yl]methanol which upon exposure to Hg(OAc)2 and NaBH4 afforded tetrahydropyrano[4,3-b]indoles. A number of the 2- and 3-aryl indoles displayed noteworthy antimicrobial activity, with compound 13a displaying the most significant activity (3.9 μg/mL) against the Gram-positive micro-organism Bacillus cereus.

Computer-aided rational drug design: A novel agent (SR13668) designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signaling

Indole-3-carbinol (I3C) is a naturally occurring anticancer agent and has entered clinical trials for cancer prevention. However, the clinical development of I3C has been impeded by its poor metabolic profile. The active components of I3C were used to develop a novel class of indole analogs to optimize I3C's anticancer actions, including blocking growth factor-stimulated Akt activation. The most promising of these analogs, SRI3668, exhibited potent oral anticancer activity against various cancers and no significant toxicity.