14441-08-8

Usage

Uses

Used in Pharmaceutical Research and Development:
(S)-N-Z-3-AMINO 3-PHENYLPROPIONIC ACID is used as a building block for the synthesis of bioactive molecules and pharmaceutical drugs. Its unique structural properties and potential biological activities make it a valuable compound in the development of new medications.
Used in Medicinal Chemistry and Drug Discovery:
In the field of medicinal chemistry and drug discovery, (S)-N-Z-3-AMINO 3-PHENYLPROPIONIC ACID is utilized as a key intermediate due to its stereochemistry and specific functional groups. These characteristics enable the compound to play a significant role in the design and synthesis of novel pharmaceutical agents.
Used in Organic Synthesis:
(S)-N-Z-3-AMINO 3-PHENYLPROPIONIC ACID is also employed in organic synthesis, where its structural properties and functional groups are harnessed to produce a wide range of pharmaceutical compounds. Its versatility as an intermediate makes it a valuable asset in the development of new and innovative medications.

Upstream product

• 245323-41-5 tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoate 
• 17609-52-8 Z-D-phenylglycine 
• 32975-59-0 methyl (S)-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate 
• 103-26-4 Methyl cinnamate 
• 159173-92-9 methyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-phenylpropanoate 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 100-52-7 benzaldehyde 
• 37088-68-9 methyl (S)-3-amino-3-phenylpropanoate tartaric salt 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 103-26-4 methyl cinnamate 
• 126575-05-1 DL-3-(N-formylamino)-3-phenylpropionic acid 
• 40856-45-9 D-3-(N-formylamino)-3-phenylpropionic acid 
• 245323-35-7 (4S)-3-((2S)-4-(tert-butoxy)-4-oxo-2-phenylbutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one 

Downstream Products

• 22839-32-3 Benzyloxycarbonyl-L-β-amino-β-phenyl-propionyl-L-α-amino-buttersaeuremethylester 
• 245323-41-5 tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoate 
• 875574-86-0 (S)-methyl 2-((S)-3-(benzyloxycarbonylamino)-3-phenylpropanamido)-5-(1,3-dioxolan-2-yl)pentanoate 
• 1419075-37-8 (S)-benzyl [5-(1,3-dioxoisoindolin-2-yl)-3-oxo-1-phenylpentyl]carbamate 
• 1419075-39-0 (S)-benzyl [2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1,3-dioxan-2-yl)-1-phenylethyl]carbamate 
• 1419075-40-3 (S)-benzyl [2-(2-(2-aminoethyl)-1,3-dioxan-2-yl)-1-phenylethyl]carbamate 
• 1419075-42-5 (S)-benzyl [1-phenyl-2-(2-(2-(2,2,2-trifluoroacetamido)ethyl)-1,3-dioxan-2-yl)ethyl]carbamate 
• 1419075-43-6 (S)-N-(2-(2-(2-amino-2-phenylethyl)-1,3-dioxan-2-yl)ethyl)-2,2,2-trifluoroacetamide 
• 1419075-24-3 2,2,2-trifluoro-N-[(4E)-3-oxo-5-phenylpent-4-en-1-yl]acetamide 
• 947530-18-9 (S)-benzyl [3-oxo-1-phenylpent-4-en-1-yl]carbamate 
• 1419075-36-7 (S)-benzyl [1-phenyl-3-(4-morpholinyl)-3-oxopropyl]carbamate 
• 947530-23-6 (S,E)-benzyl [3-oxo-1-phenyl-hex-4-enyl]carbamate 
• 947530-24-7 C₂₀H₂₁NO₃ 
• 874141-25-0 (-)-(3S)-3-(N-benzyloxycarbonylamino)-3-phenyl-(N'-methoxy-N'-methylpropananamide) 

Relevant academic research and scientific papers

Structure-Based Design and Development of Chemical Probes Targeting Putative MOR-CCR5 Heterodimers to Inhibit Opioid Exacerbated HIV-1 Infectivity

Crystal structures of ligand-bound G-protein-coupled receptors provide tangible templates for rationally designing molecular probes. Herein, we report the structure-based design, chemical synthesis, and biological investigations of bivalent ligands targeting putative mu opioid receptor C-C motif chemokine ligand 5 (MOR-CCR5) heterodimers. The bivalent ligand VZMC013 possessed nanomolar level binding affinities for both the MOR and CCR5, inhibited CCL5-stimulated calcium mobilization, and remarkably improved anti-HIV-1BaL activity over previously reported bivalent ligands. VZMC013 inhibited viral infection in TZM-bl cells coexpressing CCR5 and MOR to a greater degree than cells expressing CCR5 alone. Furthermore, VZMC013 blocked human immunodeficiency virus (HIV)-1 entry in peripheral blood mononuclear cells (PBMC) cells in a concentration-dependent manner and inhibited opioid-accelerated HIV-1 entry more effectively in phytohemagglutinin-stimulated PBMC cells than in the absence of opioids. A three-dimensional molecular model of VZMC013 binding to the MOR-CCR5 heterodimer complex is constructed to elucidate its mechanism of action. VZMC013 is a potent chemical probe targeting MOR-CCR5 heterodimers and may serve as a pharmacological agent to inhibit opioid-exacerbated HIV-1 entry.

Efficient synthesis of β'-amino-α, β-unsaturated ketones

A general and simple procedure to access chiral β'-amino-α, β-enones, in seven steps, from an α,β unsaturated ester has been described. The use of a Horner-Wadsworth-Emmons reaction as a key step for generating the β'-amino-α,β-enones, permits access to a range of substrates under mild conditions and in moderate to high yield.

Stereoselective synthesis and in vivo evaluation of the analgesic activity of polysubstituted bispidines

Hetero-Michael addition on a chiral β'-amino α,β- unsaturated ketone gave, after some structural modifications, β,β'-diamino ketals. Mannich-type reactions of these diamines with an aldehyde led, with high diastereoselectivity, to trisubstituted piperidines. Another highly stereoselective Mannich cyclization, with an N-acyliminium ion generated in situ from the corresponding imide, allowed the preparation of original polycyclic bispidine derivatives. The antinociceptive effect of the three compounds prepared was evaluated in vivo by using the writhing test. If the biological results for the analgesic properties were disappointing, compared with the bispidine HZ2, which has a high affinity for opioid receptors, the modularity of the approach offered the possibility of introducing many substituents for new applications, which was promising because the bispidine core has been described to have many different activities. Total stereoselective synthesis of bispidine derivatives is achieved by using as two successive Mannich reactions key steps. This process constitutes a powerful approach toward the preparation of a polycyclic bispidine backbone with high enantioselectivity.

Development of a bulk enabling route to maraviroc (UK-427,857), a CCR-5 receptor antagonist

A bulk enabling synthesis of the CCR-5 receptor antagonist, Maraviroc (UK-427,857) (1), is presented. Synthesis of the three key fragments, β-amino ester 3,4,4-difluorohexanecarboxylic acid (2), and 1,3,4-triazole-substituted tropane fragment 4 are described. Coupling strategies for these fragments are discussed and described, including synthetic challenges, protection strategies, impurity generation, and final scale-up of the developed route to 1.

Homologation of α-amino acids to β-amino acids: 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Nα-protected aminoacyldiazomethanes

An efficient and stereospecific homologation of urethane-protected α-amino acids to β-amino acids by Arndt-Eistert approach using an equimolar mixture of Fmoc-/Boc-/Z-α-amino acid and 9-fluorenylmethyl chloroformate for the acylation of diazomethane synth

THIADIAZOLE AMIDE MMP INHIBITORS

The present invention provides novel thiadiazole amide derivatives represented by formula I The compounds of the present invention inhibit various enzymes from the matrix metalloproteinase family, predominantly stromelysins, and hence are useful f

A general method for the synthesis of enantiomerically pure β- substituted, β-amino acids through α-substituted succinic acid derivatives

A general procedure for the synthesis of enantiopure β-substituted, β- amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert- butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (≥ 93;7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected β-amino esters 6 in good yields (74-79%).

THIADIAZOLE AMIDE MMP INHIBITORS

The present invention provides novel thiadiazole amide derivatives represented by formula I STR1 The compounds of the present invention inhibit various enzymes from the matrix metalloproteinase family, predominantly stromelysins, and hence are useful for

Analogues of 2'(3')-O-L-phenylalanyladenosine as substrates and inhibitors of ribosomal peptidyltransferase

The chemical syntheses of 2'(3')-O-(L-3-amino-3-phenylpropionyl)adenosine (2e), the corresponding D stereoisomer 2f, 2'(3')-O-(DL-phenylglycyl)adenosine (2g), 2'(3')-O-(N-benzylglycyl)adenosine (2h), and 9-(2-O-L-phenylalanyl-β-D-xylofuranosyl)adenine (3b) are described. Compounds 2e-h were obtained by acylation of 5'-O(4-methoxytrityl)adenosine with the appropriate N-benzyloxycarbonyl or N-tert-butoxycarbonyl amino acids with dicyclohexylcarbodiimide in pyridine. The corresponding reaction of N-(benzyloxycarbonyl)-D-phenylglycine led to an almost complete racemization of the aminoacyl residue (compounds 2c and 2g). Subsequent chromatographic separation and deprotection of intermediates 2a-d afforded the desired target derivatives 2e-h. Product 3b was obtained by a similar acylation of 9-(3,5-O-isopropylidene-β-D-xylofuranosyl)adenine with N-(benzyloxycarbonyl)-L-phenylalanine, followed by deblocking. The NMR spectra of 2' and 3' isomers of stereoisomers 2a and 2b are discussed. Compounds 2g and 3b are both substrates and inhibitors of Escherichia coli ribosomal peptidyltransferase, although the activity of 3b is low. Derivatives 2e,f,h do not accept AcPhe from N-AcPhe-tRNA in a peptidyltransferase-catalyzed reaction, but they inhibit the puromycin reaction in the same system. The order of inhibitory activity is 2e>2f>2h. The implications of these findings for the mechanism of peptidyltransferase and comparison of the latter with the action of chymotrypsin are discussed.