26349-75-7

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
METHYL N-(THIOXOMETHYLENE)-L-ALANINATE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds due to its structural similarity to L-alanine and its potential reactivity in organic synthesis. Its unique functional groups can be exploited to create novel drug molecules with specific therapeutic properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, METHYL N-(THIOXOMETHYLENE)-L-ALANINATE is used as a building block for the design and synthesis of new bioactive molecules. Its thioxomethylene group can be a key structural element in the development of compounds with improved pharmacological profiles.
Used in Chemical Biology:
METHYL N-(THIOXOMETHYLENE)-L-ALANINATE is also used in chemical biology for the study of protein synthesis and the exploration of new biochemical pathways. Its interaction with enzymes and other biomolecules can provide insights into the mechanisms of various biological processes and lead to the discovery of new therapeutic targets.

InChI:InChI=1/C5H7NO2S/c1-4(6-3-9)5(7)8-2/h4H,1-2H3/t4-/m0/s1

Upstream product

• 463-71-8 thiophosgene 
• 13515-97-4 methyl 2-aminopropanoate monohydrochloride 
• 75-15-0 carbon disulfide 
• 10065-72-2 L-Alanine methyl ester 
• 2491-20-5 L-alanine methyl ester hydrochloride 

Downstream Products

• 1309465-28-8 (4S,5R)-methyl 1-(diphenylphosphinoyl)-5-(2-furyl)-4,5-dimethyl-2-thioxoimidazolidine-4-carboxylate 
• 1309465-21-1 (4S,5S)-methyl 1-(diphenylphosphinoyl)-5-(2-furyl)-4,5-dimethyl-2-thioxoimidazolidine-4-carboxylate 
• 1309465-08-4 (4S,5S)-methyl 5-(4-bromophenyl)-1-(diphenylphosphinoyl)-4,5-dimethyl-2-thioxoimidazolidine-4-carboxylate 
• 1309465-09-5 (4S,5R)-methyl 5-(4-bromophenyl)-1-(diphenylphosphinoyl)-4,5-dimethyl-2-thioxoimidazolidine-4-carboxylate 
• 1309465-23-3 (4S,5S)-methyl 1-(diphenylphosphinoyl)-5-(4-fluorophenyl)-4,5-dimethyl-2-thioxoimidazolidine-4-carboxylate 
• 1309465-12-0 (4S,5R)-methyl 1-(diphenylphosphinoyl)-5-(4-fluorophenyl)-4,5-dimethyl-2-thioxoimidazolidine-4-carboxylate 
• 1309465-16-4 (4S,5R)-methyl 1-(diphenylphosphinoyl)-4,5-dimethyl-5-(4-methoxyphenyl)-2-thioxoimidazolidine-4-carboxylate 
• 1309465-25-5 (4S,5S)-methyl 5-(benzo[d][1,3]dioxol-5-yl)-1-(diphenylphosphinoyl)-4,5-dimethyl-2-thioxoimidazolidine-4-carboxylate 
• 1309465-18-6 (4S,5R)-methyl 5-(benzo[d][1,3]dioxol-5-yl)-1-(diphenylphosphinoyl)-4,5-dimethyl-2-thioxoimidazolidine-4-carboxylate 
• 1309465-20-0 (4S,5R)-methyl 1-(diphenylphosphinoyl)-4,5-dimethyl-5-(3-thienyl)-2-thioxoimidazolidine-4-carboxylate 

Relevant academic research and scientific papers

Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent

Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3 N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO? ) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L-and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.

Co-Catalyzed Transannulation of Pyridotriazoles with Isothiocyanates and Xanthate Esters

An efficient radical transannulation reaction of pyridotriazoles with isothiocyanates and xanthate esters was developed. This method features conversion of pyridotriazoles into two N-fused heterocyclic aromatic systems-imino-thiazolopyridines and oxo-thia

T3P - A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates

A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41-94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P (propane phosphonic acid anhydride) as a new and efficient desulfurating agent.

Chiral recognition of carboxylates by a static library of thiourea receptors with amino acid arms

Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and α-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.

A facile one-pot synthesis of selenoureidopeptides employing lialhseh through staudinger aza-wittig-type reaction

A one-pot protocol for the synthesis of selenoureidopeptides employing lithium aluminum hydride hydroselenide (LiAlHSeH) as a selenating agent via a Staudinger aza-Wittig-type reaction is reported. The protocol involves the use of Nα-protected aminoalkyl azides and isothicyanato esters to afford the desired products in good yields. This protocol is a direct approach to the synthesis of selenourea compounds that avoids the synthesis of isoselenocyanates and does not require multistep synthesis.

Chiral isothiocyanates-An approach to determination of the absolute configuration using circular dichroism measurement

Chiral alkyl 2-isothiocyanates have been obtained from enantiopure, aliphatic amines. ECD measurements allowed us to correlate an absolute configuration at C-2 with a sign of the Cotton effect (CE) observed for n-π- transition at the longer-wavelength range of the spectrum. Chirooptical data calculated for all enantiomers were consistent with the measured CE values and indicated that the weak absorption band at 240 nm could give an important information concerning the stereochemistry of simple, chiral isothiocyanates. Optically active esters of 2-isothiocyanatocarboxylic acids, prepared from α-amino acids, showed two absorption bands located over 195 nm. The more intensive band near 200 nm and the weak absorption located at 250 nm were related to n-π- transitions in NCS group. TD DFT calculations carried out for methyl esters of 2-isothiocyanatocarboxylic acids showed the correlation between signs of CE determined for both absorption bands, and the absolute configuration on C-2.

A facile synthesis of N-Z/Boc-protected 1,3,4-oxadiazole-based peptidomimetics employing peptidyl thiosemicarbazides

Synthesis of 1,3,4-oxadiazole containing peptidomimetics is described by a p-TsCl/pyridine-mediated cyclization of the corresponding dipeptidyl thiosemicarbazides, which are readily prepared by coupling N-protected amino acid hydrazides with amino acid-derived isothiocyanato esters. Further, the protocol has also been extended for the synthesis of orthogonally protected 1,3,4-oxadiazole tethered mimetics as well. The synthetic route is simple and mild conditions are used so that the chirality of the starting amino acids is retained.

SYNTHESIS OF CHIRAL THIOCARBAMOYLPHOSPHINES DERIVED FROM AMINO ACIDS

The methylester hydrochlorides of the (S)-amino acids L-alanine (1a), L-phenylalanine (1b), L-valine (1c) and L-lysine (1d) were converted to the corresponding isothiocyanates 2a-d by thiophosgenation. 2a-d React with secondary phosphines and phosphine oxides to give the thiocarbamoylphosphines 3a-d and P-oxides 4a, b.