484-49-1

Basic information

• Product Name: 1,5-DIMETHYL-6H-PYRIDO[4,3-B]CARBAZOLE
• Synonyms: 1,5-DIMETHYL-6H-PYRIDO[4,3-B]CARBAZOLE;OLIVACINE;Olivacin;6H-Pyrido[4,3-B]carbazole, 1,5-dimethyl-;Inchi=1/C17H14N2/C1-10-12-7-8-18-11(2)14(12)9-15-13-5-3-4-6-16(13)19-17(10)15/H3-9,19H,1-2h
• CAS NO: 484-49-1
• Molecular Formula: C17H14N2
• Molecular Weight: 246.31
• Product Categories: Indoles and derivatives
• Mol File: 484-49-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 317-325°
• Boiling Point: 493.9°Cat760mmHg
• Flash Point: 226.3°C
• Appearance: /
• Density: 1.257g/cm³
• Vapor Pressure: 2.04E-09mmHg at 25°C
• Refractive Index: 1.777
• CAS DataBase Reference: 1,5-DIMETHYL-6H-PYRIDO[4,3-B]CARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIMETHYL-6H-PYRIDO[4,3-B]CARBAZOLE(484-49-1)
• EPA Substance Registry System: 1,5-DIMETHYL-6H-PYRIDO[4,3-B]CARBAZOLE(484-49-1)

Safety Data

• Hazardous Substances Data: 484-49-1(Hazardous Substances Data)

Usage

Description

This alkaloid has recently been shown to exhibit a marked antineoplastic activity. Administration of 25 or 50 mg/kg intraperitoneally on alternate days or daily until death to mice which had been inoculated with a single intraperitoneal dose of 106 -102 LI2l0 leukemia cells increased the survival time by 89-229 per cent compared with control animals.Japanese workers have recently reported the synthesis of olivacine by heating indole with 4(1-hydroxyethyl)-3-methoxymethyl-2-methylpyridine in 47 per cent HBr.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 1751, 1990 DOI: 10.1002/jhet.5570270645

References

Regina et al., Cienc. Cult. (Sao Paulo), 26, 517 (1974)Synthesis: Kametani et al., J. Chern. Soc., Perkin I, 2102 (1975)

InChI:InChI=1/C17H14N2/c1-10-12-7-8-18-11(2)14(12)9-15-13-5-3-4-6-16(13)19-17(10)15/h3-9,19H,1-2H3

Upstream product

• 61253-30-3 N-acetyl-2-(1-methyl-9H-carbazol-2-yl)ethylamine 
• 79820-57-8 indole-2-yl-1-(4-pyridyl)-ethanol 
• 40899-89-6 1-(1-benzenesulfonyl indole-2-yl)-1-(4-pyridyl)-ethanol 
• 5531-70-4 2-(1-methyl-9H-carbazol-2-yl)ethan-1-amine 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 17017-63-9 9-benzyl-2,3,4,9-tetrahydro-1H-carbazole 
• 131920-17-7 (2,2-Dimethoxy-ethyl)-[1-(1-methyl-9H-carbazol-3-yl)-ethyl]-amine 
• 40899-71-6 1-benzenesulfonylindole 
• 79820-58-9 indole-2-yl-1-(4-pyridylmethiodide)-ethanol 
• 797050-73-8 6-benzyl-3-methoxyolivacine 
• 797050-74-9 3-methoxyolivacine 
• 2122-23-8 3-hydroxyolivacine 
• 797050-76-1 trifluoro-methanesulfonic acid 1,5-dimethyl-6H-pyrido[4,3-b]carbazol-3-yl ester 
• 917-54-4 methyllithium 

Downstream Products

• 2744-45-8 (+/-)-guatambuine 

Relevant articles and documents

A new efficient synthesis of pyridocarbazoles

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Total synthesis of ellipticine quinones, olivacine, and calothrixin b

A direct route to the synthesis of biologically active ellipticine quinones, olivacine, and calothrixin B is described. The prominent key steps involved are Friedel-Crafts hydroxyalkylation followed by oxidation and directed ortho-lithiation reactions of readily available indole-2-carboxylate esters with appropriately substituted pyridine and quinoline carboxaldehydes.

Synthesis and activity against mycobacterium tuberculosis of olivacine and oxygenated derivatives

The tetracyclic pyrido[4,3-b]carbazole olivacine and four of its oxygenated derivatives have been synthesized by a late-stage palladium-catalyzed Heck-type cyclization of the pyrrole ring as a key step. In a test for the inhibition of the growth of Mycobacterium tuberculosis, 9-methoxyolivacine showed the most significant inhibitory activity against Mycobacterium tuberculosis, with an MIC90 value of 1.5 μM.

Benzannulation of indoles to carbazoles and its applications for syntheses of carbazole alkaloids

A novel and efficient method for the benzannulation of indoles to carbazoles is reported. γ-Carbonyl tert-butylperoxide is applied as a new diene building block for the π-extension of simple indoles. The synthetic utility of this method is demonstrated by concise and selective total syntheses of naturally occurring carbazole alkaloids, olivacine, and asteropusazole A.