172595-67-4

Usage

Uses

Used in Organic Synthesis:
5-CHLORO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate in organic synthesis for the production of various organic compounds. Its reactivity and structural features allow for the creation of a wide array of chemical entities, facilitating the advancement of chemical research and development.
Used in Pharmaceutical Research and Development:
In the pharmaceutical industry, 5-CHLORO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER is utilized as a building block for the synthesis of pharmaceutical drugs. Its unique properties contribute to the discovery and development of new therapeutic agents, potentially leading to innovative treatments for various diseases and conditions.
Used in Chemical Research:
5-CHLORO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER is employed as a research tool in chemical laboratories, where its properties are studied to understand its behavior in different chemical reactions. This knowledge aids in the design of new synthetic pathways and the optimization of existing ones, contributing to the broader field of chemistry.
Used in Material Science:
5-CHLORO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER may also find applications in material science, where its unique structural attributes could be leveraged to develop new materials with specific properties. For instance, it could be incorporated into the synthesis of polymers or other materials with tailored characteristics for use in various industries.

Upstream product

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Relevant academic research and scientific papers

Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1

The ligand-sensing transcription factor nuclear receptor related 1 (Nurr1) evolves as an appealing target to treat neurodegenerative diseases. Despite its therapeutic potential observed in various rodent models, potent modulators for Nurr1 are lacking as pharmacological tools. Here, we report the structure-activity relationship and systematic optimization of indole-based inverse Nurr1 agonists. Optimized analogues decreased the receptor's intrinsic transcriptional activity by up to more than 90% and revealed preference for inhibiting Nurr1 monomer activity. In orthogonal cell-free settings, we detected displacement of NCoRs and disruption of the Nurr1 homodimer as molecular modes of action. The inverse Nurr1 agonists reduced the expression of Nurr1-regulated genes in T98G cells, and treatment with an inverse Nurr1 agonist mimicked the effect of Nurr1 silencing on interleukin-6 release from LPS-stimulated human astrocytes. The indole-based inverse Nurr1 agonists valuably extend the toolbox of Nurr1 modulators to further probe the role of Nurr1 in neuroinflammation, cancer, and beyond.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Identification of azepinone fused tetracyclic heterocycles as new chemotypes with protein kinase inhibitory activities

The design and synthesis of small tetracyclic heterocycles which bear two new regioisomeric 2-carboxyethyl-1H-pyrrole-annulated indoloazepinone scaffolds is described. An azepinone motif, which is inherent in the structures of many well studied protein kinase inhibitors, serves as prominent structural feature of the new compounds. Concise access to the new regioisomeric tetracyclic derivatives was accomplished through amide coupling of appropriate pyrrole and indole precursors followed by an intramolecular Heck coupling reaction of the intermediate amide conjugates. Preliminary evaluation of newly synthesized tetracyclic molecules against a panel of protein kinases indicated their inhibitory activities and revealed promising selectivity profiles. The new compounds displayed no significant antiproliferative activity against MCF-7 cancer cells. Interestingly, derivative 19a exhibited selective TAK1 kinase inhibitory activity and figures as a promising chemotype for the discovery of new TAK1 inhibitors.

Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E

We have developed a concise one-pot synthesis of phaitanthrin E derivatives, where simple starting materials undergo an acid-catalyzed intermolecular amination/intramolecular cyclization cascade.

Palladium-catalyzed oxidative coupling of aromatic primary amines and alkenes under molecular oxygen: Stereoselective assembly of (Z)-enamines

An efficient Pd-catalyzed oxidative coupling of aromatic primary amines and alkenes under molecular oxygen is disclosed. Under mild reaction conditions, it provides a rapid access to (Z)-enamine compounds with exceptional functional group tolerance and ex

Ionic diamine rhodium complex catalyzed reductive N-heterocyclization of 2-nitrovinylarenes

Ionic diamine rhodium complex (1) catalyzes the reductive N-cyclization of 2-vinylnitroarenes using carbon monoxide as a reducing agent to afford functionalized indoles. The catalytic system allows direct access to indoles with ester and ketone groups at the 2- or 3-position, in good yields.

Unexpected products from the Fp2-catalyzed reductive cyclization of nitroaromatics bearing pendant unsaturation

A representative o-nitroenone (Z=O) was cyclized by reduction with CO and [CpFe(CO)2]2 (Fp2) as the catalyst to give the corresponding 4-quinolone. In contrast, Baylis-Hillman adducts derived from o-nitrobenzaldehydes were

Indole derivatives useful to treat estrogen-related neoplasms and disorders

The present invention relates to novel indole derivatives useful in down-regulating estrogen receptor expression. Also included are methods for the treatment of neoplasms or of controlling the growth of a neoplasm in a patient afflicted with a neoplastic disease, especially estrogen-dependent neoplasms such as those associated with breast, ovarian and cervical tissue. Another embodiment of the present invention is a method of prophylactically treating a patient at risk of developing a neoplastic disease state. Also provided is a method for treating autoimmune diseases. Also included are pharmaceutical compositions of the novel indole derivatives.