882169-91-7

Basic information

• Product Name: (S)-tert-butyl 1-(5-bromopyridin-3-yloxy)-3-(1H-indol-3-yl)propan-2-ylcarbamate
• Synonyms: (S)-tert-butyl 1-(5-bromopyridin-3-yloxy)-3-(1H-indol-3-yl)propan-2-ylcarbamate;tert-butyl N-[(2S)-1-[(5-broMopyridin-3-yl)oxy]-3-(1H-indol-3-yl)propan-2-yl]carbaMate;CarbaMic acid, [(1S)-2-[(5-broMo-3-pyridinyl)oxy]-1-(1H-indol-3-ylMethyl)ethyl]-, 1,1-diMethylethyl ester;CarbaMic acid, [(1S)-2-[(5-broMo-3-pyridinyl)oxy]-1-(1H-indol-3-ylMethyl)ethyl]-, 1,1-diMethylethyl ester (9CI)
• CAS NO: 882169-91-7
• Molecular Formula: C₂₁H₂₄BrN₃O₃
• Molecular Weight: 446
• Mol File: 882169-91-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-tert-butyl 1-(5-bromopyridin-3-yloxy)-3-(1H-indol-3-yl)propan-2-ylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 1-(5-bromopyridin-3-yloxy)-3-(1H-indol-3-yl)propan-2-ylcarbamate(882169-91-7)
• EPA Substance Registry System: (S)-tert-butyl 1-(5-bromopyridin-3-yloxy)-3-(1H-indol-3-yl)propan-2-ylcarbamate(882169-91-7)

Safety Data

• Hazardous Substances Data: 882169-91-7(Hazardous Substances Data)

Usage

General Description

The chemical (S)-tert-butyl 1-(5-bromopyridin-3-yloxy)-3-(1H-indol-3-yl)propan-2-ylcarbamate is a compound that consists of a tert-butyl group, a bromopyridin-3-yloxy group, and an indol-3-yl group, as well as a propan-2-ylcarbamate moiety. It is a chiral molecule, with the (S)-stereoisomer being the specific form mentioned in the name. This chemical may have potential applications in organic synthesis, pharmaceuticals, or agrochemicals due to its structural features, which could confer specific biological or chemical properties. Its precise uses and properties would need to be further investigated through experimental studies and evaluations.

Upstream product

• 74115-13-2 5-bromopyridine-3-ol 
• 110659-38-6 N-t-butoxycarbonyl-tryptophanol 

Downstream Products

• 552330-15-1 tert-butyl (1S)-2-(1H-indol-3-yl)-1-[({5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-yl}oxy)methyl]ethylcarbamate 
• 552330-73-1 tert-butyl (1S)-2-{[5-(4-cyanophenyl)pyridin-3-yl]oxy}-1-(1H-indol-3-ylmethyl)ethylcarbamate 
• 882170-48-1 [1-{5-[2-(2-benzylamino-pyridin-4-yl)-vinyl]-pyridin-3-yloxymethyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 
• 882170-43-6 [1-{5-[2-(2-benzylsulfanyl-pyridin-4-yl)-vinyl]-pyridin-3-yloxymethyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 
• 882170-42-5 (2-(1H-indol-3-yl)-1-{5-[2-(2-phenylsulfanyl-pyridin-4-yl)-vinyl]-pyridin-3-yloxymethyl}-ethyl)-carbamic acid tert-butyl ester 
• 882170-41-4 (2-(1H-indol-3-yl)-1-{5-[2-(2-phenoxy-pyridin-4-yl)-vinyl]-pyridin-3-yloxymethyl}-ethyl)-carbamic acid tert-butyl ester 
• 882170-21-0 [2-(1H-indol-3-yl)-1-(5-styryl-pyridin-3-yloxymethyl)-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis and SAR of indazole-pyridine based protein kinase B/Akt inhibitors

A series of heteroaryl-pyridine containing inhibitors of Akt are reported. The synthesis and structure-activity relationships are discussed, leading to the discovery of a indazole-pyridine analogue (Ki = 0.16 nM). These compounds bind in the ATP binding site, are potent, ATP competitive, and reversible inhibitors of Akt activity. No selectivity amongst the Akt isoforms is observed for this analogue, but there is good selectivity against an panel of other kinases. It is least selective for other members of the AGC family of kinases but is nonetheless 40-fold selective for Akt over PKA. The compound shows cellular activity and significantly slows tumor growth in vivo.

Isoquinoline-pyridine-based protein kinase B/Akt antagonists: SAR and in vivo antitumor activity

The structure-activity relationships of a series of isoquinoline-pyridine-based protein kinase B/Akt antagonists have been investigated in an effort to improve the major short-comings of the lead compound 3, including poor pharmacokinetic profiles in several species (e.g., mouse iv t1/2 = 0.3 h, po F = 0%). Chlorination at C-1 position of the isoquinoline improved its pharmacokinetic property in mice (iv t1/2 = 5.0 h, po F = 51%) but resulted in >500-fold drop in potency. In a mouse MiaPaCa-2 xenograft model, an amino analog 10y significantly slowed the tumor growth, however was accompanied by toxicity.