58189-33-6

Usage

Uses

Used in Pharmaceutical Industry:
Imerubrine is used as a pharmaceutical agent for its potential therapeutic effects. Its unique chemical structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Cosmetic Industry:
Imerubrine is used as an active ingredient in cosmetic products for its potential skin benefits. Its unique properties may contribute to improved skin health and appearance.
Used in Research and Development:
Imerubrine is used as a research compound for studying its biological activities and potential applications. Its unique structure and properties make it an interesting subject for scientific investigation.

InChI:InChI=1/C20H17NO5/c1-23-14-6-5-10-12(9-13(14)22)17-15-11(7-8-21-17)18(24-2)20(26-4)19(25-3)16(10)15/h5-9H,1-4H3

Upstream product

• 186581-53-3 diazomethane 
• 74631-22-4 grandirubrine 
• 191414-83-2 6b,7,8,9-tetrahydro-4,5,6,8,8-pentamethoxyindeno<1,2,3-ij>cyclopropa<1,2-c>isoquinolin-9(9H)-one 
• 74631-22-4 grandirubrine 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 338730-21-5 16-aza-10,11,12-trimethoxy-18-oxapentacyclo[7.7.1.1^2,6.0^2,8.0^13,17]octadeca-1⁽¹⁶⁾,7,9⁽¹⁰⁾,11,13⁽¹⁷⁾,14-hexaen-4-one 
• 171925-85-2 3-aza-9,10,11-trimethoxy-5-oxo-6-amino-5H-cycloheptatrienoacenaphthylene 
• 172335-93-2 granditropone 
• 338730-13-5 N-tert-butoxycarbonyl-8-ethynyl-5,6,7-trimethoxy-1-(2,4-oxazolyl)-1,2-dihydro-isoquinoline 
• 338730-17-9 N-tert-butoxycarbonyl-1-cyano-8-ethynyl-5,6,7-trimethoxy-1,2-dihydroisoquinoline 
• 338730-18-0 8-ethynyl-1-formyl-5,6,7-trimethoxy-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 338730-12-4 4,5,6-trimethoxy-9-oxa-1-aza-cyclopenta[a]acenaphthylene 
• 338730-16-8 8-ethynyl-5,6,7-trimethoxyisoquinoline 

Relevant academic research and scientific papers

Preparation And Antileukemic Activity Of Congeners Of Tropoloisoquinoline Alkaloids From Abuta Concolor

Antileukemic tropoloisoquinoline alkaloids, pareirubine A (1) and grandirubrine (2), at first have been isolated from Abuta concolor (Menispermaceae).Methylation of 1 and 2, existing in solution as a mixture of tautomers gave the corresponding four methyl derivatives (3 - 6).Thioimerubrine (7) and thioisoimerubrine (8) were prepared by the nucleophilic substitutions of the methoxyl groups at C-11 and -10, respectively.Acetylation of 1 and 2 produced the corresponding mono-acetyl tautomers (9 and 10).Antileukemic activity of these derived tropoloisoquinoline alkaloids is also reported.

Regiocontrolled Total Synthesis of Imerubrine - the First Total Synthesis of a Tropoloisoquinoline Alkaloid

The known dihydroazafluoranthene 6 is elaborated to the ?-homo-o-benzoquinone monoacetal 9 which reacts with trifluoroacetic acid to give the title alkaloid 1.

Total synthesis of tropoloisoquinolines: Imerubrine, isoimerubrine, and grandirubrine

A unified, ready access to the tropoloisoquinoline alkaloids imerubrine (1), grandirubrine (2), and isoimerubrine (3) is delineated and features sequential application of the intramolecular Diels - Alder reaction of an acetylene-tethered oxazole and the [

Total synthesis of granditropone, grandirubrine, imerubrine, and isoimerubrine

Concise total syntheses of the naturally occurring tropoloisoquinolines grandirubrine (1), imerubrine (2), and isoimerubrine (3) are detailed. The regioselective total synthesis of grandirubrine (1) is based on the [4 + 2]cycloaddition reaction of the α-p

Regiocontrolled Total Syntheses of the Tropoloisoquinoline Alkaloids Imerubrine and Grandirubrine

The previously reported dihydroazafluoranthene (8) has been converted, over a number of steps, into the ?-homo-o-benzoquinone monoacetal (5).The structure of compound (5) was established by X-ray crystallographic methods and treatment of this material with trifluoroacetic acid resulted in formation of the tropoloisoquinoline alkaloid imerubrine (1).Alternatively, acetal (5) could be hydrolysed to the corresponding diketone (6) which proved to be unstable and isomerised to grandirubrine (2) on heating.Both tropoloisoquinolines (1) and (2) were tested for antitubulinactivity, and weak inhibition of polymerisation was observed only with the former compound.

GRANDIRUBRINE, A NEW TROPOLOISOQUINOLINE ALKALOID

Grandirubrine, a new alkaloid from Abuta grandifolia (Martius) Sandwith (Menispermaceae), has been assigned the tropoloisoquinoline structure I.