29635-81-2

Basic information

• Product Name: (S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one
• Synonyms: (S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one;(5S)-2-Thioxo-3-phenyl-5-isopropylimidazolidine-4-one;(5S)-2-Thioxo-3-phenyl-5α-isopropylimidazolidine-4-one;(5S)-5-Isopropyl-3-phenyl-2-thioxo-4-imidazolidinone
• CAS NO: 29635-81-2
• Molecular Formula: C₁₂H₁₄N₂OS
• Molecular Weight: 234.31736
• EINECS: 249-736-6
• Mol File: 29635-81-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 322.5°Cat760mmHg
• Flash Point: 148.8°C
• Appearance: /
• Density: 1.24g/cm³
• Refractive Index: 1.553
• CAS DataBase Reference: (S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one(29635-81-2)
• EPA Substance Registry System: (S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one(29635-81-2)

Safety Data

• Hazardous Substances Data: 29635-81-2(Hazardous Substances Data)

Usage

Description

(S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one is a chemical compound belonging to the thioxoimidazolidinone class, characterized by its unique molecular formula C13H16N2OS. (S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one features a chiral center at the 5th carbon, existing solely in its (S) enantiomeric form. Its structure has garnered interest due to its potential pharmacological properties, which include antibacterial, antifungal, and antitumor activities. The distinctive attributes of this compound render it a promising candidate for further exploration and development within the pharmaceutical sector.

Uses

Used in Pharmaceutical Industry:
(S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one is used as a potential therapeutic agent for its demonstrated antibacterial, antifungal, and antitumor properties. (S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one's unique structure and chiral center contribute to its potential effectiveness in targeting various medical conditions, making it a valuable asset for pharmaceutical research and development.
Used in Antimicrobial Applications:
In the field of antimicrobials, (S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one is utilized as an active ingredient to combat bacterial and fungal infections. Its specific mode of action and targeted approach to eliminating pathogens make it a promising candidate for the development of new antimicrobial drugs.
Used in Anticancer Applications:
(S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one is also used as an anticancer agent, where it may exhibit inhibitory effects on tumor growth and progression. Its potential to modulate various oncological signaling pathways could lead to the development of novel cancer treatments, particularly for solid malignancies.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic outcomes of (S)-5-(1-methylethyl)-3-phenyl-2-thioxoimidazolidin-4-one, it is employed in the development of innovative drug delivery systems. These systems, which may include organic and metallic nanoparticles as carriers, aim to improve the compound's delivery to target sites, ultimately enhancing its efficacy in treating various diseases.

InChI:InChI=1/C12H14N2O2/c1-8(2)10-11(15)14(12(16)13-10)9-6-4-3-5-7-9/h3-8,10H,1-2H3,(H,13,16)

Upstream product

• 68858-20-8 Fmoc-Val-OH 
• 103-72-0 phenyl isothiocyanate 
• 1219279-20-5 BF₄^(1-)*C₂₄H₃₀N₅OS⁽¹⁺⁾ 
• 49645-33-2 phenyl thioisocyanate 
• 72-18-4 L-valine 

Downstream Products

• 126530-30-1 (S)-3,N-Dimethyl-2-(3-phenyl-thioureido)-butyramide 
• 1350820-11-9 (S)-N-acetyl-4-isopropyl-1-phenylimidazolidin-2-thione 
• 1350820-12-0 (2R,3R)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methyl-3-phenylpropan-1-one 
• 1350820-13-1 (2R,3R)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methyl-3-p-tolylpropan-1-one 
• 1350820-14-2 (2R,3R)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-3-(4-methoxyphenyl)-2-methylpropan-1-one 
• 1350820-15-3 (2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one 
• 1350820-17-5 (2R,3S)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpentan-1-one 
• 1350820-18-6 (2R,3S)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2,4-dimethylpentan-1-one 
• 1350820-19-7 (2R,3S,E)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methyl-5-phenylpent-4-en-1-one 
• 1350820-20-0 (R)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-3-phenylpropan-1-one 
• 1350820-21-1 (R)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-3-p-tolylpropan-1-one 
• 1350820-22-2 (R)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-3-(4-methoxyphenyl)propan-1-one 
• 1350820-23-3 (R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]propan-1-one 
• 1350820-24-4 (R)-3-(4-bromophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]propan-1-one 

Relevant articles and documents

Simple and Efficient Synthesis of 5-Substituted-3-phenyl-2-thioxoimidazolidin-4-one Derivatives from S -Amino Acids and Phenylisothiocyanate in et 3N/DMF-H 2O

A concise approach for the transformation of various S-amino acids into the 5-alkyl-3-phenyl-2-thioxoimidazolidin-4-one heterocycles using phenylisothiocyanate is described. Phenylthiohydantoins of amino acid were synthesized at room temperature in Et3N/DMF-H2O with easy workup and excellent yields.

Modulation of the pharmacological activities of secretory phospholipase A2 from Crotalus durissus cascavella induced by naringin

In this work we have characterized the action of the naringin, a flavonoid found in grapefruit and known for its various pharmacological effects, which include antioxidant, blood lipid lowering and anticancer activity, on the structure and biochemical activities of a secretory phospholipase A (sPLA2) from Crotalus durissus cascavella, an important protein involved in the releasinge of arachidonic acid in phospholipid membranes. sPLA2 was incubated with naringin (mol:mol) at 37 °C and a discrete reduction in the UV scanning signal and a modification of the circular dichroism spectra were observed after treatment with naringin, suggesting modifications of the secondary structure of the protein. This flavonoid was able to decrease enzymatic activity and some pharmacological effects, such as myonecrosis, platelet aggregation, and neurotoxic activity caused by sPLA2, however, the inflammatory effect was not affected by naringin. In addition, small angle X-ray scattering (SAXS) data were collected for sPLA2 and naringin-treated sPLA2 to evaluate possible modifications of the protein structure. These structural investigations have shown that sPLA2 is an elongated dimer in solution and after treatment with naringin a conformational change in the dimeric configuration was observed. Our results suggest that structural modification may be correlated with the loss of enzymatic activity and alterations in pharmacological properties.

Traceless approach for the synthesis of 3,5-disubstituted thiohydantoins on functionalized ionic-liquid support

A traceless approach for the synthesis of 3,5-disubstituted thiohydantoins on a novel functionalized ionic-liquid support, 5, is described. Acylation of benzylamine functionalized ionic-liquid support with amino acids yielded ionic-liquid-supported amino acids, which reacted with isothiocyanates to afford ionic-liquid-supported thioureas. Following intramolecular cyclization cleavage from the ionic-liquid support by trifluoroacetic acid (TFA), the desired 3,5-disubstituted thiohydantoins were obtained in good yields and purities. The efficiency of this ionic-liquid-phase strategy facilitated isolation and analysis of intermediates and removal of excess reagents and by-products during the reaction process.