29181-65-5

Basic information

• Product Name: 1-methyl-2-thioxoimidazolidin-4-one
• CAS NO: 29181-65-5
• Molecular Formula: C₄H₆N₂OS
• Molecular Weight: 130.1682
• Mol File: 29181-65-5.mol

Chemical Properties

• Density: 1.4g/cm³
• Refractive Index: 1.634
• CAS DataBase Reference: 1-methyl-2-thioxoimidazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-2-thioxoimidazolidin-4-one(29181-65-5)
• EPA Substance Registry System: 1-methyl-2-thioxoimidazolidin-4-one(29181-65-5)

Safety Data

• Hazardous Substances Data: 29181-65-5(Hazardous Substances Data)

Usage

Type of compound

cyclic organic compound

Key elements in the structure

sulfur atom, nitrogen atom

Usage

building block in organic synthesis, found in pharmaceuticals and agrochemicals, potential antimicrobial and anticancer properties, stabilizer in polymers, intermediate in the production of rubber chemicals.

Upstream product

• 16696-88-1 acetyl dithiocarbamic acid methyl ester 
• 52605-49-9 sarcosine ethyl ester hydrochloride 
• 57901-77-6 2-benzoylimino-3-methyl-thiazolidin-5-one 
• 87544-36-3 5-benzoyl-3-methyl-4-thio-hydantoic acid ethyl ester 
• 333-20-0 potassium thioacyanate 
• 35404-74-1 3-methyl-4-thiohydantoic acid 
• 107-97-1 sarcosine 
• 1147550-11-5 ammonium thiocyanate 
• 131543-46-9 Glyoxal 
• 598-52-7 1-(methyl)-thiourea 

Downstream Products

• 35404-74-1 3-methyl-4-thiohydantoic acid 
• 620174-59-6 5-(3-bromobenzylidene)-1-methyl-2-thioxoimidazolidin-4-one 
• 620174-57-4 5-(3,4-dichlorobenzylidene)-1-methyl-2-thioxoimidazolidin-4-one 
• 867309-66-8 5-(4-fluoro-benz-(Z)-ylidene)-1-methyl-2-thioxo-imidazolidin-4-one 
• 1190367-77-1 C₂₅H₂₄N₄O₂S 
• 1190367-84-0 C₂₅H₂₇N₅O₃S 
• 1331778-99-4 5-(4-benzyloxy-3-methoxy)benzylidene-1-methyl-2-thiohydantoin 
• 51009-60-0 (E)-5-(benzylidene)-1-methyl-2-thioxoimidazolidin-4-one 
• 1334337-81-3 (5Z)-5-(3,4-dimethoxybenzylidene)-1-methyl-2-thioxoimidazolidin-4-one 
• 1334337-82-4 (5Z)-5-(3,5-dimethoxybenzylidene)-1-methyl-2-thioxoimidazolidin-4-one 
• 154052-53-6 (Z)-5-<<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>methylene>-1-methyl-2-thioxo-4-imidazolidinone 

Relevant articles and documents

Facile synthesis of hydantoins and thiohydantoins in aqueous solution

A series of hydantoins and thiohydantoins have been synthesized in water at room temperature from urea (or N-methylurea, or thiourea) and simple aldehydes (as glyoxal, and its simple derivatives) in the presence of phosphoric anhydride. The reaction time is 10 min using an equimolar amount of P 4O10 with respect to the other reagents, but the reaction occurs also, even if with longer reaction times, with very small amounts of P4O10. In addition, this method provides a clean and 'green' approach to hydantoins, compounds of great interest in biological and pharmacological fields.

Syntheses and NMR Studies of Specifically Labeled Phosphocreatine, Creatinine, and Related 15N-Labeled Compounds

Creatine, creatinine, creatinine, phosphocreatinine, phosphocreatinine, phosphocreatine, and phosphocreatine have been synthesized. 1H and 15N NMR analyses of the labeled creatinines have established that creatinine is protonated at low pH exclusively at the unmethylated ring nitrogen (N-3) and indicate that in the predominant resonance from at low pH, conjugation to the carbonyl is present. 31P and 15N NMR analyses of the labeled phosphocreatinines establish that the site of phosphorylation of phosphocreatinine is on the exocyclic nitrogen.The 31P-15N one-bond coupling constant in phosphocreatine is 18 Hz, not 3 Hz as reported for doubly 15N-labeled phosphocreatine by Brindle et al..Finally, 31P and 15N NMR analyses indicated that no spontaneous 15N/14N-positional isotope exchange occurs in specifically labeled phosphocreatine.The relatively large J31p-15N value and the lack of chemical scrambling are prerequisites for the use of phosphocreatine in positional isotope exchange studies in enzymatic reactions.

Design, synthesis, DFT, molecular modelling studies and biological evaluation of novel 3-substituted (E)-5-(arylidene)-1-methyl-2-thioxoimidazolidin-4-ones with potent cytotoxic activities against breast MCF-7, liver HepG2, and lung A549

We report the synthesis of novel 3-substituted (E)-5-(arylidene)-1-methyl-2-thioxoimidazolidin-4-ones 6-11, and their biological evaluation. Based on structural and pharmacophore analyses of known inhibitors such as fluorouracil (5-FU), we envisioned interesting 2-thioxoimidazolidin-4-one compounds, 3-substituted (E)-5-(arylidene)-1-methyl-2-thioxoimidazolidin-4-ones 6-11 that would be expected to well match the structural features in 5-FU. Efficient synthesis of twenty-four target compounds 6-11 were achieved through the synthetic pathway of 5 → 6 → 7 → 10 → 11, established after consideration of several plausible synthetic pathways. A series of (E)-5-(arylidene)-1-methyl-2-thioxoimidazolidinoneones 5a-d were synthesized via the reaction of 1-methyl-2-thioxoimidazolidin-4-one (3), which in turn was prepared via the reaction of N-methyl glycine (2) with NH4SCN, followed by Knoevenagel condensation. N-alkylation and N-glycosylation were carried via the reaction of 5a-d with alkyl bromides and α-glycopyranosyl bromides 9a,b under alkaline and glycoside conditions, respectively. The N-alkylated and N-glycosylated structures have been selected for the products. Conformational analysis has been studied by homonuclear and heteronuclear two-dimensional NMR methods (DQF-COSY, HMQC, and HMBC). The N site of alkylation and glycosylation were determined from the 1H, 13C heteronuclear multiple-quantum coherence (HMQC) experiments. Molecular modelling and DFT calculations using B3LYP/6-31+G (d, p) level were performed to study the electronic and geometric properties obtained from the stable structure of the investigated compounds. A good correlation between the quantum chemical descriptors and experimental observations was found. The synthesized derivatives exhibited good binding interactions towards the cyclin-dependent kinase 2, especially compound 11b, which have better key interactions than the co-crystallized ligand. Additionally, it had potent cytotoxic activities with IC50 = 4.30, 5.53, 9.43 against MCF-7, HepG2, and A549, respectively.

Quinolinone compound and application thereof

The invention discloses a quinolinone compound containing rhodanine and similar fragments thereof and pharmaceutically acceptable salts thereof, and relates to the technical field of organic chemistry. The quinolinone compound is shown as general formula I in the specification, wherein substituent groups R1, X and R2 have meanings given in the specification. The invention also relates to application of the compound shown as the general formula I and the pharmaceutically acceptable salts thereof in preparing medicines for treating diseases caused by abnormal expression of IDO, in particular toapplication in preparing medicines for treating and/or preventing cancers.

2-GUANIDINO-4-OXO-IMIDAZOLINE DERIVATIVES AS ANTIMALARIAL AGENTS, SYNTHESIS AND METHODS OF USE THEREOF

The present invention relates to new 2-guanidino-4-oxo-imidazoline derivatives (deoxo-IZ), methods of making these compounds, compositions containing the same, and methods of using the same to prevent, treat, or inhibit malaria in a subject.

A practical approach to new (5Z) 2-alkylthio-5-arylmethylene-1-methyl-1,5- dihydro-4H-imidazol-4-one derivatives

A practical protocol for the preparation of (5Z)-2-alkylthio-5- arylmethylene-1-methyl-1,5-dihydro-4H-imidazol-4-one derivatives is reported. The new compounds were obtained in good yield and stereoselectivity in two steps, namely a solvent-free Knoevenag

Synthesis and antimalarial activity of 2-guanidino-4-oxoimidazoline derivatives

A series of 2-guanidino-4-oxoimidazoline (deoxo-IZ) derivatives was prepared and showed potent antimalarial activities in rodent and Rhesus models. Compound 8e, the most potent analogues of this series, is the first non-8-aminoqinoline antimalarial that demonstrated radical curative activity in non-human primate by oral route and showed causal prophylactic activity comparable to that of the commonly used clinical drugs in Rhesus monkeys infected with sporozoites of Plasmodium cynomolgi. The metabolic stability and metabolites profile indicated that the new deoxo-IZ derivatives (8) may act as prodrugs of the corresponding IZ (1 and 2) derivatives.

ARYLMETHYLIDENE HETEROCYCLES AS NOVEL ANALGESICS

The present invention relates to Arylmethylidene heterocycles, compositions comprising an Arylmethylidene heterocycle, and methods useful for treating or preventing pain comprising administering an effective amount of an Arylmethylidene heterocycle as dep

Synthesis and structural study of substituted arylideneimidazolidines and arylidenebenzothiazines

Synthesis and physico-chemical properties of six 5-arylidene-3-benzyl-1- methyl-2-thioxoimidazolidin-4-ones and three 2-arylidene-6-nitro-2H-1,4- benzothiazin-3(4H)-ones have been described. These new compounds were synthetised by Knoevenagel condensation