85753-43-1

Basic information

• Product Name: K-252C
• Synonyms: K-252C;STAUROSPORINE AGLYCONE;Staurosporinone;6,7,12,13-Tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one;Staurosporine Aglycone >99%;Staurosporinone, K-252c;K-252c(Staurosporinone);Staurosporinone, Staurosporine Aglycone
• CAS NO: 85753-43-1
• Molecular Formula: C₂₀H₁₃N₃O
• Molecular Weight: 311.34
• Product Categories: Inhibitor
• Mol File: 85753-43-1.mol

Chemical Properties

• Appearance: /solid
• Storage Temp.: −20°C
• Solubility: DMSO: 10 mg/mL, soluble
• Water Solubility: Soluble in DMSO at 25mM. Also soluble in methanol. Insoluble in water.
• CAS DataBase Reference: K-252C(CAS DataBase Reference)
• NIST Chemistry Reference: K-252C(85753-43-1)
• EPA Substance Registry System: K-252C(85753-43-1)

Safety Data

• Safety Statements: 22-24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 85753-43-1(Hazardous Substances Data)

Usage

Uses

Inhibits protein kinase C

Biological Activity

Inhibitor of protein kinase C (IC 50 = 2.45 μ M) that displays ~ 10-fold selectivity over protein kinase A (IC 50 = 25.7 μ M). Also inhibits β -lactamase, malate dehydrogenase and chymotrypsin (IC 50 values are 8, 8 and 10 μ M respectively). Exhibits antiviral activity against GCV-sensitive and -resistant strains of human cytomegalovirus (HCMV) (IC 50 values range from 0.13-0.32 μ M). Shows no activity against herpes simplex virus (HSV).

references

1. fabre s, prudhomme m, rapp m. protein kinase c inhibitors; structure-activity relationships in k252c-related compounds. bioorg med chem 1993,1:193-196.2. hashimoto s. k-252a, a potent protein kinase inhibitor, blocks nerve growth factor-induced neurite outgrowth and changes in the phosphorylation of proteins in pc12h cells. j cell biol 1988,107:1531-1539.3. raychaudhuri sp, sanyal m, weltman h, kundu-raychaudhuri s. k252a, a high-affinity nerve growth factor receptor blocker, improves psoriasis: an in vivo study using the severe combined immunodeficient mouse-human skin model. j invest dermatol 2004,122:812-819.

Upstream product

• 132148-42-6 4-(2'-Nitrophenyl)-2,3-dihydro-2H,6H-pyrrolo<3,4-c>carbazol-1-one 
• 85753-78-2 3,4-bis(3-1H-indolyl)-2,5-dihydro-1H-2-pyrrolone 
• 51925-58-7 3-diazopyrrolidine-2,4-dione 
• 40899-99-8 2,2'-biindole 
• 150044-68-1 3,4-bis(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid 
• 934506-81-7 12-benzyl-5-cyano-11,12-dihydroindolo[2,3-a]carbazole 
• 934506-84-0 12-benzyl-5-(aminomethyl)-11,12-dihydroindolo[2,3-a]carbazole 
• 934506-85-1 12-benzyl-5-[N-(2,6-dimethylbenzyl)aminomethyl]-11,12-dihydroindolo[2,3-a]carbazole 
• 115684-58-7 6,7,12,13-tetrahydro-5,7-dioxo-5H-indolo<2,3-a>furo<3,4-c>carbazole 
• 1504-65-0 3-(2-nitrophenyl)prop-2-en-1-ol 
• 75059-00-6 (2-Nitrocinnamyl)amine 
• 138956-09-9 Ethyl 3-<glyoxylyl>indole-2-acetate 
• 1466-88-2 2-nitrocinnamaldehyde 
• 1466-88-2 2-nitrocinnamic aldehyde 

Relevant articles and documents

INDOLE-YNONE MEDIATED BENZOANNULATION PROCESS FOR THE PREPARATION OF CARBAZOLES- CARBAZOMYCIN A, CALOTHRIXIN B AND STAUROSPORINONE

The present invention relates to carbazoles of general formula (I), and process for the preparation thereof: wherein 'R1' is H, C1-C6 alkyl, benzyl, or allyl; R2 is H, C1-C6 alkyl, cyclopropyl, phenyl, aryl, heteroaryl, or NO2; R3 is H, C1-C6 alkyl, cyclopropyl, phenyl aryl, heteroaryl, 4-methoxy phenyl, 4-ethyl phenyl, 2-methyl phenyl, or 2-Fluoro phenyl; R4 is H, benzoyl, -CO2Et, -CHO, Br, or -OMe; R5 is OH, OMOM, OMe, CN, or OTf; R6 is H, or O-alkyl; and R3-R4 is -CHNCH2CH2-. This invention also relates to the process for the preparation of carbazomycin A of Formula (1), calothrixin B of Formula (2) and staurosporinone of Formula (3) involving carbazoles of general formula (I) as an intermediate.

A General Carbazole Synthesis via Stitching of Indole-Ynones with Nitromethanes: Application to Total Synthesis of Carbazomycin A, Calothrixin B, and Staurosporinone

A new, one-pot domino benzannulation reaction between indole-3-ynones and various nitromethane derivatives has been explored for a general entry to diversely functionalized carbazole frameworks (28 examples). The scope of this new benzannulation has been

Br?nsted Acid Catalyzed One-Pot Benzannulation of 2-Alkenylindoles under Aerial Oxidation: A Route to Carbazoles and Indolo[2,3- a]carbazole Alkaloids

A one-pot, protecting-group-free benzannulation of 2-alkenylindoles with readily available 1,3-dicarbonyls is demonstrated to construct structurally diverse carbazoles. The use of a cheap Br?nsted acid catalyst and air as the sole oxidant exemplifies the economic viability of this protocol. The execution of four different reactions successively to generate the medicinally important indolocarbazole core is also achieved. This one-pot protecting-group-free method paved the way for the total synthesis of three medicinally important alkaloids, namely staurosporinone, arcyriaflavin A, and 7-hydroxy-K252c.

The total synthesis of K-252c (staurosporinone) via a sequential C-H functionalisation strategy

A synthesis of the bioactive indolocarbazole alkaloid K-252c (staurosporinone) via a sequential C-H functionalisation strategy is reported. The route exploits direct functionalisation reactions around a simple arene core and comprises of two highly-select

Synthetic studies on indolocarbazoles: A facile synthesis of staurosporinone analogues

Synthesis of indolocarbazoles was achieved through thermal electrocyclization followed by triethyl phosphite-mediated nitrene insertion reactions. Total synthesis of staurosporinone analogues was achieved from commercially available 2-methylindole. The CD

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.

Rapid room-temperature 11C-methylation of arylamines with [ 11C]methyl iodide promoted by solid inorganic-bases in DMF

[11C]Methyl iodide is the most widely used reagent for labeling radiotracers with carbon-11 (t1/2 = 20.4 min) for molecular imaging with positron emission tomography. However, some substrates for labeling, especially primary arylamin

Synthetic studies on indolocarbazoles: Total synthesis of staurosporine aglycon

A synthesis of staurosporine aglycon and its analogs was achieved in a 28-36% overall yield starting from 2-methylindole. The prominent key steps for the synthesis of the indolocarbazole alkaloids involved electrocyclization and nitrene insertion reactions.

Synthetic staurosporines via a ring closing metathesis strategy as potent JAK3 inhibitors and modulators of allergic responses

The synthesis and biological evaluation of JAK3 based staurosporine compounds is described. The compounds are constructed completely de novo, and a ring closing metathesis strategy is used to assemble the sugar mimetic portion. These analogs show potent J

Synthesis of N-protected staurosporinones

We report a method for the synthesis of N-protected staurosporinones, which are useful for the synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazole alkaloids and related compounds. An interaction of gramine methiodide (2) with 3-(N-benzyl)indolylacetonitrile