Thalidomide-5-propargyl

• CAT Number: I040736
• CAS Number: 2226303-74-6
• Molecular Formula: C16H12N2O5
• Molecular Weight: 312.28
• Purity: ≥95%
• Synonyms: 2-(2,6-dioxopiperidin-3-yl)-5-prop-2-ynoxyisoindole-1,3-dione
• InChI: InChI=1S/C16H12N2O5/c1-2-7-23-9-3-4-10-11(8-9)16(22)18(15(10)21)12-5-6-13(19)17-14(12)20/h1,3-4,8,12H,5-7H2,(H,17,19,20)
• InChIKey: GDWXJPQKRQMMQW-UHFFFAOYSA-N
• SMILES: C#CCOC1=CC2=C(C=C1)C(=O)N(C2=O)C3CCC(=O)NC3=O

Thalidomide-5-propargyl is a propargyl-modified Thalidomide (HY-14658), that acts as a Cereblon ligand to recruit CRBN proteins. Thalidomide-5-propargyl use alkynyl group at the end to be directly used in the synthesis of triazoles in the synthesis of PROTAC molecules, and is a key intermediate in the synthesis of PROTAC molecules based on CRBN design[1].

Reference

[1]. Crew, et al. Preparation of tau-protein targeting bifunctional compounds (PROTACS) as E3 ubiquitin ligase binding useful in treatment and prevention of diseases. United States, US20180125821 A1. 2018-05-10.