166104-20-7

Basic information

• Product Name: 1-Boc-5-aminoindole
• Synonyms: 5-AMINO-1-BOC-BENZIMIDAZOLE;5-AMINO-1-BOC-BENZOIMIDAZOLE;5-AMINO-BENZOIMIDAZOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;5-AMINO-INDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-BOC-5-AMINOINDOLE;tert-butyl 5-amino-1H-indole-1-carboxylate;5-Aminoindole, N1-BOC protected;1-BOC-5-AMINOINDOLE, 98+%
• CAS NO: 166104-20-7
• Molecular Formula: C₁₃H₁₆N₂O₂
• Molecular Weight: 232.28
• Product Categories: pharmacetical
• Mol File: 166104-20-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 384.15 °C at 760 mmHg
• Flash Point: 186.128 °C
• Appearance: /
• Density: 1.167 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.28±0.10(Predicted)
• CAS DataBase Reference: 1-Boc-5-aminoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-5-aminoindole(166104-20-7)
• EPA Substance Registry System: 1-Boc-5-aminoindole(166104-20-7)

Safety Data

• Hazardous Substances Data: 166104-20-7(Hazardous Substances Data)

Usage

General Description

1-Boc-5-aminoindole is a chemical compound with the molecular formula C14H20N2O2. It is commonly used as a building block in organic synthesis and pharmaceutical research due to its unique structure and reactivity. The compound consists of a 5-aminoindole core, which is protected by a Boc (tert-butyloxycarbonyl) group at the amino group, making it a versatile starting material for the synthesis of various pharmaceuticals and bioactive compounds. 1-Boc-5-aminoindole has potential applications in the development of new drugs, agrochemicals, and materials. Its properties and reactivity make it an important compound in the field of organic chemistry and drug discovery.

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

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

Downstream Products

• 5192-03-0 5-amino-1H-indole 
• 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 

Relevant articles and documents

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.

IMINOSUGARS USEFUL FOR THE TREATMENT OF VIRAL DISEASES

Formula IA, ad their use for treating viral infections.