1265908-22-2

Basic information

• Product Name: (4S)-2-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid
• Synonyms: (4S)-2-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid;(4S)-2-(4-hydroxy-3-methoxy-phenyl)thiazolidine-4-carboxylic acid
• CAS NO: 1265908-22-2
• Molecular Formula: C11H13NO4S
• Molecular Weight: 255.29022
• Mol File: 1265908-22-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4S)-2-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-2-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid(1265908-22-2)
• EPA Substance Registry System: (4S)-2-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid(1265908-22-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1265908-22-2(Hazardous Substances Data)

Usage

Description

(4S)-2-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid is a thiazolidine carboxylic acid compound belonging to the thiazolidinedione class of drugs. It has a molecular formula of C11H13NO4S and features a thiazolidine ring structure with a carboxylic acid group and a hydroxy-methoxyphenyl group. These structural elements may contribute to its biological activity, which is currently under investigation for potential therapeutic applications.

Uses

Used in Pharmaceutical Industry:
(4S)-2-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid is used as a potential therapeutic agent for the treatment of type 2 diabetes. Its ability to lower blood sugar levels and improve insulin sensitivity makes it a promising candidate for further research and development in this field.
Used in Research and Development:
In the field of pharmaceutical research and development, (4S)-2-(4-Hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid serves as a valuable compound for studying its pharmacological properties and exploring its potential therapeutic uses beyond type 2 diabetes treatment. This may include investigating its effects on other metabolic disorders or diseases where insulin sensitivity plays a role.

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Relevant articles and documents

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.)

Design, synthesis and biological evaluation of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors

Herein we describe the design, synthesis and biological activities of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors. The target compounds 2a-2j were designed and synthesized from the structural characteristics of N-phenylthiourea, tyrosinase inhibitor and tyrosine, and l-DOPA, the natural substrates of tyrosinase. Among them, (2R/S,4R)-2-(2,4-dimethoxyphenyl)thiazolidine-4-carboxylic acid (2g) caused the greatest inhibition 66.47% at 20 μM of l-DOPA oxidase activity of mushroom tyrosinase. Kinetic analysis of tyrosinase inhibition revealed that 2g is a competitive inhibitor. We predicted the tertiary structure of tyrosinase, and simulated the docking of mushroom tyrosinase with 2g. These results suggest that the binding affinity of 2g with tyrosinase is high. Also, 2g effectively inhibited tyrosinase activity and reduced melanin levels in B16 cells treated with α-MSH. These data strongly suggest that 2g can suppress the production of melanin via the inhibition of tyrosinase activity.

Synthesis and evaluation of novel thiazolidine derivatives as thromboxane A2 receptor antagonists

A series of 3-benzoyl or 3-phenylsulfonyl-2-substituted thiazolidine derivatives were synthesized, and evaluated for their thromboxane A2 (TXA2) receptor-antagonizing effect on (15S)-15-hydroxy-11α,9α- (epoxymethano)prosta-5(Z),13(E)-dienoic acid (U-46619)-induced aggregation of rabbit platelet-rich plasma (PRP). A simple 2-arylthiazolidine derivative, 3- benzoyl-2-(4-hydroxy-3-methoxyphenyl)thiazolidine (5a), showed mild TXA2 receptor antagonist activity. Modification of 5a led to 2-chloro-4-[3-(4- chlorophenylsulfonyl)thiazolidin-2-ylmethyl]phenoxyaretic acid (29d), which showed 10 times more potent TXA2 receptor antagonist activity than 5a.