916870
4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid
≥95%
Synonym(s):
Semi-flexible linker for PROTAC® development
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About This Item
Empirical Formula (Hill Notation):
C17H23NO4
CAS Number:
Molecular Weight:
305.37
MDL number:
UNSPSC Code:
12352106
Quality Level
Assay
≥95%
form
powder
reaction suitability
reagent type: linker
functional group
Boc
carboxylic acid
storage temp.
2-8°C
SMILES string
O=C(N(CC1)CCC1C(C=C2)=CC=C2C(O)=O)OC(C)(C)C
InChI
1S/C17H23NO4/c1-17(2,3)22-16(21)18-10-8-13(9-11-18)12-4-6-14(7-5-12)15(19)20/h4-7,13H,8-11H2,1-3H3,(H,19,20)
InChI key
YCNVQGGUCDVTIZ-UHFFFAOYSA-N
Application
4-(1-(tert-Butoxycarbonyl)piperidin-4-yl)benzoic acid is a 4-aryl piperidine useful as a semi-flexible linker in PROTAC development for targeted protein degradation. Incorporation of rigidity into the linker region of bifunctional protein degraders may impact the 3D orientation of the degrader and thus ternary complex formation as well as optimization of drug-like properties.
Other Notes
Legal Information
PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1
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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Andrei A Krysko et al.
Bioorganic & medicinal chemistry letters, 21(19), 5971-5974 (2011-08-20)
The novel RGD mimetics with phthalimidine central fragment were synthesized with the use of 4-piperidine-4-yl-butyric, 4-piperidine-4-yl-benzoic, 4-piperazine-4-yl-benzoic and 1,2,3,4-tetrahydroisoquinoline-7-carboxylic acids as surrogates of Arg motif. The synthesized compounds potently inhibited platelet aggregation in vitro and blocked FITC-Fg binding to α(IIb)β(3)
Dillon T Flood et al.
Journal of the American Chemical Society, 141(25), 9998-10006 (2019-05-29)
DNA Encoded Libraries have proven immensely powerful tools for lead identification. The ability to screen billions of compounds at once has spurred increasing interest in DEL development and utilization. Although DEL provides access to libraries of unprecedented size and diversity
Dominik K Kölmel et al.
ACS combinatorial science, 21(8), 588-597 (2019-07-10)
A new catalytic manifold that merges photoredox with nickel catalysis in aqueous solution is presented. Specifically, the combination of a highly active, yet air-stable, nickel precatalyst with a new electron-deficient pyridyl carboxamidine ligand was key to the development of a
Weilin Sun et al.
Journal of medicinal chemistry, 62(6), 3122-3134 (2019-03-16)
Imatinib mesylate, 1a, inhibits production of β-amyloid (Aβ) peptides both in cells and in animal models. It reduces both the β-secretase and γ-secretase cleavages of the amyloid precursor protein (APP) and mediates a synergistic effect, when combined with a β-secretase
Andrei A Krysko et al.
Bioorganic & medicinal chemistry letters, 26(7), 1839-1843 (2016-02-26)
A series of 2-piperazin-1-yl-quinazolines were synthesized and evaluated for their antiaggregative activity. The synthesized small molecule compounds have potently inhibited platelet aggregation in vitro and blocked FITC-Fg binding to αIIbβ3 integrin in a suspension of washed human platelets. The key
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