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34157-83-0

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34157-83-0 Usage

Pharmacological effects

Tripterine is a natural product with a variety of biological activity. It has a strong antioxidant effect, anti-cancer neovascularization effect as well as anti-rheumatoid effect. It is mainly isolated from the root bark of the celastraceae plant, Tripterygium wilfordii. It is one of the active ingredients contained in the rheumatoid-treatment drug Tripterygium tablet, Tripterygium Glycosides tablets and other preparations. The major activity and pharmacological effects of Tripterine: Cytotoxic activity. In vitro, it has non-specific cytotoxic activity against P388 and a group of human cancer cell lines. Immune regulation. It could significantly inhibit the formation of hemolytic plaque cells in mouse spleen cells and significantly inhibit the mice delayed-type hypersensitivity. Anti-inflammatory effect. At a dose of 0.5mg/kg, it could result in significant inhibition of the formation of rat cotton granuloma. At a dose of 0.1~1.0μg/mL, it could suppress the production of PGE2 induced by the yeast sugar; at a dose of 1.0μg/mL, it can inhibit the macrophage phagocytosis. The anti-oxidation effect of tripterine is 15 times that of tocopherol with an IC50 of 7μM. Inhibit the peroxidation occurring inside and outside of the mitochondrial membrane, direct removing the free radicals. Tripterine can extend the sleep time of mice triggered by the pentobarbital sodium. Immunosuppressive effect: inhibit the spleen cell proliferation of mice induced by PHA, ConA and LPS, further inhibiting the lymphocyte proliferation. It can inhibit the in vitro sperm fertilization capacity of guinea pig with the activity being significantly stronger than acetic acid gossypol. Anti-arthritic effect, it will inhibit the activity of interleukin-1 of inside and outside the mouse intraperitoneal macrophages, inhibit the production of interleukin-2 by mouse spleen cells and lower the level of PGE2 produced by rabbit synovial cells. Source: lookchem Editorial.

Application

Celastrol is an effective proteasome inhibitor. It has been confirmed that it is capable of inducing apoptosis of cancer cells through inhibiting proteasome activity.

Description

Celastrol (34157-83-0) displays potent antioxidant and anti-inflammatory activity. Inhibits NFkB (IC50=270 nM). ?It induces heat shock response and cytoprotection in various cells. Inhibits 20S proteasome chymotrypsin activity (IC50=2.5 mM). Induces autophagy by targeting AR/miR-101 in prostate cancer cells.4 Induces UPR-dependent cell death in cancer cells.5 Cell permeable.

Chemical Properties

Orange Red Solid

Uses

Different sources of media describe the Uses of 34157-83-0 differently. You can refer to the following data:
1. antineoplastic, NO synthesis inhibitor, chaperone stimulant
2. Celastrol can be used as an antioxidant onstrated to have antiangiogenic activity, and be inhibitory against mice tumor growth by a few recent studies.
3. An antioxidant natural product Celastrol inhibits the growth of human glioma xenografts in nude mice through suppressing VEGFR expression. Used for clinical treatment for rheumatoid arthritis, was demonstrated to have antiangiogenic activity, and be
4. Celastrol is an antioxidant natural product which inhibits the growth of human glioma xenografts in nude mice through suppressing VEGFR expression. Used for clinical treatment for rheumatoid arthritis, was demonstrated to have antiangiogenic activity, and be inhibitory against mice tumor growth by a few recent studies. Celastrol also has been shown to have the power to kill tumor cells and can work as an anticarcinogen. It is also a leptin sensitizer with the potential to reduce weight in obesity.

Definition

ChEBI: A pentacyclic triterpenoid that is 24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid bearing an oxo substituent at position 2, a hydroxy substituent at position 3 and two methyl groups at positions 9 and 13. An antioxidant and anti-inflammatory agent. otently inhibits lipid peroxidation in mitochondria and inhibits TNF-alpha-induced NFkappaB activation. Also shown to inhibit topoisomerase II activity in vitro (IC50 = 7.41 muM).

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biological Activity

Antioxidant and anti-inflammatory agent. Potently inhibits lipid peroxidation in mitochondria and inhibits TNF- α -induced NF κ B activation. Also shown to inhibit topoisomerase II activity in vitro (IC 50 = 7.41 μ M).

Biochem/physiol Actions

Celastrol is a potent antioxidant, and anti-inflammatory agent. It is a novel HSP90 inhibitor (disrupts Hsp90/Cdc37 complex), that exhibits anticancer (anti-angiogenic - suppresses VEGFR expression); antioxidant (inhibits lipid peroxidation) and anti-inflammatory activity (suppresses iNOS and inflammatory cytokine production).

References

1) Sethi et al. (2007), Celastrol, a novel triterpene, potentiates TNF-induced apoptosis and suppresses invasion of tumor cells by inhibiting NF-κC-regulated gene products and TAK1-mediated NF-κB activation; Blood, 109 2727 2) Westerheide et al. (2004), Celastrols as inducers of the heat shock response and cytoprotection; J. Biol. Chem., 279 56053 3) Yang et al. (2006), Celastrol, a triterpene extracted from the Chinese “Thunder of God Vine” is a potent proteasome inhibitor and suppresses human prostate cancer cell growth in nude mice; Cancer Res., 66 4758 4) Guo et al. (2015), Celastrol Induces Autophagy by targeting AR/miR-101 in Prostate Cancer Cells; PLoS One, 10(10) e0140745 5) Fribley et al. (2015), Celastrol induces unfolded protein response-dependent cell death in head and neck cancer; Exp. Cell Res., 330 412

Check Digit Verification of cas no

The CAS Registry Mumber 34157-83-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,4,1,5 and 7 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 34157-83:
(7*3)+(6*4)+(5*1)+(4*5)+(3*7)+(2*8)+(1*3)=110
110 % 10 = 0
So 34157-83-0 is a valid CAS Registry Number.
InChI:InChI=1/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1

34157-83-0 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (C2737)  Celastrol  >98.0%(HPLC)

  • 34157-83-0

  • 25mg

  • 1,990.00CNY

  • Detail
  • Sigma

  • (C0869)  Celastrol  ≥98% (HPLC), solid

  • 34157-83-0

  • C0869-10MG

  • 1,904.76CNY

  • Detail
  • Sigma

  • (C0869)  Celastrol  ≥98% (HPLC), solid

  • 34157-83-0

  • C0869-50MG

  • 7,628.40CNY

  • Detail

34157-83-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name celastrol

1.2 Other means of identification

Product number -
Other names Tripterine

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:34157-83-0 SDS

34157-83-0Synthetic route

C39H55N3O10S

C39H55N3O10S

A

GLUTATHIONE
70-18-8

GLUTATHIONE

B

celastrol
34157-83-0

celastrol

Conditions
ConditionsYield
In aq. phosphate buffer; dimethyl sulfoxide Equilibrium constant;
C31H44O5S

C31H44O5S

A

celastrol
34157-83-0

celastrol

B

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

Conditions
ConditionsYield
In aq. phosphate buffer; dimethyl sulfoxide Equilibrium constant;
celastrol
34157-83-0

celastrol

Dihydrocelastrol

Dihydrocelastrol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃;100%
With sodium tetrahydroborate In d(4)-methanol at 20℃; for 0.5h;99%
With sodium tetrahydroborate In d(4)-methanol at 20℃; for 0.5h;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(7-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(7-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;99%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
celastrol
34157-83-0

celastrol

5-methyl-1H-indole
614-96-0

5-methyl-1H-indole

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(5-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(5-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;99%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
6-methylindole
3420-02-8

6-methylindole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(6-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(6-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;99%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4-a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxamide
1361057-85-3

(2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4-a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxamide

Conditions
ConditionsYield
With ammonium chloride; N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;98%
With O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;91%
indole
120-72-9

indole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Reagent/catalyst; Solvent; Friedel-Crafts Alkylation; Sealed tube;97%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h;78%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 5h;122.2 mg
6-chloroindole
17422-33-2

6-chloroindole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-8-(6-chloro-1H-indol-3-yl)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-8-(6-chloro-1H-indol-3-yl)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;97%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
4-methoxy-1H-indole
4837-90-5

4-methoxy-1H-indole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(4-methoxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(4-methoxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;97%
celastrol
34157-83-0

celastrol

methyl iodide
74-88-4

methyl iodide

pristimerin
1258-84-0

pristimerin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;96.8%
With sodium tetrahydroborate In N,N-dimethyl-formamide at 20℃; for 48h;95.4%
With sodium carbonate In N,N-dimethyl-formamide at 20℃;90%
5-methoxylindole
1006-94-6

5-methoxylindole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(5-methoxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(5-methoxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;95%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
6-fluoro-1H-indole
399-51-9

6-fluoro-1H-indole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-8-(6-fluoro-1H-indol-3-yl)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-8-(6-fluoro-1H-indol-3-yl)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;95%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
7-methoxy-1H-indole
3189-22-8

7-methoxy-1H-indole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(7-methoxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(7-methoxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;94%
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 5h;
celastrol
34157-83-0

celastrol

5-chloro-1H-indole
17422-32-1

5-chloro-1H-indole

(2R,4aS,6aS,12bR,14aS,14bR)-8-(5-chloro-1H-indol-3-yl)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-8-(5-chloro-1H-indol-3-yl)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;94%
celastrol
34157-83-0

celastrol

1-halopentane

1-halopentane

C34H48O4

C34H48O4

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;94%
celastrol
34157-83-0

celastrol

1-(halomethyl)-3-chlorobenzene

1-(halomethyl)-3-chlorobenzene

C36H43ClO4

C36H43ClO4

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;93%
celastrol
34157-83-0

celastrol

1-halo-2-methylpropane

1-halo-2-methylpropane

3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid isobutyl ester

3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid isobutyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;93%
celastrol
34157-83-0

celastrol

[(halomethoxy)methyl]benzene

[(halomethoxy)methyl]benzene

C37H46O5

C37H46O5

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;93%
celastrol
34157-83-0

celastrol

ethyl halide

ethyl halide

3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid ethyl ester
1105067-39-7

3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;93%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;84%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-8-(5-bromo-1H-indol-3-yl)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-8-(5-bromo-1H-indol-3-yl)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;92%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
celastrol
34157-83-0

celastrol

1-halohexane

1-halohexane

C35H50O4

C35H50O4

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;92%
celastrol
34157-83-0

celastrol

halocyclopropane

halocyclopropane

C32H42O4

C32H42O4

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;92%
celastrol
34157-83-0

celastrol

1-(halomethyl)-4-bromobenzene

1-(halomethyl)-4-bromobenzene

C36H43BrO4

C36H43BrO4

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;91%
celastrol
34157-83-0

celastrol

2-halobutane

2-halobutane

C33H46O4

C33H46O4

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;91%
celastrol
34157-83-0

celastrol

butyl halide

butyl halide

butyl 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oate
842143-39-9

butyl 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oate

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;91%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;75%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;
celastrol
34157-83-0

celastrol

ethyl 2-halomoacetate

ethyl 2-halomoacetate

C33H44O6

C33H44O6

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;91%
celastrol
34157-83-0

celastrol

methyl halide

methyl halide

pristimerin
1258-84-0

pristimerin

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;91%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;74%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;
celastrol
34157-83-0

celastrol

propyl halide

propyl halide

3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid propyl ester
1239313-00-8

3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid propyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;91%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;81%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;
indol-5-ol
1953-54-4

indol-5-ol

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(5-hydroxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(5-hydroxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;90%
celastrol
34157-83-0

celastrol

(halomethyl)benzene

(halomethyl)benzene

benzyl 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oate
842143-38-8

benzyl 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oate

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;90%
celastrol
34157-83-0

celastrol

1-(halomethyl)-4-nitrobenzene

1-(halomethyl)-4-nitrobenzene

C36H43NO6

C36H43NO6

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;90%

34157-83-0Upstream product

34157-83-0Relevant articles and documents

Celastrol binds to its target protein via specific noncovalent interactions and reversible covalent bonds

Zhang, Duo,Chen, Ziwen,Hu, Chaochao,Yan, Siwei,Li, Zhuoer,Lian, Baohuan,Xu, Yang,Ding, Rong,Zeng, Zhiping,Zhang, Xiao-kun,Su, Ying

supporting information, p. 12871 - 12874 (2018/11/30)

Celastrol is one of the most studied natural products. Our studies show for the first time that celastrol can bind to its target protein via specific noncovalent interactions that position celastrol next to the thiol group of the reactive cysteine for reversible covalent bond formation. Such specific noncovalent interactions confer celastrol binding specificity and demonstrate the feasibility of improving the efficacy and selectivity of celastrol for therapeutic applications.

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