222404-24-2

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-(4-HYDROXY-PHENYL)-THIAZOLIDINE-4-CARBOXYLIC ACID is used as a therapeutic agent for the treatment of diabetes and metabolic disorders, due to its insulin-sensitizing and anti-inflammatory properties. It modulates the body's response to insulin, potentially improving glucose tolerance and managing blood sugar levels.
Used in Neuroprotective Applications:
In the field of neuroscience, (R)-2-(4-HYDROXY-PHENYL)-THIAZOLIDINE-4-CARBOXYLIC ACID is used as a neuroprotective agent, potentially safeguarding neurons from damage and degeneration. Its antioxidant properties may contribute to the prevention of oxidative stress-related neurodegenerative diseases.
Used in Antioxidant Formulations:
(R)-2-(4-HYDROXY-PHENYL)-THIAZOLIDINE-4-CARBOXYLIC ACID is utilized as an antioxidant in various formulations, particularly in the health and wellness industry. Its ability to neutralize free radicals may help in preventing cellular damage and promoting overall health.

Upstream product

• 52-89-1 l-cysteine hydrochloride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 52-90-4 L-Cysteine 

Downstream Products

• 637032-06-5 (4R)-3-(tert-butoxycarbonyl)-2-(4-hydroxyphenyl)thiazolidine-4-carboxylic acid 
• 1609535-72-9 dimethyl (3R)-3-(4-acethoxyphenyl)-5-methyl-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylate 
• 1609535-73-0 (3R)-6,7-bis(hydroxymethyl)-3-(4-hydroxyphenyl)-5-methyl-1H,3H-pyrrolo[1,2-c]thiazole 

Relevant academic research and scientific papers

Discovery of cysteine and its derivatives as novel antiviral and antifungal agents

Based on the structure of the natural product cysteine, a series of thiazolidine-4-carboxylic acids were designed and synthesized. All target compounds bearing thiazolidine-4-carboxylic acid were characterized by1 H-NMR,13 C-NMR, and

Purple acid phosphatase inhibitors as leads for osteoporosis chemotherapeutics

Purple acid phosphatases (PAPs) are metalloenzymes that catalyse the hydrolysis of phosphate esters under acidic conditions. Their active site contains a Fe(III)Fe(II) metal centre in mammals and a Fe(III)Zn(II) or Fe(III)Mn(II) metal centre in plants. In humans, elevated PAP levels in serum strongly correlate with the progression of osteoporosis and metabolic bone malignancies, which make PAP a target suitable for the development of chemotherapeutics to combat bone ailments. Due to difficulties in obtaining the human enzyme, the corresponding enzymes from red kidney bean and pig have been used previously to develop specific PAP inhibitors. Here, existing lead compounds were further elaborated to create a series of inhibitors with Ki values as low as ～30 μM. The inhibition constants of these compounds were of comparable magnitude for pig and red kidney bean PAPs, indicating that relevant binding interactions are conserved. The crystal structure of red kidney bean PAP in complex with the most potent inhibitor in this series, compound 4f, was solved to 2.40 ? resolution. This inhibitor coordinates directly to the binuclear metal centre in the active site as expected based on its competitive mode of inhibition. Docking simulations predict that this compound binds to human PAP in a similar mode. This study presents the first example of a PAP structure in complex with an inhibitor that is of relevance to the development of anti-osteoporotic chemotherapeutics.

Thiazolidine chemistry revisited: A fast, efficient and stable click-type reaction at physiological pH

We describe the fast reaction kinetics between 1,2-aminothiols and aldehydes. Under physiological conditions such a click-type reaction afforded a thiazolidine product that remains stable and did not require any catalyst. This type of bioorthogonal reacti

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

3-Propionyl-thiazolidine-4-carboxylic acid ethyl esters: A family of antiproliferative thiazolidines

Cancer results from unregulated cell growth. Reactivating the process of the programmed cell death, i.e. apoptosis, is a classical anticancer therapeutic strategy. The apoptosis-inducing property of the (2RS,4R)-2-phenyl-3-propionyl-thiazolidine-4-carboxylic acid ethyl ester (ALC 67) molecule has recently been discovered. We analyzed in this study the impact of the phenyl moiety of this molecule on its biological activity by synthesizing and evaluating analogues where this substituent was replaced by a series of aromatic and aliphatic groups. The results demonstrated that the molecule's antiproliferative property resisted such modifications. Thus, in addition to developing a family of thiazolidine compounds with promising anticancer properties; our investigation revealed that the second position of the thiazolidine ring can be used either to tune the physicochemical properties of ALC67 or to introduce a fluorescent tag to the structure in order to track it in cells and determine its exact molecular mechanism of action.

Targeting triple-negative breast cancer cells with 6,7-bis(hydroxymethyl)- 1H,3H-pyrrolo[1,2-c]thiazoles

Further studies on 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles as anticancer agents against breast cancer are reported, allowing to demonstrate the potential of these compounds for the therapy of the triple-negative breast cancer, the most challe

NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR

Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

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, structure and structure-activity relationship analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives as potential antibacterial agents

Nine 2-arylthiazolidine-4-carboxylic acid derivatives and nine 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives were synthesized to screen for their antibacterial activities. Compounds 5, 14-18 were first reported. Their chemical str

SAR studies of 2-arylthiazolidine-4-carboxylic acid amides: A novel class of cytotoxic agents for prostate cancer

In our continuing efforts to develop novel chemotherapeutic agents for prostate cancer, recently we reported the discovery of 2-arylthiazolidine-4- carboxylic acid amides (ATCAAs) as a new class of cytotoxic agents. Several of them were very effective in