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staurosporine,62996-74-1
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62996-74-1 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,10R,11R,13R)-
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High Quality Antifungal Agent Powder CAS 62996-74-1 Staurosporine
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62996-74-1 Usage

Uses

A protein Kinase C inhibitor that induces apoptosis in many cell types

Occurrence

A complex alkaloid. staurosporine has been isolated from a strain of Streptomyces.

Uses

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.

Biological Activity

Broad spectrum protein kinase inhibitor. Enzymes inhibited include protein kinase C (IC 50 = 3 nM), protein kinase A (IC 50 = 7 nM), p 60v-src tyrosine protein kinase (IC 50 = 6 nM) and CaM kinase II (IC 50 = 20 nM). Also available as part of the Mixed Kinase Inhibitor Tocriset? .

Chemical Properties

Light Yellow Solid
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)/p+1/t17-,20-,26-,28+/m1/s1

62996-74-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name staurosporine

1.2 Other means of identification

Product number -
Other names Antibiotic 230

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:62996-74-1 SDS

62996-74-1Synthetic route

C37H36N4O5
188028-33-3

C37H36N4O5

staurosporine
62996-74-1

staurosporine

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

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

6-(O-triisopropylsilyl)-L-glucal

A

C27H24N4O3
160256-55-3

C27H24N4O3

B

staurosporine
62996-74-1

staurosporine

Conditions
ConditionsYield
With Benzyloxymethyl chloride; thiophosgene; di-tert-butyl dicarbonate; 2,3,4,5,6-pentafluorophenol; trichloroacetonitrile; p-methoxybenzyl chloride; dimethyl sulfate In dichloromethaneA 39%
B 39%
7-carbonyl staurosporin

7-carbonyl staurosporin

A

staurosporine
62996-74-1

staurosporine

B

isostaurosporine

isostaurosporine

Conditions
ConditionsYield
With sodium tetrahydroborate; Benzeneselenol; toluene-4-sulfonic acid 1.) EtOH, RT, 2.) CH2Cl2, RT; Yield given. Multistep reaction. Yields of byproduct given;
C36H34N4O5
188028-11-7

C36H34N4O5

staurosporine
62996-74-1

staurosporine

Conditions
ConditionsYield
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
C37H34N4O6
195617-12-0

C37H34N4O6

staurosporine
62996-74-1

staurosporine

Conditions
ConditionsYield
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
formaldehyd
50-00-0

formaldehyd

staurosporine
62996-74-1

staurosporine

(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
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
ConditionsYield
With sodium cyanoborohydride Methylation;100%
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

staurosporine
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

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
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 48h;97%
benzoyl chloride
98-88-4

benzoyl chloride

staurosporine
62996-74-1

staurosporine

N-benzoylstaurosporine

N-benzoylstaurosporine

Conditions
ConditionsYield
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;
staurosporine
62996-74-1

staurosporine

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

2,2,2-Trichloroethyl chloroformate

C31H27Cl3N4O5
135384-24-6

C31H27Cl3N4O5

Conditions
ConditionsYield
92%
With triethylamine In dichloromethane at 0 - 20℃;92%
succinic acid anhydride
108-30-5

succinic acid anhydride

staurosporine
62996-74-1

staurosporine

C32H30N4O6

C32H30N4O6

Conditions
ConditionsYield
Inert atmosphere;92%
With dmap In dimethyl sulfoxide at 20℃; for 30h;91%
With dmap In dimethyl sulfoxide Inert atmosphere;90%
benzoic acid anhydride
93-97-0

benzoic acid anhydride

staurosporine
62996-74-1

staurosporine

N-benzoylstaurosporine

N-benzoylstaurosporine

Conditions
ConditionsYield
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;
staurosporine
62996-74-1

staurosporine

7-oxoylidenestaurosporine

7-oxoylidenestaurosporine

Conditions
ConditionsYield
With potassium tert-butylate; oxygen In dimethyl sulfoxide at 20℃; for 6h;88.6%
staurosporine
62996-74-1

staurosporine

7-carbonyl staurosporin

7-carbonyl staurosporin

Conditions
ConditionsYield
With potassium tert-butylate; oxygen In dimethyl sulfoxide at 20℃; for 6h;88.6%
staurosporine
62996-74-1

staurosporine

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

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

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

Conditions
ConditionsYield
In tetrahydrofuran for 12h; Reflux;84%
4-Fluorobenzenesulfonyl chloride
349-88-2

4-Fluorobenzenesulfonyl chloride

staurosporine
62996-74-1

staurosporine

3'-N-p-fluorobenzenesulfonylstaurosporine

3'-N-p-fluorobenzenesulfonylstaurosporine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;83.3%
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;83.3%
1,1'-Thiocarbonyldiimidazole
6160-65-2

1,1'-Thiocarbonyldiimidazole

staurosporine
62996-74-1

staurosporine

3'-N-(1-imidazolylthioformyl)staurosporine

3'-N-(1-imidazolylthioformyl)staurosporine

Conditions
ConditionsYield
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%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

staurosporine
62996-74-1

staurosporine

3'-N-(tert-butoxycarbonyl)staurosporine

3'-N-(tert-butoxycarbonyl)staurosporine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;82%
With triethylamine In tetrahydrofuran at 10℃; for 0.5h;76%
1H-imidazole
288-32-4

1H-imidazole

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

staurosporine
62996-74-1

staurosporine

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

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

Conditions
ConditionsYield
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%
staurosporine
62996-74-1

staurosporine

chlorambucil
305-03-3

chlorambucil

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

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

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;80%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;80%
1H-imidazole
288-32-4

1H-imidazole

staurosporine
62996-74-1

staurosporine

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

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

Conditions
ConditionsYield
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%
4-oxo-4-(prop-2-yn-1-ylamino)butanoic acid
342022-20-2

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

staurosporine
62996-74-1

staurosporine

C35H33N5O5

C35H33N5O5

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide56%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

staurosporine
62996-74-1

staurosporine

bis-Boc staurosporine

bis-Boc staurosporine

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 25℃; for 48h; Inert atmosphere;55%
tert-butyl N-(2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethyl)carbamate

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

staurosporine
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

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
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 17h;50%
bromocyane
506-68-3

bromocyane

staurosporine
62996-74-1

staurosporine

3'-N-cyanostauroporine
1415406-02-8

3'-N-cyanostauroporine

Conditions
ConditionsYield
Stage #1: staurosporine With potassium carbonate In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: bromocyane In tetrahydrofuran at 20℃; for 3h;
38%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

staurosporine
62996-74-1

staurosporine

KIST301135
1326539-88-1

KIST301135

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 12h;13%
staurosporine
62996-74-1

staurosporine

methyl iodide
74-88-4

methyl iodide

4'-N-methylstaurosporine methiodide

4'-N-methylstaurosporine methiodide

Conditions
ConditionsYield
With tributyl-amine In N,N-dimethyl-formamide Ambient temperature;
staurosporine
62996-74-1

staurosporine

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

(+)-RK-286c

Conditions
ConditionsYield
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
staurosporine
62996-74-1

staurosporine

staurosporine
155416-34-5

staurosporine

Conditions
ConditionsYield
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
staurosporine
62996-74-1

staurosporine

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

3'-demethylamino-3'-oxostaurosporine

Conditions
ConditionsYield
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
staurosporine
62996-74-1

staurosporine

C27H21N3O3
169756-23-4

C27H21N3O3

Conditions
ConditionsYield
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
staurosporine
62996-74-1

staurosporine

C27H23N3O3

C27H23N3O3

Conditions
ConditionsYield
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
staurosporine
62996-74-1

staurosporine

C27H21N3O4
169756-27-8

C27H21N3O4

Conditions
ConditionsYield
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

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