167631-21-2

Usage

Uses

Used in Pharmaceutical Research and Development:
Ethyl 5-fluoro-3-iodo-1H-indole-2-carboxylate is used as a research compound for its potential therapeutic properties. It is studied for its biological activities, which may contribute to the development of new drugs for the treatment of various medical conditions.
Used in Chemical Industry:
In the chemical industry, Ethyl 5-fluoro-3-iodo-1H-indole-2-carboxylate is used as a building block or intermediate in the synthesis of other complex organic molecules. Its unique structure, including fluorination and iodination, makes it a valuable component in the development of new chemical entities with specific properties and applications.
Used in Drug Discovery:
Ethyl 5-fluoro-3-iodo-1H-indole-2-carboxylate is used as a potential drug candidate in drug discovery. Its biological activities are investigated to identify its potential as a therapeutic agent for treating various diseases and medical conditions.
Used in Drug Development:
In drug development, Ethyl 5-fluoro-3-iodo-1H-indole-2-carboxylate is used to optimize the properties of new drug molecules. Its unique structural features can be incorporated into drug candidates to improve their efficacy, selectivity, and pharmacokinetic properties, leading to the development of more effective and safer medications.

InChI:InChI=1/C11H9FINO2/c1-2-16-11(15)10-9(13)7-5-6(12)3-4-8(7)14-10/h3-5,14H,2H2,1H3

Upstream product

• 348-36-7 ethyl 5-fluoro-1H-indole-2-carboxylate 
• 61272-76-2 4-fluoro-2-iodoaniline 

Downstream Products

• 1034110-39-8 ethyl 1-(benzenesulfonyl)-5-fluoro-1H-3-iodoindole-2-carboxylate 
• 1362861-20-8 ethyl 3-(2,5-bis(methoxymethoxy)phenyl)-5-fluoro-1H-indole-2-carboxylate 

Relevant academic research and scientific papers

INDOLE DERIVATIVES AND USES THEREOF FOR TREATING A CANCER

The present invention relates to indole derivatives of formula (I') as CK2 inhibitor and pharmaceutical compositions comprising the same. The present invention further relates to the use of such compounds of formula (I) for use for preventing and/or treating a cancer.

Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM

In this study, we screen three heterocyclic structures as potential inhibitors of UDP-galactopyranose mutase (UGM), an enzyme involved in the biosynthesis of the cell wall of Mycobacterium tuberculosis. In order to understand the binding mode, docking simulations are performed on the best inhibitors. Their activity on Mycobacterium tuberculosis is also evaluated. This study made it possible to highlight an “oxazepino-indole” structure as a new inhibitor of UGM and of M. tuberculosis growth in vitro.

Synthesis and Reactivity of Oxazinoindolones via Regioselective 6-exo-dig Iodolactonization

An efficient protocol for the facile construction of 3,4-dihydro-10-iodo-3-iodomethylene-[1,4]-oxazino[4,3-a]indol-1-ones has been developed by using a regio- and stereoselective iodolactonization reaction. Subsequent palladium cross-coupling reactions of 3,4-dihydro-10-iodo-3-iodomethylene-[1,4]-oxazino[4,3-a]indol-1-ones readily afforded functionalized oxazinoindolones.

Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: A novel DYRK1A inhibitor class

A library of substituted chromeno[3,4-b]indoles was developed as Lamellarin isosters. Synthesis was achieved from indoles after a four-step pathway sequence involving C-3 iodination, a Suzuki cross-coupling reaction, and a one pot deprotection/lactonisation step. Twenty final compounds were tested in order to determine their activity against topoisomerase I and kinases, the two major biological activities of Lamellarins. One newly synthesized derivative exhibited a strong topoisomerase activity comparable to reference compounds such as campthotecin and Lamellarin with only a weak kinase inhibition. Two other lead compounds were identified as new nanomolar DYRK1A inhibitors and several other drugs affected the kinases in the sub-micromolar range. These results will enable us to use the chromeno[3,4-b]indole as a pharmacophore to develop potent treatments for neurological or oncological disorders in which DYRK1A is fully involved.

New C5-alkylated indolobenzazepinones acting as inhibitors of tubulin polymerization: Cytotoxic and antitumor activities

A series of 5-alkylindolobenzazepin-7-ones was synthesized by Suzuki coupling between 3-iodoindole-2-carboxylates and the appropriate α-alkylbenzylamino α-boronic acids followed by cyclization to the lactam. Derivatives having a linear alkyl chain at C5 were found to be highly cytotoxic to KB cells with IC50 values in the 30-80 nM range. These compounds also inhibited the polymerization of tubulin with IC50's of 1-2 μM. Compound 4f ((S)-5-ethyl) showed comparable antiproliferative activities (IC50's of 30-70 nM) in a variety of cancer cell lines, cell growth being arrested at the G2/M phase. Compound 4f induced apoptosis in a dose-dependent manner in three different cancer cell lines and was shown to affect cell morphology in a manner consistent with its inhibitory action on tubulin polymerization. Using the experimental model of glioma grafted on the chick chorio-allantoic membrane, local treatment with compound 4f markedly reduced tumor progression.

Synthesis of indolobenzazepinones by application of an isocyanide-based multicomponent reaction

Application of a Ugi multicomponent reaction to oxo acids 4 allows the formation of potentially antimitotic indolobenzazepinones of type 5 in good yields of up to 72%, whereas the same transformation from the starting substrate 6 gives access to analogues of paullone with yields of up to 89%. The reaction could be applied to a wide range of isocyanides, thereby ensuring introduction of molecular diversity at the key C-5 position. Use of cyclohexenyl isocyanide allows post-condensation modifications, while careful choice of the amine and the indole protecting groups proved to be important for providing the deprotected compounds necessary for biological tests. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.