141579-87-5

Basic information

• Product Name: 1-{(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl}-1-hydroxyurea
• Synonyms: urea, N-[(1R)-3-[5-(4-fluorophenoxy)-2-furanyl]-1-methyl-2-propyn-1-yl]-N-hydroxy-
• CAS NO: 141579-87-5
• Molecular Formula: C₁₅H₁₃FN₂O₄
• Molecular Weight: 304.2731
• Mol File: 141579-87-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 472.9°C at 760 mmHg
• Flash Point: 239.8°C
• Density: 1.42g/cm³
• Vapor Pressure: 9.5E-10mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: 1-{(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl}-1-hydroxyurea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-{(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl}-1-hydroxyurea(141579-87-5)
• EPA Substance Registry System: 1-{(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl}-1-hydroxyurea(141579-87-5)

Safety Data

• Hazardous Substances Data: 141579-87-5(Hazardous Substances Data)

Usage

Explanation

The molecular formula represents the number of atoms of each element present in a molecule of the compound.
2. Hydroxyurea derivative

Explanation

It is a compound derived from hydroxyurea, which is a well-known drug used in the treatment of certain cancers and sickle cell disease.
3. Contains a furan ring
4. Contains a fluorophenyl group

Explanation

The fluorophenyl group, which is a phenyl group (a six-membered aromatic ring) with a fluorine atom substitution, adds to the compound's unique properties and potential for interaction with biological targets.
5. Contains an ethynyl group

Explanation

The ethynyl group, a two-carbon functional group with a triple bond between the carbons, provides structural diversity and may influence the compound's reactivity and biological activity.

Explanation

The stereochemistry of the compound is important for its biological activity, as the (2R) configuration indicates the specific arrangement of atoms in three-dimensional space.
7. Potential drug candidate

Explanation

Due to its structure and the known properties of hydroxyurea derivatives, this compound may have potential therapeutic applications in the treatment of various diseases, including cancer and sickle cell disease.
8. Biomedical and pharmaceutical research

Explanation

The specific structure and properties of 1-(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl-1-hydroxyurea make it a valuable compound for further research and development in the fields of biomedical and pharmaceutical sciences.

Stereochemistry

(2R) configuration

Upstream product

• 141598-93-8 N,O-bis(phenoxycarbonyl)-N-<4-<5-(4-fluorophenoxy)-2-furyl>-3-butyn-2-yl>hydroxylamine 
• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 33342-17-5 5-(4'-fluorophenyl)furan-2-carbaldehyde 
• 141580-63-4 (5-(4-fluorophenoxy)-2-furyl)acetylene 
• 141580-54-3 2-[5-(4-fluorophenoxy)-furan-2-yl]-1,1-dibromoethene 
• 141580-64-5 4-<5-(4-fluorophenoxy)-2-furyl>-3-butyn-2-ol 
• 141579-67-1 A-78773 
• 169059-39-6 (S)-4-(5-(4-fluorophenoxy)-2-furyl)-3-butyn-2-ol 
• 169059-37-4 4-(5-(4-fluorophenoxy)-2-furyl)-3-butyn-2-one 
• 1026984-69-9 C₂₁H₂₃NO₅Si 
• 149609-87-0 5-(4-fluorophenoxy)-2-furancarboxylic acid 
• 141580-53-2 5-(4-fluorophenoxy)furan-2-carboxaldehyde 
• 371-41-5 4-Fluorophenol 
• 154355-92-7 (R)-(+)-N-hydroxy-N-(3-butyn-2-yl)urea 

Relevant articles and documents

Synthesis of A-79175: A second generation 5-lipoxygenase inhibitor

A convergent, high yielding, and scalable synthesis of A-79175, with a key step involving a mild and efficient Cu-Pd catalyzed coupling reaction of a terminal acetylene with a substituted 2-iodofuran is discussed.

Asymmetric synthesis of (R)-N-3-butyn-2-yl-N-hydroxyurea, a key intermediate for 5-lipoxygenase inhibitors

An efficient asymmetric synthesis of (R)-N-3-butyn-2-yl-N-hydroxyurea from crotyl alcohol is described. The process involves asymmetric Sharpless epoxidation to establish the stereochemistry, formation of (S)-3-butynol and hydroxyl substitution with inversion by the masked N-hydroxyurea reagent N,O-bis(phenoxycarbonyl)hydroxylamine in a Mitsunobu reaction.

(R)-(+)-N-[3-[5-[(4-fluorophenyl)methyl]-2-thienyl]-1-methyl-2-propynyl]- N-hydroxyurea (ABT-761), a second-generation 5-lipoxygenase inhibitor

Structure-activity optimization of inhibitory potency and duration of action of N-hydroxyurea containing 5-lipoxygenase inhibitors was conducted. The lipophilic heteroaryl template and the link group connecting the template to the N-hydroxyurea pharmacophore were modified. Inhibition of 5- lipoxygenase was evaluated in vitro in a human whole blood assay. An in vitro assay using liver microsomes from monkey was used to evaluate congeners for comparative rates of glucuronidation. (3-Heteroaryl-1-methyl-2-propynyl)-N- hydroxyureas were found to be more resistant to in vitro glucuronidation. The promising inhibitor N-[3-[5-(4-fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]- N-hydroxyurea (6) was found to have stereoselective glucuronidation in monkey and man. The R enantiomer 7 provided longer duration of inhibition as evaluated by an ex vivo whole blood assay. Further optimization of the lipophilic template led to the discovery of (R)-(+)-N-[3-[5-[(4- fluorophenyl)methyl]-2-thienyl]-1-methyl-2-propynyl]-N-hydroxyurea (11) with more effective and prolonged inhibition of leukotriene biosynthesis than zileuton (1) and 7 in monkey and man. The optimized 5-lipoxygenase inhibitor 11 was selected for development as an investigational drug for leukotriene- mediated disorders.