628319-03-9

Basic information

• Product Name: 2H-Imidazole-2-thione, 4-(cyclohexylmethyl)-1,3-dihydro-5-(1-methylethyl)-
• CAS NO: 628319-03-9
• Molecular Formula: C13H22N2S
• Molecular Weight: 238.397
• Mol File: 628319-03-9.mol

Chemical Properties

• CAS DataBase Reference: 2H-Imidazole-2-thione, 4-(cyclohexylmethyl)-1,3-dihydro-5-(1-methylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Imidazole-2-thione, 4-(cyclohexylmethyl)-1,3-dihydro-5-(1-methylethyl)-(628319-03-9)
• EPA Substance Registry System: 2H-Imidazole-2-thione, 4-(cyclohexylmethyl)-1,3-dihydro-5-(1-methylethyl)-(628319-03-9)

Safety Data

• Hazardous Substances Data: 628319-03-9(Hazardous Substances Data)

Upstream product

• 27527-05-5 L-cyclohexylalanine 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 628319-07-3 4-cyclohexylmethyl-5-isopropyl-2-methylsulfanyl-1H-imidazole 
• 668475-80-7 5-cyclohexylmethyl-4-isopropyl-1H-imidazole 
• 859537-28-3 2-(5-cyclohexylmethyl-4-isopropyl-1H-imidazol-2-ylsulfanyl)-acetamide 
• 668475-87-4 5-cyclohexylmethyl-4-isopropylimidazole-1-sulfonic acid dimethylamide 
• 668475-90-9 5-cyclohexylmethyl-2-hydroxymethyl-4-isopropylimidazole-1-sulfonic acid dimethylamide 

Relevant articles and documents

Synthesis of 2-methylsulfanyl-1H-imidazoles as novel non-nucleoside reverse transcriptase inhibitors (NNRTIs)

α-Aminoketone hydrochlorides 2a-d were synthesized by Dakin-West reaction from L-phenylalanine and L-cyclohexylalanine followed by hydrolysis in acidic medium. Treatment of 2 a-d with aqueous potassium thiocyanate afforded 1,3-imidazole-2-thiones 3 a-d which were alkylated with methyl iodide to give 2-methylsulfanyl-1 H-imidazoles 4 a-d with 4-benzyl/4-cyclohexylmethyl and 5-ethyl/5-isopropyl substituents. Coupling of 4 a-d with ethoxymethyl chloride or benzyloxymethyl chloride furnished N-1 5 a-d and N-3 6 a-h alkylated products. The synthesised compounds were tested for their activity against HIV-1. The most active compounds have a cyclohexylmethyl group in the 5-position of 6 and showed an activity against HIV-1 comparable to the activity of Nevirapine.