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Merck
CN

911666

Pomalidomide-C6-NH2 hydrochloride

≥95%

别名:

4-((6-Aminohexyl)amino)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione hydrochloride, Crosslinker−E3 ligase ligand conjugate, Pomalidomide conjugate, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader

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关于此项目

经验公式（希尔记法）:
C19H24N4O4 · xHCl
化学文摘社编号:
2375194-37-7
分子量:
372.42 (free base basis)
MDL number:
MFCD31729298
UNSPSC Code:
12352101
NACRES:
NA.22

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产品名称

Pomalidomide-C6-NH2 hydrochloride, ≥95%

InChI

1S/C19H24N4O4.ClH/c20-10-3-1-2-4-11-21-13-7-5-6-12-16(13)19(27)23(18(12)26)14-8-9-15(24)22-17(14)25;/h5-7,14,21H,1-4,8-11,20H2,(H,22,24,25);1H

InChI key

PBGMRXNTLPSDNR-UHFFFAOYSA-N

SMILES string

O=C(C(CC1)N(C2=O)C(C3=C2C=CC=C3NCCCCCCN)=O)NC1=O.Cl

ligand

pomalidomide

assay

≥95%

form

powder

reaction suitability

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

Quality Level

200

相关类别

Application

Protein degrader building block Pomalidomide-C6-NH2 hydrochloride enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a Cereblon (CRBN)-recruiting ligand and an alkyl-chain crosslinker with pendant amine for reactivity with an acid on the target ligand. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and PROTAC, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a terminal amine, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Proteolysis Targeting Chimeras for the Selective Degradation of Mcl-1/Bcl-2 Derived from Nonselective Target Binding Ligands

Chemoselective Synthesis of Lenalidomide-Based PROTAC Library Using Alkylation Reaction

Identification of New Small-Molecule Inducers of Estrogen-related Receptor α (ERRα) Degradation

Discovery of MD-224 as a First-in-Class, Highly Potent and Efficacious PROTAC MDM2 Degrader Capable of Achieving Complete and Durable Tumor Regression

Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360D

Hazard Classifications

Repr. 1B

存储类别

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number
0000207588
0000194928
0000180658
0000139445
0000180658

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Lijie Peng et al.
ACS medicinal chemistry letters, 10(5), 767-772 (2019-05-18)
A series of (E)-3-(4-((2,4-bis(trifluoromethyl)benzyl)oxy)-3-methoxyphenyl)-2-cyanoacrylamide derivatives were designed and synthesized as new estrogen-related receptor α (ERRα) degraders based on the proteolysis targeting chimera (PROTAC) concept. One of the representative compounds 6c is capable of specifically degrading ERRα protein by >80% at
Ziqian Wang et al.
Journal of medicinal chemistry, 62(17), 8152-8163 (2019-08-08)
Proteolysis targeting chimera (PROTAC) recruits an E3 ligase to a target protein to induce its ubiquitination and subsequent degradation. We reported success in the development of two PROTACs (C3 and C5) that potently and selectively induce the degradation of Mcl-1
Xing Qiu et al.
Organic letters, 21(10), 3838-3841 (2019-05-09)
An organic base-promoted chemoselective alkylation of lenalidomide with different halides was developed, which offers a novel approach to a highly functionalized lenalidomide-based PROTAC library under mild reaction conditions. DIPEA was found to act as an efficient base to trigger facile
Yangbing Li et al.
Journal of medicinal chemistry, 62(2), 448-466 (2018-12-12)
Human murine double minute 2 (MDM2) protein is a primary endogenous cellular inhibitor of the tumor suppressor p53 and has been pursued as an attractive cancer therapeutic target. Several potent, nonpeptide, small-molecule inhibitors of MDM2 are currently in clinical development.

商品

Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

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