2215-20-5

Basic information

• Product Name: 5-phenyl-4-thiohydantoic acid
• Synonyms: 5-phenyl-4-thiohydantoic acid;1-phenyl-alpha-thiohydantoic acid;1-phenyl-alpha-thio-hydantoic acid;(3-Phenylthioureido)acetic acid;N-(Phenylthiocarbamoyl)glycine;N-[(Phenylamino)thioxomethyl]glycine;U-7130
• CAS NO: 2215-20-5
• Molecular Formula: C₉H₁₀N₂O₂S
• Molecular Weight: 210.2529
• EINECS: 218-676-2
• Mol File: 2215-20-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 379.7°Cat760mmHg
• Flash Point: 183.5°C
• Appearance: /
• Density: 1.398g/cm³
• Refractive Index: 1.704
• CAS DataBase Reference: 5-phenyl-4-thiohydantoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenyl-4-thiohydantoic acid(2215-20-5)
• EPA Substance Registry System: 5-phenyl-4-thiohydantoic acid(2215-20-5)

Safety Data

• Hazardous Substances Data: 2215-20-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H8N2OS/c12-8-6-11(9(13)10-8)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,12,13)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 56-40-6 glycine 
• 4530-20-5 BOC-glycine 
• 107-07-3 2-chloro-ethanol 

Downstream Products

• 897340-70-4 3,4-dihydroxybenzylidene-3-phenyl-2-thioxoimidazolidin-4-one 
• 874755-87-0 (5Z)-3-methyl-2-methylthio-5-(α-pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-one 
• 145693-89-6 3-phenyl-(5Z)-5-(pyridine-2-ylmethylene)-2-thioxoimidazolin-4-one 
• 1312775-96-4 2-(4-oxo-2-phenyliminothiazolidin-3-yl)acetic acid 
• 1312775-95-3 [5-(naphthalen-2-ylmethylidene)-4-oxo-2-phenyliminothiazolidin-3-yl]acetic acid 
• 1312775-93-1 [4-oxo-5-(4-phenoxyphenylmethylidene)-2-phenyliminothiazolidin-3-yl]acetic acid 
• 17452-09-4 2-mercapto-1-phenylimidazole 
• 7164-98-9 1-phenylimidazole 
• 2010-15-3 3-phenyl-2-thioxoimidazolidin-4-one 

Relevant articles and documents

An investigation on 4-thiazolidinone derivatives as dual inhibitors of aldose reductase and protein tyrosine phosphatase 1B, in the search for potential agents for the treatment of type 2 diabetes mellitus and its complications

Designed multiple ligands (DMLs), developed to modulate simultaneously a number of selected targets involved in etiopathogenetic mechanisms of a multifactorial disease, such as diabetes mellitus (DM), are considered a promising alternative to combinations of drugs, when monotherapy results to be unsatisfactory. In this work, compounds 1–17 were synthesized and in vitro evaluated as DMLs directed to aldose reductase (AR) and protein tyrosine phosphatase 1B (PTP1B), two key enzymes involved in different events which are critical for the onset and progression of type 2 DM and related pathologies. Out of the tested 4-thiazolidinone derivatives, compounds 12 and 16, which exhibited potent AR inhibitory effects along with interesting inhibition of PTP1B, can be assumed as lead compounds to further optimize and balance the dual inhibitory profile. Moreover, several structural portions were identified as features that could be useful to achieve simultaneous inhibition of both human AR and PTP1B through binding to non-catalytic regions of both target enzymes.

Identification of 5-arylidene-4-thiazolidinone derivatives endowed with dual activity as aldose reductase inhibitors and antioxidant agents for the treatment of diabetic complications

In continuing the search for more effective 5-arylidene-4-thiazolidinones as aldose reductase inhibitors, a new set of suitably substituted compounds (4, 5 and 8) was explored. Acetic acids 5, particularly 5a and 5h, proved to be interesting inhibitors of the enzyme as well as excellent antioxidant agents that are potentially able to counteract the oxidative stress associated with both diabetic complications as well as other pathologies. Molecular docking experiments supported SAR studies.

The highly enantioselective Michael addition of ketones to nitrodienes catalyzed by the efficient organocatalyst system of pyrrolidinyl-thioimidazole and chiral thioureido acid

The highly enantioselective Michael addition reaction of ketones to nitrodienes was promoted efficiently by the accessible and fine-tunable organocatalytic system of pyrrolidinyl-thioimidazole and chiral thioureido acid. The corresponding adducts were afforded in good yields with high diastereoselectivities (up to 99:1) and excellent enantioselectivities (up to 99% ee). The Royal Society of Chemistry 2010.