343-90-8

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
5-Fluorogramine is used as a research compound for its potential antitumor and anticancer properties. It has been studied for its ability to modulate neurotransmitter receptors in the central nervous system, making it a promising candidate for the development of new drugs targeting cancer and neurological disorders.
Used in Neuroscience:
5-Fluorogramine is used as a tool molecule for studying the structure and function of certain receptors and ion channels in the brain. Its ability to modulate neurotransmitter receptors allows researchers to gain insights into the underlying mechanisms of various neurological conditions and develop targeted therapies.
Used in Anticancer Applications:
5-Fluorogramine is used as an anticancer agent, particularly for its potential to target and inhibit the growth of tumor cells. Its antitumor properties make it a valuable compound in the development of novel cancer therapies.
Used in Drug Delivery Systems:
To enhance the therapeutic potential of 5-Fluorogramine, researchers are exploring various drug delivery systems, such as nanoparticles and other carriers, to improve its bioavailability, delivery, and overall efficacy in treating cancer and neurological disorders.

InChI:InChI=1/C11H13FN2/c1-14(2)7-8-6-13-11-4-3-9(12)5-10(8)11/h3-6,13H,7H2,1-2H3

Upstream product

• 348-36-7 ethyl 5-fluoro-1H-indole-2-carboxylate 
• 782-10-5 (5-fluoro-2-nitro-phenyl)-pyruvic acid 
• 399-52-0 5-fluoro-1H-indole 
• 33797-51-2 eschenmoser's salt 
• 50-00-0 formaldehyd 
• 506-59-2 N,N-dimethylammonium chloride 
• 351-64-4 ethyl 2-[2-(4-fluorophenyl)hydrazinylidene]propanoate 
• 399-76-8 5-fluoroindole-2-carboxylic acid 
• 124-40-3 dimethyl amine 

Downstream Products

• 215997-93-6 di(5-fluoro-1H-indole-3-yl)methane 
• 154-08-5 DL-5-fluorotryptophan 
• 154170-01-1 ethyl 2-amino-3-(5-fluoro-1H-indol-3-yl)propanoate 
• 16626-02-1 5-fluoro-L-tryptophan 
• 114926-41-9 (S)-2-((tert-butoxycarbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)propanoic acid 
• 73139-85-2 2-(5-fluoro-1H-indol-3-yl)acetonitrile 
• 443-73-2 (5-fluoroindol-3-yl)acetic acid 

Relevant academic research and scientific papers

SMALL MOLECULES THAT TARGET THE RNA THAT CAUSES ALS

Disclosed herein are compounds that selectively bind an expanded transcribed repeat r(G4C2)exp, prevent sequestration of RNA-binding proteins, and inhibit translation of repeat associated non-ATG (RAN) translation responsible for generation of toxic dipeptide repeats underlying diseases such as amyotrophic lateral sclerosis (ALS) and frontotemporal dementia (FTD). The compounds and their pharmaceutical compositions are useful in treating a disease or condition characterized by an expanded G4C2 repeat RNA (r(G4C2)exp), such as ALS and FTD.

Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides

We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed in situ from substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements in the presence of a rhodium and a copper catalyst, respectively. The combined experimental and density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving a metal-free ylide in the rhodium catalyzed reaction favoring [2,3]-rearrangement, and a metal-coordinated ion-pair in the copper catalyzed [1,2]-rearrangement that recombines in the solvent-cage. The application of our methodology was demonstrated in the first total synthesis of the indole alkaloid (±)-sorazolon B, which enabled the stereochemical reassignment of the natural product. Further functional group transformations of the rearrangement products to generate valuable synthetic intermediates were also demonstrated.

NOVEL DUAL MODE OF ACTION SOLUBLE GUANYLATE CYCLASE ACTIVATORS AND PHOSPHODIESTERASE INHIBITORS AND USES THEREOF

The present invention relates to compounds of formula (I), or pharmaceutically acceptable salt, solvate or hydrate thereof, wherein said compound of formula (I) comprises at least one covalently bound -ONO2 or -ONO moiety and at most four covalently bound -ONO2 or -ONO moieties, and wherein AR, R1, X, R3 and R4 are as defined in claim 1; and pharmaceutical compositions thereof, and their use in methods of treating or preventing a disease alleviated by inhibition of PDE5 in a human or in a non-human mammal.

Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles

A highly selective rhodium-catalyzed cyclization of tethered 3-allenylindoles is reported. In a smooth reaction, 1-vinyltetrahydrocarbazoles are obtained in excellent yields and enantioselectivities. Aside from a great functional group tolerance, this method requires neither the Schlenk technique nor the use of anhydrous solvents. Preliminary mechanistic investigations proved that the reaction proceeds via an intermediary formed spiroindolenine which rapidly undergoes an acid-catalyzed stereospecific migration.

Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines

A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction's synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.

General Synthesis of Unsymmetrical 3,3′-(Aza)diindolylmethane Derivatives

Diindolylmethane (DIM) and its derivatives have recently been in the focus of interest due to their significant biological activities, specifically in cancer prevention and therapy. Molecular targets of DIM have been identified, e.g., the immunostimulatory G protein-coupled receptor GPR84. However, most of the reported and investigated DIM derivatives are symmetrical because general methods for obtaining unsymmetrical DIMs have been lacking. To optimize the interaction of DIM derivatives with their protein targets, unsymmetrical substitution is required. In the present study we developed a new, mild and efficient access to unsymmetrically substituted 3,3′-DIMs by reaction of (3-indolylmethyl)trimethylammonium iodides with a wide range of substituted indole derivatives. 7-Azaindole also led to the 3,3′-connected DIM analogue, while 4- and 5-azaindoles reacted at the N1-nitrogen atom as confirmed by X-ray crystallography. The reactions were performed in water without the requirement of a catalyst or other additives. Wide substrate scope, operational simplicity, environmentally benign workup, and high yields are further advantages of the new method. The synthetic protocol proved to be suitable for upscaling to yield gram amounts for pharmacological studies. This procedure will allow the preparation of a broad range of novel, unsymmetrical DIM derivatives to exploit their potential as novel drugs.

Biosynthesis of violacein, structure and function of L-tryptophan oxidase VioA from chromobacterium violaceum

Violacein is a natural purple pigment of Chromobacterium violaceum with potential medical applications as antimicrobial, antiviral, and anticancer drugs. The initial step of violacein biosynthesis is the oxidative conversion of L-tryptophan into the corresponding α-imine catalyzed by the flavoenzyme L-tryptophan oxidase (VioA). A substrate-related (3-(1H-indol-3-yl)-2-methylpropanoic acid) and a product-related (2-(1H-indol-3-ylmethyl)prop-2-enoic acid) competitive VioA inhibitor was synthesized for subsequent kinetic and x-ray crystallographic investigations. Structures of the binary VioA?FADH2 and of the ternary VioA?FADH2 ?2-(1H-indol-3-ylmethyl)prop-2-enoic acid complex were resolved. VioA forms a "loosely associated" homodimer as indicated by small-angle x-ray scattering experiments. VioA belongs to the glutathione reductase family 2 of FAD-dependent oxidoreductases according to the structurally conserved cofactor binding domain. The substrate-binding domain of VioA is mainly responsible for the specific recognition of L-tryptophan. Other canonical amino acids were efficiently discriminated with a minor conversion of L-phenylalanine. Furthermore, 7-aza-tryptophan, 1-methyl-tryptophan, 5-methyl-tryptophan, and 5-fluoro-tryptophan were efficient substrates of VioA. The ternary product-related VioA structure indicated involvement of protein domain movement during enzyme catalysis. Extensive structure-based mutagenesis in combination with enzyme kinetics (using L-tryptophan and substrate analogs) identified Arg64 , Lys269 , and Tyr309 as key catalytic residues of VioA. An increased enzyme activity of protein variant H163A in the presence of L-phenylalanine indicated a functional role of His163 in substrate binding. The combined structural and mutational analyses lead to the detailed understanding of VioA substrate recognition. Related strategies for the in vivo synthesis of novel violacein derivatives are discussed.

Advances toward new antidepressants with dual serotonin transporter and 5-HT1A receptor affinity within a class of 3-aminochroman derivatives. Part 2

Novel compounds combining a 5-HT1A moiety (3-aminochroman scaffold) and a 5-HT transporter (indole analogues) linked through a common basic nitrogen via an alkyl chain attached at the 1- or 3-position of the indole were evaluated for dual affin

INDOLES FOR USE AS DPP-IV INHIBITORS

The present invention relates to indole derivatives useful as dipeptidyl peptidase IV (DPP-IV) inhibitors. Formula (I).