60755-86-4

Usage

General Description

1-Methoxycanthinone is a naturally occurring alkaloid that belongs to the canthinone family. It is found in certain plants and has been studied for its potential pharmacological properties. 1-Methoxycanthinone has been reported to exhibit anti-inflammatory, anti-tumor, and anti-microbial activities. It has also been investigated for its potential use in treating various diseases, including cancer and inflammation. Additionally, 1-Methoxycanthinone has shown promise as a potential therapeutic agent for certain skin conditions and as a potential lead compound for the development of new drugs. Further research is needed to fully understand the pharmacological properties and potential therapeutic uses of 1-Methoxycanthinone.

InChI:InChI=1/C15H10N2O2/c1-19-12-8-16-10-6-7-13(18)17-11-5-3-2-4-9(11)14(12)15(10)17/h2-8H,1H3

Upstream product

• 141-78-6 ethyl acetate 
• 92631-69-1 4-methoxy-β-carboline-1-carbaldehyde 
• 117908-36-8 methyl 2,3,6,11-tetrahydro-3,6-dioxo-1H-indolizino<8,7-b>indole-11b(5H)-carboxylate 
• 117908-37-9 11,11b-dihydro-1H-indolizino<8,7-b>indole-3,6(2H,5H)-dione 
• 79888-13-4 methyl 2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate 
• 343-94-2 tryptamine hydochloride 
• 60807-25-2 4-methoxy-β-carboline-1-carboxylic acid methyl ester 
• 80787-59-3 1-hydroxy-canthin-6-one 
• 77-78-1 dimethyl sulfate 
• 117908-39-1 4,5-dihydro-1-methoxy-6H-indolo<3,2,1-de><1,5>naphthyridin-6-one 
• 117908-38-0 methyl 4-methoxy-9H-pyrido<3,4-b>indole-1-propanoate 

Relevant academic research and scientific papers

SYNTHESIS OF 1-METHOXY CANTHINE-6-ONE

The six step synthesis of the cytotoxic antileukemic alkaloid 1-methoxy canthine-6-one 2 is described.The pivotal steps are represented by the oxidation (DDQ) of 9 to afford the 3-acylindole 14 and the conversion of 11 into the 4-methoxy-1-alkyl β-carboline 15.

1-HYDROXYCANTHIN-6-ONE, AN ALKALOID FROM AILANTHUS GIRALDII

A new alkaloid has been isolated from the heartwood of Ailanthus giraldii and its structure determined as 1-hydroxycanthin-6-one.Key Word Index - Ailanthus giraldii, Simaroubaceae; 1-hydroxycanthin-6-one; alkaloid.

A total synthesis of 1-methoxycanthin-6-one: An efficient one-pot synthesis of the canthin-6-one skeleton from β-carboline-1-carbaldehyde

A total synthesis of naturally occurring 1-methoxycanthin-6-one is described. In this synthesis, we achieved one-pot conversion from β-carboline-1-carbaldehyde to the canthin-6-one skeleton by the sequential addition of lithium ketene acetal in LiHMDS solution followed by the addition of EtOH in the reaction mixture.

DDQ Oxidations in the Indole Area. Synthesis of 4-Alkoxy-β-carbolines Including the Natural Products Crenatine and 1-Methoxycanthin-6-one

The seven-step synthesis of the cytotoxic, antileukemic alkaloid 1-methoxycanthin-6-one (2b) is described.The pivotal steps are represented by the oxidation (DDQ, aqueous THF, room temperature) of 1-(methoxycarbonyl)-1,2,3,4-tetrahydro-β-carboline (10) to provide the 4-oxo-substituted derivative 14 in 78percent yield, and conversion of the 4-oxo analogue 7 into 4-methoxy-1-alkyl-β-carboline (23) via a methoxylation-oxidation process .This four-step, one-pot reaction has been shown to be general; 4-oxo-1,2,3,4-tetrahydro-β-carboline (18) was converted into the corresponding 4-methoxy-, 4-ethoxy-, 4-(allyloxy)-, and 4-(benzyloxy)-β-carbolines (19a-d, respectively) on heating in the appropriate alcohol in the presence of pTSA and a trialkyl orthoformate (Table II).The proposed mechanism for this intriguing transformation is outlined in Scheme IV.Execution of this process has also resulted in a four-step preparation of crenatine (1a), a 4-methoxy-1-ethyl-β-carboline alkaloid.Finally, steric and electronic parameters have also been successfully manipulated to direct the DDQ oxidation of 1,2,3,4-tetrahydro-β-carbolines to position 1, regiospecifically.The conversion of tetrahydro-β-carboline 25 into 2-acylindole 38 and benzamide 26 into 1-oxotetrahydro-β-carboline 27 (Table I), respectively, is in agreement with the proposed mechanism for this process.