73148-70-6

Usage

Uses

Used in the Food Industry:
α(L)-aminobenzylacetonitrile is used as a flavoring agent to enhance the taste and aroma of various food products, contributing to a more appealing consumer experience.
Used in Pharmaceutical Synthesis:
α(L)-aminobenzylacetonitrile is utilized as a key intermediate in the synthesis of a range of pharmaceuticals, leveraging its chemical properties to facilitate the creation of new and improved medications.
Used in Agrochemical Production:
α(L)-aminobenzylacetonitrile is also employed in the production of agrochemicals, where it serves as a building block for the development of effective crop protection products and other agricultural applications.

Upstream product

• 70591-26-3 2-(Benzhydrylidene-amino)-3-phenyl-propionitrile 
• 63-91-2 L-phenylalanine 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 21947-21-7 (S)-N-benzyloxycarbonyl-2-amino-3-phenyl-propionitrile 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 155385-83-4 (-)-1-<(1-cyano-2-phenylethyl)amino>-2R-methyl-5R-(1-methylethenyl)cyclohexane-1R,3R-dicarbonitrile 
• 99281-90-0 (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanenitrile 
• 59937-72-3 (S)-2-(2-Nitro-phenylsulfanylamino)-3-phenyl-propionamide 

Downstream Products

• 1159488-91-1 (S)-2-[(S)-1-(4-bromo-phenyl)-2,2,2-trifluoro-ethylamino]-N-[(S)-1-cyano-2-phenyl-ethyl]-3-methyl-butyramide 
• 5241-58-7 L-Phenylalanine amide 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 18942-49-9 Boc-D-Phe-OH 

Relevant academic research and scientific papers

Optimization strategy of single-digit nanomolar cross-class inhibitors of mammalian and protozoa cysteine proteases

Cysteine proteases (CPs) are involved in a myriad of actions that include not only protein degradation, but also play an essential biological role in infectious and systemic diseases such as cancer. CPs also act as biomarkers and can be reached by active-

Sulfur(VI) Fluoride Exchange (SuFEx)-Enabled High-Throughput Medicinal Chemistry

Optimization of small-molecule probes or drugs is a synthetically lengthy, challenging, and resource-intensive process. Lack of automation and reliance on skilled medicinal chemists is cumbersome in both academic and industrial settings. Here, we demonstr

N-Sulfonyl dipeptide nitriles as inhibitors of human cathepsin S: In silico design, synthesis and biochemical characterization

A library of cathepsin S inhibitors of the dipeptide nitrile chemotype, bearing a bioisosteric sulfonamide moiety, was synthesized. Kinetic investigations were performed at four human cysteine proteases, i.e. cathepsins S, B, K and L. Compound 12 with a t

Synthesis and structure-activity relationship of nitrile-based cruzain inhibitors incorporating a trifluoroethylamine-based P2 amide replacement

The structure-activity relationship for nitrile-based cruzain inhibitors incorporating a P2 amide replacement based on trifluoroethylamine was explored by deconstruction of a published series of inhibitors. It was demonstrated that the P3 biphenyl substituent present in the published inhibitor structures could be truncated to phenyl with only a small loss of affinity. The effects of inverting the configuration of the P2 amide replacement and linking a benzyl substituent at P1 were observed to be strongly nonadditive. We show that plotting affinity against molecular size provides a means to visualize both the molecular size efficiency of structural transformations and the nonadditivity in the structure-activity relationship. We also show how the relationship between affinity and lipophilicity, measured by high-performance liquid chromatography with an immobilized artificial membrane stationary phase, may be used to normalize affinity with respect to lipophilicity.

Carbohydrates as efficient catalysts for the hydration of α-amino nitriles

Directed hydration of α-amino nitriles was achieved under mild conditions using simple carbohydrates as catalysts exploiting temporary intramolecularity. A broadly applicable procedure using both formaldehyde and NaOH as catalysts efficiently hydrated a variety of primary and secondary susbtrates, and allowed the hydration of enantiopure substrates to proceed without racemization. This work also provides a rare comparison of the catalytic activity of carbohydrates, and shows that the simple aldehydes at the basis of chemical evolution are efficient organocatalysts mimicking the function of hydratase enzymes. Optimal catalytic efficiency was observed with destabilized aldehydes, and with difficult substrates only simple carbohydrates such as formaldehyde and glycolaldehyde proved reliable.

Identification of potent and reversible cruzipain inhibitors for the treatment of Chagas disease

Identification of potent and reversible cruzipain inhibitors for the treatment of Chagas disease is described. The identified inhibitors bearing an amino nitrile warhead in P1 exhibit low nanomolar in vitro potency against cruzipain. Further SAR in P2 por

Design and synthesis of dipeptidyl nitriles as potent, selective, and reversible inhibitors of cathepsin C

A series of dipeptide nitriles with a thienyl alanine in P2 were identified as potent and selective cathepsin C inhibitors. Incorporation of a substituted cyclopropyl moiety in P1 effectively protects these derivatives against hydrolase activity in whole blood.

Primary amides as selective inhibitors of cathepsin K

The nitrile warhead used in a series of cathepsin K inhibitors can be replaced by a less electrophilic primary amide. The accompanying loss of potency can be partially recovered by introducing a substituent α to the amide. The potency gain resulting from this addition is not achieved with the nitrile derivatives due to a different geometry of the cysteine adduct in the enzyme active site. This study led to the identification of the primary amide 2g, which is an inhibitory substrate, with an IC50 of 10 nM against cathepsin K and excellent selectivity versus the other cathepsins.

Regioselective hydration and deprotection of chiral, dissymmetric iminodinitriles in the scope of an asymmetric strecker strategy

The controlled, selective decomposition of dissymmetric iminodinitriles (DIDN) of formula RCH(CN)-NH-C(CN)R′R″ (considered as N-protected alpha-aminonitriles), is a critical issue for an original asymmetric Strecker strategy previously outlined by us for the enantioselective synthesis of amino acids. This strategy, derived from Harada's work, involves a double sequence of (i) stereoselective Strecker condensation of a chiral ketone R′R″CO with NH3 and HCN, followed by (ii) stereoselective Strecker condensation with an aldehyde RCHO and HCN, then (iii) regioselective retro-Strecker decomposition of the DIDN intermediate to release the target alpha-aminonitrile. In addition to the use of quite simple, cheap cyclic ketones (e.g. carvone derivatives) as chiral auxiliaries, another great advantage of this strategy is that step (iii) enables the recovery of the chiral ketone and hence its reuse. While our previous investigations on step (iii) under various conditions, either preceded or followed by the hydration of the secondary nitrile group RH(CN)- into an amide, had shown insufficient selectivity, we succeeded in the regioselective hydration of the secondary nitrile of DIDN without significant racemisation, by using a large excess of hydrogen peroxide in methanolic/aqueous ammonia (pH 12.5) at low temperature. The resulting imino nitrile/amide compound was then classically decomposed in acidic medium through a retro-Strecker reaction, affording the chiral alpha-amino amide. Alternately, the regioselective retro-Strecker decomposition of the tertiary moiety of the DIDN was achieved by reaction with silver cation in aqueous nitric acid, also without significant racemisation, thus establishing an original, enantioselective synthesis of alpha-aminonitriles. In both reactions, the chiral ketonic auxiliary resulting from DIDN decomposition was recovered in good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

An efficient procedure for the preparation of 4-substituted 5-aminoimidazoles

The preparation of O-methylimidates from α-aminonitriles and their subsequent co-cyclization with primary amines to afford 4-substituted 5-aminoimidazoles was studied. It was found that the mildly acidic pyridinium p-toluenesulfonate efficiently catalyzed each stage of the reaction sequence: (a) the formation of the O-methylimidates, (b) their co-cyclization with a variety of primary amines, and (c) certain derivatizations of the resultant heterocycles. The developed reaction conditions tolerate a wide variety of α-aminonitriles and primary amine co-reactants. Thus, it is possible to easily prepare a diverse array of substituted heterocyclic compounds in good yield. The requisite α-aminonitriles were synthesized either from amino acids or by phase-transfer alkylation of a glycine anion equivalent. The unstable free 5-aminoimidazoles were normally protected in situ to provide derivatives (methyl imidates or N,N-dimethylamidines) that were amenable to characterization.