3747-47-5

Usage

Type of compound

Derivative of urea

Medical use

Antineoplastic and antiviral agent

Mechanism of action

Inhibits DNA synthesis in cancer cells, causing them to stop growing and dividing

Treatment of blood disorders

Sickle cell anemia and polycythemia vera

Industrial use

Production of certain chemical compounds

Hazardous nature

Considered a hazardous substance

Safety precautions

Should be handled with care to avoid toxic effects if not used properly

InChI:InChI=1/C9H12N2O2/c12-7-6-10-9(13)11-8-4-2-1-3-5-8/h1-5,12H,6-7H2,(H2,10,11,13)

Upstream product

• 102-12-5 N-2-hydroxyethyl-N'-phenylthiourea 
• 103-71-9 phenyl isocyanate 
• 141-43-5 ethanolamine 
• 3422-02-4 N-(benzyloxycarbonyl)aniline 
• 60-29-7 diethyl ether 
• 4930-03-4 phenyl N-phenylcarbamate 
• 65-85-0 benzoic acid 
• 495-18-1 Benzohydroxamic acid 
• 62-53-3 aniline 
• 98-88-4 benzoyl chloride 

Downstream Products

• 27151-01-5 4,5-dihydro-N-phenyl-2-oxazolamine 
• 1848-69-7 1-phenylimidazolidin-2-one 
• 1240326-67-3 C₁₅H₁₈N₂O₆ 

Relevant academic research and scientific papers

ANTIMICROBIAL CATIONIC POLYAMINES

Antimicrobial, non-hemolytic cationic polyamines were prepared by treating partially N-acylated polyethylenimines and/or partially oxidized polyethylenimines with a protic acid. The cationic polyamines can have a linear or branched polyethylenimine backbone structure. Preferably, the cationic polyamines comprise pendant urea groups, which can be introduced via a cyclic carbonate comprising a pendant urea group. The cationic polyamines can be active against a tuberculosis mycobacterium at low concentration. The cationic polyamines are also effective against Gram-negative Escherichia coli and Pseudomonas aeruginosa, Gram-positive Staphylococcus aureus, and fungus Candida albicans in solution and in the form of a film.

Ethyl 2-cyano-2-(4-nitrophenylsulfonyloxyimino)acetate-mediated lossen rearrangement: Single-pot racemization-free synthesis of hydroxamic acids and ureas from carboxylic acids

Ethyl 2-cyano-2-(4-nitrophenylsulfonyloxyimino)acetate (4-NBsOXY) mediated Lossen rearrangement and its application for the synthesis of ureas is demonstrated. Required hydroxamic acids for the Lossen rearrangements were synthesized from carboxylic acids using the same reagent. Finally, reaction of an amine with the produced isocyanate resulted in urea. Good yields without racemization were achieved under milder and simpler reaction conditions. Reactions are compatible with common N-protecting groups, such as Boc, Fmoc, Cbz, and benzyl, as well as various OH protecting groups, such as tBu and Bzl. Conversion from carboxylic acid to urea is achieved in one pot. Most importantly, byproducts Oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate] and 4-nitrobenzenesulfonic acid can be recovered easily and can be recycled to prepare the reagent. Thus, the method is environmentally friendly and cost-effective.

Synthesis and evaluation in vitro of 1-[2-(10-dihydroartemisininoxy) ethyl]-3-phenylurea derivatives as potential agents against cancer

In order to develop potent and selective anticancer agents, a series of novel artemisinin derivatives bearing urea moiety 1a-n were facilely synthesized herein and screened for their activities in vitro against ten human tumor cell lines (HeLa, MCF-7, U937, K562, HL60, HCT116, HepG2, A549, A375-S2, and HT1080). The pharmacological results indicated that some compounds showed excellent activity against cancer cell lines and good selectivity, especially the compound 1c which proved to be the most active against the cancer cells as well as distinctive patterns of selectivity.

ANTIMICROBIAL HYDROGELS, METHODS OF PREPARATION THEREOF, AND ARTICLES THEREFROM

A covalently crosslinked hydrogel comprises a) three or more divalent poly(alkylene oxide) chains P′ covalently linked at respective first end units to a branched first core group C′, b) three or more divalent poly(alkylene oxide) chains P″ covalently linked at respective first end units to a branched second core group C″, the chains P″ comprising respective second end units which are covalently linked to between 0% and 100% of respective second end units of chains P′ by divalent linking groups L″, and c) at least one pendant cationic block copolymer chain A′-B′. A′-B′ comprises i) a divalent block A′ comprising a poly(alkylene oxide) backbone chain having an end unit covalently linked to a second end unit of one of the chains P′ by a divalent linking group L′, and ii) a monovalent block B′ comprising a first repeat unit, the first repeat unit comprising a backbone carbonate group and a cationic side chain group.

Synthesis of 1-Hydroxyalkyl-3-Substituted Ureas and Thioureas, Substrates for Alcohol Dehydrogenase

A series of 1-(2-hydroxyethyl)- and 1-(3-hydroxyethyl)-3-substituted ureas and thioureas were synthesized. 1-(3-Hydroxyethyl)-3-acylthioureas were shown to be specific substrates for alcohol dehydrogenase in vitro.

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.

The Aminolysis of Carbamates. I. The Kinetics of the Aminolysis of Benzyl N-phenylcarbamate with Ethanolamine

Die Kinetik der Aminolyse des Benzyl-N-phenylurethans im Bereich von 135 bis 165 deg C in Gegenwart eines Ueberschusses an Monoethanolamin mit und ohne Loesungsmittel (Benzylalkohol) konnte als Folgereaktion erster Ordnung erfasst werden: Die Abhaenigkeit der Geschwindigkeitskonstante k1 von der Monoethanolaminkonzentration weist auf eine Reaktion 2.Ordnung hin, und es wurde eine lineare Abhaenigkeit der relativen Reaktivitaet R = k1/k2 von der Konzentration festgestellt.Der Einfluss der Temperatur auf R und die Aktivierungsenergie der beiden Reaktionsschritte wurde ermittelt.Die Analyse der Reaktanten und Zwischenprodukte erfolgte mit Hilfe der Hochdruckfluessigkeitschromatographie.Moegliche Mechanismen werden besprochen.