RU 58841

Base Information

• Chemical Name: RU 58841
• CAS No.: 154992-24-2
• Molecular Formula: C17H18F3N3O3
• Molecular Weight: 369.343
• Hs Code.: 2933990090
• UNII: 0D8FJQ0ADW
• DSSTox Substance ID: DTXSID20165781
• Nikkaji Number: J584.909H
• Wikipedia: RU-58841
• Wikidata: Q16943512
• Pharos Ligand ID: TJAM52Y9FSBG
• ChEMBL ID: CHEMBL9337
• Mol file: 154992-24-2.mol

Synonyms:4-(4,4-Dimethyl-2,5-dioxo-3-(4-hydroxybutyl)1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile;4-[3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-trifluoromethylbenzonitrile;RU 58841;

Chemical Property of RU 58841

Chemical Property:

• Vapor Pressure: 1.47E-10mmHg at 25°C
• Refractive Index: 1.559
• Boiling Point: 493.588 °C at 760 mmHg
• PKA: 15.09±0.10(Predicted)
• Flash Point: 252.313 °C
• PSA: 84.64000
• Density: 1.397 g/cm³
• LogP: 2.89968
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 369.13002593
• Heavy Atom Count: 26
• Complexity: 611

Purity/Quality:

98%,99%, ^*data from raw suppliers

RU58841 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=O)N(C(=O)N1CCCCO)C2=CC(=C(C=C2)C#N)C(F)(F)F)C
• Description: RU-58841 is a non-steroidal antiandrogen that binds to the androgen receptor (Kd = 1.8, 1.1, 5.6, 1.3, and 1.4 nM for human, rat, mouse, hamster prostate, and hamster flank organ receptors, respectively). In vivo, topical administration of RU-58841 (1-100 μg per animal) reduces size of the flank organ withoutaffecting sex organs in a dose-dependent manner in hamsters. It has no effect on sex organ weight in intact rats when administered percutaneously, subcutaneously, or orally at doses up to 1 mg per animal. RU-58841 (5% v/v) also induces hair regrowth in the bald frontal scalps of postpubertal stumptailed macaques, a model for male pattern baldness. RU-58841 is a non-steroidal antiandrogen that binds to the androgen receptor (Kd = 1.8, 1.1, 5.6, 1.3, and 1.4 nM for human, rat, mouse, hamster prostate, and hamster flank organ receptors, respectively). In vivo, topical administration of RU-58841 (1-100 μg per animal) reduces size of the flank organ without affecting sex organs in a dose-dependent manner in hamsters. It has no effect on sex organ weight in intact rats when administered percutaneously, subcutaneously, or orally at doses up to 1 mg per animal. RU-58841 (5% v/v) also induces hair regrowth in the bald frontal scalps of postpubertal stumptailed macaques, a model for male pattern baldness.
• Uses: RU58841 (Roussel Uclaf) is a nonsteroidal topical antiandrogen without significant systemic effects apparently due to its metabolism in the skin. This appears to be a promising new hair growth agent that promotes hair growth on the scalp as well as retards hair growth of both beard and body hair follicles. RU58841 has produced highly efficacious results in stumptailed macaques. The synergistic effects of RU58841 and minoxidil topical solution (2% and 5%) have also been reported in stumptailed macaques. The effect of combined treatment was most remarkable early on, but by 1 year no significant benefit of combined treatment was apparent relative to either treatment alone. Avoid hair loss: RU58841 is a non-steroidal antiandrogenic medication that was initially developed in the 1980s as a topical treatment remedy for acne and male pattern baldness – androgenetic alopecia. RU 58841, is a specific androgen receptor antagonist or anti-androgen, that has shown to have effect on hair growth.

Technology Process of RU 58841

There total 8 articles about RU 58841 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

4-Bromobutyl acetate (4753-59-7) + 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile (143782-20-1) → 4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile (154992-24-2)

Guidance literature:

4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; for 0.25h;

4-Bromobutyl acetate; In N,N-dimethyl-formamide; mineral oil; at 50 ℃; for 2h;

DOI:10.1039/c4ra00332b

Reference yield:

toluene ethanol + 4-Bromobutyl acetate (4753-59-7) + 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile (143782-20-1) → 4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile (154992-24-2)

Guidance literature:

In N-methyl-acetamide; methanol; ethanol; dichloromethane; water;

Reference yield:

4-amino-2-trifluoromethylbenzonitrile (654-70-6) → 4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile (154992-24-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate / 1,2-dichloro-ethane / 14 h / 20 °C

2.1: sodium nitrite / N,N-dimethyl-formamide / 14 h / 20 °C

3.1: iron; hydrogenchloride / isopropyl alcohol; ethanol; water / 1 h / 90 °C

4.1: potassium carbonate / 1,2-dichloro-ethane / 14 h

5.1: sodium nitrite / N,N-dimethyl-formamide / 14 h / 20 °C

6.1: N,N-dimethyl-formamide / 7 h / 110 °C

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h

7.2: 2 h / 50 °C

With hydrogenchloride; iron; sodium hydride; potassium carbonate; sodium nitrite; In ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol; mineral oil;

DOI:10.1039/c4ra00332b

upstream raw materials:

4-Bromobutyl acetate

4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile

4-amino-2-trifluoromethylbenzonitrile

2-bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methylpropanamide

Downstream raw materials:

4-(4,4-dimethyl-2,5-dioxo-3-(4-iodobutyl)-1-imidazolidinyl)-2-(trifluoromethyl)-benzonitrile

bis-2-propyl carbonate

dicyclohexyl carbonate

Refernces

• 1、 -. "Phenylimidazolidine preparation process". . . Retrieved 2008/06/13.