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Usage

Uses

Used in Pharmaceutical Industry:
2-(2-Methoxyphenyl)-thiazolidine-4-carboxylic acid is used as a reactant in the preparation of N-(mercaptoacyl)thiazolidinecarboxylic acids. These compounds exhibit antihypertensive activity, making them valuable for the development of medications aimed at treating high blood pressure. The synthesis of these bioactive molecules leverages the unique structural features of 2-(2-methoxyphenyl)-thiazolidine-4-carboxylic acid, highlighting its utility in medicinal chemistry.

Upstream product

• 52-90-4 L-Cysteine 
• 135-02-4 ortho-anisaldehyde 
• 52-89-1 l-cysteine hydrochloride 

Relevant academic research and scientific papers

X-ray crystal structures and anti-breast cancer property of 3-tert -butoxycarbonyl-2-arylthiazolidine-4-carboxylic acids

Diastereomeric '2RS,4R'-2-arylthiazolidine-4-carboxylic acids (ATCAs) were synthesized and their resolution to chiraly pure N-BOC derivatives was attempted by column chromatography. The absolute stereochemistry of the resolved compounds was ascertained by X-ray single crystal structures. Further application of the synthesized compounds was studied for their in vitro anti-breast cancer activity against MCF7 cell line using DOX as a standard by MTT assay method. Cell morphology analysis was carried out by fluorescence microscopy. The compounds containing '2S' absolute configuration in thiazolidine ring and presence of 2-NO2, 2,6-Cl groups on '2R'-aryl substituent showed significant anti-breast cancer activity where some of the compounds were found to be more active than DOX in terms of induced apoptosis mode of MCF7 cell death.

New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives

Aromatic aldehydes reacted readily with (R)-cysteine in boiling acidified methanol to give diastereomeric mixtures of the corresponding 2-(aryl substituted) thiazolidine-4-carboxylic acids. 4-Nitrobenzaldehyde under similar conditions afforded one isomer of 2-(4-nitrophenyl)-thiazolidine-4-carboxylic acid, which epimerized in the NMR solvents into a diastereomeric mixture. 2-Nitrobenzaldehyde reacted with (R)-cysteine to afford 3,5-bis-(2-nitrophenyl)-tetrahydro-1H-thiazolo[3,4-c]oxazol-1-one as the sole product, which collapsed in the NMR solvent into a diastereomeric mixture of the thiazolidine-4-carboxylic acids. The thiazolidine derivatives reacted smoothly with phenyl isothiocyanate to give single isomers of the corresponding thiohydantoins.

The cysteine releasing pattern of some antioxidant thiazolidine-4-carboxylic acids

Oxidative stress that corresponds to a significant increase in free radical concentration in cells can cause considerable damage to crucial biological macromolecules if not prevented by cellular defense mechanisms. The low-molecular-weight thiol glutathio

Crystal structure, computational studies, and stereoselectivity in the synthesis of 2-aryl-thiazolidine-4-carboxylic acids via in situ imine intermediate

ABSTRACT: This article presents the synthesis of (2R/2S,4R)-2-aryl-thiazolidine-4-carboxylic acids via nucleophilic addition of L-Cysteine on aromatic aldehydes involving a yield and time-effective room temperature reaction in an aqueous DMSO medium in the presence of NaHCO3 as a base. The synthesized diastereomers were spectroscopically characterized and quantified for diastereomeric excess by liquid chromatography-mass spectrometry analysis. The impact of the type and position of substituent in aromatic aldehydes on reaction time, % yield, 1H NMR shift at newly formed chiral center [C(2)-H], and diastereomeric excess (de%) have been investigated. A plausible mechanism for stereoselectivity via an in situ imine intermediate is proposed using real-time IR monitoring of the synthetic reaction based on the significant signals at 1597, 1593 cm?1 for imine (C=N) stretching. The imine mechanism for stereoselectivity was further supported by NMR studies of azomethine 13C NMR signals at 159, 160 δ ppm and by the single crystal structure of hitherto unknown (2S,4R)-3-(tert-butoxycarbonyl)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid (3a) obtained as a major diastereomer in the synthesis of the butyloxy carbonyl (BOC) derivative of (2R/2S,4R)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid. The significant ortho-OH effect of phenolic hydroxyl group leading to strong hydrogen bondings plays a vital role in the formation of 2S,4R BOC derivative stereoselectively. The frontier molecular orbitals, possible electronic excitations, IR band characterizations, and reactivity parameters of newly reported compound (3a) have been predicted using quantum chemical descriptors from density functional theory. The theoretical exploration of experimental spectra using time-dependent DFT indicated a (π–π*) transition between HOMO and LUMO in the ultraviolet region. (Figure presented.)

Synthesis, characterization and antibacterial activities of N-tert-butoxycarbonyl-thiazolidine carboxylic acid

A possible mechanism of dynamic kinetic resolution by the formation of N-tert-butoxycarbonyl-thiazolidine carboxylic acid was proposed and validated by a quantitative density functional theoretical calculation according to Curtin-Hammett principle. Such a

Synthesis, in vitro structure-activity relationship, and in vivo studies of 2-arylthiazolidine-4-carboxylic acid amides as anticancer agents

A series of (2RS,4R)-2-arylthiazolidine-4-carboxylic acid amide (ATCAA) was synthesized. Antiproliferative activity against melanoma and prostate cancer cells compared with control cells (fibroblast and RH7777, respectively) was evaluated. Compound 3id sh

AMIDO ANTI-VIRAL COMPOUNDS

Disclosed are compounds, stereoisomers, tautomers, pharmaceutically acceptable salts, or prodrugs thereof of having Formula (I), their preparation, use, and compositions thereof for treating an infection mediated at least in part by a virus in the Flaviviridae family of viruses, wherein A, R3, X, V, W, T, Z, R, Y1, and p are as defined herein.

Synthesis and Chiroptical Properties of N-Acetyl-2-aryl-4-thiazolidinecarboxylic Acids

(4R)-2-Aryl-4-thiazolidinecarboxylic acids 3, derived from aromatic aldehydes 1 and L-cysteine (2), could be diastereoselectively converted into (2R,4R)- or (2S,4R)-N-acetyl-2-aryl-4-thiazolidinecarboxylic acids (4 and 5, resp.).The diastereomers can be d