6843-49-8

Basic information

• Product Name: 5-METHYL-5-PHENYLHYDANTOIN
• Synonyms: 2,4-Imidazolidinedione, 5-methyl-5-phenyl-;5-Methyl-5-phenyl-2,4-imidazolidinedione;5-methyl-5-phenyl-4-imidazolidinedione;5-methyl-5-phenyl-hydantoi;cb1664;5-METHYL-5-PHENYLHYDANTOIN;5-methyl-5-phenylimidazolidine-2,4-dione;Hydantoin, 5-methyl-5-phenyl.
• CAS NO: 6843-49-8
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.2
• EINECS: 229-928-6
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines
• Mol File: 6843-49-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: 199-201 °C(lit.)
• Boiling Point: 325.7°C (rough estimate)
• Flash Point: 9℃
• Appearance: White/Crystalline Powder
• Density: 1.2167 (rough estimate)
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 8.60±0.10(Predicted)
• CAS DataBase Reference: 5-METHYL-5-PHENYLHYDANTOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-5-PHENYLHYDANTOIN(6843-49-8)
• EPA Substance Registry System: 5-METHYL-5-PHENYLHYDANTOIN(6843-49-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 24/25-26
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• RTECS: MU2625500
• Hazardous Substances Data: 6843-49-8(Hazardous Substances Data)

Usage

Description

5-METHYL-5-PHENYLHYDANTOIN is a chemical compound that serves as an important reactant in the synthesis of various pharmaceutical agents and inhibitors.

Uses

Used in Pharmaceutical Industry:
5-METHYL-5-PHENYLHYDANTOIN is used as a reactant for the synthesis of beta-amino alcohols, which are inhibitors of the anti-tubercular target N-acetyltransferase. This makes it a valuable component in the development of treatments for tuberculosis.
Used in Synthesis of Chlorohydantoins:
5-METHYL-5-PHENYLHYDANTOIN is also utilized in the synthesis of chlorohydantoins, which are compounds with potential applications in the pharmaceutical industry.
Used in Development of Specific MMP Inhibitors:
Furthermore, 5-METHYL-5-PHENYLHYDANTOIN is employed in the development of specific inhibitors for matrix metalloproteinases (MMPs). These inhibitors have potential therapeutic applications in treating various diseases, including cancer and inflammatory conditions, by regulating the activity of MMPs.

InChI:InChI=1/C10H16N2O2/c1-10(7-5-3-2-4-6-7)8(13)11-9(14)12-10/h7H,2-6H2,1H3,(H2,11,12,13,14)/t10-/m0/s1

Upstream product

• 506-87-6 ammonium carbonate 
• 98-86-2 acetophenone 
• 773837-37-9 sodium cyanide 
• 71-43-2 benzene 
• 124-38-9 carbon dioxide 
• 4355-46-8 α-amino-α-methylphenylacetonitrile 
• 74-90-8 hydrogen cyanide 
• 1066-33-7 ammonium bicarbonate 

Downstream Products

• 726-88-5 5-Methyl-5-phenyl-3-hydantoinyl acetic acid 
• 23187-03-3 5-methyl-5-phenyl-imidazolidine-2,4-dithione 
• 6326-77-8 5-cyclohexyl-5-methylhydantoin 
• 6844-34-4 3,5-dimethyl-5-phenylimidazolidine-2,4-dione 
• 565-07-1 2-amino-2-phenylpropanoic acid 
• 733-98-2 (4-methyl-2,5-dioxo-4-phenyl-imidazolidin-1-yl)-acetic acid ethyl ester 
• 13398-26-0 (S)-2-methyl-2-phenylglycine 
• 27539-12-4 (S)-5-methyl-5-phenyl-2,4-imidazolidinedione 
• 1224939-47-2 3-(3-chloropropyl)-5-methyl-5-phenylimidazolidine-2,4-dione 
• 1061470-81-2 C₁₄H₁₈N₂O₂ 
• 1608154-32-0 C₁₆H₂₁BrN₂O₂ 
• 1608154-38-6 3,5-dimethyl-5-phenyl-1-(5-(4-phenylpiperazin-1-yl)pentyl)imidazolidine-2,4-dione 
• 1608154-39-7 1-(5-(4-(2-fluorophenyl)piperazin-1-yl)pentyl)-3,5-dimethyl-5-phenylimidazolidine-2,4-dione 
• 1608154-40-0 1-(5-(4-(2-methoxyphenyl)piperazin-1-yl)pentyl)-3,5-dimethyl-5-phenylimidazolidine-2,4-dione 

Relevant articles and documents

Novel serotonin 5-HT2A receptor antagonists derived from 4-phenylcyclohexane-5-spiro-and 5-methyl-5-phenyl-hydantoin, for use as potential antiplatelet agents

Background: Antiplatelet drugs have been used in the treatment of acute coronary syndromes and for the prevention of recurrent events. Unfortunately, many patients remain resistant to the available antiplatelet treatment. Therefore, there is a clinical need to synthesize novel antiplatelet agents, which would be associated with different pathways of platelet aggregation, to develop an alternative or additional treatment for resistant patients. Recent studies have revealed that 5-HT2A receptor antagonists could constitute alternative antiplatelet therapy. Methods: Based on the structures of the conventional 5-HT2A receptor ligands, two series of compounds with 4-phenylcyclohexane-5-spiro- or 5-methyl-5-phenyl-hydantoin core linked to various arylpiperazine moieties were synthesized and their affinity for 5-HT2A receptor was assessed. Further, we evaluated their antagonistic potency at 5-HT2A receptors using isolated rat aorta and cells expressing human 5-HT2A receptors. Finally, we studied their anti-aggregation effect and compared it with ketanserin and sarpogrelate, the reference 5-HT2A receptor antagonists. Moreover, the structure–activity relationships were studied following molecular docking to the 5-HT2A receptor model. Results: Functional bioassays revealed some of the synthesized compounds to be moderate antagonists of 5-HT2A receptors. Among them, 13, 8-phenyl-3-(3-(4-phenylpiperazin-1-yl)propyl)-1,3-diazaspiro[4.5]decane-2,4-dione, inhibited collagen stimulated aggregation (IC50 = 27.3?μM) being more active than sarpogrelate (IC50 = 66.8?μM) and comparable with ketanserin (IC50 = 32.1?μM). Moreover, compounds 2–5, 9–11, 13, 14 inhibited 5-HT amplified, ADP- or collagen-induced aggregation. Conclusions: Our study confirmed that the 5-HT2A antagonists effectively suppress platelet aggregation and remain an interesting option for the development of novel antiplatelet agents with an alternative mechanism of action.

Computer-aided studies for novel arylhydantoin 1,3,5-triazine derivatives as 5-HT6 serotonin receptor ligands with antidepressive-like, anxiolytic and antiobesity action in vivo

This study focuses on the design, synthesis, biological evaluation, and computer-aided structure-activity relationship (SAR) analysis for a novel group of aromatic triazine-methylpiperazines,with an hydantoin spacer between 1,3,5-traizine and the aromatic fragment. New compounds were synthesized and their affinities for serotonin 5-HT6, 5-HT1A, 5-HT2A, 5-HT7, and dopamineD2 receptorswere evaluated. The induced-fit docking (IFD) procedure was performed to explore the 5-HT6 receptor conformation space employing two lead structures. It resulted in a consistent binding mode with the activity data. For the most active compounds found in each modification line, anti-obesity and anti-depressive-like activity in vivo, as well as "druglikeness" in vitro, were examined. Two 2-naphthyl compounds (18 and 26) were identified as themost active 5-HT6R agents within each leadmodification line, respectively. The 5-(2-naphthyl)hydantoin derivative 26, themost active one in the series (5-HT6R: Ki = 87 nM), displayed also significant selectivity towards competitive G-protein coupled receptors (6-197-fold). Docking studies indicated that the hydantoin ring is stabilized by hydrogen bonding, but due to its different orientation, the hydrogen bonds formwith S5.44 and N6.55 or Q6.58 for 18 and 26, respectively. Compound 26 exerted anxiolytic-like and antidepressant-like activities. Importantly, it demonstrated anti-obesity properties in animals fed palatable feed, and did not show toxic effects in vitro.

Supramolecular structure of 5-methyl-5-phenyl hydantoin and hydrogen-bonding patterns in 5,5′-substituted hydantoins

The crystal structure of heterocyclic compound 5-methyl-5-phenyl hydantoin has been determined from X-ray single crystal structural characterization. This material crystallizes in the orthorhombic system and noncentrosymmetric space group P21 (N°4). The crystal packing is governed by N–H···O hydrogen bond-type intermolecular interactions, forming chains and edge-fused 12-membered rings with graph-set C(4) C(5) C22(8) R33(12) in a similar hydrogen-bonding pattern of another chiral 5,5′-substituted hydantoins.