552866-98-5

Usage

Uses

Used in Pharmaceutical Synthesis:
4-FLUORO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE is used as a building block for the synthesis of various pharmaceutical drugs. Its unique chemical structure allows for the creation of new compounds with potential therapeutic properties.
Used in Analytical Chemistry:
As a reference standard, 4-FLUORO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE is employed in analytical chemistry to ensure the accuracy and reliability of experimental results. Its consistent properties make it an ideal benchmark for comparison and calibration.
Used in Drug Discovery and Development:
4-FLUORO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE is utilized in drug discovery and development processes due to its potential biological activity. Researchers use 4-FLUORO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE to explore its therapeutic potential and identify new drug candidates for various medical conditions.
Used in Research Applications:
In research settings, 4-FLUORO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE serves as a valuable tool for studying the properties and interactions of indole-based compounds. Its use in research helps to advance the understanding of chemical and biological processes related to this class of molecules.
Used in Solubility Enhancement:
The hydrochloride salt form of 4-FLUORO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE is used to improve the solubility of the compound in water. This enhanced solubility is beneficial for certain applications, such as drug delivery and formulation development, where water solubility is a critical factor.

InChI:InChI=1/C8H8FN/c9-7-2-1-3-8-6(7)4-5-10-8/h1-3,10H,4-5H2

Upstream product

• 387-43-9 4-fluoroindole 
• 769-10-8 1-fluoro-2-methyl-3-nitrobenzene 
• 344790-94-9 1-(2-(2-fluoro-6-nitrophenyl)vinyl)pyrrolidine 

Downstream Products

• 860024-83-5 1-(4-fluoroindolin-1-yl)ethanone 
• 1337532-29-2 GSK2656157 
• 915953-78-5 C₁₈H₁₉FN₂ 
• 915953-69-4 C₁₉H₂₁N₂F 
• 915953-65-0 C₁₉H₂₂N₂F₂ 
• 915953-60-5 C₁₉H₂₃N₂F 
• 1167056-95-2 4-fluoro-7-nitro-1H-indole 
• 1003858-66-9 4-fluoro-1H-indol-5-amine 
• 1003858-69-2 4-fluoro-5-nitro-1H-indole 
• 1620581-32-9 2-(5-((4-fluoroindolin-1-yl)sulfonyl)-2-methoxyphenyl)-2-isobutyl-4-methylpentanenitrile 

Relevant academic research and scientific papers

PERK INHIBITING INDOLINYL COMPOUNDS

Provided herein are compounds of formula (I), compositions, and methods useful for inhibiting PERK and for treating related conditions diseases, and disorders, wherein Q is selected from (Ia), (Ib) ou (Ic).

Synthesis method of 4-fluoro-7-nitroindole or derivatives of 4-fluoro-7-nitroindole

The invention is applicable to the technical field of chemical synthesis, and provides a synthesis method of 4-fluoro-7-nitroindole or derivatives thereof, which comprises the following steps: reacting 4-fluoroindole or derivatives thereof, glacial acetic acid and sodium cyanoborohydride to obtain 4-fluoroindoline or derivatives thereof, reacting the 4-fluoroindoline or derivatives thereof, glacial acetic acid and acetic anhydride to obtain N-acetyl-4-fluoroindoline or a derivative thereof, carrying out nitration reaction on N-acetyl-4-fluoroindoline or a derivative thereof to obtain N-acetyl4-fluoro-7-nitroindoline or a derivative thereof, reacting N-acetyl-4-fluorine 7-nitroindoline or derivatives thereof, sodium hydroxide and 1, 4-dioxane to obtain 4-fluoro-7-nitroindoline or derivatives thereof, and reacting 4-fluoro-7-nitroindoline or derivatives thereof, trichloromethane and manganese dioxide to obtain 4-fluoro-7-nitroindoline or derivatives thereof. The synthesis method provided by the invention is mild in reaction condition and easy to operate.

Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations

Herein, nickel-catalyzed synthesis of polyarylcarbazole through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indole C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indoline. This methodology is not limited to aromatic internal alkynes as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed. We have also studied the photophysical properties of these highly conjugated molecules.

Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles

We disclose herein a photocatalytic difluoroalkylation and cyclization cascade reaction of N-(but-2-enoyl)indoles with broad substrate scopes in up to 90% isolated yield. This method provides sustainable and efficient access to synthesize difluoroalkylated pyrrolo[1,2-a]indoles with a quaternary carbon center under mild conditions.

5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

4,5,6,7-TETRAHYDRO-1 H-PYRAZOLO[4,3-C]PYRIDIN-3-AMINE COMPOUNDS AS CBP AND/OR EP300 INHIBITORS

The present invention relates to compounds of formula (I) or formula (II): and to salts thereof, wherein R1-R4 of formula (I) and R1-R3 of formula (II) have any of the values defined herein, and compositions and uses thereof. The compounds are useful as inhibitors of CBP and/or EP300. Also included are pharmaceutical compositions comprising a compound of formula (I) of formula (II) or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various CBP and/or EP300-mediated disorders.

INDOLINE DERIVATIVES AS INHIBITORS OF PERK

The invention is directed to substituted indoline derivatives. Specifically, the invention is directed to compounds according to Formula I: (I) wherein R1, R2 and R3 are defined herein. The compounds of the invention are inhibitors of PERK and can be usef

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.

Discovery of a novel series of indoline carbamate and indolinylpyrimidine derivatives as potent GPR119 agonists

GPR119 has emerged as an attractive target for anti-diabetic agents. We identified a structurally novel GPR119 agonist 22c that carries a 5-(methylsulfonyl)indoline motif as an early lead compound. To generate more potent compounds of this series, structural modifications were performed mainly to the central alkylene spacer. Installation of a carbonyl group and a methyl group on this spacer significantly enhanced agonistic activity, resulting in the identification of 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]propyl 7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole-1-carboxylate (20). To further expand the chemical series of indoline-based GPR119 agonists, several heterocyclic core systems were introduced as surrogates of the carbamate spacer that mimic the presumed active conformation. This approach successfully produced an indolinylpyrimidine derivative 37, 5-(methylsulfonyl)-1-[6-({1-[3-(propan-2- yl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl}oxy)pyrimidin-4-yl]-2, 3-dihydro-1H-indole, which has potent GPR119 agonist activity. In rat oral glucose tolerance tests, these two indoline-based compounds effectively lowered plasma glucose excursion and glucose-dependent insulin secretion after oral administration.

Discovery of GSK2656157: An optimized PERK inhibitor selected for preclinical development

We recently reported the discovery of GSK2606414 (1), a selective first in class inhibitor of protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK), which inhibited PERK activation in cells and demonstrated tumor growth inhibition in a human tumor xenograft in mice. In continuation of our drug discovery program, we applied a strategy to decrease inhibitor lipophilicity as a means to improve physical properties and pharmacokinetics. This report describes our medicinal chemistry optimization culminating in the discovery of the PERK inhibitor GSK2656157 (6), which was selected for advancement to preclinical development.