21778-77-8

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxy-1H-indole-2-Methanol is used as a precursor in the synthesis of pharmaceutical compounds for its potential to contribute to the development of new medications.
Used in Medicinal Chemistry Research:
5-Methoxy-1H-indole-2-Methanol is utilized as a subject of study for its antioxidant and anti-inflammatory properties, which may lead to its application in the treatment of various diseases and conditions.
Used in Drug Development:
Due to its potential pharmacological activities, 5-Methoxy-1H-indole-2-Methanol is used in drug development to explore its efficacy in treating specific health issues and to enhance the therapeutic options available.

Upstream product

• 4792-58-9 ethyl 5-methoxy-1H-indole-2-carboxylate 
• 67929-86-6 methyl 5-methoxyindole-2-carboxylate 
• 4382-54-1 5-methoxy-1H-indole-2-carboxylic acid 

Downstream Products

• 1006-94-6 5-methoxylindole 
• 1272970-94-1 (5-methoxy-1-(1-phenylvinyl)-1H-indol-2-yl)methanol 
• 1427311-14-5 N-cyclohexyl-1-(5-methoxy-1H-indol-2-yl)-3-oxo-2-propylisoindoline-1-carboxamide 
• 1427311-22-5 N-cyclohexyl-10-methoxy-5-oxo-6-propyl-6,7-dihydro-5H-benzo[6,7][1,4]diazepino[1,2-a]indole-7-carboxamide 
• 1427311-30-5 N-cyclohexyl-11-methoxy-5-oxo-6-propyl-5,6,7,8-tetrahydrobenzo[5,6]azepino[3,4-b]indole-7-carboxamide 
• 1427311-16-7 2-benzyl-N-butyl-1-(5-methoxy-1H-indol-2-yl)-3-oxoisoindoline-1-carboxamide 
• 1616101-43-9 6-methoxy-1,2-bis(4-methoxyphenyl)-4-phenyl-9H-carbazole 
• 1427311-41-8 C₂₈H₂₈IN₃O₃ 
• 1427311-40-7 C₂₉H₃₀IN₃O₃ 
• 1427311-38-3 C₂₇H₃₂IN₃O₃ 
• 1427311-33-8 N-butyl-11-methoxy-5-oxo-6-phenyl-5,6,7,8-tetrahydrobenzo[5,6]azepino[3,4-b]indole-7-carboxamide 
• 1427311-25-8 N-butyl-10-methoxy-5-oxo-6-phenyl-6,7-dihydro-5H-benzo[6,7][1,4]diazepino[1,2-a]indole-7-carboxamide 
• 1427311-17-8 N-butyl-1-(5-methoxy-1H-indol-2-yl)-3-oxo-2-phenylisoindoline-1-carboxamide 
• 1427311-24-7 6-benzyl-N-butyl-10-methoxy-5-oxo-6,7-dihydro-5H-benzo[6,7][1,4]diazepino[1,2-a]indole-7-carboxamide 

Relevant academic research and scientific papers

Modulation of the Antitumor Activity by Methyl Substitutions in the Series of 7H-Pyridocarbazole Monomers and Dimers

The structure of the dimeric antitumor drug ditercalinium (NSC 366241) -1,1'-diyldi-2,1-ethanediyl)biscarbazolium>tetramethanesulfonate> was modified by introduction of methyl groups in various positions of the aromatic ring.Monomeric analogues with the nitrogen atom of the pyridinic ring in different positions have also been synthesized.Pharmacological properties and DNA interactions of the new compounds are reported.In contrast with the monomeric analogue of ditercalinium, which was inactive, methyl substitutions on the 10 methoxy-7H-pyridocarbazolium in positions 6 and 7 led to monomers endowed with small but significant activity.As expected, dimerization of the methyl-substituted pyridocarbazoles yielded DNA bisintercalators with affinity slightly higher than that of the unsubstituted parent compounds.These dimers, characterized by a relatively better therapeutic index, have the same mechanism of action as ditercalinium.Otherwise, in monomeric and dimeric series, methyl substitution in position 4 or 5 provided inactive compounds unable to intercalate into DNA.All these results are in agreement with the previously proposed geometry for the complex of ditercalinium with DNA.

Synthesis of Indole- and Pyrrole-Fused Seven-Membered Nitrogen Heterocycles via Acid-Base Switchable Cyclization Involving Cleavage of Amide C?N Bonds

We report the method for synthesis of indole- and pyrrole-fused seven-membered nitrogen heterocycles by means of acid-base switchable cyclization reactions. The reactions involved cleavage of amide C?N bonds, chemoselective N-1 or C-3 acylation, and 1,4-M

Polycyclic compound for inhibiting DHX33 helicase

The invention relates to a polycyclic compound for inhibiting DHX33 helicase. In particular, the invention relates to a compound shown as a formula I in the specification or a pharmaceutically acceptable form thereof, a pharmaceutical composition containing the compound or the pharmaceutically acceptable form thereof, a preparation method of the compound or the pharmaceutically acceptable form thereof, and medical application of the compound or the pharmaceutically acceptable form thereof and the pharmaceutical composition to prevention and/or treatment of DHX33-related diseases.

Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility

Indolecarboxamides are potent but poorly soluble mycobactericidal agents. Here we found that modifying the incipient scaffold by amide-amine substitution and replacing the indole ring with benzothiophene or benzoselenophene led to striking (10-20-fold) im

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.

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones

The aromatic nitrogen atoms of heteroarylaldehydes are activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products are afforded in good to excellent yields and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichemicals for plant protection.

Addition of a Carbene Catalyst to Indole Aryl Aldehyde Activates a Remote δ-sp2 Carbon for Protonation and Formal [4+2] Reaction

The addition of a carbene catalyst to an indole aryl aldehyde leads to the activation of a remote sp2 carbon that is five atoms away from the catalyst. The unsaturated Breslow intermediate formed between the catalyst and substrate undergoes an internal redox reaction and remote carbon protonation to generate an analogous azolium vinyl enolate intermediate. Subsequent [4+2] reaction with cyclic imine substrates eventually affords multicyclic pyridoindoles as nearly single diastereomers with excellent enantioselectivities.

Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells

We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

Facile Synthesis of 3-Halobenzo-heterocyclic-2-carbonyl Compounds via in situ Halogenation-Oxidation

A facile method to synthesize 3-halobenzo-heterocyclic-2-carbonyl compounds is described. Mechanistic studies suggested that a halo-cyclization process, which generated the unstable spiro-acetal transition state and readily convertible to the corresponding carbonyl compound might be involved. Diverse 3-halobenzo-heterocyclic-2-carbonyl compounds could be synthesized with up to 95 % yield in mild conditions with inexpensive starting materials. (Figure presented.).

Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity

Methuosis is a form of nonapoptotic cell death characterized by an accumulation of macropinosome-derived vacuoles with eventual loss of membrane integrity. Small molecules inducing methuosis could offer significant advantages compared to more traditional anticancer drug therapies that typically rely on apoptosis. Herein we further define the effects of chemical substitutions at the 2-and 5-indolyl positions on our lead compound 3-(5-methoxy-2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propene-1-one (MOMIPP). We have identified a number of compounds that induce methuosis at similar potencies, including an interesting analogue having a hydroxypropyl substituent at the 2-position. In addition, we have discovered that certain substitutions on the 2-indolyl position redirect the mode of cytotoxicity from methuosis to microtubule disruption. This switch in activity is associated with an increase in potency as large as 2 orders of magnitude. These compounds appear to represent a new class of potent microtubule-active anticancer agents.