774-14-1

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromoindole-3-acetonitrile is used as a key intermediate in the synthesis of various pharmaceuticals for its potent biological activity. It contributes to the development of new drugs by serving as a building block for the production of other chemical compounds with therapeutic properties.
Used in Agrochemical Industry:
5-Bromoindole-3-acetonitrile is utilized as a precursor in the manufacturing of agrochemicals, specifically in the creation of pesticides and other agricultural products. Its reactivity and biological activity make it a valuable component in enhancing crop protection and yield.
Used in Organic Synthesis:
5-Bromoindole-3-acetonitrile is employed as a versatile building block in organic synthesis, allowing for the production of a wide range of chemical compounds. Its unique structure and reactivity enable the synthesis of various organic molecules for different applications across various industries.

Upstream product

• 773837-37-9 sodium cyanide 
• 10075-50-0 5-bromo-1H-indole 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 92557-51-2 5-Bromo-indole-3-carbinol 
• 830-93-3 N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine 
• 7677-24-9 trimethylsilyl cyanide 
• 151-50-8 potassium cyanide 

Downstream Products

• 1419874-03-5 tert-butyl 5-bromo-3-(cyanomethyl)-1H-indole-1-carboxylate 
• 1613334-48-7 (Z)-2-(5-bromo-1H-indol-3-yl)-3-(4-(4-(trifluoromethyl)phenyl)pyridin-3-yl)acrylonitrile 
• 1613334-45-4 (Z)-2-(5-bromo-1H-indol-3-yl)-3-(4-(4-fluorophenoxy)pyridin-3-yl)acrylonitrile 
• 142273-20-9 kenpaullone 
• 40432-84-6 (5-bromo-1H-indol-3-yl)-acetic acid 
• 117235-22-0 methyl 2-(5-bromo-1H-indole-3-yl)acetate 
• 196081-79-5 2-(5-bromo-1H-indol-3-yl)acetamide 

Relevant academic research and scientific papers

Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst

Asymmetric dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeds under mild reaction conditions to provide fluoropyrroloindoline derivatives in a highly enantioselective manner. Various substitution patterns on the indole ring are well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water is essential, and its possible role is discussed.

Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5 μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day.

SELECTIVE ANTI-CANCER COMPOUNDS

A compound of formula I, wherein the compound of formula I has the structure: wherein R1 to R5, Y, L, Z and X1 to X7 have meanings given in the description, said compounds having utility in the treatment of hyperproliferative disease.

4,5,6,7-TETRAHYDRO-1 H-PYRAZOLO[4,3-C]PYRIDIN-3-AMINE COMPOUNDS AS CBP AND/OR EP300 INHIBITORS

The present invention relates to compounds of formula (I) or formula (II): and to salts thereof, wherein R1-R4 of formula (I) and R1-R3 of formula (II) have any of the values defined herein, and compositions and uses thereof. The compounds are useful as inhibitors of CBP and/or EP300. Also included are pharmaceutical compositions comprising a compound of formula (I) of formula (II) or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various CBP and/or EP300-mediated disorders.

Use of derivatives of indoles for the treatment of cancer

The present invention relates to the use of derivatives of indoles having a general formula (I) as follow: for the manufacture of a pharmaceutical composition intended for the treatment of cancer.

New synthetic approach to paullones and characterization of their SIRT1 inhibitory activity

A series of 7,12-dihydroindolo[3,2-d][1]benzazepine-6(5H)-ones (paullones) substituted at C9/C10 (Br) and C2 (Me, CF3, CO2Me) have been synthesized by a one-pot Suzuki-Miyaura cross-coupling of an o-aminoarylboronic acid and methyl 2-iodoindoleacetate followed by intramolecular amide formation. Other approaches to the paullone scaffold based on Pd-catalyzed C-H activation were unsuccessful. In vitro enzymatic assay with recombinant human SIRT-1 indicated a strong inhibitory profile for the series, in particular the analogue with a methoxycarbonyl group at C2 and a bromine at C9. These compounds are, in general, inducers of granulocyte differentiation of the U937 acute leukemia cell line and cause a marked increase in pre-G1 of the cell cycle.

SMALL MOLECULE INHIBITORS OF ISOPRENYLCYSTEINE CARBOXYL METHYLTRANSFERASE WITH POTENTIAL ANTICANCER ACTIVITY

The present invention generally relates to inhibitors of isoprenylcysteine carboxyl methyltransferase (Icmt), in particularly to compounds that inhibit Icmt activity and pharmaceutical compositions thereof. The invention also relates to methods of disease treatment using the same.

Amino derivatives of indole as potent inhibitors of isoprenylcysteine carboxyl methyltransferase

The enzyme isoprenylcysteine carboxyl methyltransferase (Icmt) plays an important role in the post-translational modification of proteins that are involved in the regulation of cell growth. The indole acetamide cysmethynil is by far the most potent and widely investigated Icmt inhibitor, but it has modest antiproliferative activity and may have pharmacokinetic limitations due to its lipophilic character. We report here that cysmethynil can be structurally modified to give analogues that are as potent in inhibiting Icmt but with significantly greater antiproliferative activity. Key modifications were the replacement of the acetamide side chain by tertiary amino groups, the n-octyl side chain by isoprenyl and the 5-m-tolyl ring by fluorine. Moreover, these analogues have lower lipophilicities that could lead to improved pharmacokinetic profiles.

INHIBITORS OF ISOPRENYLCYSTEINE CARBOXYL METHYLTRANSFERASE

The present invention relates, in general, to isoprenylcysteine carboxyl methyltransferase (Icmt) and, in particular, to inhibitors of Icmt and to methods of disease treatment using same.

Synthesis of new melatonin analogues from dimers of azaindole and indole by use of Suzuki homocoupling

N-{2-[3′-(2-Acetylaminoethyl)-1H,1′H-[5,5′]biindol-3-yl]- and N-{2-[1′-(2-acetylaminoethyl)-1′H-[5, 5′]biindol-1-yl]ethyl}acetamide (2,3) and their analogues in 7-azaindole series (4,5) were synthesized by palladium catalysed reaction starting from indole or 7-azaindole using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, as catalyst.