163487-27-2

Basic information

• Product Name: (1H-indol-5-yl)-carbamic acid 4-nitro-phenyl ester
• Synonyms: (1H-indol-5-yl)-carbamic acid 4-nitro-phenyl ester
• CAS NO: 163487-27-2
• Molecular Weight: 297.27
• Mol File: 163487-27-2.mol

Chemical Properties

• CAS DataBase Reference: (1H-indol-5-yl)-carbamic acid 4-nitro-phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1H-indol-5-yl)-carbamic acid 4-nitro-phenyl ester(163487-27-2)
• EPA Substance Registry System: (1H-indol-5-yl)-carbamic acid 4-nitro-phenyl ester(163487-27-2)

Safety Data

• Hazardous Substances Data: 163487-27-2(Hazardous Substances Data)

Upstream product

• 5192-03-0 5-amino-1H-indole 
• 7693-46-1 4-Nitrophenyl chloroformate 

Downstream Products

• 1185258-52-9 (+)-(1H-indol-5-yl)-carbamic acid (2R)-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl ester 
• 1366394-92-4 (+)-(S)-3-(1-benzyl-1H-indol-5-yl)-4-(benzyloxymethyl)oxazolidin-2-one 

Relevant articles and documents

New indolic non-peptidic HIV protease inhibitors from (S)-glycidol: synthesis and preliminary biological activity

A series of non-peptidic HIV protease inhibitors were synthesized starting from the same optically active precursor, (S)-glycidol. The substrate was easily converted into different indolic sulfonamides or amines by regioselective reactions. The preliminary inhibitory activity was evaluated.

Synthesis and biological evaluation of new simple indolic non peptidic HIV Protease inhibitors: The effect of different substitution patterns Dedicated to CINMPIS on the occasion of its 20th anniversary.

New structurally simple indolic non peptidic HIV Protease inhibitors were synthesized from (S)-glycidol by regioselective methods. Following the concept of targeting the protein backbone, different substitution patterns were introduced onto the common stereodefined isopropanolamine core modifying the type of functional group on the indole, the position of the functional group on the indole and the type of the nitrogen containing group (sulfonamides or perhydroisoquinoline), alternatively. The systematic study on in vitro inhibition activity of such compounds confirmed the general beneficial effect of the 5-indolyl substituents in presence of arylsulfonamide moieties, which furnished activities in the micromolar range. Preliminary docking analysis allowed to identify several key features of the binding mode of such compounds to the protease.

Stereoselective intramolecular cyclization to 4-(hydroxymethyl)-3-(1H- indolyl)oxazolidin-2-ones

A simple high-yield three-steps route to optically active 4-hydroxymethyl-3-(1H-indolyl)oxazolidin-2-ones from (S)-glycidol is described. The key intermediates (R)-oxiran-2-ylmethyl 1H-indol-4/-5-ylcarbamates are obtained in high yields from (S)-glycidol.