125471-00-3

Basic information

• Product Name: N-BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID
• Synonyms: BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID;N-BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID;(R)-3-Boc-thiazolidine-2-carboxylic acid, 97%;(R)-3-(tert-Butoxycarbonyl)thiazolidine-2-carboxylic acid
• CAS NO: 125471-00-3
• Molecular Formula: C9H15NO4S
• Molecular Weight: 233.28
• Mol File: 125471-00-3.mol

Chemical Properties

• Melting Point: 90-93℃
• Boiling Point: 385.3±42.0 °C(Predicted)
• Appearance: /
• Density: 1.305±0.06 g/cm3(Predicted)
• PKA: 3.05±0.20(Predicted)
• CAS DataBase Reference: N-BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID(125471-00-3)
• EPA Substance Registry System: N-BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID(125471-00-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 125471-00-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
N-BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID serves as a fundamental building block in the synthesis of various pharmaceuticals and agrochemicals. Its presence in these industries is crucial for the development of new drugs and chemical products that can address a range of health and agricultural needs.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of asymmetric synthesis, N-BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID is utilized as a chiral auxiliary. This role is pivotal for assisting in the creation of enantiomerically pure compounds, which are essential for the production of high-quality pharmaceuticals with specific desired effects.
Used in Drug Development for Anti-Inflammatory and Antidiabetic Properties:
N-BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID has demonstrated anti-inflammatory and antidiabetic properties, making it a valuable asset in drug development. These characteristics are particularly important for the creation of medications aimed at treating inflammation and diabetes, respectively, thereby contributing to improved patient care and treatment options.
Overall, N-BOC-(R)-THIAZOLIDINE-2-CARBOXYLIC ACID is a multifaceted chemical with applications that span across different sectors, highlighting its importance in both the synthesis of new compounds and the advancement of medical treatments.

Upstream product

• 16310-13-7 DL-3-thiazolidine-4-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1419390-25-2 C₄₁H₅₀N₂O₁₀S₂ 

Relevant articles and documents

[2 + 2] Cycloaddition reactions of imines with cyclic ketenes: Synthesis of 1,3-thiazolidine derived spiro-β-lactams and their transformations

Unsymmetric cyclic ketenes were generated from N-acyl-1,3-thiazolidine-2- carboxylic acids 1a-c by means of Mukaiyama's reagent, and then reacted with imines 2a-c to the new, isomeric spiro-β-lactams 3 and 4 via [2 + 2] cycloaddition (Staudinger ketene-imine reaction; Scheme 1). The reactions were stereoselective (Table 1) and mainly afforded the spiro-β-lactams with a relative trans configuration. The spiro-β-lactams could be transformed into the corresponding monocyclic β-lactams by means of thiazolidine ring opening or into substituted thiazolidines via hydrolysis of the β-lactam ring.

BIOCONJUGATION OF POLYPEPTIDES

Certain embodiments of the present invention relate to methods of forming and manipulating bioconjugates. Particularly, but not exclusively certain embodiments relate to methods of reversible carbon-carbon bond bioconjugation using aldol based chemical reactions at physiological conditions.

Palladium-unleashed proteins: Gentle aldehyde decaging for site-selective protein modification

Protein bioconjugation frequently makes use of aldehydes as reactive handles, with methods for their installation being highly valued. Here a new, powerful strategy to unmask a reactive protein aldehyde is presented. A genetically encoded caged glyoxyl aldehyde, situated in solvent-accessible locations, can be rapidly decaged through treatment with just one equivalent of allylpalladium(ii) chloride dimer at physiological pH. The protein aldehyde can undergo subsequent oxime ligation for site-selective protein modification. Quick yet mild conditions, orthogonality and powerful exposed reactivity make this strategy of great potential in protein modification.

HETEROCYCLE CARBOXAMIDE DERIVATIVES HAVING ADAMANTYL GROUP, PROCESS FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to a heterocyclic carboxamide derivative having an adamantyl group represented by chemical formula 1 which inhibits the activity of 11andbeta;-hydroxysteroid dehydrogenase type 1 (11andbeta;-HSD1), a prodrug of the same, a solvate of the same, a stereoisomer or a pharmaceutically acceptable salt of the same, a preparation method of the same, and a pharmaceutical composition comprising the same as an active ingredient. In the chemical formula 1, W, X, R_1, R_2, L, a, and b are as defined in the specification of the present invention.COPYRIGHT KIPO 2017

Thiazolidine-Masked α-Oxo Aldehyde Functionality for Peptide and Protein Modification

α-Oxo aldehyde-based bioconjugation chemistry has been widely explored in peptide and protein modifications for various applications in biomedical research during the past decades. The generation of α-oxo aldehyde via sodium periodate oxidation is usually limited to the N-terminus of a target protein. Internal-site functionalization of proteins with the α-oxo aldehyde handle has not been achieved yet. Herein we report a novel method for site-specific peptide and protein modification using synthetically or genetically incorporated thiazolidine-protected α-oxo aldehyde. Efficient unmasking of the aldehyde was achieved by silver ion-mediated hydrolysis of thiazolidine under mild conditions for the first time. A model peptide and a recombinant protein were used to demonstrate the utility of this new method, which were site-specifically modified by oxime ligation with an oxyamine-functionalized peptide labeling reagent. Therefore, our current method has enriched the α-oxo aldehyde synthetic tool box in peptide and protein bioconjugation chemistry and holds great potential to be explored in novel applications in the future.

Synthesis and 11β hydroxysteroid dehydrogenase 1 inhibition of thiazolidine derivatives with an adamantyl group

A new series of thiazolidine derivatives with an adamantyl group was synthesized and evaluated for their ability to inhibit 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1). Our initial compound 5a showed a weak inhibitory activity. Significant improvements in potency were achieved by substituent modification. The potent compound 8g (E) showed good in vitro inhibitory activity toward human 11β-HSD1, selectivity toward 11β-HSD2, metabolic stability, pharmacokinetic, and safety profile. Furthermore, this compound significantly inhibited 11β-HSD1 activity in rat and monkey models, and showed improved glycemic control in KKAy mice.

N-HYDROXYAMIDE DERIVATIVES POSSESSING ANTIBACTERIAL ACTIVITY

Described herein are N-hydroxyamlde antibacterial compounds, methods for making the compounds, pharmaceutical compositions containing the compounds and methods of treating bacterial infections utilizing the compounds and pharmaceutical compositions compound of Formula (I): or a salt, solvate ti hydrate thereof, wherein A is (a) eachindicates a point of attachment.

Design and synthesis of non-hydroxamate histone deacetylase inhibitors: Identification of a selective histone acetylating agent

A series of suberoylanilide hydroxamic acid (SAHA)-based non-hydroxamates was designed, synthesized, and evaluated for their histone deacetylase (HDAC) inhibitory activity. Among these, methyl sulfoxide 15 inhibited HDACs in enzyme assays and caused hyperacetylation of histone H4 while not inducing the accumulation of acetylated α-tubulin in HCT116 cells.

Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them

The invention relates to new derivatives of 2-(iminomethyl)amino-phenyl which are NO synthase inhibitors and can trap reactive oxygen species. These compounds can notably be used for the treatment of stroke, of neurodegenerative diseases and of ischemic or hemorragic cardiac or cerebral infarctions. These compounds include: N-{4-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-{3-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-(4-{[{[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}(methyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-(3-{[(3,5-di-tert-butyl-4-hydroxybenzyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-[3-({[3-(4-hydroxy-3,5-diisopropylphenyl)propyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-(3-{[(4-hydroxy-3,5-diisopropylbenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(4-hydroxy-3,5-diisopropylphenyl)ethyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-2-(3,5-di-tert-butyl-4-hydroxybenzoyl)-N-1-(4-{[imino(thien-2-yl)methyl]amino}phenyl)-L-leucinamide; and pharmaceutically acceptable salts thereof.

New derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them

The invention relates to new derivatives of 2-(iminomethyl)amino-phenyl which are NO synthase inhibitors and can trap reactive oxygen species. These compounds can notably be used for the treatment of stroke, of neurodegenerative diseases and of ischemic or hemorragic cardiac or cerebral infarctions. These compounds include: N-{4-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-{3-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-(4-{[{[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}(methyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-(3-{[(3,5-di-tert-butyl-4-hydroxybenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-[3-({[3-(4-hydroxy-3,5-diisopropylphenyl)propyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-(3-{[(4-hydroxy-3,5-diisopropylbenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(4-hydroxy-3,5-diisopropylphenyl)ethyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-2-(3,5-di-tert-butyl-4-hydroxybenzoyl)-N-1-(4-{[imino(thien-2-yl)methyl]amino}phenyl)-L-leucinamide; and pharmaceutically acceptable salts thereof.