166104-20-7

Usage

Uses

Used in Pharmaceutical Research and Development:
1-Boc-5-aminoindole is used as a key intermediate in the synthesis of new drugs, contributing to the development of innovative pharmaceuticals with potential therapeutic applications. Its protected amino group allows for selective reactions and functional group manipulations, facilitating the creation of diverse drug candidates.
Used in Agrochemical Development:
1-Boc-5-aminoindole is utilized as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique reactivity and structural features enable the production of bioactive compounds that can be used to protect crops and enhance agricultural productivity.
Used in Material Science:
1-Boc-5-aminoindole is employed as a building block in the development of new materials with specific properties, such as conductivity, magnetism, or optical characteristics. Its versatility in organic synthesis allows for the creation of materials with tailored properties for various applications.

InChI:InChI=1/C13H16N2O2/c1-13(2,3)17-12(16)15-7-6-9-8-10(14)4-5-11(9)15/h4-8H,14H2,1-3H3

Upstream product

• 6146-52-7 5-nitroindole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 166104-19-4 5-nitroindole-1-carboxylic acid tert-butyl ester 

Downstream Products

• 1266338-28-6 N-(1-(2-chloro-4-fluorobenzoyl)-1H-indol-5-yl)picolinamide 
• 1266338-29-7 N-(1-(2-methoxybenzoyl)-1H-indol-5-yl)picolinamide 
• 495-48-7 azoxybenzene 

Relevant academic research and scientific papers

Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions

Azobenzenes are widely used as dyes and photochromic compounds, with the Baeyer-Mills reaction serving as the most common method for their preparation. This transformation is often plagued by low yields due to the formation of undesired azoxybenzene. Here, we explore electronic effects dictating the formation of the azoxybenzene side-product. Using calculated oxidation potentials, we were able to predict reaction outcomes and improve reaction efficiency simply by modulating the oxidation potential of the arylamine component.

Ring-opening of five-membered heterocycles conjugated 4-isopropylresorcinol scaffold-based benzamides as HSP90 inhibitors suppressing tumor growth in vitro and in vivo

A series of ring-opened dihydroxybenzamides have been designed and synthesized as heat shock protein 90 inhibitors. One of derivatives, compound 6b ((N-ethyl-2,4-dihydroxy-5-isopropyl-N-(pyridin-3-yl)benzamide)) demonstrated remarkable antiproliferative activity against in human KRAS mutant A549 and EGFR T790 M mutant H1975 lung cancer cell lines with GI50 values of 0.07 and 0.05 μM, respectively. It is also active against in other cancer cell lines, such as colorectal HCT116 (GI50 = 0.09 μM), liver Hep3B (GI50 = 0.20 μM) and breast MDA-MB-231 (GI50 = 0.09 μM), and shows no evidence of toxicity in normal cell line. Compound 6b has an IC50 of 110.18 nM in HSP90α inhibitory activity, slightly better than reference compound 1 (17-AAG, IC50 = 141.62 nM) and achieves the degradation of multiple HSP90 client proteins in a dose- and time-dependent manner and downstream signaling of Akt in a concentration- and time-dependent manner in the human A549 lung cancer cell line. In the Boyden chamber assay, compound 6b can efficiently inhibit the migration of A549 cells when compared to the reference compound 1. It also induce significant activity through the apoptotic pathway. Treatment with 6b showed no vision toxicity (IC50 > 10 μM) on 661w photoreceptor cells as compared to AUY922 (3a) with a 0.04 μM values of IC50 and has no effect in hERG test. In a bidirectional Caco-2 permeability assay, compound 6b was classified as a highly permeable compound which is not a substrate of efflux transporters. In a pharmacokinetic study in rats, 6b showed an F = 17.8% of oral bioavailability. The effect of metabolic stability of compound 6b in human hepatocytes showed a T1/2 of 67.59 min. Compound 6b (50 mg/kg, po, daily) exhibits antitumor activity with a 72% TGD (tumor growth delay) in human A549 lung xenograft. The combination of 6b and afatinib, orally administered, showed tumor growth suppression with 67.5% of TGI in lung H1975 xenograft model. Thus compound 6b is a lead compound for further development of potential agents to treat lung cancer.

ARYL-PHOSPHORUS-OXYGEN COMPOUND AS EGFR KINASE INHIBITOR

Disclosed is a class of new aryl-phosphorus-oxygen compounds as shown in formula (I) as EGFR kinase inhibitors, and pharmaceutically acceptable salts thereof.

Pyrazoles containing substituted methanone compound and its composition and use thereof

The invention relates to a pyrazolo compound containing substituted ketone, a composition thereof and application thereof to preparation of medicaments for treating diseases associated with an Xa factor. In particular, the invention relates to a novel pyr

IMINOSUGARS USEFUL FOR THE TREATMENT OF VIRAL DISEASES

Formula IA, ad their use for treating viral infections.

AZABENZIMIDAZOLES AND THEIR USE AS AMPA RECEPTOR MODULATORS

Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, [formula (I) should be inserted here]. Also provided herein are pharmaceutical compositions comprising compounds of Formula (I) and methods

Re-engineering of the duocarmycin structural architecture enables bioprecursor development targeting CYP1A1 and CYP2W1 for biological activity

A library of duocarmycin bioprecursors based on the CPI and CBI scaffolds was synthesized and used to probe selective activation by cells expressing CYP1A1 and 2W1, CYPs known to be expressed in high frequency in some tumors. Several CPI-based compounds w

Discovery, synthesis, and structure-activity relationship development of a series of N-(4-acetamido)phenylpicolinamides as positive allosteric modulators of metabotropic glutamate receptor 4 (mGlu4) with CNS exposure in rats

Herein we report the discovery, synthesis, and evaluation of a series of N-(4-acetamido)-phenylpicolinamides as positive allosteric modulators of mGlu4. Compounds from the series show submicromolar potency at both human and rat mGlu4. In addition, pharmacokinetic studies utilizing subcutaneous dosing demonstrated good brain exposure in rats.

AMINOPIPERIDINYL DERIVATIVES AND USES THEREOF

This application discloses aminopiperidinyl compounds of generic Formulae I-II: or pharmaceutically acceptable salts thereof, wherein m, r, Q1, Q2, Q3, R, Ra, R1, R2a, R2b, and R3 are defined as described herein, useful for treatment of diseases associated with monoamine reuptake inhibitors. Also provided are pharmaceutical compositions, methods of using, and methods of preparing the compounds.

QUINAZOLINONE AND FUSED PYRIMIDINONE COMPOUNDS AND THEIR USE IN TREATING SODIUM CHANNEL-MEDIATED DISEASES OR CONDITIONS

This invention is directed to compounds of formula (I): wherein (A), n, R1, R2 and R3 are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain.