864293-75-4

Usage

Chemical structure

1-Piperidinecarboxylic acid, 4-[[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]amino]-, phenylmethyl ester

Chemical structure

The compound has a piperidine ring at the 1-position, a carboxyl group at the 4-position, and various functional groups attached to the lysine residue.

Role in organic synthesis and peptide chemistry

acts as a protecting group for the side chain amino group of lysine during peptide synthesis

Role in organic synthesis and peptide chemistry

The compound is used to protect the side chain amino group of lysine during peptide synthesis, which allows for selective deprotection and modification of other functional groups in the peptide.

Derivative of

lysine, an important amino acid

Derivative of

The compound is derived from lysine, an essential amino acid that plays a crucial role in protein structure and function.

Functional groups

Fmoc (9-fluorenylmethoxycarbonyl) protecting group, Mtt (2,2,2-trifluoroethoxycarbonyl) protecting group, and phenylmethyl ester moiety

Functional groups

The Fmoc protecting group is a 9-fluorenylmethoxycarbonyl group, the Mtt protecting group is a 2,2,2-trifluoroethoxycarbonyl group, and the phenylmethyl ester moiety allows for attachment of the lysine residue to a solid support during solid-phase peptide synthesis.

Upstream product

• 120278-07-1 benzyl 4-aminopiperidine-1-carboxylate 
• 89711-08-0 N-(t-butoxycarbonyl)glycinal 
• 19099-93-5 benzyl 4-oxo-1-piperidinecarboxylate 
• 57260-73-8 N-BOC-1,2-diaminoethane 

Relevant academic research and scientific papers

INDOLE DERIVATIVES AS EFFLUX PUMP INHIBITORS

Disclosed herein are compounds of formula (I): and salts thereof. Also disclosed are compositions comprising compounds of formula I and compounds of formula I for use in treating or preventing bacterial infections.

BETA-LACTAMASE INHIBITORS

Described herein are compounds and compositions that modulate the activity of beta-lactamases. In some embodiments, the compounds described herein inhibit beta-lactamase. In certain embodiments, the compounds described herein are useful in the treatment of bacterial infections.

Discovery of a tetrahydropyrimidin-2(1 H)-one derivative (TAK-442) as a potent, selective, and orally active factor Xa inhibitor

Coagulation enzyme factor Xa (FXa) is a particularly promising target for the development of new anticoagulant agents. We previously reported the imidazo[1,5-c]imidazol-3-one derivative 1 as a potent and orally active FXa inhibitor. However, it was found that 1 predominantly undergoes hydrolysis upon incubation with human liver microsomes, and the human specific metabolic pathway made it difficult to predict the human pharmacokinetics. To address this issue, our synthetic efforts were focused on modification of the imidazo[1,5-c] imidazol-3-one moiety of the active metabolite 3a, derived from 1, which resulted in the discovery of the tetrahydropyrimidin-2(1H)-one derivative 5k as a highly potent and selective FXa inhibitor. Compound 5k showed no detectable amide bond cleavage in human liver microsomes, exhibited a good pharmacokinetic profile in monkeys, and had a potent antithrombotic efficacy in a rabbit model without prolongation of bleeding time. Compound 5k is currently under clinical development with the code name TAK-442.

CYCLIC AMIDE DERIVATIVES, AND THEIR PRODUCTION AND USE AS ANTITHROMBOTIC AGENTS

The present invention provides a cyclic amide derivative useful as a drug for treating thrombosis, which is represented by the formula (I): wherein R1 represents an optionally substituted cyclic hydrocarbon group or an optionally substituted heterocyclic group, W represents a bond or an optionally substituted divalent chain hydrocarbon group, a represents 0, 1, or 2, X1 represents an optionally substituted lower alkylene or an optionally substituted lower alkenylene, Y1 represents -C(O)-, -S(O)- or -S(O)2-, A represents a piperazine ring which may be further substituted or a piperidine ring which may be further substituted, X2 represents a bond or an optionally substituted lower alkylene, Y2 represents -C(O)-, -S(O)-, -S(O)2- or -C(=NR7)-, X3 represents an optionally substituted C1-4 alkylene or an optionally substituted C2-4 alkenylene, Z3 represents -N(R4)-, -O- or a bond, Z1 represents -C(R2)(R2')-, -N(R2)-, etc., and Z2 represents -C(R3)(R3')-, -N(R3)-, etc., or a salt thereof.