3093-97-8

Usage

Uses

Used in Pharmaceutical Research:
1H-Indole-2-carboxylicacid, 6-fluorois used as a research compound for its potential therapeutic properties. It serves as an inhibitor of various enzymes and receptors, which is valuable in drug development. The fluorinated structure of 1H-Indole-2-carboxylicacid, 6-fluoro- contributes to its improved bioavailability and pharmacokinetics, making it a promising candidate for the creation of new medications.
Used in Organic Synthesis:
In the field of organic synthesis, 1H-Indole-2-carboxylicacid, 6-fluorois employed as a building block or intermediate in the synthesis of more complex organic molecules. Its unique structure, including the fluorine atom, allows for the development of new chemical entities with specific biological activities or improved drug-like properties.

InChI:InChI=1/C9H6FNO2/c10-6-2-1-5-3-8(9(12)13)11-7(5)4-6/h1-4,11H,(H,12,13)

Upstream product

• 348-37-8 6-fluoro-1H-indole-2-carboxylic acid ethyl ester 
• 459-57-4 4-fluorobenzaldehyde 
• 136818-43-4 methyl 6-fluoroindole-2-carboxylate 

Downstream Products

• 1260430-46-3 2-(6-fluoroindole-2-yl)-4-benzylthiazoline 
• 1260430-47-4 2-(6-fluoroindole-2-yl)-4-phenylthiazoline 
• 933746-81-7 6-fluoro-1H-indole-2-carbaldehyde 
• 136818-43-4 methyl 6-fluoroindole-2-carboxylate 
• 348-37-8 6-fluoro-1H-indole-2-carboxylic acid ethyl ester 
• 1265234-08-9 3-(6-Fluoro-1-(phenylsulfonyl)-1H-indol-2-yl)3-oxopropanenitrile 
• 1429473-84-6 methyl 3-((4-chlorophenyl)thio)-6-fluoro-1H-indole-2-carboxylate 
• 2836-69-3 6-fluoro N,N-Diethyltryptamine 
• 52579-22-3 1'-deoxy-1'-(6-fluoroindolyl)-β-D-ribofuranose 
• 882043-81-4 1-(2'-deoxy-5'-O-tert-butyldiphenylsilyl-3'-O-mesyl-β-D-erythro-pentofuranosyl)-6-fluoroindole 
• 943524-15-0 1-(2'-deoxy-5'-O-tert-butyldiphenylsilyl-β-D-erythro-pentofuranosyl)-6-fluoroindole 

Relevant academic research and scientific papers

Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway

A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 μM) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 μM) and 5-Fu (IC50 = 24.80 μM) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent.

Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4- phenylpyridine derivatives in vitro

A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 × 103- and 2.0 × 103- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 μM), respectively.

Synthesis and structure of fluoroindole nucleosides

Chemically modified bases are frequently used to stabilize nucleic acids, to study the driving forces for nucleic acid structure formation, and to tune DNA and RNA hybridization conditions. Nucleoside analogues are chemical means to investigate hydrogen bonds, base stacking, and solvation as the three predominant forces that are responsible for the stability of nucleic acids. To obtain deeper insight into the contributions of these interactions to RNA stability, we decided to synthesize some novel nucleic acid analogues where the nucleobases are replaced by fluoroindoles. Fluorinated indoles can be compared with fluorinated benzimidazoles to determine the role of nitrogen in five-membered ring systems. The synthesis of fluoroindole ribonucleosides as well as the X-ray crystal structures of all synthesized fluoroindole ribonucleosides are reported here. These compounds could also be building blocks for a variety of biologically active RNA analogues.

Synthesis of fluorinated indoles as RNA analogues

Nucleoside analogues are chemical means to investigate hydrogen bonds, base stacking, and solvation as the three predominant forces that are responsible for the stability of secondary structure of nucleic acids. To obtain deeper insight into the contributions of these interactions to RNA stability apart from the ones exerted by the predominant nucleosides we decided to synthesize some novel nucleic acid analogues where the nucleobases are replaced by fluoroindoles. Fluorinated indoles can be compared to fluorinated benzimidazoles to determine the role of nitrogen in five membered ring system. The synthesis of fluoroindole ribonucleosides is described here. Copyright Taylor & Francis Group, LLC.

Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines

A series of fluorinated analogues of the hallucinogenic tryptamines N,N-diethyltryptamine (DET), 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT, psilocin), and 5-methoxy-DMT was synthesized to investigate possible explanations for the inactivity of 6-fluoro-DET as a hallucinogen and to determine the effects of fluorination on the molecular recognition and activation of these compounds at serotonin receptor subtypes. The target compounds were evaluated using in vivo behavioral assays for hallucinogen-like and 5-HT(1A) agonist activity and in vitro radioligand competition assays for their affinity at 5-HT(2A), 5-HT(2C), and 5-HT(1A) receptor sites. Functional activity at the 5-HT(2A) receptor was determined for all compounds. In addition, for some compounds functional activity was determined at the 5-HT(1A) receptor. Hallucinogen-like activity, evaluated in the two-lever drug discrimination paradigm using LSD-trained rats, was attenuated or abolished for all of the fluorinated analogues. One of the tryptamines, 4-fluoro-5-methoxy-DMT (6), displayed high 5-HT(1A) agonist activity, with potency greater than that of the 5-HT(1A) agonist 8-OH-DPAT. The ED50 of 6 in the two-lever drug discrimination paradigm using rats trained to discriminate the 5-HT(1A) agonist LY293284 was 0.17μmol/kg, and the K(i) at [3H]8-OH-DPAT-labeled 5-HT(1A) receptors was 0.23 nM. The results indicate that fluorination of hallucinogenic tryptamines generally has little effect on 5-HT(2A/2C) receptor affinity or intrinsic activity. Affinity at the 5-HT(1A) receptor was reduced, however, in all but one example, and all of the compounds tested were full agonists but with reduced functional potency at this serotonin receptor subtype. The one notable exception was 4-fluoro-5-methoxy-DMT (6), which had markedly enhanced 5-HT(1A) receptor affinity and functional potency. Although it is generally considered that hallucinogenic activity results from 5-HT(2A) receptor activation, the present results suggest a possible role for involvement of the 5-HT(1A) receptor with tryptamines.

Tricyclic compounds having fungicidal activity, their preparation and their use

Compounds of formula (I): STR1 ?wherein: R1 represents halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, or cycloalkyloxy; R2 represents hydrogen or halogen; R3 represents hydrogen, alkyl, or cycloalkyl; and the dotted line represents a single or double carbon--carbon bond!; and salts thereof have valuable fungicidal activities which make them of considerable value in agriculture and horticulture.

Anti-aids piperazines

The present invention includes diaromatic substituted heterocyclic compounds (III) STR1 which are useful in treating individuals infected with the HIV virus. The invention includes certain previously generically disclosed anti-AIDS piperazinyl compounds (V) and a method of treating HIV infected individuals with the indoles of formula (V) and the anti-AIDS amines (X).