118458-54-1

Basic information

• Product Name: ARCYRIAFLAVIN A
• Synonyms: ARCYRIAFLAVIN A;ARCYRIAFLAVIN A, SYNTHETIC;12,13-DIHYDRO-5H-INDOLO[2,3-A]PYRROLO[3,4-C]CARBAZOLE-5,7(6H)-DIONE
• CAS NO: 118458-54-1
• Molecular Formula: C₂₀H₁₁N₃O₂
• Molecular Weight: 325.32
• Product Categories: Cell Cycle Regulation
• Mol File: 118458-54-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: >200 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.621g/cm³
• Refractive Index: 1.96
• Storage Temp.: Store at -20°C
• Solubility: Soluble in DMSO
• PKA: 10.74±0.20(Predicted)
• CAS DataBase Reference: ARCYRIAFLAVIN A(CAS DataBase Reference)
• NIST Chemistry Reference: ARCYRIAFLAVIN A(118458-54-1)
• EPA Substance Registry System: ARCYRIAFLAVIN A(118458-54-1)

Safety Data

• Hazardous Substances Data: 118458-54-1(Hazardous Substances Data)

Usage

Uses

Arcyriaflavin A is a potent inhibitor of CDK4/cyclin D1.

Biological Activity

Potent inhibitor of cdk4/cyclin D1 (IC 50 = 59 nM). Also active against CaM kinase II (IC 50 = 25 nM) but displays selectivity over several other kinases in vitro (IC 50 values for inhibition of PKA and PKC are > 2 and > 100 μ M respectively). Inhibits human cytomegalovirus (HCMV) replication in vitro (IC 50 = 200 nM).

in vitro

arcyriaflavin a is a potent, selective inhibitor of hcmv replication in cell culture, and the anti-hcmv activity appeared no relation to the inhibition of protein kinase c. the imide nh was identified to be essential for anti-hcmv activity [1]. arcyriaflavin a also has been showed the inhibitory activity against d1/cdk4 with a ic50 of 59 nm. based on x-ray co-crystal structure of staurosporine and the human cdk2, the acidic proton of the maleimide moiety and the carbonyl group play critical roles by acting as a hydrogen bond donor and acceptor in the atp binding pocket of cdk2 [2].

IC 50

0.2 μm for hcmv [1], 0.14 μm for d1–cdk4 [2]

references

[1] slater mj, cockerill s, baxter r, bonser rw, gohil k, gowrie c, robinson je, littler e, parry n, randall r, snowden w. indolocarbazoles: potent, selective inhibitors of human cytomegalovirus replication. bioorg med chem. 1999 jun;7(6):1067-74.[2] zhu g, conner s, zhou x, shih c, brooks hb, considine e, dempsey ja, ogg c, patel b, schultz rm, spencer cd, teicher b, watkins sa. synthesis of quinolinyl/isoquinolinyl[a]pyrrolo [3,4-c] carbazoles as cyclin d1/cdk4 inhibitors. bioorg med chem lett. 2003 apr 7;13(7):1231-5.

InChI:InChI=1/C20H11N3O2/c24-19-15-13-9-5-1-3-7-11(9)21-17(13)18-14(16(15)20(25)23-19)10-6-2-4-8-12(10)22-18/h1-8,21-22H,(H,23,24,25)

Upstream product

• 541-59-3 maleiimide 
• 229956-58-5 [1,2]dithiino[4,3-b:5,6-b']diindole 
• 100-63-0 phenylhydrazine 
• 150044-68-1 3,4-bis(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid 
• 944472-34-8 methyl 3-(2-nitrophenyl)-2-oxobut-3-enoate 
• 81787-94-2 1-benzylindole-2-carbaldehyde 
• 118458-40-5 5,6-Bis-(phenyl-hydrazono)-hexahydro-isoindole-1,3-dione 

Downstream Products

• 85753-43-1 staurosporine aglycone 
• 118458-61-0 12,13-dihydro-3,9-dibromo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)-dione 
• 118458-60-9 tjipanazole L 
• 152628-27-8 12-ethyl-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5,7(6H)-dione 

Relevant articles and documents

A short synthesis of staurosporinone (K-252c)

A new, simple, high-yield synthesis of the indolo[2,3-a]carbazole alkaloid staurosporinone is described.

A novel synthesis of arcyriaflavin-A via an intramolecular sulfur extrusion reaction

2,3-[2',2''-Biindolyl-3',3''-dimercapto]maleimide, derived from 2,2'-biindolyl-3,3'-dithiete, dibromomaleimide and n-Bu3P, undergoes an intramolecular reaction to provide arcyriaflavin-A. (C) 2000 Elsevier Science Ltd.

A Diels-Alder, retro-Diels-Alder approach to arcyriaflavin-A

2,2'-Bi-indolyl-3,3'-dithiete and maleimide participate in a [4 + 2] cycloaddition reaction to provide arcyriaflavin-A.

A facile synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazoles via oxidative photocyclization of bisindolylmaleimides

A simple and inexpensive oxidative photocyclization of the bisindolylmaleimides in the presence of a catalytic amount of iodine leading to indolo[2,3-a]pyrrolo[3,4-c]carbazoles in 84-90% yields is described.

Oxidative cyclisations with palladium acetate. A short synthesis of staurosporine aglycone

A palladium acetate mediated oxidative cyclisation has been used as the key step for the syntheses staurosporine aglycone and related analogues.

Formal [1 + 2 + 3] Annulation: Domino Access to Carbazoles and Indolocarbazole Alkaloids

A new formal [1 + 2 + 3] annulation of o-alkenyl arylisocyanides with α, β-unsaturated ketones under metal-, base-, and acid-free conditions is disclosed. This domino reaction provides a general protocol for the efficient and practical synthesis of a wide range of carbazole derivatives from readily available starting materials in a single operation. Furthermore, this methodology was used as the key step in a protecting-group-free synthesis of indolocarbazole alkaloids arcyriaflavin A and racemosin B.

Simplified staurosporine analogs as potent JAK3 inhibitors

Simplification of bottom ring and regioselective functionalization of the indolocarbazole unit of staurosporine (2) are described. The modification led to a new series of simplified staurosporine analogs, which exhibited significant inhibitory activity ag

Molecular iodine assisted electrocyclisation: Synthesis of arcyriaflavin A and formal synthesis of staurosporinone

A new method for the synthesis of the indolocarbazole alkaloid arcyriaflavin A is described. The synthetic strategy employs a graphite-catalysed alkenation, one-pot oxidation-Wittig reaction, iodine-catalysed electrocyclisation and nitrene insertion as th

Friedel-Crafts alkylation on indolocarbazoles catalyzed by two dimethylallyltryptophan synthases from Aspergillus

Prenylated indolocarbazoles have been reported neither from natural sources, nor by chemical synthetic approaches. In this Letter, we report a regiospecific prenylation of indolocarbazoles at the para-position of the indole N-atom by two recombinant enzymes from the dimethylallyltryptophan synthase (DMATS) superfamily, that is, 5-DMATS from Aspergillus clavatus and FgaPT2 from Aspergillus fumigatus.