Staurosporine, from Streptomyces sp.

Base Information

• Chemical Name: Staurosporine, from Streptomyces sp.
• CAS No.: 62996-74-1
• Molecular Formula: C28H26N4O3
• Molecular Weight: 466.539
• Hs Code.: 29419090
• European Community (EC) Number: 613-127-7,638-872-5
• Nikkaji Number: J1.482.863J
• Wikipedia: Staurosporine
• Pharos Ligand ID: 4UXA8QJ761JD
• ChEMBL ID: CHEMBL1537489
• Mol file: 62996-74-1.mol

Synonyms:MLS000028832;SMR000058536;622996-74-1;62996-74-1;CGP-39360;C28-H26-N4-O3;Antibiotic AM-2282;STS;AM-2282;Staurosporine, from Streptomyces sp.;Opera_ID_1924;Genbank aao27471(9ci);CHEMBL1537489;SCHEMBL13659665;BDBM32337;cid_5311103;REGID_for_CID_5311103;MFCD18252446;SMP1_000279;SR-01000721921-2

Chemical Property of Staurosporine, from Streptomyces sp.

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 3.25E-18mmHg at 25°C
• Melting Point: 270 °C
• Boiling Point: 677.523 °C at 760 mmHg
• PKA: 14.25±0.70(Predicted)
• Flash Point: 363.553 °C
• PSA: 69.45000
• Density: 1.562 g/cm³
• LogP: 5.07370
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• Water Solubility.: Soluble in DMSO or ethanol.Soluble in dimethyl sulfoxide , dimethyl formamide, ethyl acetate, hot acetone and ethanol. Slightly
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 466.20049070
• Heavy Atom Count: 35
• Complexity: 901

Purity/Quality:

99.9% by HPLC ^*data from raw suppliers

Staurosporin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; T; Xi
• Hazard Codes: Xn,T,Xi
• Statements: 40-45-36/37/38-46
• Safety Statements: 36/37-53-36-26-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12C(C(CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)NC)OC
• Isomeric SMILES: C[C@@]12[C@H]([C@H](C[C@@H](O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)NC)OC
• Description: Staurosporine (Stsp) is potent inhibitor of protein kinase C (PKC) from rat brain, exhibiting an IC50 value of 2.7 nM. It inhibits rat recombinant PKC-α approximately 100- and 1,000-fold better than PKC-δ and PKC-ζ, respectively. However, Stsp is non-selective in that it also inhibits the activity of a variety of other protein kinases, not only PKC isoforms. The biological effects of Stsp include cytotoxicity, relaxation of smooth muscle, and regulation of eNOS gene expression.
• Uses: Staurosporine is a protein Kinase C inhibitor that induces apoptosis in many cell types. A protein Kinase C inhibitor that induces apoptosis in many cell types Staurosporine is an unusual indolocarbazole alkaloid produced by a range of actinomycete species. It is a potent antitumour active, inducing apoptosis in a variety of cell lines. Staurosporine is a potent inhibitor of many kinases including protein kinase C, tyrosine kinase, CDK2/cyclin A and CDK4/cyclin D. At submicromolar concentrations, staurosporine inhibits both IKKalpha and IKKbeta.

Technology Process of Staurosporine, from Streptomyces sp.

There total 15 articles about Staurosporine, from Streptomyces sp. which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

C37H36N4O5 (188028-33-3) → staurosporine (62996-74-1)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; for 48h;

DOI:10.1021/ja971304x

Reference yield: 39.0%

1-<(benzyloxy)methyl>-3,4-dihydro-4-(1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione (160256-37-1) + 6-(O-triisopropylsilyl)-L-glucal → C27H24N4O3 (160256-55-3) + staurosporine (62996-74-1)

Guidance literature:

With Benzyloxymethyl chloride; thiophosgene; di-tert-butyl dicarbonate; 2,3,4,5,6-pentafluorophenol; trichloroacetonitrile; p-methoxybenzyl chloride; dimethyl sulfate; In dichloromethane;

Reference yield:

C37H34N4O6 (195617-12-0) → staurosporine (62996-74-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 mg / H₂ / PtO₂ / aq. acetic acid

2: 2.) BH₃*DMS / 1) THF; 2) THF, toluene, reflux, 2 h

3: 70 percent / TFA, anisole / 48 h

With dimethylsulfide borane complex; hydrogen; methoxybenzene; trifluoroacetic acid; platinum(IV) oxide; In acetic acid;

DOI:10.1021/ja971304x

upstream raw materials:

ent-7-oxostaurosporine

3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine

6-N-<(benzyloxy)methyl>-3'-O-desmethyl-4'-N-desmethyl-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine

6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine

Downstream raw materials:

7-carbonyl staurosporin

7-oxoylidenestaurosporine

Refernces

• 1、 -. "COMPOUNDS FOR IMMUNOPOTENTIATION". Page/Page column 140. . Retrieved 2010/02/15.
• 2、 Link,Raghavan, Subharekha,Gallant, Michel,Danishefsky, Samuel J.,Chou,Ballas, Lawrence M.. "Staurosporine and ent-staurosporine: The first total syntheses, prospects for a regioselective approach, and activity profiles". . p. 2825 - 2842. Retrieved 2007/10/03.