653589-25-4

Usage

Derivative of

Piperidine

Usage

Synthesis of pharmaceuticals and other organic compounds

Physical form

White to light yellow crystalline solid at room temperature

Solubility

Soluble in organic solvents such as ethanol and acetone

Potential use

Building block in the development of new drugs and research chemicals

Upstream product

• 20515-15-5 methyl (2E)-4-methylpent-2-enoate 
• 1008510-48-2 tert-butyl 4,6-dioxo-2-isopropylpiperidine-1-carboxylate 
• 126301-18-6 [(2S)-2-(tert-butoxycarbonylamino)-3-methyl-butyl] methanesulfonate 
• 172695-23-7 (R)-3-<(tert-butoxycarbonyl)amino>-4-methylpentanenitrile 
• 79069-14-0 (S)-2-<(tert-butoxycarbonyl)amino>-3-methylbutan-1-ol 
• 66866-46-4 C₁₅H₂₇NO₆ 
• 13734-41-3 t-Boc-L-valine 
• 183990-64-9 (R)-3-tert-butoxycarbonylamino-4-methyl-pentanoic acid 
• 653589-13-0 tert-butyl (2S)-2-isopropyl-4,6-dioxo-1-piperidinecarboxylate 

Downstream Products

• 653589-30-1 (2S,4S)-4-hydroxy-2-isopropyl-6-oxopiperidine 
• 653589-30-1 (2S,4R)-4-hydroxy-2-isopropyl-6-oxopiperidine 

Relevant academic research and scientific papers

First Cdc7 kinase inhibitors: Pyrrolopyridinones as potent and orally active antitumor agents. 2. Lead discovery

Cdc7 kinase is a key regulator of the S-phase of the cell cycle, known to promote the activation of DNA replication origins in eukaryotic organisms. Cdc7 inhibition can cause tumor-cell death in a p53-independent manner, supporting the rationale for devel

Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations

Abstract A flexible route to piperidine-2,4-diones variously substituted at the 6-, 5,6- and 2,6-positions, both with and without 1-substitution, is described; no N-protective group is required. A related regioselective Dieckmann cyclisation is also described that uses Davies' α-methylbenzylamine auxiliary and affords 6-substituted piperidine-2,4-diones enantioselectively.

A multifaceted secondary structure mimic based on piperidine-piperidinones

Minimalist secondary structure mimics are typically made to resemble one interface in a protein-protein interaction (PPI), and thus perturb it. We recently proposed suitable chemotypes can be matched with interface regions directly, without regard for secondary structures. Here we describe a modular synthesis of a new chemotype 1, simulation of its solution-state conformational ensemble, and correlation of that with ideal secondary structures and real interface regions in PPIs. Scaffold 1 presents amino acid side-chains that are quite separated from each other, in orientations that closely resemble ideal sheet or helical structures, similar non-ideal structures at PPI interfaces, and regions of other PPI interfaces where the mimic conformation does not resemble any secondary structure. 68 different PPIs where conformations of 1 matched well were identified. A new method is also presented to determine the relevance of a minimalist mimic crystal structure to its solution conformations. Thus dld-1-faf crystallized in a conformation that is estimated to be 0.91 kcal-mol-1 above the minimum energy solution state. Do we know, when designing a new peptidomimetic scaffold like the one shown, how it can resemble secondary structures? Design and modular synthesis of this elongated mimic is reported, and the structure is related to ideal and real structures at PPI interfaces.

PYRIDYLPYRROLE DERIVATIVES ACTIVE AS KINASE INHIBITORS

Pyridylpyrrole derivatives of formula (I) and pharmaceutically acceptable salts thereof, as defined in the specification, and pharmaceutical compositions comprising them are disclosed; the compounds of the invention may be useful, in therapy, in the treat

PYRIMIDYLPYRROLE DERIVATIVES ACTIVE AS KINASE INHIBITORS

Pyrimidylpyrrole derivatives of formula (1) and pharmaceutically acceptable salts thereof, as defined in the specification, process for their preparation and pharmaceutical compositions comprising them are disclosed; the compounds of the invention may be

Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor

tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-OtBu and other β-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy δ-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo- 1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).