78860-34-1

Usage

Uses

Used in Pharmaceutical Industry:
DMAQ B1 is used as a therapeutic agent for the treatment of diabetes and related metabolic disorders. Its ability to activate insulin receptor tyrosine kinase and induce glucose uptake in adipocytes and skeletal muscle cells without promoting cell proliferation makes it a promising candidate for managing blood glucose levels and improving insulin sensitivity.
Used in Research Applications:
DMAQ B1 is used as a research tool for studying the mechanisms of insulin signaling and glucose metabolism. Its high specificity for insulin receptor tyrosine kinase and its ability to bind GAPDH in vitro make it a valuable compound for investigating the roles of these proteins in cellular processes related to glucose homeostasis.
Used in Drug Development:
DMAQ B1 is used as a lead compound in the development of new drugs targeting insulin resistance and related metabolic disorders. Its unique properties, such as its ability to activate insulin receptor tyrosine kinase and induce glucose uptake without promoting cell proliferation, offer potential advantages over existing treatments and may lead to the discovery of novel therapeutic agents.

Biological Activity

Selective insulin receptor (IR) activator/mimetic (EC 50 values are 3-6 μ M for IRTK and 100 μ M for IGF1R and EGFR). Increases IR β subunit tyrosine phosphorylation and downstream activation of PI 3-kinase and Akt, but not ERK. Induces glucose uptake in adipocytes and skeletal muscle in vitro , without enhancing vascular proliferation. Binds GAPDH.

InChI:InChI=1/C32H30N2O4/c1-6-32(4,5)31-23(20-11-7-8-13-22(20)34-31)25-29(37)27(35)24(28(36)30(25)38)21-16-33-26-18(15-14-17(2)3)10-9-12-19(21)26/h6-14,16,33-35,38H,1,15H2,2-5H3

Upstream product

• 120-72-9 indole 
• 488-48-2 tetrabromobenzoquinone 
• 339094-45-0 2,5-dibromo-3-[2-(1,1-dimethylallyl)-1H-indol-3-yl]-6-[7-(3-methylbut-2-enyl)-1H-indol-3-yl][1,4]benzoquinone 
• 245112-21-4 4-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-3-hydroxy-6-[7-(3-methyl-but-2-enyl)-1H-indol-3-ylmethylene]-pyran-2,5-dione 
• 78860-52-3 2-[2-(1,1-Dimethyl-allyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-hydroxy-3-methyl-butyl)-1H-indol-3-yl]-[1,4]benzoquinone 
• 78708-35-7 asterriquinone B1 
• 245112-28-1 oxalic acid 3-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-oxo-propyl ester ethyl ester 
• 245112-23-6 4-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-3-hydroxy-pyran-2,5-dione 
• 245112-27-0 1-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-3-hydroxy-propan-2-one 
• 245112-25-8 methyl 2-(1,1-dimethylallyl)-3-indoleacetate 
• 245112-26-9 [2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-acetyl chloride 
• 1912-34-1 methyl 2-(2-chloro-1H-indol-3-yl)acetate 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 477883-71-9 2,3,5-tribromo-6-[2-(1,1-dimethylallyl)-1H-indol-3-yl][1,4]benzoquinone 

Downstream Products

• 78708-35-7 asterriquinone B1 

Relevant academic research and scientific papers

Methyl scanning: Total synthesis of demethylasterriquinone B1 and derivatives for identification of sites of interaction with and isolation of its receptor(s)

The principle of methyl scanning is proposed for determination of the sites of interaction between biologically active small molecules and their macromolecular target(s). It involves the systematic preparation of a family of methylated derivatives of a co

Total syntheses of demethylasterriquinone B1, an orally active insulin mimetic, and demethylasterriquinone A1.

Two total syntheses of the unsymmetrical bis-indolylquinone natural product demethylasterriquinone B1 (also known as L-783,281) have been accomplished. The first exploits a known base-promoted condensation of indoles with bromanil, which stops at monoaddition using the sterically hindered 2-isoprenylindole. This permits addition of the second indole, 7-prenylindole, which gives both meta- and para-substituted bis-indolylquinone products. This regiochemical control problem was solved by extension of a method we recently developed for acid-promoted addition of indoles to 2,5-dichlorobenzoquinone. Under our original mineral acid conditions, reaction of 2-isoprenylindole with dichlorobenzoquinone fails, but it succeeds with 3-bromo-2,5-dichlorobenzoquinone using acetic acid as the promoter. The regiochemistry established in such selectively bromine-substituted quinones can be exploited in Stille couplings. As a model system, the synthesis of demethylasterriquinone A1 was accomplished using as the key step a Stille coupling of a 2,5-dibromobenzoquinone with an (N-isoprenylindol-3-yl)tin, producing the para-substituted bis-indolylquinone exclusively. Use of a (7-prenylindole)tin in coupling with a bromo-2,5-dichloro-4-indolylbenzoquinone gives the demethylasterriquinone B1 precursor. The dihaloquinone products of these indole/quinone coupling processes can be hydrolyzed to the dihydroxyquinone natural products. Demethylasterriquinone B1 is of high recent interest as a small molecule insulin mimetic with oral anti-diabetic activity in mice.

Total synthesis of asterriquinone B1

This communication describes the first total synthesis of asterriquinone B1, a representative member of a group of anti-tumor metabolites of Aspergillus terreus. The synthesis described herein is potentially applicable to other members of the asterriquinone family.

METABOLIC PRODUCTS OF ASPERGILLUS TERREUS. V. DEMETHYLATION OF ASTERRIQUINONES

Demethylation of asterriquinones (AQ, bisindolyl-dimethoxyl benzoquinones) was investigated in connection with the determination of their structures and studies of their antitumor activity.Usually, the demethylation proceeded smoothly with KOH, but several types of side reactions were observed with acidic reagents.Keywords-demethylation; asterriquinones; Aspergillus terreus; IFO 8835; benzoquinone; indolyl; dimethylallyl