76497-43-3

Usage

Uses

Used in Pharmaceutical Synthesis:
3-METHYLAMINO-3-PHENYL-PROPIONIC ACID is used as an intermediate in the synthesis of various pharmaceutical goods. Its unique chemical structure allows it to be a key component in the creation of a wide range of medications, contributing to the development of new treatments and therapies.
Used in Platelet Fibrinogen Receptor Antagonists:
In the field of cardiovascular medicine, 3-METHYLAMINO-3-PHENYL-PROPIONIC ACID is used as a precursor in the preparation of antagonists of the platelet fibrinogen receptor. These antagonists play a crucial role in preventing blood clot formation, which can lead to conditions such as heart attacks and strokes. By targeting the platelet fibrinogen receptor, these antagonists can help reduce the risk of thrombotic events and improve patient outcomes.

InChI:InChI=1/C10H13NO2/c1-11-9(7-10(12)13)8-5-3-2-4-6-8/h2-6,9,11H,7H2,1H3,(H,12,13)

Upstream product

• 141-82-2 malonic acid 
• 622-29-7 N-Benzylidenemethylamine 
• 593-51-1 methylamine hydrochloride 
• 100-52-7 benzaldehyde 
• 1010128-92-3 methyl 3-[(diphenylphosphoryl)(methyl)amino]-3-phenylpropanoate 
• 4192-77-2 ethyl cinnamate 
• 64-17-5 ethanol 
• 39629-54-4 (+/-)-3-methylamino-3-phenyl-propionic acid ethyl ester 

Downstream Products

• 4458-62-2 1-methyl-4-phenylazetidin-2-one 
• 31925-48-1 methyl-3-methylamino-3-phenylpropionate 
• 3834-44-4 methyl 3-amino-4,4,4-trifluoro-3-methylbutanoate 
• 31925-64-1 3-[(3-{3-[(2-Cyano-ethyl)-methyl-amino]-3-phenyl-propionylamino}-propyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 31925-65-2 3-[(3-{3-[(3-Amino-propyl)-methyl-amino]-3-phenyl-propionylamino}-propyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 31925-67-4 3-[(3-{3-[(3-Amino-propyl)-methyl-amino]-3-phenyl-propionylamino}-propyl)-methyl-amino]-3-phenyl-propionic acid 
• 31925-50-5 3-[(3-Benzyloxycarbonylamino-propionyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 31925-51-6 3-[(3-Benzyloxycarbonylamino-propionyl)-methyl-amino]-3-phenyl-propionic acid 
• 32063-92-6 3-[(3-Benzyloxycarbonylamino-propyl)-methyl-amino]-3-phenyl-propionic acid 
• 31925-63-0 3-[(3-Benzyloxycarbonylamino-propyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 31948-95-5 3-[(2-Cyano-ethyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 31948-96-6 3-[(3-Amino-propyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 857812-95-4 5-bromo-1-methyl-6-phenyl-dihydro-pyrimidine-2,4-dione 
• 39629-54-4 (S)-ethyl 3-(methylamino)-3-phenylpropanoate 

Relevant academic research and scientific papers

Phosphinamide-directed benzylic lithiation. application to the synthesis of peptide building blocks

N-Benzyldiphenylphosphinamides are deprotonated at the NCα position diastereospecifically upon treatment with f-BuLi in diethyl ether at low temperature. The reaction of the anions with alkyl, acyl, and tin halides, aliphatic and aromatic aldehydes, and Michael acceptors allowed installation of a variety of functional groups into the benzylic arm in excellent yields. Cleavage of the P-N linkage affords 1,2-amino alcohols and α-, β-, and γ-amino acids.

Discovery of an orally active non-peptide fibrinogen receptor antagonist based on the hydantoin scaffold

Antagonists of the platelet fibrinogen receptor (GP IIb/IIIa receptor) are expected to be a promising new class of antithrombotic agents. The binding of fibrinogen to the fibrinogen receptor depends on an Arg-Gly-Asp-Ser (RGDS) tetrapeptide recognition motif. Structural modifications of the RGDS lead have led to the discovery of a non-peptide RGD mimetic GP IIb/IIIa antagonist 44 (S 1197). Compound 44 inhibited, in a dose dependent and reversible manner, human and dog platelet aggregation as well as 125I-fibrinogen binding to ADP-activated human gel filtered platelets and isolated GP IIb/IIIa with Ki values of 9 nM and 0.17 nM, respectively. A pharmacophore mapping procedure with QXP and a 3D-QSAR analysis applying the GRID/GOLPE methodology yielded a stable, rather predictive model and revealed structural features which are important for binding. Hydrophobic substitutions both at the hydantoin nucleus and at the C-terminus increase the affinity toward the fibrinogen receptor. The crystalline ethyl ester prodrug 48 (HMR 1794) is an orally active antithrombotic agent which is a promising drug candidate for the treatment of thrombotic diseases in humans.

Synthesis of the Alkaloid Homaline in (+/-) and Natural (S,S)-(-) Forms, using Amination and Transamidative Ring Expansion in Liquid Ammonia

Synthesis of the alkaloid homaline in (+/-) and natural (S,S)-(-) forms is reported.Linking of 2-azacyclooctanone units either directly or successively using 1,4-dihalogenobutanes or 1,4-dihalogenobut-2-ynes is examined. (+/-)-5-Methyl-4-phenyl-1,5-diazacyclooctan-2-one is first made by a 2,2'-dithiodipyridine/triphenylphosphine-mediated cyclisation, and then by amination and transamidative ring expansion from N-(3-chloropropyl)-4-phenylazetidin-2-one in liquid ammonia, followed by N-methylation.Coupling through a 1,4-dihalogenobutane of either the N-methylated azalactam, or the unmethylated azalactam followed by methylation, gave homaline in (+/-) and meso forms. (R)-(-)-Phenylglycine was converted via (S)-β-phenyl-β-alanine into an (S)-β-lactam which was then alkylated with 1-bromo-3-chloropropane, and aminated and ring expanded in liquid ammonia.Coupling of the homochiral azalactam (2 mol) so formed with 1,4-dibromobutane, followed by N-methylation, gave (S,S)-(-)-homaline identical with the natural material.

Cyclic diones

A 2-benzoylcyclic-1,3-dione derivative of the formula: STR1 wherein X represents methylene, oxygen, sulphur or --NR4 --, Y represents --C(R5) (R6)-- or oxygen, R1 represents hydrogen or alkyl optionally substitu