19714-15-9

Basic information

• Product Name: 1H-Indole, 3-(1H-imidazol-1-ylmethyl)-
• Synonyms: 3-Imidazol-1-ylmethyl-1H-indole;3-(1H-imidazol-1-ylmethyl)indole;3-(1H-1-imidazolylmethyl)-1H-indole;3-(1-imidazolylmethyl)-indole;3-(1H-imidazol-1-ylmethyl)-1H-indole;3-(imidazol-1-ylmethyl)-indole
• CAS NO: 19714-15-9
• Molecular Formula: C12H11N3
• Molecular Weight: 197.23600
• Mol File: 19714-15-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 3-(1H-imidazol-1-ylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 3-(1H-imidazol-1-ylmethyl)-(19714-15-9)
• EPA Substance Registry System: 1H-Indole, 3-(1H-imidazol-1-ylmethyl)-(19714-15-9)

Safety Data

• Hazardous Substances Data: 19714-15-9(Hazardous Substances Data)

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 58550-78-0 N-benzenesulfonyl-3-(bromomethyl)indole 
• 58550-84-8 N-(phenylsulphonyl)-3-methylindole 
• 83-34-1 3-Methylindole 
• 700-06-1 indole-3-carbinol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 143703-41-7 1-benzenesulfonyl-3-(1H-imidazol-1-ylmethyl)indole 

Relevant articles and documents

The reaction of carbonyldiimidazole with alcohols to form carbamates and N-alkylimidazoles

The reactions of non-benzylic primary and secondary aliphatic alcohols with carbonyldiimidazole (CDI) afford the corresponding carbamates but not N-alkylimidazoles. For benzylic primary alcohols, formation of N-alkylimidazoles proceeds reasonably at 170 °C in several different solvents and occurs by way of the initially formed carbamate. However, under these rather forcing conditions, or even at lower reaction temperatures, elimination is a significant side reaction for benzylic secondary alcohols with β-hydrogen atoms. With one exception, reactions of six N,N-disubstituted β-aminoalcohols with CDI to form N-alkylimidazoles proceed under relatively mild conditions and may occur by way of an aziridinium intermediate.

Comparison of the in-vitro aromatase inhibitory activity of 3-(azolylmethyl)-1H-indoles

The synthesis of 3-(imidazol-1-ylmethyl)-N-R-alkyl-1H-indoles [R = H (1), ethyl (2), benzyl (3)], N-benzyl-3-(triazol-1-ylmethyl)-1H-indole (4) and N-benzyl-3-(triazol-4-yl-methyl)1H-indole (5) is described. The compounds were tested for human placental aromatase inhibition in-vitro, using [1β-3H]androstenedione and [1β,2β-3H]testosterone as substrates for the aromatase enzyme. Inhibition of androgen aromatization by compounds 1-5 was effective in both enzyme systems. The most interesting compounds were 3 (imidazole derivative) and 4 (triazole derivative) showing comparable percent inhibition values with both androgen substrates. The absence of a substituent (1) or the presence of an ethyl group (2) gave weak inhibitors in imidazole-substituted indoles. Triazole derivatives 4 and 5, with an N-benzyl group, were less potent aromatase inhibitors than compound 3, the imidazole analogue. The 4-triazole derivative 5 was the least active inhibitor in the series. The simultaneous introduction of benzyl and imidazole (rather than triazole) moieties was found to enhance the inhibitory profile of these 3-azolylmethylindole derivatives.