69739-20-4

Basic information

• Product Name: 2-PHENYLTHIAZOLIDINE-4-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 2-PHENYLTHIAZOLIDINE-4-CARBOXYLIC ACID METHYL ESTER
• CAS NO: 69739-20-4
• Molecular Formula: C11H13NO2S
• Molecular Weight: 223.29
• Mol File: 69739-20-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 358.3°C at 760 mmHg
• Flash Point: 170.5°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 2.58E-05mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: 2-PHENYLTHIAZOLIDINE-4-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLTHIAZOLIDINE-4-CARBOXYLIC ACID METHYL ESTER(69739-20-4)
• EPA Substance Registry System: 2-PHENYLTHIAZOLIDINE-4-CARBOXYLIC ACID METHYL ESTER(69739-20-4)

Safety Data

• Hazardous Substances Data: 69739-20-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13NO2S/c1-14-11(13)9-7-15-10(12-9)8-5-3-2-4-6-8/h2-6,9-10,12H,7H2,1H3/t9-,10?/m1/s1

Upstream product

• 100-52-7 benzaldehyde 
• 5714-80-7 D-cysteine methyl ester hydrochloride 
• 5714-80-7 cysteine methyl ester hydrochloride 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 196930-46-8 (4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 

Downstream Products

• 7113-10-2 2-phenyl-1,3-thiazole-4-carboxylic acid 
• 195135-11-6 (R)-3-acetyl-4-methoxycarbonyl-2-phenylthiazolidine 
• 164986-94-1 (2R,4R)-4-(hydroxymethyl)-2-phenylthiazolidine 
• 131570-64-4 (3S,4aR,8aR,9R,9aS)-9-Methyl-8-oxo-3-phenyl-hexahydro-thiazolo[3,4-a]indole-9a-carboxylic acid methyl ester 

Relevant articles and documents

Chemoselectivity and stereoselectivity of cyclisation pathways leading to bicyclic tetramates controlled by ring-chain tautomerisation in thiazolidines

Chemoselective Dieckmann cyclisation reactions on N-malonyl thiazolidine templates derived from cysteine and pivaldehyde or aromatic aldehydes may be used to access bicyclic tetramates, for which different pathways operate as a result of differing ring-chain tautomeric behaviour of the respective intermediate imines.

Intramolecular Aldol Ring Closures of Cysteine Derivatives Leading to Densely Functionalised Pyroglutamates

The synthesis of densely functionalised pyroglutamates derived from cysteine by an aldol cyclisation strategy has been achieved.

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.