137102-30-8

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
[(1S)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER is used as a potential drug candidate for the treatment of various conditions due to its potential biological activity and therapeutic effects.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, [(1S)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER is utilized for its potential to contribute to the discovery and development of new therapeutic agents, given its unique chemical properties and interactions with biological targets.
Used in Pharmacology:
Pharmacology benefits from the use of [(1S)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER as it may provide insights into the mechanisms of action of drugs and help in understanding the interactions between drugs and biological systems, thereby enhancing the development of more effective and safer medications.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 941602-11-5 tert-butyl N-(2-nitro-1-phenylethyl)carbamate 
• 1242073-15-9 [(1S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester 
• 177723-19-2 (S)-2-N-tert-butoxycarbonylamino-2-phenylethanenitrile 
• 312532-37-9 {(S)-2-[2-((S)-1-Hydroxy-2,2-dimethyl-propyl)-4-oxo-4H-quinazolin-3-ylamino]-1-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 137102-29-5 (S)-(+)-1-<(butoxycarbonyl)amino>-1-phenylethyl azide 
• 102-96-5 (2-nitroethenyl)benzene 
• 73025-50-0 (Z)-2-nitro-1-phenylethen-1-amine 
• 479687-23-5 1,2,3-oxathiazolidine-3-carboxylic acid, 4-phenyl 1,1-dimethylethyl ester-2,2-dioxide 
• 4248-19-5 tert-butyl carbazate 
• 100-52-7 benzaldehyde 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 110143-62-9 (S)-(+)-<2-<(methylsulfonyl)oxy>-1-phenylethyl>carbamic acid 1,1-dimethylethyl ester 

Downstream Products

• 662143-00-2 [(1S)-2-[[(4-methylphenyl)sulfonyl]amino]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester 
• 1245908-76-2 (S)-tert-butyl 2-formamido-1-phenylethylcarbamate 
• 1354694-87-3 (S)-(2-acetylamino-1-phenylethyl)carbamic acid tert-butyl ester 
• 1390672-77-1 (S)-(9H-fluoren-9-yl)methyl 2-[(S)-2-(tert-butoxycarbonylamino)-2-phenylethylcarbamoyl]pyrrolidine-1-carboxylate 
• 1390672-78-2 C₂₈H₂₉N₃O₃*ClH 

Relevant academic research and scientific papers

Development of Chiral Organosuperbase Catalysts Consisting of Two Different Organobase Functionalities

In the field of chiral Br?nsted base catalysis, a new generation of chiral catalysts has been highly anticipated to overcome the intrinsic limitation of pronucleophiles that are applicable to the enantioselective reactions. Herein, we reveal conceptually new chiral Br?nsted base catalysts consisting of two different organobase functionalities, one of which functions as an organosuperbase and the other as the substrate recognition site. Their prominent activity, which stems from the distinctive cooperative function by the two organobases in a single catalyst molecule, was demonstrated in the unprecedented enantioselective direct Mannich-type reaction of α-phenylthioacetate as a less acidic pronucleophile. The present achievement would provide a new guiding principle for the design and development of chiral Br?nsted base catalysts and significantly broaden the utility of Br?nsted base catalysis in asymmetric organic synthesis.

Discovery and Optimization of Phosphopantetheine Adenylyltransferase Inhibitors with Gram-Negative Antibacterial Activity

In the preceding manuscript [Moreau et al. 2018, 10.1021/acs.jmedchem.7b01691] we described a successful fragment-based lead discovery (FBLD) strategy for discovery of bacterial phosphopantetheine adenylyltransferase inhibitors (PPAT, CoaD). Following several rounds of optimization two promising lead compounds were identified: triazolopyrimidinone 3 and 4-azabenzimidazole 4. Here we disclose our efforts to further optimize these two leads for on-target potency and Gram-negative cellular activity. Enabled by a robust X-ray crystallography system, our structure-based inhibitor design approach delivered compounds with biochemical potencies 4-5 orders of magnitude greater than their respective fragment starting points. Additional optimization was guided by observations on bacterial permeability and physicochemical properties, which ultimately led to the identification of PPAT inhibitors with cellular activity against wild-type E. coli.

NOVEL NICOTINAMIDE DERIVATIVES OR SALTS THEREOF

An object of the present invention is to provide to a compound and a pharmaceutical composition, which have excellent Syk-inhibitory activity. Th e present invention provides a nicotinamide derivative represented by the follo wing formula (I) (wherein R 1 represents a halogen atom; R 2 represents a C 1-12 alkyl group, a C 2-12 alkenyl group, a C 2-12 alkynyl group, a C 3-8 cycloalkyl g roup, an aryl group, an ar-C 1-6 alkyl group or a heterocyclic group, each opti onally having at least one substituent; R 3 represents an aryl group or a hetero cyclic group each optionally having at least one substituent; and R 4 and R 5 e ach independently represent a hydrogen atom; and R 2 and R 4 may form a cyc lic amino group optionally having at least one substituent together with the ni trogen atom to which they bind) or a salt thereof, and a pharmaceutical comp osition for use in the treatment of a Syk-related disease which comprises the nicotinamide derivative or a salt thereof.

A Continuous-Flow, Two-Step, Metal-Free Process for the Synthesis of Differently Substituted Chiral 1,2-Diamino Derivatives

The enantioselective organocatalytic reduction of aryl-substituted nitroenamines was successfully performed under continuous-flow conditions. After a preliminary screening with a 10-μL microreactor, to establish the best reaction conditions, the reduction was scaled up in a 0.5-mL mesoreactor, without appreciable loss of enantioselectivity, that remained constantly higher than 90%. The in-flow nitro reduction was also accomplished, either by Raney nickel catalyzed hydrogenation or by a metal-free methodology based on the use of the very inexpensive and readily available reducing agent trichlorosilane. The final aim is to develop a two-step, continuous-flow process for the stereoselective, metal-free, catalytic synthesis of differently functionalized chiral 1,2-diamines.

SYNTHESIS OF ARYL CYCLOHEXANE CARBOXAMIDE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS

Synthesis methods to produce a series of carboxamides built off of an (S)-2-amino acid backbone or an (R)-2-amino acid backbone, depending upon the desired diastereomer of the end product.

Novel α-amino acid-derived phase-transfer catalyst application to a highly enantio- and diastereoselective nitro-Mannich reaction

New quaternary ammonium types of bifunctional asymmetric phase-transfer catalysts bearing multiple hydrogen-bonding donors derived from α-amino acids were readily prepared and found to be highly efficient in the asymmetric nitro-Mannich reactions of amidosulfones. Very broad substrate generality was observed, and the products were achieved in high enantio-/diastereoselectivities (90->99.9% ee, 90:10 to 92:8 dr). Compared with previous reports, the enantioselectivity of aliphatic amidosulfones has been improved to a high level (91-93% ee).

Novel bifunctional thiourea-ammonium salt catalysts derived from amino acids: Application to highly enantio- and diastereoselective aza-Henry reaction

The development of new efficient and easily accessible catalysts has been one of the focuses in asymmetric phase-transfer catalysis. In this paper, a novel class of chiral bifunctional thiourea-ammonium phase-transfer catalysts were synthesized from commercially available α-amino acids. The structural modularity of these catalysts permits facile tunings to achieve optimum results, which was demonstrated in catalyzing the aza-Henry reaction with excellent enantioselectivities (up to 99.5% ee) and diastereoselectivities (up to >25:1 dr).

A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst

A tripeptide-like prolinamide-thiourea catalyst with (S)-proline, (1S,2S)-diphenylethylenediamine and (S)-di-tert-butyl aspartate as building blocks provides the products of the reaction between ketones and aromatic aldehydes in high to quantitative yields and high stereoselectivities (up to 99:1 dr and 99% ee). Both the chiral centers of the diamine unit are essential, while the thiourea hydrogen originating from the amine and the amide hydrogen play a predominant role for the catalyst efficiency.

Highly enantioselective nitro-mannich reaction catalyzed by cinchona alkaloids and N-benzotriazole derived ammonium salts

The catalytic enantio- and diastereoselective nitro-Mannich reaction of α-amido sulfones in the mixed solvent of toluene/H2O has been realized using a phase-transfer catalyst (PTC) derived from cinchona alkaloids and N-benzotriazole. It performed well over a wide range of substrates to give the desired products in good yields (up to 94%) with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99:1).

Isoselenocyanates derived from Boc/Z-amino acids: Synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The 1H NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenoureido derivatives is free from racemization.