108320-78-1

Basic information

• Product Name: (11-methyl-6H-pyrido[4,3-b]carbazol-5-yl)methanol
• Synonyms: 6H-Pyrido[4,3-b]carbazole, 5-hydroxymethyl-11-methyl-
• CAS NO: 108320-78-1
• Molecular Formula: C₁₇H₁₄N₂O
• Molecular Weight: 262.3059
• Mol File: 108320-78-1.mol

Chemical Properties

• Boiling Point: 563.5°C at 760 mmHg
• Flash Point: 294.6°C
• Density: 1.356g/cm³
• Vapor Pressure: 1.56E-13mmHg at 25°C
• Refractive Index: 1.811
• CAS DataBase Reference: (11-methyl-6H-pyrido[4,3-b]carbazol-5-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (11-methyl-6H-pyrido[4,3-b]carbazol-5-yl)methanol(108320-78-1)
• EPA Substance Registry System: (11-methyl-6H-pyrido[4,3-b]carbazol-5-yl)methanol(108320-78-1)

Safety Data

• Hazardous Substances Data: 108320-78-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(11-methyl-6H-pyrido[4,3-b]carbazol-5-yl)methanol is used as a pharmaceutical compound for its potential biological activities. (11-methyl-6H-pyrido[4,3-b]carbazol-5-yl)methanol's carbazole core and additional functional groups may contribute to its anticancer, antimicrobial, and anti-inflammatory properties, making it a valuable asset in the development of new drugs and therapies.
Used in Synthetic Chemistry:
In the field of synthetic chemistry, (11-methyl-6H-pyrido[4,3-b]carbazol-5-yl)methanol is used as a building block or intermediate in the synthesis of more complex organic compounds. Its unique structure and functional groups can be utilized to create novel molecules with specific properties and applications.
Used in Material Science:
(11-methyl-6H-pyrido[4,3-b]carbazol-5-yl)methanol is used in material science for its potential to contribute to the development of new materials with unique properties. (11-methyl-6H-pyrido[4,3-b]carbazol-5-yl)methanol's structure and functional groups may be employed to design and synthesize advanced materials for various applications, such as sensors, optoelectronics, and nanotechnology.

Upstream product

• 108320-77-0 5-carbomethoxy-11-methyl-6H-pyrido<4,3-b>carbazole 
• 77251-57-1 11-methyl-6H-pyrido<4,3-b>carbazole-5-carbaldehyde 
• 18073-35-3 nitro-9 ellipticine 
• 954375-96-3 C₂₇H₃₂N₂O₄S 
• 519-23-3 ellipticine 
• 65266-47-9 N-(1,4-dimethylcarbazol-3-ylmethyl) aminoacetaldehyde diethyl acetal 
• 108320-73-6 3-[1-(2-Methoxycarbonylmethyl-1H-indol-3-yl)-vinyl]-1-(4-nitro-benzyl)-pyridinium; bromide 
• 108320-76-9 2-(p-nitrobenzyl)-5-carbomethoxy-11-methyl-6H-pyrido<4,3-b>carbazolium bromide 
• 91653-14-4 1-<2-(carbomethoxymethyl)-3-indolyl>-1-(3-pyridyl)ethene 
• 21422-40-2 methyl 1H-indole-2-acetate 
• 87896-88-6 5-(1',3'-dithian-2'-yl)-11-methyl-6H-pyrido<4,3-b>carbazole 

Downstream Products

• 77251-57-1 11-methyl-6H-pyrido<4,3-b>carbazole-5-carbaldehyde 

Relevant articles and documents

Cytochrome b5 increases cytochrome P450 3A4-mediated activation of anticancer drug ellipticine to 13-hydroxyellipticine whose covalent binding to DNA is elevated by sulfotransferases and N,O-acetyltransferases

The antineoplastic alkaloid ellipticine is a prodrug, whose pharmacological efficiency is dependent on its cytochrome P450 (P450)- and/or peroxidase-mediated activation in target tissues. The P450 3A4 enzyme oxidizes ellipticine to five metabolites, mainly to 13-hydroxy- and 12- hydroxyellipticine, the metabolites responsible for the formation of ellipticine-13-ylium and ellipticine-12-ylium ions that generate covalent DNA adducts. Cytochrome b5 alters the ratio of ellipticine metabolites formed by P450 3A4. While the amounts of the detoxication metabolites (7-hydroxy- and 9-hydroxyellipticine) were not changed with added cytochrome b5, 12-hydroxy- and 13-hydroxyellipticine, and ellipticine N 2-oxide increased considerably. The P450 3A4-mediated oxidation of ellipticine was significantly changed only by holo-cytochrome b5, while apo-cytochrome b5 without heme or Mn-cytochrome b5 had no such effect. The change in amounts of metabolites resulted in an increased formation of covalent ellipticine-DNA adducts, one of the DNA-damaging mechanisms of ellipticine antitumor action. The amounts of 13-hydroxy- and 12-hydroxyellipticine formed by P450 3A4 were similar, but more than 7-fold higher levels of the adduct were formed by 13-hydroxyellipticine than by 12-hydroxyellipticine. The higher susceptibility of 13-hydroxyellipticine toward heterolytic dissociation to ellipticine-13-ylium in comparison to dissociation of 12-hydroxyellipticine to ellipticine-12-ylium, determined by quantum chemical calculations, explains this phenomenon. The amounts of the 13- hydroxyellipticine-derived DNA adduct significantly increased upon reaction of 13-hydroxyellipticine with either 3′-phosphoadenosine-5′- phosphosulfate or acetyl-CoA catalyzed by human sulfotransferases 1A1, 1A2, 1A3, and 2A1, or N,O-acetyltransferases 1 and 2. The calculated reaction free energies of heterolysis of the sulfate and acetate esters are by 10-17 kcal/mol more favorable than the energy of hydrolysis of 13-hydroxyellipticine, which could explain the experimental data.

An efficient modification of ellipticine synthesis and preparation of 13-hydroxyellipticine

A simple modification of a previously published ellipticine synthesis is reported, which decreases the reaction time and increases the yield and purity of the product. Benzylic oxidations of 1,4-dimethylcarbazole and ellipticine derivatives were studied and 13-hydroxyellipticine was prepared.

CHEMISTRY OF 6H-PYRIDOCARBAZOLES. PART 12. SYNTHESIS OF POTENTIAL BISINTERCALATING DRUGS BEARING TWO ELLIPTICINE UNITS

A number of bisellipticines have been synthesized in an attempt to increase the potency of the parent tetracycles as anti-cancer drugs through bis-intercalation into the same strand of DNA.The compounds described are structures in which two pyridoc

Synthesis and Biological Properties of Some 6H-Pyridocarbazoles

The effect of methyl substitution on the biological properties of the ellipticines was reexamined. 9-Hydroxy-6H-pyridocarbazole was synthesized and shown to be devoid of antitumor activity in murine P388 lymphocytic leukemia in mice. 5-(Hydroxymeth

SYNTHESIS OF 5-HYDROXYMETHYL-11-METHYL-6H-PYRIDOCARBAZOLE AND 5-FORMYL-11-METHYL-6H-PYRIDOcarbazole (17-OXOELLIPTICINE)

A synthesis of 5-hydroxymethyl-11-methyl-6H-pyridocarbazole and the corresponding 5-formyl derivative, 17-oxoellipticine, is described, the key feature of which is the use of the Krohnke aldehyde synthesis to effect the debenzylation of a p-nitrobe