73139-85-2

Basic information

• Product Name: 5-FLUOROINDOLE-3-ACETONITRILE
• Synonyms: 5-FLUOROINDOLE-3-ACETONITRILE;2-(5-fluoro-1H-indol-3-yl)acetonitrile
• CAS NO: 73139-85-2
• Molecular Formula: C₁₀H₇FN₂
• Molecular Weight: 174.17
• Mol File: 73139-85-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 377.3 °C at 760 mmHg
• Flash Point: 182 °C
• Appearance: /
• Density: 1.316 g/cm³
• Vapor Pressure: 6.83E-06mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 5-FLUOROINDOLE-3-ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUOROINDOLE-3-ACETONITRILE(73139-85-2)
• EPA Substance Registry System: 5-FLUOROINDOLE-3-ACETONITRILE(73139-85-2)

Safety Data

• Hazardous Substances Data: 73139-85-2(Hazardous Substances Data)

Usage

Description

5-Fluoroindole-3-acetonitrile, a chemical compound with the molecular formula C10H7FN2, is a derivative of the indole family. It is distinguished by the presence of a fluorine atom at the 5th position of the indole ring and an acetonitrile group at the 3rd position. This unique structure and reactivity make it a valuable intermediate in the synthesis of pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
5-Fluoroindole-3-acetonitrile is used as a key intermediate in the synthesis of various drugs and chemical compounds. Its unique structure allows for the development of new pharmaceuticals with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Fluoroindole-3-acetonitrile serves as an essential intermediate for the production of agrochemicals. Its reactivity and structural properties contribute to the creation of effective compounds for agricultural use.
Used in Medicinal Chemistry Research:
5-Fluoroindole-3-acetonitrile is also utilized in medicinal chemistry research for studying its potential biological activities and pharmacological properties. This exploration aims to uncover new avenues for drug discovery and development.

InChI:InChI=1/C10H7FN2/c11-8-1-2-10-9(5-8)7(3-4-12)6-13-10/h1-2,5-6,13H,3H2

Upstream product

• 399-52-0 5-fluoro-1H-indole 
• 343-90-8 3-dimethylaminomethyl-5-fluoroindole 
• 74-88-4 methyl iodide 
• 773869-43-5 5-fluoroindole-3-carbinol 
• 50-00-0 formaldehyd 
• 7677-24-9 trimethylsilyl cyanide 
• 2338-71-8 5-fluoro-1H-indole-3-carbaldehyde 
• 190182-61-7 N,N-diethyl-3-aminomethyl-5-fluoro-1H-indole 
• 87-52-5 3-(Dimethylaminomethyl)indole 

Downstream Products

• 1110273-52-3 N-[(S)-2-(3-cyanomethyl-5-fluoroindol-1-yl)-1-methylethyl]-2,4-dimethyl-6-nitrobenzenesulfonamide 
• 497258-29-4 methyl 2-(5-fluoro-1H-indol-3-yl)acetate 
• 443-73-2 (5-fluoroindol-3-yl)acetic acid 

Relevant articles and documents

Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5 μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day.

SMALL MOLECULE INHIBITORS OF ISOPRENYLCYSTEINE CARBOXYL METHYLTRANSFERASE WITH POTENTIAL ANTICANCER ACTIVITY

The present invention generally relates to inhibitors of isoprenylcysteine carboxyl methyltransferase (Icmt), in particularly to compounds that inhibit Icmt activity and pharmaceutical compositions thereof. The invention also relates to methods of disease treatment using the same.

Amino derivatives of indole as potent inhibitors of isoprenylcysteine carboxyl methyltransferase

The enzyme isoprenylcysteine carboxyl methyltransferase (Icmt) plays an important role in the post-translational modification of proteins that are involved in the regulation of cell growth. The indole acetamide cysmethynil is by far the most potent and widely investigated Icmt inhibitor, but it has modest antiproliferative activity and may have pharmacokinetic limitations due to its lipophilic character. We report here that cysmethynil can be structurally modified to give analogues that are as potent in inhibiting Icmt but with significantly greater antiproliferative activity. Key modifications were the replacement of the acetamide side chain by tertiary amino groups, the n-octyl side chain by isoprenyl and the 5-m-tolyl ring by fluorine. Moreover, these analogues have lower lipophilicities that could lead to improved pharmacokinetic profiles.