60941-76-6

Usage

Uses

Used in Organic Synthesis:
(1-Benzyl-1H-Indol-3-yl)-Methanol is used as a reactant in dearomative indole (3 + 2) cycloaddition reactions. This application is valuable for the synthesis of complex organic molecules and the development of novel chemical entities with potential applications in various fields.
Used in Pharmaceutical Industry:
(1-Benzyl-1H-Indol-3-yl)-Methanol is used as a key intermediate in the synthesis of inhibitors of P450 aromatase. Aromatase inhibitors are important in the treatment of hormone-dependent cancers, such as breast cancer, by reducing estrogen levels. (1-BENZYL-1H-INDOL-3-YL)-METHANOL's ability to be incorporated into these inhibitors highlights its significance in medicinal chemistry and drug development.

Upstream product

• 10511-51-0 1-Benzylindole-3-carboxaldehyde 
• 487-89-8 Indole-3-carboxaldehyde 
• 100-44-7 benzyl chloride 
• 120-72-9 indole 
• 3377-71-7 N-benzylindole 
• 109-97-7 pyrrole 

Downstream Products

• 256391-50-1 N,N'-dibenzyl-3,3'-diindolylmethane 
• 1185056-90-9 C₄₈H₃₉N₃ 
• 1592897-29-4 N-benzyl-3-(t-butyldimethylsilyl)oxymethylindole 
• 118959-33-4 1-benzyl-1H-indole-3-carbonitrile 
• 22051-19-0 N-benzyl-3-(p-methoxybenzyl)indole 

Relevant academic research and scientific papers

Synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives via reductive heteroarylation

An efficient and general reductive heteroarylation approach toward the synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives has been developed. Thus, treatment of acylpyrrole or acylindole derivatives with indoles or pyrroles in the presence of a combination of sodium borohydride and acetic acid resulted in the formation of the title compounds in moderate to excellent isolated yields.

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

The palladium-catalyzed synthesis of indole/benzofurancontaining diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

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.

Synthesis and Docking of Novel 3-Indolylpropyl Derivatives as New Polypharmacological Agents Displaying Affinity for 5-HT1AR/SERT

A series of novel 3-indolylpropyl derivatives was synthesized and evaluated for their binding affinities at the serotonin-1A receptor subtype (5-HT1AR) and the 5-HT transporter (SERT). Compounds 11b and 14b exhibited the highest affinities at the 5-HT1AR (Ki = 43 and 56 nM), whereas compounds 11c and 14a were the most potent analogs at the SERT (Ki = 34 and 17 nM). On the other hand, compounds 14b and 11d showed potent activity at both targets, displaying a profile that makes them promising leads for the search for novel potent ligands with a dual mechanism of action. Molecular docking studies in all the compounds unveiled relevant drug–target interactions, which allowed rationalizing the observed affinities.

Analogues and derivatives of oncrasin-1, a novel inhibitor of the C-terminal domain of RNA polymerase II and their antitumor activities

To optimize the antitumor activity of oncrasin-1, a small molecule RNA polymerase II inhibitor, we evaluated 69 oncrasin-1 analogues for their cytotoxic activity against normal human epithelial cells and K-Ras mutant tumor cells. About 40 of those compoun

3-(Azolylmethyl)-1H-indoles as selective P450 aromatase inhibitors

The synthesis of 1-(halobenzyl) and 1-tosyl-3-(1H-imidazol-1-ylmethyl)-1H-indoles, 1-(halobenzyl) and 1-tosyl-3-(1H-1,2,4-triazol-1-ylmethyl)-1H-indoles and 1-(halobenzyl)-3-(4H-1,2,4-triazol-4-ylmethyl)-1H-indoles is described. 3-(Azolylmethyl)-1H-indoles were obtained in three steps from 1H-indole-3-carbaldehyde (1) by benzylation or tosylation, reduction and azole moiety fixation. In an alternative method, the bromo intermediates issued from the corresponding alcohols were condensed with the azolium sodium salts. Inhibitory activity against P450(arom) and P450(17α), and influence on retinoic acid metabolism were evaluated. Three imidazole compounds exhibited potent and selective aromatase inhibitory activity.

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.

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.