34351-19-4

Usage

Uses

Used in Organic Chemistry:
(3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride is used as a building block for the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of molecules with different properties and functions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride is utilized for the development of pharmaceuticals and bioactive molecules. Its presence of functional groups makes it a promising candidate for the design and synthesis of new drugs with potential therapeutic applications.
Used in Drug Development:
(3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride is employed in drug development as a key intermediate in the synthesis of various pharmaceutical agents. Its versatility and reactivity contribute to the creation of novel drug candidates with improved efficacy and safety profiles.
Used in Research:
(3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride is also used in research settings to study the structure-activity relationships of different molecules and to explore new chemical reactions and synthetic pathways. Its unique properties make it a valuable tool for advancing scientific knowledge and understanding in the fields of chemistry and medicine.

Upstream product

• 102123-74-0 (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 74-97-5 chlorobromomethane 
• 339190-43-1 N-benzylidene (S)-phenylalanine methyl ester 
• 286019-77-0 (3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanone 
• 149206-46-2 (4S)-4-Benzyl-N-tert-butyloxycarbonyl-1,3-oxazolidin-5-one 
• 119153-87-6 (C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅) 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 120238-42-8 methyl (S)-2-(diphenylmethylideneamino)-3-phenylpropanoate 
• 291279-17-9 N-Boc-4-benzyl-5-chloromethyl-5-hydroxy-3-oxazolidine 
• 60398-41-6 (3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate 

Downstream Products

• 127231-58-7 (3S)-<amino>-1-chloro-4-phenyl-2-butanone 
• 155847-91-9 [(S)-1-((S)-1-Benzyl-3-chloro-2-oxo-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 214826-45-6 Boc-Lys(Z)-Phe-CH₂Cl 
• 214826-48-9 Boc-Dap(Z)-Phe-CH₂Cl 
• 214826-46-7 Boc-Orn(Z)-Phe-CH₂Cl 
• 214826-47-8 Boc-Dab(Z)-Phe-CH₂Cl 
• 102123-74-0 (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 176972-61-5 (S)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid methyl ester 
• 137150-40-4 (S)-2-((S)-2-Acetylamino-4-methyl-pentanoylamino)-N¹-((S)-1-benzyl-3-chloro-2-oxo-propyl)-succinamide 
• 127231-59-8 (3S)-<amino>-1-chloro-4-phenyl-2-butanone 
• 127231-43-0 (3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone 

Relevant academic research and scientific papers

Creation of an artificial metalloprotein with a Hoveyda-Grubbs catalyst moiety through the intrinsic inhibition mechanism of α-chymotrypsin

An l-phenylalanyl chloromethylketone-based inhibitor equipped with a Hoveyda-Grubbs catalyst moiety was regioselectively incorporated into the cleft of α-chymotrypsin through the intrinsic inhibition mechanism of the protein to construct an artificial organometallic protein. The Royal Society of Chemistry 2012.

REDUCTION OF ALDEHYDES AND KETONES TO ALCOHOLS

The embodiments described herein provide a reduction of an aldehyde or a ketone, such as a Meerwein-Ponnorf-Verley (MPV) reaction of an aldehyde or ketone. In some embodiments, the reaction occurs in the presence of A1[OC(CH3)3]. In some embodiments, the reaction occurs in the presence of an aprotic solvent. In some embodiments, the aldehyde or ketone is an amino aldehyde or an amino ketone wherein the amine is group is protected such that the nitrogen of the amine has no proton. Other embodiments related to compositions and compounds related to the reduction reaction, or to the preparation or use of the aldehyde, the ketone, or the resulting alcohol.

Process for producing alpha-aminoketones

An amino group of an α-amino acid ester is protected as an imine, and it is then reacted with a halomethyllithium to obtain an N-protected-α-aminohalomethylketone. Further, this N-protected-α-aminohalomethylketone is treated with an acid to obtain an α-aminohalomethylketone. This process is suited for industrial production, and can produce an α-aminohalomethylketone and its related compounds economically and efficiently.

Practical synthesis of α-aminoalkyl-α′-chloromethylketone derivatives. Part 1: Chloromethylation of N-protected 3-oxazolidin-5-ones

Reaction of N-protected 3-oxazolidin-5-ones with in situ-generated chloromethyllithium afforded N-protected 5-chloromethyl-5-hydroxy-3-oxazolidines without racemization. They were easily hydrolyzed to give α-aminoalkyl-α′-chloromethylketone derivatives, which are useful intermediates for several protease inhibitors.

Practical synthesis of α-aminoalkyl-α′-chloromethylketone derivatives. Part 2: Chloromethylation of N-imine-protected amino acid esters

Chloromethylation of N-imine-protected amino acid esters followed by acid hydrolysis gave α-aminoalkyl-α′-chloromethylketone as a HCl salt form in good yield without racemization. The amino group was conveniently protected with carbamate protecting reagents to give various useful intermediates for the protease inhibitors.

Amino acids and peptides. LII. Design and synthesis of opioid mimetics containing a pyrazinone ring and examination of their opioid receptor binding activity

An amino group was introduced to the 3 or 6 position of a pyrazinone ring by cyclization of dipeptidyl chloromethyl ketones. Boc-Tyr-OH was coupled with the amino function, followed by removal of the Boc group to give pyrazinone ring-containing tyrosine derivatives. Of the various tyrosine derivatives prepared, 5-methyl-6-β-phenethyl-3-tyrosylaminobutyl-2(1H)- pyrazinone exhibited strong binding to the μ-opioid receptor with a K(i) value of 55.8 nM and to the δ-opioid receptor with a K(i) value of 2165 nM and with a K(i)μ/K(i)δ value of 0.026.

Amino acids and peptides. XLI. Facile synthesis of 5-methyl-2(1H)-pyrazinone derivatives from dipeptidyl chloromethyl ketones

5-Methyl-2(1H)-pyrazinone derivatives were easily synthesized by short reflux of dipeptidyl chloromethyl ketone hydrochlorides in MeOH.

Development of active center-directed plasmin and plasma kallikrein inhibitors and studies on the structure-inhibitory activity relationship

The molecule of trans-4-aminomethylcyclohexanecarbonylphenylalanine 4- carboxymethylanilide (8), which is a potent and selective inhibitor of plasma kallikrein, can be divided into three parts (P1, P1 and P2), each of which contains one of the rings. In order to study the role of each part in the manifestation of potent and selective inhibitory activity and the relationship between the structure and inhibitory activities toward plasmin, plasma kallikrein, urokinase and thrombin, each part was substituted with various other moieties to give many kinds of analogs and their inhibitory activities against the above enzymes were examined. Among them, trans-4- aminomethylcyclohexanecarbonyl-O-2-bromobenzyloxycarbonyltyrosine 4- acetylanilide (12) inhibited plasmin and plasma kallikrein with IC50 values of 2.3 x 10-7 M and 3.7 x 10-7 M, and K(i) values of 1.2 x 10-7 M and 1.3 x 10-7 M, respectively.

New hydroxyethylamine HIV protease inhibitors that suppress viral replication

The synthesis of analogues of AcSerLeuAsn[Phe-HEA-Pro]IleValOMe (1, JG- 365; where HEA stands for the hydroxyethylamine unit 2), a tight-binding inhibitor of HIVP, are reported. Systematic modification of the P3 and P3' regions of the inhibitors has led to smaller HIVP inhibitors that inhibit viral replication in HIV-infected and SIV-infected cell cultures. Six aliphatic and/or aromatic derivatives were prepared by replacing residues in the P3 regions of BocLeuAsn[Phe-HEA-Pro]IleValOMe. Aromatic side chains at P3 gave better inhibitors than aliphatic side chains. The better inhibitors in this series contained a β-naphthylalanine or a biphenyl unit at P3. A second series of HIVP inhibitors were obtained by converting the P3 group into acyl groups. CbzAsn[Phe-HEA-Pro]IlePheOMe and Qua-Asn-[Phe-HEA-Pro]-Ile- Phe-OMe (where Qua = quinolin-2-ylcarbonyl) are potent HIVP inhibitors with K(i) values equal to 1.0 and 0.1 nM, respectively. The inhibition constants were determined by using the continuous fluorometric assay developed by Toth and Marshall. The activities of the protease inhibitors for inhibition of SIV replication were determined in vitro using CEMx174 cells. Inhibition of HIV infection was determined essentially as reported by Pauwels and co-workers. The anti-HIV assay was carried out in culture using CEM cells (a CD4+ lymphocyte line) infected with virus strain HTLV-III(b) with a multiplicity of infection of 0.1. Several analogues inhibited the cytopathic effect at concentrations of 0.1-0.8 μg/mL. These results establish that good inhibitors of HIV protease that inhibit viral replication in infected lymphocytes in in vitro cell assays can be obtained from JG-365 when the AcSerLeu unit is replaced by aromatic acyl derivatives.