65444-05-5

Upstream product

• 91702-98-6 3-acetylthio-2-benzylpropanoic acid 
• 5669-19-2 2-Benzyl-2-propenoic acid 
• 607-81-8 diethyl 2-benzylmalonate 
• 616-75-1 2-benzylmalonic acid 
• 116111-79-6 (R)-3-(acetylthio)-2-benzylpropanoic acid 
• 507-09-5 tiolacetic acid 

Downstream Products

• 116112-38-0 Sodium; 2-(2-acetylsulfanylmethyl-3-phenyl-propionylamino)-benzenesulfonate 
• 111510-74-8 N-<3-(acetylthio)-2-benzylpropanoyl>-S-ethyl-L-cysteine 
• 116111-88-7 N-<3-(acetylthio)-2-benzylpropionyl>taurine sodium salt 
• 116111-78-5 Sodium; 2-[(2-acetylsulfanylmethyl-3-phenyl-propionyl)-methyl-amino]-ethanesulfonate 
• 116112-33-5 Sodium; 3-(2-acetylsulfanylmethyl-3-phenyl-propionylamino)-propane-1-sulfonate 
• 116111-90-1 Sodium; (2-acetylsulfanylmethyl-3-phenyl-propionylamino)-methanesulfonate 
• 116112-39-1 Sodium; 4-(2-acetylsulfanylmethyl-3-phenyl-propionylamino)-naphthalene-1-sulfonate 
• 116112-34-6 Sodium; [4-(2-acetylsulfanylmethyl-3-phenyl-propionylamino)-phenyl]-methanesulfonate 
• 116112-32-4 Sodium; 2-[(2-acetylsulfanylmethyl-3-phenyl-propionyl)-cyclopropyl-amino]-ethanesulfonate 
• 116112-37-9 Sodium; 3-(2-acetylsulfanylmethyl-3-phenyl-propionylamino)-benzenesulfonate 
• 116112-36-8 Sodium; 4-(2-acetylsulfanylmethyl-3-phenyl-propionylamino)-benzenesulfonate 
• 115370-30-4 (R)-2-((R)-2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-3-(4-methyl-benzylsulfanyl)-propionic acid 
• 115370-31-5 (R)-2-((S)-2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-3-(4-methyl-benzylsulfanyl)-propionic acid 
• 126349-29-9 (S)-2-(2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-4-phenylcarbamoyl-butyric acid tert-butyl ester 

Relevant academic research and scientific papers

Method for preparing racecadotril through one-pot process

The invention belongs to the technical field of drug synthesis, and particularly relates to a method for preparing racecadotril through a one-pot process. The method comprises the followings steps: firstly, adding 2-benzyl-3-ethanethioyl crylic acid, orga

Challenges in the Development of a Thiol-Based Broad-Spectrum Inhibitor for Metallo-β-Lactamases

Pathogens, expressing metallo-β-lactamases (MBLs), become resistant against most β-lactam antibiotics. Besides the dragging search for new antibiotics, development of MBL inhibitors would be an alternative weapon against resistant bacterial pathogens. Inhibition of resistance enzymes could restore the antibacterial activity of β-lactams. Various approaches to MBL inhibitors are described; among others, the promising motif of a zinc coordinating thiol moiety is very popular. Nevertheless, since the first report of a thiol-based MBL inhibitor (thiomandelic acid) in 2001, no steps in development of thiol based MBL inhibitors were reported that go beyond clinical isolate testing. In this study, we report on the synthesis and biochemical characterization of thiol-based MBL inhibitors and highlight the challenges behind the development of thiol-based compounds, which exhibit good in vitro activity toward a broad spectrum of MBLs, selectivity against human off-targets, and reasonable activity against clinical isolates.

Structural studies of racecadotril and its process impurities by NMR and mass spectroscopy

Three unknown impurities in racecadotril bulk drug at levels below 0.5% were detected by simple reverse phase isocratic high performance liquid chromatography (HPLC). Structures for these impurities were proposed by molecular ion information and their fragmentation pattern obtained by LC-MS and these impurities were confirmed by NMR spectroscopy. The impurities I, II and III were characterized as benzyl 2-methyl carboximido acetate, benzyl 2-phenyl ethyl carboximido acetate, and benzyl 2-(1-benzyl vinyl carboximido) acetate. These structures were further confirmed by co-injecting of synthetic standards of impurities with racecadotril. The mechanism of the formation of these process related impurities is discussed.

PROCESS FOR THE ASYMMETRIC SYNTHESIS OF S-ACYL DERIVATIVES OF 2-MERCAPTOMETHYL -3- PHENYL PROPANOIC ACID, APPLICATION TO THE SYNTHESIS OF N-(MERCAPTOACYL) AMINO ACID DERIVATIVES

Process for the asymmetric synthesis of S-acyl derivatives of 2-mercaptomethyl-3-phenylpropanoic acid of formula (I): characterized in that it comprises the steps consisting in:a) preparing the diol (VI) by reduction of a malonic ester (V) in the presence of a hydride; b) preparing the monoacetates (VII R) or (VII S) respectively; c) subjecting these monoacetates to an oxidation in order to form the acids (IX S) or (IX R);d) saponifying the compounds (IX S) or (IX R) in order to form the hydroxy acids (X S) or (X R);e) thioacylating the hydroxy acids (X S) or (X R) with a mercapto acid R. sub.1 SH (XI), according to a Mitsunobu-type reaction, in order to lead to the desired acids (I R) (I S) respectively and application to the synthesis of N-(mercaptoacyl)amino acid derivatives (II). STR1

New orally active enkephalinase inhibitors: Their synthesis, biological activity, and analgesic properties

A series of (4s)-4-[(2S)-benzyl-3-mercaptopropionylamino]-4-(N- phenylcarbamoyl)-butyric acids has been identified as potent systemically active enkephalinase inhibitors. Structure-activity relationships (SAR) are discussed. Further chemical modification of the inhibitors was carried out in order to identify the inhibitors which are orally active in an animal model. Compounds of particular interest are the prodrug-like analogues, including 5b (ONO-9902). Their analgesic effects after oral administration were evaluated.

Mercaptoacyl amino acid inhibitors of atriopeptidase. 1. Structure- activity relationship studies of methionine and S-alkylcysteine derivatives

A broad series of N-(3-mercaptoacyl) amino acid derivatives was evaluated for their ability to inhibit atriopeptidase (neutral endopeptidase, EC 3.4.24.11) in vitro and in vivo. Structural parameters studied were (i) the substituent on the 2-position of the 3-mercaptopropionyl moiety, (ii) the amino acid component, (iii) the S-terminal derivative, and (iv) the C- terminal derivative. Optimum activity was observed for derivatives of methionine and S-alkylcysteines. N-[3-Mercapto-2(S)-[(2- methylphenyl)methyl]-1-oxopropyl]-L-methionine was identified as a highly effective inhibitor of atriopeptidase meriting evaluation as a potential cardiovascular therapeutic agent.

A novel class of enkephalinase inhibitors containing a C-terminal sulfo group

A new series of sulfonic acids were synthesized and tested for their enkephalinase inhibitory activity. Among them, the most potent was N-(2- benzyl-3-mercaptopropionyl)metanilic acid 10i with an IC50 value of 0.27 nM. Several other analogues (10a,b,j,n,o,gg,hh) showed the inhibitory activity comparable to or greater than thiorphan (IC50 = 2.6 nM), a C- terminal carboxyl-containing inhibitor of enkephalinase. Thus compounds containing a C-terminal sulfo group, instead of the C-terminal carboxyl group, were found to show a remarkably high level of inhibition of enkephalinase. The analgesic activity of 10b, (S)-10b, and (R)-10b was also evaluated by the phenylbenzoquinone writhing test.

Method of relieving pain with mercaptoalkanamides

Novel ω-mercaptopropanamides and their homologs of the formula STR1 wherein R1 is selected from the group consisting of hydrogen and STR2 R1 ' is selected from the group consisting of alkyl of 1 to 5 carbon atoms and aryl optionally

Mercapto-acylamino acids as antihypertensives

Novel mercapto-acylamino acids useful as analgesic, as well as in the treatment of hypertension and congestive heart failure and combinations of mercapto acylamino acids and atrial natriuretic factors or angiotensin converting enzyme inhibitors useful for

COMPOUNDS FOR ALLEVIATING ANGIOTENSIN RELATED HYPERTENSION

Compounds for alleviating or reducing angiotensin related hypertension in hypertensive mammals comprising angiotensin converting enzyme inhibitors selected from a group of mercaptoacyl aminoacids.