LCL-161

Product Name: LCL-161
CAS No.: 1005342-46-0
Chemical Name: LCL-161
Synonyms: CS-987;LCL-161;LCL-161; LCL161;LCL-161 USP/EP/BP;LCL161, 10 mM in DMSO;LCL161, inhibitor of Apoptosis Protein (IAP) family of proteins;LCL161, 98%, inhibitor of Apoptosis Protein (IAP) family of proteins;(S)-N-((S)-1-Cyclohexyl-2-((S)-2-(4-(4-fluorobenzoyl)thiazol-2-yl)pyrrolidin-1-yl)-2-oxoethyl);N-[(1S)-1-Cyclohexyl-2-{(2S)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]-1-pyrrolidinyl}-2-oxoethyl]-N2-MethylalaninaMide;(2S)-N-[(1S)-1-Cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-2-thiazolyl]-1-pyrrolidinyl]-2-oxoethyl]-2-(methylamino)-propanamide
CBNumber: CB62650157
Molecular Formula: C26H33FN4O3S
Formula Weight: 500.63
MOL File: 1005342-46-0.mol

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LCL-161 Property

Boiling point:: 713.7±60.0 °C(Predicted)
Density: 1.245±0.06 g/cm3(Predicted)
storage temp.: Store at -20°C
solubility: ≥25.05 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH
form: solid
pka: 14.25±0.46(Predicted)
color: White to yellow
InChIKey: UFPFGVNKHCLJJO-SSKFGXFMSA-N
SMILES: C(N[C@@H](C1CCCCC1)C(N1CCC[C@H]1C1=NC(C(=O)C2=CC=C(F)C=C2)=CS1)=O)(=O)[C@@H](NC)C

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Safety

RIDADR: 3077
HS Code: 29341000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 22420
Product name: LCL-161
Purity: ≥98%
Packaging: 5mg
Price: $160
Updated: 2024/03/01

Cayman Chemical

Product number: 22420
Product name: LCL-161
Purity: ≥98%
Packaging: 10mg
Price: $286
Updated: 2024/03/01

Cayman Chemical

Product number: 22420
Product name: LCL-161
Purity: ≥98%
Packaging: 25mg
Price: $515
Updated: 2024/03/01

Cayman Chemical

Product number: 22420
Product name: LCL-161
Purity: ≥98%
Packaging: 50mg
Price: $869
Updated: 2024/03/01

TRC

Product number: L270000
Product name: LCL161
Packaging: 25mg
Price: $475
Updated: 2021/12/16

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LCL-161 Chemical Properties,Usage,Production

Description

LCL-161 is a small molecule Smac mimetic that inhibits multiple inhibitor of apoptosis (IAP) family proteins.

Uses

LCL 161 is a second mitochondria-derived activator of caspases (SMAC) inhibitor used to prolong patient survival by increasing apoptosis of anti-tumor drugs.

Synthesis

1005342-82-4

1005342-46-0

General procedure for the synthesis of (S)-N-((S)-1-cyclohexyl-2-((S)-2-(4-(4-fluorobenzoyl)thiazol-2-yl)pyrrolidin-1-yl)-2-oxoethyl)-2-(methylamino)propanamide from B6 to B7 (Compound (I)) using Compound (CAS:1005342-82-4) as a raw material. To a 2L Argonaut reactor containing 120 g (20 mmol) of crude B6 was added 360.8 g (400 mL) of ethyl acetate. The solution was heated to 45±3°C and 109.1 g (120 mL) of isopropanol solution of 5-6N HCl was slowly added while maintaining the temperature at 45±3°C for 30 min. Stirring was continued at 45±3°C for 2 hours. Samples were taken for process control analysis. If the process control analysis passed, the reaction mixture was cooled to 18±3°C. The solution was slowly added to another 2L Argonaut reactor, which was pre-filled with 500g of water and 82.9g of potassium carbonate, while controlling the temperature at 5 ± 3°C. After stirring at 5±3°C for 30 minutes, 451 g (500 mL) of ethyl acetate was added. The solution was warmed to 20±3°C and kept for 1 hour. The two layers were separated and the upper organic phase was retained as B7 was present in this phase. The organic layer was washed with 286.6 g (250 mL) of brine and the lower aqueous phase was discarded. The upper organic phase was concentrated under reduced pressure to 500 mL at 30 °C. 1368 g (2 L) of heptane was slowly added while maintaining the temperature at 30 ± 3 °C. The suspension was cooled to 18 °C and the temperature was set at 30 ± 3 °C. The suspension was cooled to 18±3°C and held for 1 hr. The solids were collected by filtration and washed with 136 g (200 mL) of simvastatin-containing heptane. The solid was dried in an oven at 45°C for 16 hours to give 80 g of B7 in 80% yield.

in vivo

Tumor-bearing mice are treated with vehicle or LCL161 p.o. at a dose of 50 mg/kg/day, or SC-2001 p.o. at a dose of 10 mg/kg/day, 5 days a week, or in combination for the duration of the study. Tumor growth is significantly inhibited by co-treatment with SC2001 and LCL161 and tumor size in the co-treatment group is only one third of that of the control group at the end of the study^[2]. LCL161 is a first-in-class oral Smac mimetic shown to induce degradation of cIAP1 and cleavage of caspase 3 in mouse xenograft models^[4].

References

[1] Patent: WO2011/18474, 2011, A1. Location in patent: Page/Page column 42

LCL-161 Preparation Products And Raw materials

Raw materials

Preparation Products

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LCL-161 Suppliers

China 132 India 2 United States 18 Global 152

DKMbiochem.Co. Ltd

Tel: 15901859516
Fax: 15901859516
Email: sales@DKMbiochem.com
Country: China
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Changsha Fuzhen Biotechnology Co.，LTD

Tel: 0731-13823398 15111215862
Email: 313359644@qq.com
Country: China
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Shanghai Boyle Chemical Co., Ltd.

Tel
Fax: 86-21-57758967
Email: sales@boylechem.com
Country: China
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Dalian Meilun Biotech Co., Ltd.

Tel: 0411-62910999 13889544652
Email: sales@meilune.com
Country: China
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Shanghai Hope Chem Co., Ltd.，

Tel: +21-18501659228 18501659228
Fax: sales@hope-chem.com
Email: info@hope-chem.com
Country: China
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NCE Biomedical Co.,Ltd.

Tel: 4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
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Country: China
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Haoyuan Chemexpress Co., Ltd.

Tel: 021-58950125
Fax: (86) 21-58955996
Email: info@chemexpress.com
Country: China
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Shanghai Aladdin Bio-Chem Technology Co.,LTD

Tel: 400-6206333 13167063860
Fax: 021-50323701
Email: anhua.mao@aladdin-e.com
Country: China
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MedChemexpress LLC

Tel: 021-58955995
Fax: 609-228-5909
Email: sales@medchemexpress.cn
Country: United States
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Shanghai Witofly Chemical Co.,Ltd

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Email: sales@witofly.com
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View Lastest Price from LCL-161 manufacturers

Career Henan Chemical Co

Product: N-[(1S)-1-Cyclohexyl-2-{(2S)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]-1-pyrrolidinyl}-2-oxoethyl]-N2-methylalaninamide 1005342-46-0
Price: US $1.00/KG
Min. Order: 1KG
Purity: Min98% HPLC
Supply Ability: g/kg/ton
Release date: 2019-12-30

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LCL-161

N-[(1S)-1-Cyclohexyl-2-{(2S)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]-1-pyrrolidinyl}-2-oxoethyl]-N2-MethylalaninaMide

(2S)-N-[(1S)-1-Cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-2-thiazolyl]-1-pyrrolidinyl]-2-oxoethyl]-2-(methylamino)-propanamide

(S)-N-((S)-1-Cyclohexyl-2-((S)-2-(4-(4-fluorobenzoyl)thiazol-2-yl)pyrrolidin-1-yl)-2-oxoethyl)

N-[(1S)-1-cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-2-thiazolyl]-1-pyrrolidinyl]-2-oxoethyl]-2-(methylamino)-(2S)-propanamide

(2S)-N-[(1S)-1-Cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-2-thiazolyl]-1-pyrrolidinyl]-2-oxoethyl]-2-(methylamino)-propanamide LCL 161

LCL161, 98%, inhibitor of Apoptosis Protein (IAP) family of proteins

CS-987

LCL-161; LCL161

Propanamide, N-[(1S)-1-cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-2-thiazolyl]-1-pyrrolidinyl]-2-oxoethyl]-2-(methylamino)-, (2S)-

LCL-161 USP/EP/BP

LCL161, inhibitor of Apoptosis Protein (IAP) family of proteins

LCL161, 10 mM in DMSO

1005342-46-0

C26H33FN4O3S

Inhibitors