21193-77-1

Basic information

• Product Name: indolmycin
• Synonyms: indolmycin
• CAS NO: 21193-77-1
• Molecular Formula: C14H15N3O2
• Molecular Weight: 257.2878
• Mol File: 21193-77-1.mol

Chemical Properties

• Boiling Point: 420.8°C at 760 mmHg
• Flash Point: 208.3°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 2.75E-07mmHg at 25°C
• Refractive Index: 1.669
• CAS DataBase Reference: indolmycin(CAS DataBase Reference)
• NIST Chemistry Reference: indolmycin(21193-77-1)
• EPA Substance Registry System: indolmycin(21193-77-1)

Safety Data

• Hazardous Substances Data: 21193-77-1(Hazardous Substances Data)

Usage

Uses

Indolmycin is an antibiotic that inhibits bacterial tryptophanyl-tRNA synthetase.

InChI:InChI=1/C14H15N3O2/c1-8(12-13(18)17-14(15-2)19-12)10-7-16-11-6-4-3-5-9(10)11/h3-8,12,16H,1-2H3,(H,15,17,18)

Upstream product

• 74639-50-2 N-benzyloxycarbonyl-indole-3-carbaldehyde 
• 182194-46-3 2-Dimethylamino-5-[1-(1H-indol-3-yl)-ethyl]-4-oxo-4,5-dihydro-oxazole-5-carboxylic acid benzyl ester 
• 103871-31-4 1-(N-carbobenzoxyindol-3-yl)ethanol 
• 103871-33-6 N-carbobenzoxy-3-(l-chloroethyl)indole 
• 42352-13-6 3-[1-(dimethylamino)ethyl]-1H-indole 
• 487-89-8 Indole-3-carboxaldehyde 
• 74-89-5 methylamine 
• 103871-34-7 5-<1-(1H-indol-3-yl)ethyl>-2-(dimethylamino)-4(5H)-oxazolone 

Relevant articles and documents

Total synthesis of (±) indolmycin

A practical and short synthesis of a novel antibiotic, (±) indolmycin, has been accomplished. The overall process requires only 4 chemical steps by starting from gramine derivative 3 and oxazolinone 2.

Structure-activity dependency of new bacterial tryptophanyl tRNA synthetase inhibitors

Analogues of the aminoacyl tRNA synthetase inhibitor, indolmycin, have been synthesised in which the side chain methyl group is replaced by a wide range of substituents. Their antibacterial and enzyme inhibitory potency is related to steric properties and

New Total Synthesis of (+/-)-Indolmycin

A convergent total synthesis of the antibiotic (+/-)-indolmycin (1) is presented.N-Carbobenzoxy-3-(1-chloroethyl)indole (12) is prepared in three steps from indole-3-carboxaldehyde (9).Alkylation of the lithium anion of 2-(dimethylamino)-4(5H)-oxazolone (4) with chloride (12) provides a mixture of the (+/-)-2-dimethylamino derivative of indolmycin (13) and its diastereomer (14) in a ratio of 2.2:1.Amine exchange is effected by treatment of 13 with methylamine, affording (+/-)-1 in five steps from commercially available 9.Efforts to extend this technology toward an asymmetric synthesis of (-)-1 are described.