23073-31-6

Usage

Uses

Used in Pharmaceutical Research:
4-Fluoro-1H-Indole-3-carbaldehyde is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure and fluoro substituent make it a valuable building block in the synthesis of new drugs and medicinal agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-Fluoro-1H-Indole-3-carbaldehyde serves as a key intermediate for the preparation of a wide range of chemical products. Its versatility and reactivity in chemical reactions contribute to its importance in the synthesis of various organic compounds.
Used in Research and Development:
4-Fluoro-1H-Indole-3-carbaldehyde is utilized in research and development settings to explore its potential applications and properties. This may include studying its interactions with other molecules, evaluating its stability, and investigating its potential use in new chemical processes or applications.

InChI:InChI=1/C9H6FNO/c10-7-2-1-3-8-9(7)6(5-12)4-11-8/h1-5,11H

Upstream product

• 387-43-9 4-fluoroindole 
• 68-12-2 N,N-dimethyl-formamide 
• 100-97-0 hexamethylenetetramine 
• 50-00-0 formaldehyd 

Downstream Products

• 863407-42-5 [4-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde 
• 110221-04-0 (S)-2-amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid 
• 1369571-01-6 (S)-1-tosyl-4-fluorotryptophan methyl ester 
• 1369570-94-4 4-fluoro-3-hydroxymethyl-1-tosylindole 
• 1369570-96-6 3-bromomethyl-4-fluoro-1-tosylindole 
• 1369570-99-9 (3S,6R)-3-((4-fluoro-1-tosyl-3-indolyl)methyl)-3,6-dihydro-6-isopropyl-2,5-dimethoxypyrazine 
• 1422433-16-6 C₂₃H₂₀FN₃O₃ 
• 1422432-53-8 C₂₁H₁₆FN₃O₃ 
• 1428969-91-8 1-(4-fluoro-1H-indol-3-yl)-2-((3-methoxy-phenyl)amino)-2-phenylethanone 
• 23077-42-1 4-fluoro-1H-indole-3-carboxylic acid 
• 1011484-22-2 4-fluoro-3-methyl-1H-indole 
• 863407-47-0 trans-3-[4-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide 

Relevant academic research and scientific papers

Amphiphilic Indole Derivatives as Antimycobacterial Agents: Structure-Activity Relationships and Membrane Targeting Properties

Antibacterials that disrupt cell membrane function have the potential to eradicate “persister” organisms and delay the emergence of resistance. Here we report the antimycobacterial activities of 4-fluoro and 6-methoxyindoles bearing a cationic amphiphilic motif represented by a lipophilic n-octyl side chain at position 1 and a positively charged azepanyl or 1,4-dioxa-8-azaspiro[4.5]decane moiety at position 3. These analogues exhibited balanced profiles of potency (Mycobacterium bovis BCG, M tuberculosis H37Rv), selective activity, solubility, and metabolic stability. Bacteriological mechanism of action investigations on a representative analogue revealed cell membrane permeabilization and depolarization in M bovis BCG. These membrane-related changes preceded cell death indicating that the loss in membrane integrity was not an epiphenomenon. Bactericidal activity was observed against both growing and nongrowing mycobacterial cultures. The analogue also upregulated cell envelope stress-inducible promoters piniBAC and pclgR, implicating the involvement of envelope-related targets in its mode of action.

Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles

A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.

Access to Polycyclic Thienoindolines via Formal [2+2+1] Cyclization of Alkynyl Indoles with S8and K2S

The syntheses of polycyclic thienoindolines bearing a dihydrothiophene or tetrahydrothiophene subunit have not been reported, despite the fact that such compounds may have interesting medicinal properties. Herein, we report a protocol for accessing polycyclic dihydrothiophenes by means of formal [2+2+1] intramolecular dearomatizing cyclization of alkynyl indoles with K2S and S8 as the sources of sulfide. In addition, tetrahydrothienoindolines were stereoselectively synthesized via a one-pot, two-step protocol involving AgNO3-catalyzed alkenyl dearomatization followed by two nucleophilic addition reactions involving K2S.

N-Alkylation-Initiated Redox-Neutral [5 + 2] Annulation of 3-Alkylindoles with o-Aminobenzaldehydes: Access to Indole-1,2-Fused 1,4-Benzodiazepines

Described herein is an unprecedented N-Alkylation-initiated redox-neutral [5 + 2] annulation of 3-Alkylindoles with o-Aminobenzaldehydes via a cascade N-Alkylation/dehydration/[1,5]-hydride transfer/Friedel-Crafts alkylation sequence. A series of indole-1,2-fused 1,4-benzodiazepines are facilely constructed in moderate to good yields in one step. This protocol features excellent regioselectivity, metal-free conditions, high step economy, and wide substrate scope.

Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)

The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)

ANTIBACTERIAL COMPOUNDS

Novel compounds having antimicrobial activitiy, in particular against Pseudomonas aeruginosa, Burkholderia cepaciaand/or Clostridium difficile, and a pharmaceutical composition containing the novel compound.

Synthesis of polycyclic spirooxindoles via an asymmetric catalytic one-pot stepwise Aldol/chloroetherification/aromatization procedure

A general method for the synthesis of chiral pentacyclic spirooxindoles containing a tetrahydropyrano[2,3-b]indole scaffold through a one-pot stepwise sequence from 3-(3-indolomethyl)oxindole, paraformaldehyde and NCS is reported. Furthermore, the pentacyclic spirooxindoles could be transformed to bispirooxindole and other structurally diverse spirocyclic oxindoles.

IMIDAZOLYL-SUBSTITUTED INDOLE DERIVATIVES BINDING 5-HT7 SEROTONIN RECEPTOR AND PHARMACEUTICAL COMPOSITIONS THEREOF

The invention relates to a new class of substituted indole derivatives that are able to activate 5-HT7 serotonin receptor. These compounds bind 5-HT7 serotonin receptor with high affinity and selectivity, while possessing favourable physicochemical properties. The compounds of the invention are the first described low-basicity 5-HT7 receptor agonists. The invention also relates to use of such compounds in the treatment or prevention of 5-HT7 receptor-related disorders, especially of the central nervous system. The invention also relates to the isotopically labelled compounds for use in the in vivo diagnostics or imaging of a 5-HT7 serotonin receptor.

Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.

5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE

Provided are 5-HT2C receptor agonists. Also provided are methods for weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction, pathological gambling, reward deficiency syndrome, and sex addiction), obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders (including insomnia, fragmented sleep architecture, and disturbances of slow-wave sleep), urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea. Also provided are compositions comprising a selective 5-HT2C receptor agonist, optionally in combination with a supplemental agent, and methods for reducing the frequency of smoking tobacco in an individual attempting to reduce frequency of smoking tobacco; aiding in the cessation or lessening of use of a tobacco product in an individual attempting to cease or lessen use of a tobacco product; aiding in smoking cessation and preventing associated weight gain; controlling weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; reducing weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; treating nicotine dependency, addiction and/or withdrawal in an individual attempting to treat nicotine dependency, addiction and/or withdrawal; or reducing the likelihood of relapse use of nicotine by an individual attempting to cease nicotine use comprising administering a selective 5-HT2C receptor agonist, optionally in combination with a supplemental agent.