28697-11-2

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C14H17NO4/c16-13(17)12-8-4-5-9-15(12)14(18)19-10-11-6-2-1-3-7-11/h1-3,6-7,12H,4-5,8-10H2,(H,16,17)/t12-/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 1723-00-8 (R)-(+)-pipecolic acid 
• 1068012-41-8 (R)-N-(benzyloxycarbonyl)-2-formylpiperidine 
• 25662-28-6 1-(carboxymethoxy)cyclopentadiene 
• 1399282-25-7 (R)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)piperidin-2-one 
• 3105-95-1 pipecolinic acid 
• 212557-00-1 (S)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester 
• 212556-95-1 (S)-N-(benzyloxycarbonyl)-2-formylpiperidine 
• 28697-07-6 N-benzyloxycarbonyl D/L-pipecolinic acid 
• 105706-75-0 1-benzyloxycarbonyl-2-hydroxymethylpiperidine 
• 3433-37-2 piperidin-2-ylmethanol 
• 108-20-3 di-isopropyl ether 
• 1885-14-9 phenyl chloroformate 
• 4043-87-2 pipecolic Acid 

Downstream Products

• 78058-39-6 (R)-2-Carbamoyl-piperidine-1-carboxylic acid benzyl ester 
• 98189-15-2 BzOCO-D-Pip-L-His-OMe 
• 154499-13-5 benzyl (R)-2-(hydroxymethyl)piperidine-1-carboxylate 
• 3197-44-2 (2R)-piperidin-2-ylmethanol 
• 125279-72-3 (1R,2R,8aR)-lentiginosine 
• 160169-49-3 (1R,2S,8aR)-1,2-dihydroxy-hexahydroindolizin-3(5H)-one 
• 1068012-41-8 (R)-N-(benzyloxycarbonyl)-2-formylpiperidine 
• 160169-47-1 (R)-2-((E)-2-Ethoxycarbonyl-vinyl)-piperidine-1-carboxylic acid benzyl ester 
• 160096-51-5 (R)-2-((1R,2S)-2-Ethoxycarbonyl-1,2-dihydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 19889-77-1 (+)-2R-Piperidine-2-carboxylic acid amide 
• 111492-04-7 Z-D-PipCHN₂ 
• 1266174-40-6 C₃₆H₅₅N₅O₅S 
• 1174764-24-9 (4R)-4-[((R)-2-{3-[methyl-(N-methyl-(R)-pipecolyl-(S)-isoleucyl)-amino]-4-methyl-pentyl}-thiazole-4-carbonyl)-amino]-5-phenyl-pentanoic acid trifluoroacetic acid salt 
• 1219930-75-2 methyl (2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoate 

Relevant academic research and scientific papers

Synthesis method of 3-hydroxy-2-piperidinecarboxylic acid compound and synthesis method of hydrochloride thereof

The invention discloses a synthesis method of 3-hydroxy-2-piperidinecarboxylic acid compound and a synthesis method of hydrochloride thereof. According to the invention, (S)-piperidine-2-formic acid is used as an initial raw material, (2S)-N-(quinoline-8-

TUBULYSIN DERIVATIVES AND METHODS FOR PREPARING THE SAME

The invention relates to novel means and methods for the synthesis of tubulysin and derivatives thereof, which find their use e.g. as cytotoxic agents in targeted drug delivery. Provided is a method for preparing a tubulysin derivative, comprising reacting compounds A, B and C in a 3- component Passerini reaction, wherein compound A is a carboxylic acid according to the general formula (A); wherein compound B is an aldehyde according to the general formula (B); and wherein compound C is an isocyanide according to the general formula (C).

Pipecolic esters as minimized templates for proteasome inhibition

Allosteric regulators of clinically important enzymes are gaining popularity as alternatives to competitive inhibitors. This is also the case for the proteasome, a major intracellular protease and a target of anti-cancer drugs. All clinically used proteasome inhibitors bind to the active sites in catalytic chamber and display a competitive mechanism. Unfortunately, inevitable resistance associated with this type of inhibition drives the search for non-competitive agents. The multisubunit and multicatalytic “proteolytic machine” such as the proteasome is occasionally found to be affected by agents with other primary targets. For example the immunosuppressive agent rapamycin has been shown to allosterically inhibit the proteasome albeit at levels far higher than its mTOR related efficacy. As part of an ongoing program to search for novel proteasome-targeting pharmacophores, we identified the binding domain of rapamycin as required for proteasome inhibition even without the macrocyclic context of the parent compound. By subsequent structure-activity relationship studies, we generated a pipecolic ester derivative compound 3 representing a new class of proteasome inhibitors. Compound 3 affects the core proteasome activities and proliferation of cancer cells with low micromolar/high nanomolar efficacy. Molecular modeling, atomic force microscopy imaging and biochemical data suggest that compound 3 binds into one of intersubunit pockets in the proteasomal α ring and destabilizes the α face and the gate. The α face is used as a docking area for proteasome-regulating protein modules and the gate is critical for controlling access to the catalytic chamber. Thus, the pipecolic ester template elicits a new and attractive mechanism for proteasome inhibition distinct from classical competitive drugs.

PIPECOLIC ESTERS FOR INHIBITION OF THE PROTEASOME

The present disclosure relates to chemical compounds that modulate proteasome activity, pharmaceutical compositions containing such compounds, and use of these compounds and compositions for the treatment of disorders of uncontrolled cellular proliferation such as, for example, a cancer. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Cis-fused ring-containing β-lactam the synthetic method of the compound of

The invention discloses a synthetic method of a beta-lactam compound with a cis condensed ring. Substituted or un-substituted pyrrole-2-formic acid, or substituted or un-substituted pyridine-2-formic acid or substituted or un-substituted indole-2-formic acid is used as a starting material, Pd(II) is adopted as a catalyst, and AgOAc or Ag2CO3 is used as an oxidant; a sp3C-H bond at a beta site of an amide substrate 2 (for example Scheme4) is activated through palladium catalysis; a key step of forming a C-N bond in a molecule to successfully construct a beta-lactam framework with the cis condensed ring is generated. According to the synthetic method disclosed by the invention, materials are simple and easily available, the price is cheap, the experiment operation is simple, the route is short and the yield is high; the synthetic method has very high atom economy, a little waste, environment friendliness, a wide scope of application of the substrate and good universality, and can be used for efficiently obtaining the beta-lactam compound with optical activity kept in a chiral manner.

A short enantioselective total synthesis of (R)- and (S)-pipecolic acid

A convenient and practical total synthesis of (R)- and (S)-pipecolic acid has been achieved by utilizing chiral cis-aziridine-2-carboxylate as the common synthetic precursor. The synthesis involves regioselective reductive cleavage of the aziridine ring and Wittig olefination as key reactions.

SORDARIN DERIVATIVES FOR PREVENTING OR TREATING INFECTIOUS DISEASES CAUSED BY PATHOGENIC MICROORGANISMS

This invention relates to a new sordarin derivative or a pharmaceutically acceptable salt thereof, which has antimicrobial activities (especially, antifungal activities), to process for preparation thereof, to a pharmaceutical composition comprising the same, and to a method for prophylactic and/or therapeutic treatment of infectious diseases in a human being or an animal.

1-Hydroxyalkyl-3-phenylthioureas as novel HDL-elevating agents

A series of 1-hydroxyalkyl-3-phenylthiourea analogs were prepared and evaluated as HDL-and Apo A-I-elevating agents. Derivatives 5h, 7j, 7n, and 7o were found to be as effective or superior to gemfibrozil (1).

Short syntheses of (S)-pipecolic acid, (R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks

The kinetic resolutions of both (±)-N-(benzyloxycarbonyl-2- (hydroxymethyl)piperidine [(±)-5] and (±)-N(tert-butoxycarbonyl)-2- (hydroxymethyl)piperidine [(±)-6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks (S)-5 and (S)- 6, respectively; which were used for the syntheses of the title natural products and derivatives of (S)-pipecolic acid. The syntheses were short (2- 4 steps) and proceeded with satisfactory overall yield.

ANTITHROMBOTIC AGENTS

This invention relates to L-arginine aldehyde derivatives, having the formula I STR1 where X and Y have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitor