288385-89-7

Basic information

• Product Name: 1H-Indole,4-fluoro-5-methoxy-(9CI)
• Synonyms: 1H-Indole,4-fluoro-5-methoxy-(9CI);1H-Indole, 4-fluoro-5-Methoxy-;4-fluoro-5-Methoxy-1H-indole;4-Fluoro-5-Methoxy-indole
• CAS NO: 288385-89-7
• Molecular Formula: C9H8FNO
• Molecular Weight: 165.166
• Product Categories: METHOXY
• Mol File: 288385-89-7.mol

Chemical Properties

• Boiling Point: 308.707°C at 760 mmHg
• Flash Point: 140.501°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 1H-Indole,4-fluoro-5-methoxy-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole,4-fluoro-5-methoxy-(9CI)(288385-89-7)
• EPA Substance Registry System: 1H-Indole,4-fluoro-5-methoxy-(9CI)(288385-89-7)

Safety Data

• Hazardous Substances Data: 288385-89-7(Hazardous Substances Data)

Usage

Uses

1H-Indole,4-fluoro-5-methoxy-(9CI) may have potential applications in the field of pharmaceuticals, agrochemicals, and materials science. However, further research and testing are necessary to fully understand the potential uses and effects of this chemical.

InChI:InChI=1/C9H8FNO/c1-12-8-3-2-7-6(9(8)10)4-5-11-7/h2-5,11H,1H3

Upstream product

• 124-41-4 sodium methylate 
• 344790-96-1 5-bromo-4-fluoro-1H-indole 
• 387-43-9 4-fluoroindole 
• 67-56-1 methanol 
• 1240113-40-9 4-fluoro-5-iodo-1H-indole 
• 947380-13-4 (2-fluoro-3-methoxy-6-nitro-phenyl)-acetonitrile 

Relevant articles and documents

A novel fluorinated tryptamine with highly potent serotonin 5-HT1A receptor agonist properties

Synthesis and biological evaluation of a novel fluorinated tryptamine analogue are described. This new compound 1-(4-fluoro-5-methoxyindol-3-yl)pyrrolidine (2) was found to be a potent serotonin 5-HT1A agonist.

Fluorinated indole-imidazole conjugates: Selective orally bioavailable 5-HT7 receptor low-basicity agonists, potential neuropathic painkillers

The 5-HT7 receptor has recently gained much attention due to its involvement in multiple physiological functions and diseases. The insufficient quality of the available molecular probes prompted design of fluorinated 3-(1-alkyl-1H-imidazol-5-yl)-1H-indoles as a new generation of selective 5-HT7 receptor agonists. A potent and drug-like agonist, 3-(1-ethyl-1H-imidazol-5-yl)-5-iodo-4-fluoro-1H-indole (AGH-192, 35, Ki 5-HT7R = 4 nM), was identified by optimizing the halogen bond formation with Ser5.42 as the supposed partner. The compound was characterized by excellent water solubility, high selectivity over related CNS targets, high metabolic stability, oral bioavailability and low cytotoxicity. Rapid absorption into the blood, medium half-life and a high peak concentration in the brain Cmax = 1069 ng/g were found after i.p. (2.5 mg/kg) administration in mice. AGH-192 may thus serve as the long-sought tool compound in the study of 5-HT7 receptor function, as well as a potential analgesic, indicated by the antinociceptive effect observed in a mouse model of neuropathic pain.

INDOLOPYRIDINES AS INHIBITORS OF THE KINESIN SPINDLE PROTEIN (EG5 )

Compounds of formula (I), in which R1, R2, R3 and R4 have the meanings indicated in the description, are effective Eg5-inhibiting compounds with anti-proliferative and/or apoptosis inducing activity.

TETRACYCLIC INDOLOPYRIDINES AS EG5 INHIBITORS

Compounds of a certain formula (I), in which R1, R2, R3 and R4 have the meanings indicated in the description, are effective Eg5-inhibiting compounds with anti-proliferative and/or apoptosis inducing activity.

INDOLOPYRIDINES AS EG5 KINESIN MODULATORS

Compounds of a certain formula (I), in which R1, R2, R3, R4, R5 and R6 have the meanings indicated in the description, are effective compounds with anti-proliferative and/or apoptosis inducing activity.

Quinoline derivatives having vegf inhibiting activity

The invention relates to compounds of formula (I) wherein: either any one of G1, G2, G3, G4 and G5 is nitrogen and the other four are —CH—, or G1, G2, G3, G4 and G5 are all —CH—; Z is —O—, —NH—, —S—, —CH2— or a direct bond; Z is linked to any one of G1, G2, G3 and G4; n is an integer from 0 to 5; m is an integer from 0 to 3; Ra represents hydrogen or fluoro; Rb, R1 and R2 are defined herein and salt thereof, process for the preparation so such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and the use of a compound of formula I in the manufacture of a medicament for the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blodded animals. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of diseases states including cancer and rheumatoid arthritis.

Cinnoline compounds

The invention relatest to compounds of the formula (I) wherein either any one of G1, G2, G3, G4 and G5 is nitrogen and the other four are —CH—, or G1, G2, G3, G4 and G5 are all —CH—; Z is —O—, —NH—, —S—, —CH2— or a direct bond; Z is linked to any one of G1, G2, G3 and G4 which is a free carbon atom; n is an integer from 0 to 5; any of the substitutents R1 may be attached at any free carbon atom of the indole, azaindole or indazole group; m is an integer from 0 to 3; Ra represents hydrogen; Rb represents hydrogen or another value as defined herein; R1 represents hydrogen, oxo, hydroxy, halogeno, C1-4alkyl, C1-4alkoxy, C1-4alkoxy, C1-4-alkyl, aminoC1-4alkyl, C1-3alkylaminoC1-4alkyl, di(C1-3alkyl)aminoC1-4alkyl, —C1-5alkyl(ring B) wherein ring B is selected from azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, N-methylpiperazinly, N-ethylpiperazinyl, morpholino and thiomorpholino; R2 represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3aklylsulphanyl, —NR3R4 (wherein R3 and R4, which may be the same or different, each represents hydrogen or C1-3alkyl), or R5X1— (wherein R5 and X1 are as defined herein) and salts thereof, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and the use of a compound of formula I in the manufacture of medicament for the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.

Chemical compounds

The invention relates to compounds of the formula (I): wherein: ring C is 9 or 10-membered bicyclic heteroaromatic group containing at least one nitrogen atom in the ring attached to Z and optionally containing a further 1-3 heteroatoms, selected independently from O, S, and N, with the proviso that ring C is not a quinazoline, quinoline or cinnoline group; either any one of G1, G2, G3, G4 and G5 is nitrogen and the other four are —CH—; or G1, G2, G3, G4 and G5 are all —CH—; Z is —O—, NH—, —S—, CH2— or a direct substituents R1 may be attached at any free carbon atom of the indole, azaindole or indazole group; m is an integer from 0 to 2; Rb represents hydrogen or another value as defined herein; R1 represents hydrogen, hydroxy, halogeno, C1-4alkyl, or any other value as defined herein; R2 represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, —NR3R4 (wherein R3 and R4, which may be the same or different, each represents hydrogen or C1-3alkyl), or R5X1— (wherein R5 and X1 are as defined herein) and salts thereof, processes for the preparation of such compounds, pharmaceutical compositions