27151-01-5

Usage

InChI:InChI=1/C9H10N2O/c1-2-4-8(5-3-1)11-9-10-6-7-12-9/h1-5H,6-7H2,(H,10,11)

Upstream product

• 102-12-5 N-2-hydroxyethyl-N'-phenylthiourea 
• 103-72-0 phenyl isothiocyanate 
• 80254-01-9 N-(2-aminoethyl)dibenzoacridinium trifluoromethanesulphonate 
• 3747-47-5 1-(2-hydroxyethyl)-3-phenylurea 
• 7144-13-0 1-(2-chloroethyl)-3-phenylurea 
• 7732-18-5 water 
• 5157-48-2 N-(2-bromoethyl)-N'-phenylurea 
• 13279-22-6 1-(phenylaminocarbonyl)aziridine 
• 103-71-9 phenyl isocyanate 
• 64-17-5 ethanol 

Downstream Products

• 83539-71-3 N-phthaloylglycine-2-phenyliminooxazolidine 
• 83539-69-9 N-benzoyl-2 phenyliminooxazolidine 
• 83539-70-2 N-p-nitrobenzoyl-2-phenyliminooxazolidine 
• 65536-52-9 N-(2-chloroethyl) O-ethyl S-(1-methylpropyl) N-phenylaminocarbonyl phosphoramidothioate 
• 83539-72-4 (3,5-Dinitro-phenyl)-{2-[(E)-phenylimino]-oxazolidin-3-yl}-methanone 

Relevant academic research and scientific papers

Selective alkylation of βII-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents

Aryl chloroethylureas (CEUs) are potent anti-neoplastic agents alkylating specific intracellular proteins such as βII-tubulin. Recently we have identified a new subset of CEU derived from compound 36 that alkylates thioredoxin isoform 1 (Trx-1), inhibits the nuclear translocation of Trx-1, and favors the accumulation of cells in G0/G1 phase. We have evaluated the effects of various substituents and their position on the aromatic ring of a series of derivatives of 36 on (i) the anti-proliferative activity, (ii) the cell cycle progression, (iii) the nuclear translocation of Trx-1, and (iv) their covalent binding to β-tubulin. The same experiments were performed on representative CEU derivatives where the 2-chloroethyl amino moiety is replaced by either an ethyl, a 2-aminooxazolinyl or a 2-chloroacetyl group. On one hand, our results suggest that CEUs substituted on the phenyl ring at position 3 or 4 by cycloalkyl and substituted cycloalkyl or cycloalkoxy groups inhibit the nuclear translocation of Trx-1 and arrest the cell cycle progression in G0/G1. On the other hand, CEUs substituted by a fused aromatic ring, an aliphatic chain, or a fused aliphatic ring are alkylating βII-tubulin but not Trx-1. Beside the expected inactivity of the ethylurea derivatives, none of the modification to the electrophilic moiety led to cross-selectivity of the drugs toward β-tubulin but increased the anti-proliferative activity and resulted in mitigated effects on Trx-1 translocation.

A mild cyclodesulfurization of N-(2-hydroxyethyl)-N′-phenylthioureas to 2-phenylamino-2-oxazolines using TsCl/NaOH

An efficient synthesis of 2-phenylamino-2-oxazolines 3 via cyclodesulfurization of N-(2-hydroxyethyl)-N′-phenylthioureas 2 by a one-pot reaction using p-toluenesulfonyl chloride (TsCl) and NaOH in very good yields is described.

Investigation of the Mitsunobu reaction of N-(2-hydroxyethyl)-N'- phenyl-ureas

The Mitsunobu reaction of N-(2-hydroxyethyl)-ureas 1 using PPh3 and EtO2CN=NCO2Et led to the mixture of N- and O-alkylation products or a single isomer depending on the substrates.

Efficient Cyclodesulfurization of N-(2-Hydroxyethyl)-N′-Arylthioureas to Δ2-Oxazolines Using Superoxide Radical Anion

Δ2-Oxazolines have been synthesized in good yields by the cyclodesulfurization of N-(2-hydroxyethyl)-N′-phenylthioureas with superoxide radical anion (O2-?) at room temperature in anhydrous acetonitrile.

A simple synthesis of Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and 2-substituted benzoxazoles

Carboxylic acids react readily at 0° ← + 24°C with amino alcohols, amino mercaptans and o-aminophenols in the presence of triphenylphosphine- or tributylphosphine dichloride (generated in situ from the reaction of the phosphines with hexacholoroethane or CCl4) and triethylamine in acetonitrile to form the corresponding Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and 2-substituted benzoxazoles in one reaction step in yields of up to 80%.

A SIMPLE SYNTHESIS OF Δ2-OXAZOLINES, Δ2-OXAZINES, Δ2-THIAZOLINES AND Δ2-IMIDAZOLINES

Carboxylic acids react with amino alcohols, amino mercaptans or diamines in the presence of triphenylphosphine, CCl4 and tert. bases to afford in 50-75percent yield the corresponding Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and Δ2-imidazolines.

TRANSFORMATIONS OF PYRIDINIUMS DERIVED FROM AMINO-ALCOHOLS AND FROM DIAMINES

Pyridiniums derived from amino alcohols cyclise to ethers or rearrange to aldehydes on heating.Monopyridiniums from diamines can be acylated or converted into ureas or thioureas: these products cyclise on heating in solution to give dihydro-thiazoles, -4H-thiazines, -oxazoles, -4H-oxazines, or tetrahydro-3H-thiazepines.