53590-47-9

Usage

Uses

Used in Pharmaceutical Industry:
(5-chloro-1H-indol-2-yl)methanol is used as a pharmaceutical intermediate for the development of drugs with potential therapeutic applications. Its anti-inflammatory and anticancer properties make it a promising candidate for the treatment of various diseases and conditions.
Used in Drug Development:
(5-chloro-1H-indol-2-yl)methanol is used as a building block in the synthesis of new drug molecules. Its unique structure and functional groups allow for the creation of novel compounds with potential therapeutic benefits.
Used in Organic Synthesis:
(5-chloro-1H-indol-2-yl)methanol is used as a key intermediate in the synthesis of various organic compounds. Its reactivity and versatility make it a valuable component in the preparation of a wide range of chemical products.
Used in Scientific Research:
(5-chloro-1H-indol-2-yl)methanol is used in scientific research to study its chemical properties, reactivity, and potential applications in various fields. Its unique structure and properties make it an interesting subject for further investigation and exploration.

Upstream product

• 87802-11-7 methyl 5-chloroindole-2-carboxylate 
• 4792-67-0 5-chloro-indole-2-carboxylic acid ethyl ester 
• 10517-21-2 5-chloro-1H-Indole-2-carboxylic acid 

Downstream Products

• 148473-21-6 5-Chloro-2-phenylsulfanylmethyl-1H-indole 
• 53590-49-1 5-chloro-1H-indole-2-carbaldehyde 
• 950513-62-9 C₁₈H₁₂NOCl 
• 148473-22-7 5-Chloro-3-phenylsulfanyl-2-phenylsulfanylmethyl-1H-indole 
• 1427311-23-6 10-chloro-N-cyclohexyl-5-oxo-6-propyl-6,7-dihydro-5H-benzo[6,7][1,4]diazepino[1,2-a]indole-7-carboxamide 
• 1427311-39-4 C₂₆H₂₉ClIN₃O₂ 
• 1616101-45-1 6-chloro-1,2,4-triphenyl-9H-carbazole 

Relevant academic research and scientific papers

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

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

NEW ISOINDOLINONE SUBSTITUTED INDOLES AND DERIVATIVES AS RAS INHIBITORS

-The present invention relates to new isoindolinone or isobenzofuranone substituted indoles and derivatives of formula (I) wherein the groups R1 to R7, R10 and n have the meanings given in the claims and specification, their use as inhibitors of RAS-family proteins and their use as medicaments, especially as agents for treatment and/or prevention of oncological diseases.

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.

Highly enantioselective synthesis of functionalized azepino[1,2-a] indoles via NHC-catalyzed [3+4] annulation

The enantioselective [3+4] annulation of 3-formylindol-2-methyl-malonates with 2-bromoenals catalyzed by NHCs is described to afford functionalized azepino[1,2-a]indoles in high yields with excellent enantioselectivities. This method, in which the 3-formyl group in indoles acts as a necessary mediating group, provided cycloaddition products under mild conditions.

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.

Synthesis and biological evaluation of potential inhibitors of the cysteine proteases cruzain and rhodesain designed by molecular simplification

Analogues of 8-chloro-N-(3-morpholinopropyl)-5H-pyrimido[5,4-b]indol-4-amine 1, a known cruzain inhibitor, were synthesized using a molecular simplification strategy. Five series of analogues were obtained: indole, pyrimidine, quinoline, aniline and pyrrole derivatives. The activity of the compounds was evaluated against the enzymes cruzain and rhodesain as well as against Trypanosoma cruzi amastigote and trypomastigote forms. The 4-aminoquinoline derivatives showed promising activity against both enzymes, with IC50values ranging from 15 to 125?μM. These derivatives were selective inhibitors for the parasitic proteases, being unable to inhibit mammalian cathepsins B and S. The most active compound against cruzain (compound 5a; IC50?=?15?μM) is considerably more synthetically accessible than 1, while retaining its ligand efficiency. As observed for the original lead, compound 5a was shown to be a competitive enzyme inhibitor. In addition, it was also active against T. cruzi (IC50?=?67.7?μM). Interestingly, the pyrimidine derivative 4b, although inactive in enzymatic assays, was highly active against T. cruzi (IC50?=?3.1?μM) with remarkable selectivity index (SI?=?128) compared to uninfected fibroblasts. Both 5a and 4b exhibit drug-like physicochemical properties and are predicted to have a favorable ADME profile, therefore having great potential as candidates for lead optimization in the search for new drugs to treat Chagas disease.

Fluorination-Oxidation of 2-Hydroxymethylindole Using Selectfluor

An unexpected fluorination-oxidation of 2-hydroxymethylindole using selectfluor under mild condi-tions without a catalyst is described. This new chemistry allows for efficient and rapid synthesis of various 3-fluoroindole-2-aldehydes and novel quaternary

OXADIAZINE COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure relates to oxadiazine compounds, pharmaceutical compositions comprising an effective amount of an oxadiazine compound and methods for using an oxadiazine compound in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of an oxadiazine compound.

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.