166104-19-4

Usage

Uses

Used in Chemical Research:
TERT-BUTYL 5-NITRO-1H-INDOLE-1-CARBOXYLATE is used as a research compound for exploring its chemical properties and potential reactions. Its unique structure allows chemists to study its reactivity and interactions with other molecules, which can lead to the development of new chemical processes and products.
Used in Pharmaceutical Development:
TERT-BUTYL 5-NITRO-1H-INDOLE-1-CARBOXYLATE is used as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its indole core and functional groups can be modified to create new drug candidates with potential therapeutic applications.
Used in Industrial Applications:
TERT-BUTYL 5-NITRO-1H-INDOLE-1-CARBOXYLATE is used as a specialty chemical in various industrial processes. Its unique properties may be harnessed for specific applications, such as in the production of dyes, pigments, or other specialty chemicals.
It is important to handle TERT-BUTYL 5-NITRO-1H-INDOLE-1-CARBOXYLATE with care due to the potential risks associated with exposure to nitro compounds. Proper safety measures should be taken to minimize any hazards during its production, use, and disposal.

InChI:InChI=1/C13H14N2O4/c1-13(2,3)19-12(16)14-7-6-9-8-10(15(17)18)4-5-11(9)14/h4-8H,1-3H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 6146-52-7 5-nitroindole 

Downstream Products

• 129487-92-9 tert-butyl 5-amino-2,3-dihydro-1H-indole-1-carboxylate 
• 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 
• 1448607-77-9 5-benzoylamino-4-bromoindole-1-carboxylic acid tert-butyl ester 
• 1350890-84-4 5-(benzoyl-tert-butoxycarbonylamino)-4-bromo-indole-1-carboxylic acid tert-butyl ester 
• 495-48-7 azoxybenzene 
• 1058739-51-7 tert-butyl 5-(3,5-dichloro-phenylsulphonylamino)-2,3-dihydro-indole-1-carboxylate 
• 1058740-18-3 C₁₄H₁₂Cl₂N₂O₂S 
• 5192-03-0 5-amino-1H-indole 
• 6146-52-7 5-nitroindole 

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

LACTAM-CONTAINING COMPOUNDS AND DERIVATIVES THEREOF AS FACTOR XA INHIBITORS

The present application describes lactam-containing compounds and derivatives thereof of Formula I: P4—P-M-M4??I or pharmaceutically acceptable salt forms thereof, wherein ring P, if present is a 5-7 membered carbocycle or heterocycle and ring M is a 5-7 membered carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

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

IMINOSUGARS USEFUL FOR THE TREATMENT OF VIRAL DISEASES

Formula IA, ad their use for treating viral infections.

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.

Palladium-catalyzed cross-couplings of lithium arylzincates with aromatic halides: Synthesis of analogues of isomeridianin G and evaluation as GSK-3β inhibitors

Several analogues of isomeridianin G have been synthesized using palladium-catalyzed cross-coupling reactions of lithium triorganozincates as a key step. The latter have been prepared by deprotonative lithiation followed by transmetalation using ZnCl