110326-14-2

Basic information

• Product Name: 1-ETHYL-1H-INDOLE-3-METHANOL
• Synonyms: 1-ETHYL-1H-INDOLE-3-METHANOL;1H-INDOLE-3-METHANOL, 1-ETHYL-
• CAS NO: 110326-14-2
• Molecular Formula: C11H13NO
• Molecular Weight: 175.23
• Mol File: 110326-14-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-ETHYL-1H-INDOLE-3-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYL-1H-INDOLE-3-METHANOL(110326-14-2)
• EPA Substance Registry System: 1-ETHYL-1H-INDOLE-3-METHANOL(110326-14-2)

Safety Data

• Hazardous Substances Data: 110326-14-2(Hazardous Substances Data)

Upstream product

• 58494-59-0 N-ethyl-3-formylindole 
• 487-89-8 Indole-3-carboxaldehyde 
• 10604-59-8 N-Ethylindole 

Relevant articles and documents

Efficient Synthesis and Biological Activity of Novel Indole Derivatives as VEGFR-2 Tyrosine Kinase Inhibitors

A series of novel indole derivatives were synthesized as potent inhibitors for the vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase. Among those, compound 10b demonstrated the highest growth inhibition rate of 66.7% against the VEGFR-2 tyrosine kinase at 10 μM which indicates that indole-benzothiazole might be the favorable structure. The binding mode of compound 10b with VEGFR-2 tyrosine kinase was evaluated by molecular docking.

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.

Synthesis and in vitro evaluation of 3-(1-Azolylmethyl)-1H-indoles and 3-(1-azoly1-1-phenylmethyl)-1H-indoles as inhibitors of P450 arom

In the challenge to develop potent inhibitors of aromatase for reducing the levels of estrogens, we found that azolyl-substituted indoles inhibit aromatase activity. 3-(1-Azolylmethyl)-1H-indoles 9-15 and 3-(1-azolyl-1- phenylmethyl)-1H-indoles 22-25 were prepared, and tested on their ability to inhibit P450 arom. Analysis of the inhibitory effect exerted by several derivatives (11, 12, 22, and 23) on microsomal aromatase in vitro activity indicates that azolyl-substituted indoles containing an imidazole moiety are more potent inhibitors than triazole derivatives. In the first series, the introduction of the N-benzyl moiety has been found to enhance the inhibitory profile of these 3-(1-azolylmethyl)-1H-indole derivatives. The corresponding 4-fluoro derivative 12 displays the highest inhibitory activity (IC50 = 0.0718 μM) of all investigated compounds; thus, 12 is 258 times as potent as aminoglutethimide (AG). The presence of a chloro grouping in para position of the phenyl ring in compounds 22 and 24 exerts a positive effect only in the triazol-1-yl sub-series: compound 25 is 4-fold more potent than 24.