924229
(S,R,S)-AHPC-Me
95%
Synonym(s):
(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)pyrrolidine-2-carboxamide, PROTAC® research ligand, VH032 methyl derivative
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About This Item
Empirical Formula (Hill Notation):
C23H32N4O3S
CAS Number:
Molecular Weight:
444.59
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
ligand
VH032
Quality Level
Assay
95%
form
powder
storage temp.
2-8°C
SMILES string
C([C@H](C(C)(C)C)N)(=O)N1[C@H](C(N[C@@H](C)C2=CC=C(C=C2)C3=C(C)N=CS3)=O)C[C@@H](O)C1
InChI
1S/C23H32N4O3S/c1-13(15-6-8-16(9-7-15)19-14(2)25-12-31-19)26-21(29)18-10-17(28)11-27(18)22(30)20(24)23(3,4)5/h6-9,12-13,17-18,20,28H,10-11,24H2,1-5H3,(H,26,29)/t13-,17+,18-,20+/m0/s1
InChI key
JOSFQWNOUSNZBP-UUZHKXTQSA-N
Application
(S,R,S)-AHPC-Me is a VH032 derivative used in the recruitment of the von Hippel-Lindau (VHL) protein for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This was previously listed under ATEH961B8E6E.
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Targeted protein degradation
Other Notes
Discovery of ERD-308 as a highly potent proteolysis targeting chimera (PROTAC) degrader of estrogen receptor (ER)
Discovery of ARD-69 as a highly potent proteolysis targeting chimera (PROTAC) degrader of androgen receptor (AR) for the treatment of prostate cancer
Design, Synthesis, and Biological Evaluation of MEK PROTACs
Antibody–PROTAC Conjugates Enable HER2-Dependent Targeted Protein Degradation of BRD4
Discovery of a First-in-Class Mitogen-Activated Protein Kinase Kinase 1/2 Degrader
Discovery of PROTAC BCL-XL degraders as potent anticancer agents with low on-target platelet toxicity
Discovery of MD-224 as a First-in-Class, Highly Potent, and Efficacious Proteolysis Targeting Chimera Murine Double Minute 2 Degrader Capable of Achieving Complete and Durable Tumor Regression
A caged E3 ligase ligand for PROTAC-mediated protein degradation with light
Discovery of SHP2-D26 as a First, Potent, and Effective PROTAC Degrader of SHP2 Protein
Selective CDK6 degradation mediated by cereblon, VHL, and novel IAP-recruiting PROTACs
Discovery of ARD-69 as a highly potent proteolysis targeting chimera (PROTAC) degrader of androgen receptor (AR) for the treatment of prostate cancer
Design, Synthesis, and Biological Evaluation of MEK PROTACs
Antibody–PROTAC Conjugates Enable HER2-Dependent Targeted Protein Degradation of BRD4
Discovery of a First-in-Class Mitogen-Activated Protein Kinase Kinase 1/2 Degrader
Discovery of PROTAC BCL-XL degraders as potent anticancer agents with low on-target platelet toxicity
Discovery of MD-224 as a First-in-Class, Highly Potent, and Efficacious Proteolysis Targeting Chimera Murine Double Minute 2 Degrader Capable of Achieving Complete and Durable Tumor Regression
A caged E3 ligase ligand for PROTAC-mediated protein degradation with light
Discovery of SHP2-D26 as a First, Potent, and Effective PROTAC Degrader of SHP2 Protein
Selective CDK6 degradation mediated by cereblon, VHL, and novel IAP-recruiting PROTACs
Legal Information
PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Marı A Maneiro et al.
ACS chemical biology, 15(6), 1306-1312 (2020-04-28)
Targeting protein degradation with Proteolysis-Targeting Chimeras (PROTACs) is an area of great current interest in drug discovery. Nevertheless, although the high effectiveness of PROTACs against a wide variety of targets has been established, most degraders reported to date display limited
Cyrille S Kounde et al.
Chemical communications (Cambridge, England), 56(41), 5532-5535 (2020-04-17)
With the intent of achieving greater spatiotemporal control of PROTAC-induced protein degradation, a light-activated degrader was designed by photocaging an essential E3 ligase binding motif in a BRD4 targeting PROTAC. Proteolysis was triggered only after a short irradiation time, the
Jiantao Hu et al.
Journal of medicinal chemistry, 62(3), 1420-1442 (2019-04-17)
The estrogen receptor (ER) is a validated target for the treatment of estrogen receptor-positive (ER+) breast cancer. Here, we describe the design, synthesis, and extensive structure-activity relationship (SAR) studies of small-molecule ERα degraders based on the proteolysis targeting chimeras (PROTAC)
Stefan Vollmer et al.
Journal of medicinal chemistry, 63(1), 157-162 (2019-12-06)
PROteolysis TArgeting Chimeras (PROTACs) targeting the degradation of MEK have been designed based on allosteric MEK inhibitors. Inhibition of the phosphorylation of ERK1/2 was less effective with the PROTACs than a small-molecule inhibitor; the best PROTACs, however, were more effective
Mingliang Wang et al.
Journal of medicinal chemistry, 63(14), 7510-7528 (2020-05-22)
Src homology 2 domain-containing phosphatase 2 (SHP2) is an attractive therapeutic target for human cancers and other human diseases. Herein, we report our discovery of potent small-molecule SHP2 degraders whose design is based upon the proteolysis-targeting chimera (PROTAC) concept. This
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