88466-74-4

Usage

Uses

(S)-1-Cbz-piperidine-3-carboxylic acid is a useful research chemical compound.

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

Upstream product

• 501-53-1 benzyl chloroformate 
• 498-95-3 (S)-nipecotic acid 
• 637337-59-8 (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-5-bromo-1-oxopentyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 637337-43-0 (4R)-3-(5-bromo-1-oxopentyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 4509-90-4 5-bromovaleroyl chloride 
• 868632-22-8 (4R)-3-({(3S)-1-[(benzyloxy)carbonyl]piperidin-3-yl}carbonyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 

Downstream Products

• 168050-84-8 (S)-3-({(S)-1-[(S)-3-Methoxycarbonyl-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-piperidine-1-carboxylic acid benzyl ester 
• 174759-65-0 (S)-3-({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-piperidine-1-carboxylic acid benzyl ester 
• 174699-11-7 (3S)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester 
• 88495-54-9 (3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid 
• 498-95-3 (S)-nipecotic acid 
• 1142005-50-2 (S)-3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester 
• 1222997-51-4 C₁₅H₂₀N₄O₃S 
• 1394170-06-9 C₁₈H₂₅N₃O₂ 
• 1394169-79-9 (S)-1-(2-(4-chlorophenyl)acetyl)-N-methyl-N-(4-(2-oxopiperidin-1-yl)phenyl)piperidine-3-carboxamide 
• 1394169-80-2 (S)-1-(4-(4-bromophenyl)thiophene-2-carbonyl)-N-methyl-N-(4-(2-oxopiperidin-1-yl)phenyl) piperidine-3-carboxamide 
• 37675-18-6 (S)-(+)-nipecotic acid ethyl ester 
• 193693-67-3 (R)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}piperidine-3-carboxylic acid 
• 193693-68-4 (S)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}piperidine-3-carboxylic acid 

Relevant academic research and scientific papers

Potent direct inhibitors of factor Xa based on the tetrahydroisoquinoline scaffold

Direct inhibition of coagulation factor Xa (FXa) carries significant promise for developing effective and safe anticoagulants. Although a large number of FXa inhibitors have been studied, each can be classified as either possessing a highly flexible or a rigid core scaffold. We reasoned that an intermediate level of flexibility will provide high selectivity for FXa considering that its active site is less constrained in comparison to thrombin and more constrained as compared to trypsin. We studied several core scaffolds including 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid for direct FXa inhibition. Using a genetic algorithm-based docking and scoring approach, a promising candidate 23 was identified, synthesized, and found to inhibit FXa with a Ki of 28 μM. Optimization of derivative 23 resulted in the design of a potent dicarboxamide 47, which displayed a Ki of 135 nM. Dicarboxamide 47 displayed at least 1852-fold selectivity for FXa inhibition over other coagulation enzymes and doubled PT and aPTT of human plasma at 17.1 μM and 20.2 μM, respectively, which are comparable to those of clinically relevant agents. Dicarboxamide 47 is expected to serve as an excellent lead for further anticoagulant discovery.

PYRROLIDINE, PIPERIDINE AND PIPERAZINE DERIVATIVES AND METHODS OF USE THEREOF

The present invention relates to novel Pyrrolidine, Piperidine and Piperazine Derivatives, pharmaceutical compositions comprising the Pyrrolidine, Piperidine and Piperazine Derivatives and the use of these compounds for treating or preventing treating allergy, an allergy-induced airway response, congestion, a cardiovascular disease, an inflammatory disease, a gastrointestinal disorder, a neurological disoder, a metabolic disorder, obesity, an obesity-related disorder, diabetes, a diabetic complication, impaired glucose tolerance or impaired fasting glucose.

INHIBITORS OF PROTEIN KINASES

Compounds of general Formula I, wherein R1, R2, R3, x, A and Ra are as defined herein are inhibitors of cyclin-dependent kinases and are useful for preventing and/or treating any type of pain, inflammatory disorders, immunological diseases, proliferative diseases, infectious diseases, cardiovascular diseases and neurodegenerative diseases.

Preparation of β2-amino acid derivatives (β2hThr, β2hTrp, β2hMet, β2hPro, β2hLys, pyrrolidine-3-carboxylic acid) by using DIOZ as chiral auxiliary

The title compounds were prepared from valine-derived N-acylated oxazolidin-2-ones, 1-3, 7, 9, by highly diastereoselective (≥ 90%) Mannich reaction (→ 4-6; Scheme 1) or aldol addition (→ 8 and 10; Scheme 2) of the corresponding Ti- or B-enolates as the key step. The superiority of the '5,5-diphenyl-4-isopropyl-1,3-oxazolidin-2-one' (DIOZ) was demonstrated, once more, in these reactions and in subsequent transformations leading to various t-Bu-, Boc-, Fmoc-, and Cbz-protected β2-homoamino acid derivatives 11-23 (Schemes 3-6). The use of ω-bromo-acyl-oxazolidinones 1-3 as starting materials turned out to open access to a variety of enantiomerically pure trifunctional and cyclic carboxylic-acid derivatives.

Methods for the stereoselective synthesis of substituted piperidines

One aspect of the present invention relates to methods of synthesizing substituted piperidines. A second aspect of the present invention relates to stereoselective methods of synthesizing substituted piperidines. The methods of the present invention will