Staurosporine supplier | CasNO.62996-74-1

Name
STAUROSPORINE
EINECS 613-127-7
CAS No. 62996-74-1
Article Data6
CAS DataBase
Density 1.562 g/cm³
Solubility Soluble in DMSO or ethanol.Soluble in dimethyl sulfoxide , dimethyl formamide, ethyl acetate, hot acetone and ethanol. Slightly soluble in chloroform and methanol. Insoluble in water.
Melting Point 270 °C
Formula C₂₈H₂₆N₄O₃
Boiling Point 677.523 °C at 760 mmHg
Molecular Weight 466.539
Flash Point 363.553 °C
Transport Information
Appearance off-white powder
Safety 36/37-53-26
Risk Codes 40-45-36/37/38
Molecular Structure
Hazard Symbols Xn; T; Xi
Synonyms 9,13-Epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one,2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, [9S-(9a,10b,11b,13a)]-;(+)-Staurosporine;AM-2282;Alkaloid AM-2282 from Streptomyces;Antibiotic 230;Antibiotic AM 2282;CGP39360;Staurosporin;Staurosporine;
PSA 69.45000
LogP 5.07370

Synthetic route

: 188028-33-3
C37H36N4O5

: 62996-74-1
staurosporine

Conditions

Conditions	Yield
With methoxybenzene; trifluoroacetic acid for 48h;	70%
With methoxybenzene; trifluoroacetic acid Yield given;

: 160256-37-1
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

: 6-(O-triisopropylsilyl)-L-glucal

A: 160256-55-3
C27H24N4O3

B: 62996-74-1
staurosporine

Conditions

Conditions	Yield
With Benzyloxymethyl chloride; thiophosgene; di-tert-butyl dicarbonate; 2,3,4,5,6-pentafluorophenol; trichloroacetonitrile; p-methoxybenzyl chloride; dimethyl sulfate In dichloromethane	A 39% B 39%

...Expand

: 7-carbonyl staurosporin

A: 62996-74-1
staurosporine

B: isostaurosporine

Conditions

Conditions	Yield
With sodium tetrahydroborate; Benzeneselenol; toluene-4-sulfonic acid 1.) EtOH, RT, 2.) CH2Cl2, RT; Yield given. Multistep reaction. Yields of byproduct given;

: 188028-11-7
C36H34N4O5

: 62996-74-1
staurosporine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) BH3*DMS / 1) THF; 2) THF, toluene, reflux, 2 h 2: 70 percent / TFA, anisole / 48 h View Scheme
Multi-step reaction with 2 steps 1: BH3*Me2S 2: CF3CO2H, anisole View Scheme

: 195617-12-0
C37H34N4O6

: 62996-74-1
staurosporine

Conditions

Conditions	Yield
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 View Scheme
Multi-step reaction with 3 steps 1: 96 percent / H2 / PtO2 2: BH3*Me2S 3: CF3CO2H, anisole View Scheme

: 50-00-0
formaldehyd

: 62996-74-1
staurosporine

: 129623-30-9
(5S,6R,7R,9R)-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-14(5h)-one

Conditions

Conditions	Yield
With sodium cyanoborohydride Methylation;	100%

: 96-32-2
bromoacetic acid methyl ester

: 62996-74-1
staurosporine

: methyl N-((5R,7R,8R,9S)-8-methoxy-9-methyl-16-oxo-6,7,8,9,15,16-hexahydro-5H,14H-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-7-yl)-N-methylglycinate

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 48h;	97%

: 98-88-4
benzoyl chloride

: 62996-74-1
staurosporine

: N-benzoylstaurosporine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 5℃; for 0.5h;	95%
With triethylamine In N,N-dimethyl-formamide Reagent/catalyst;

: 62996-74-1
staurosporine

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: 135384-24-6
C31H27Cl3N4O5

Conditions

Conditions	Yield
	92%
With triethylamine In dichloromethane at 0 - 20℃;	92%

: 108-30-5
succinic acid anhydride

: 62996-74-1
staurosporine

: C32H30N4O6

Conditions

Conditions	Yield
Inert atmosphere;	92%
With dmap In dimethyl sulfoxide at 20℃; for 30h;	91%
With dmap In dimethyl sulfoxide Inert atmosphere;	90%

: 93-97-0
benzoic acid anhydride

: 62996-74-1
staurosporine

: N-benzoylstaurosporine

Conditions

Conditions	Yield
In ethanol; water at 70℃; Product distribution / selectivity;	91.5%
In ethanol; water at 70℃; Product distribution / selectivity;	82%
In ethanol; dichloromethane at 26 - 40℃; for 35h; Solvent; Temperature;

: 62996-74-1
staurosporine

: 7-oxoylidenestaurosporine

Conditions

Conditions	Yield
With potassium tert-butylate; oxygen In dimethyl sulfoxide at 20℃; for 6h;	88.6%

: 62996-74-1
staurosporine

: 7-carbonyl staurosporin

Conditions

Conditions	Yield
With potassium tert-butylate; oxygen In dimethyl sulfoxide at 20℃; for 6h;	88.6%

: 62996-74-1
staurosporine

: 530-62-1
1,1'-carbonyldiimidazole

: 3'-N-(1H-imidazol-1-yl)carbonylstaurosporine

Conditions

Conditions	Yield
In tetrahydrofuran for 12h; Reflux;	84%

: 349-88-2
4-Fluorobenzenesulfonyl chloride

: 62996-74-1
staurosporine

: 3'-N-p-fluorobenzenesulfonylstaurosporine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	83.3%
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	83.3%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 62996-74-1
staurosporine

: 3'-N-(1-imidazolylthioformyl)staurosporine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;	82%
With triethylamine In dichloromethane at 20℃;	78%
With triethylamine In dichloromethane at 20℃;	78%
With triethylamine In dichloromethane at 20℃;	78%

: 24424-99-5
di-tert-butyl dicarbonate

: 62996-74-1
staurosporine

: 3'-N-(tert-butoxycarbonyl)staurosporine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	82%
With triethylamine In tetrahydrofuran at 10℃; for 0.5h;	76%

: 288-32-4
1H-imidazole

: 32315-10-9
bis(trichloromethyl) carbonate

: 62996-74-1
staurosporine

: 3'-N-(1H-imidazol-1-yl)carbonylstaurosporine

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; staurosporine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: 1H-imidazole With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃; for 2h;	80%

...Expand

: 62996-74-1
staurosporine

: 305-03-3
chlorambucil

: 3'-N-[4-[4-(N,N-bis(2-chloroethyl)amino)phenyl]butyryl]staurosporine

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;	80%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;	80%

: 288-32-4
1H-imidazole

: 62996-74-1
staurosporine

: 3'-N-(1H-imidazol-1-yl)carbonylstaurosporine

Conditions

Conditions	Yield
Stage #1: staurosporine With bis(trichloromethyl) carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: 1H-imidazole With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃; for 2h;	80%

: 342022-20-2
4-oxo-4-(prop-2-yn-1-ylamino)butanoic acid

: 62996-74-1
staurosporine

: C35H33N5O5

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide	56%

: 24424-99-5
di-tert-butyl dicarbonate

: 62996-74-1
staurosporine

: bis-Boc staurosporine

Conditions

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 25℃; for 48h; Inert atmosphere;	55%

: tert-butyl N-(2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethyl)carbamate

: 62996-74-1
staurosporine

: tert-butyl 2-[[(5S,6R,7R,9R)-6-methoxy-5-methyl-14-oxo-6,7,8,9,15,16-hexahydro-5H,14H-5,9-epoxy-4b,9a,15-triazadibenzo[b,h]cyclonona[1,2,3,4-jkl]cyclopenta[e]-as-indacen-7-yl]-5,8,11-trioxa-2-azatridecan-13-yl]carbamate

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 17h;	50%

: 506-68-3
bromocyane

: 62996-74-1
staurosporine

: 1415406-02-8
3'-N-cyanostauroporine

Conditions

Conditions	Yield
Stage #1: staurosporine With potassium carbonate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: bromocyane In tetrahydrofuran at 20℃; for 3h;	38%

: 32315-10-9
bis(trichloromethyl) carbonate

: 62996-74-1
staurosporine

: 1326539-88-1
KIST301135

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 12h;	13%

: 62996-74-1
staurosporine

: 74-88-4
methyl iodide

: 4'-N-methylstaurosporine methiodide

Conditions

Conditions	Yield
With tributyl-amine In N,N-dimethyl-formamide Ambient temperature;

: 62996-74-1
staurosporine

: 126572-73-4
(+)-RK-286c

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / NaBH3CN 2: 92 percent / m-chloroperoxybenzoic acid (m-CPBA) / CHCl3 3: 85 percent / 160 °C / 1 Torr 4: 65 percent / OsO4; N-methylmorpholine-N-oxide (NMO) 5: 60 percent / tetrahydrofuran 6: 47 percent / n-Bu3SnH; 2,2'-azobisisobutyronitrile (AIBN) / toluene 7: 80 percent 8: 50 percent / potassium tri-sec-butyl borohydride (K-Selectride) View Scheme

Yield

Multi-step reaction with 8 steps
1: 100 percent / NaBH3CN
2: 92 percent / m-chloroperoxybenzoic acid (m-CPBA) / CHCl3
3: 85 percent / 160 °C / 1 Torr
4: 65 percent / OsO4; N-methylmorpholine-N-oxide (NMO)
5: 60 percent / tetrahydrofuran
6: 47 percent / n-Bu3SnH; 2,2'-azobisisobutyronitrile (AIBN) / toluene
7: 80 percent
8: 50 percent / potassium tri-sec-butyl borohydride (K-Selectride)
View Scheme

: 62996-74-1
staurosporine

: 155416-34-5
staurosporine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / NaBH3CN 2: 92 percent / m-chloroperoxybenzoic acid (m-CPBA) / CHCl3 3: 85 percent / 160 °C / 1 Torr 4: 65 percent / OsO4; N-methylmorpholine-N-oxide (NMO) View Scheme

: 62996-74-1
staurosporine

: 178276-05-6
3'-demethylamino-3'-oxostaurosporine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 100 percent / NaBH3CN 2: 92 percent / m-chloroperoxybenzoic acid (m-CPBA) / CHCl3 3: 85 percent / 160 °C / 1 Torr 4: 65 percent / OsO4; N-methylmorpholine-N-oxide (NMO) 5: 60 percent / tetrahydrofuran 6: 47 percent / n-Bu3SnH; 2,2'-azobisisobutyronitrile (AIBN) / toluene 7: 80 percent View Scheme

: 62996-74-1
staurosporine

: 169756-23-4
C27H21N3O3

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / NaBH3CN 2: 92 percent / m-chloroperoxybenzoic acid (m-CPBA) / CHCl3 3: 85 percent / 160 °C / 1 Torr View Scheme

: 62996-74-1
staurosporine

: C27H23N3O3

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 100 percent / NaBH3CN 2.1: 92 percent / m-chloroperoxybenzoic acid (m-CPBA) / CHCl3 3.1: 85 percent / 160 °C / 1 Torr 4.1: BH3 4.2: 80 percent / H2O2; NaOH 5.1: 58 percent / tetrahydrofuran 6.1: 63 percent / n-Bu3SnH; 2,2'-azobisisobutyronitrile (AIBN) / toluene View Scheme

: 62996-74-1
staurosporine

: 169756-27-8
C27H21N3O4

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 100 percent / NaBH3CN 2.1: 92 percent / m-chloroperoxybenzoic acid (m-CPBA) / CHCl3 3.1: 85 percent / 160 °C / 1 Torr 4.1: BH3 4.2: 80 percent / H2O2; NaOH 5.1: 88 percent View Scheme

Staurosporine Specification

The Staurosporine, with CAS registry number 62996-74-1, belongs to the following product categories: (1)All Inhibitors; (2)Inhibitors; (3)Intermediates & Fine Chemicals; (4)Pharmaceuticals; (5)Protein Kinase Inhibitors and Activators; (6)Protein Kinase; (7)Signalling. It has the systematic name of (5S,6R,7R,9R)-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-5H,14H-5,9-epoxy-4b,9a,15-triazadibenzo[b,h]cyclonona[1,2,3,4-jkl]cyclopenta[e]-as-indacen-14-one. This chemical should be stored at the temperature of 2-8°C. The main biological activity of this chemical is the inhibition of protein kinases through the prevention of ATP binding to the kinase. And the use of this chemical is to induce apoptosis. Besides this, it is also used as a starting material in the commercial synthesis of K252C (also called staurosporine aglycone).

Physical properties of Staurosporine: (1)ACD/LogP: 5.27; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.327; (4)ACD/LogD (pH 7.4): 3.713; (5)ACD/BCF (pH 5.5): 6.798; (6)ACD/BCF (pH 7.4): 165.23; (7)ACD/KOC (pH 5.5): 20.016; (8)ACD/KOC (pH 7.4): 486.488; (9)#H bond acceptors: 7; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 69.45 Å²; (13)Index of Refraction: 1.81; (14)Molar Refractivity: 128.823 cm³; (15)Molar Volume: 298.711 cm³; (16)Polarizability: 51.07×10^-24cm³; (17)Surface Tension: 62.885 dyne/cm; (18)Enthalpy of Vaporization: 99.457 kJ/mol; (19)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
The Trimesic acid irritates to eyes, respiratory system and skin. This chemical may cause cancer. And it has limited evidence of a carcinogenic effect. Before using it, please avoid exposure - obtain special instructions before use. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: C[C@@]12[C@@H]([C@@H](C[C@@H](O1)n3c4ccccc4c5c3c6n2c7ccccc7c6c8c5C(=O)NC8)NC)OC
(2)InChI: InChI=1/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20-,26-,28+/m1/s1
(3)InChIKey: HKSZLNNOFSGOKW-FYTWVXJKBZ
(4)Std. InChI: InChI=1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20-,26-,28+/m1/s1
(5)Std. InChIKey: HKSZLNNOFSGOKW-FYTWVXJKSA-N

Product Name

STAUROSPORINE

Synthetic route

Staurosporine Specification

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