1008-07-7

Usage

Uses

Used in Pharmaceutical Development:
7-CHLORO-3-FORMYLINDOLE is used as a key intermediate in the synthesis of pharmaceuticals for its potential to contribute to the development of new drugs with enhanced therapeutic properties. Its unique structure allows for the creation of molecules that can interact with biological targets, potentially leading to the discovery of novel treatments for various diseases.
Used in Agrochemical Research:
In the agrochemical industry, 7-CHLORO-3-FORMYLINDOLE is used as a precursor in the development of new agrochemicals, such as pesticides and herbicides. Its chemical properties make it a valuable component in the design of molecules that can effectively control pests and weeds, thereby increasing crop yields and ensuring food security.
Used in Organic Synthesis:
7-CHLORO-3-FORMYLINDOLE is utilized as a building block in organic synthesis, allowing chemists to construct more complex organic molecules with diverse applications. Its reactivity and structural features facilitate the formation of new chemical bonds and the creation of innovative molecular architectures.
Used in Medicinal Chemistry Research:
7-CHLORO-3-FORMYLINDOLE serves as a starting material for medicinal chemistry research, where it is investigated for its potential biological activity. Studies on its synthesis, properties, and interactions with biological systems can provide insights into its therapeutic potential and contribute to the advancement of drug discovery efforts.
Overall, 7-CHLORO-3-FORMYLINDOLE's applications span across various fields, including pharmaceuticals, agrochemicals, organic synthesis, and medicinal chemistry, making it a versatile and valuable compound for researchers and industry professionals.

InChI:InChI=1/C9H6ClNO/c10-8-3-1-2-7-6(5-12)4-11-9(7)8/h1-5,11H

Upstream product

• 53924-05-3 7-chloro-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 852391-19-6 Nec-1s 
• 221377-37-3 7-chloro-1H-indole-3-acetonitrile 
• 1428968-84-6 1-(7-chloro-1H-indol-3-yl)-2-((2-methoxypyridin-4-yl)amino)-2-phenylethanone 
• 1428968-67-5 1-(7-chloro-1H-indol-3-yl)-2-((3-methoxyphenyl)amino)-2-phenylethanone 
• 1428969-08-7 4-(2-(7-chloro-1H-indol-3-yl)-1-((3-methoxyphenyl)amino)-2-oxoethyl)benzonitrile 
• 1422432-60-7 C₂₁H₁₆ClN₃O₃ 
• 1422433-23-5 C₂₃H₂₀ClN₃O₃ 
• 3804-16-8 2-(7-chloro-1H-indol-3-yl)ethanamine 
• 1195785-02-4 C₁₈H₁₃ClN₄ 

Relevant academic research and scientific papers

Synthesis, crystal structures and electronic properties of isomers of chloro-pyridinylvinyl-1H-indoles

Three isomers of chloro-3-(2-pyridin-3-ylvinyl)-1H-indole were synthesized and tested as inhibitors of human tryptophan 2,3-dioxygenase (hTDO). The crystal structures of two of them were solved by X-ray diffraction. The solubility of the molecules also was determined experimentally. The molecular electrostatic potentials and dipole moments of the three isomers were calculated by ab initio quantum mechanics (HF/6-311G). The single crystal X-ray analyses reveal non-planar structures. This non-coplanarity is retained during docking of the compounds into a model of hTDO, the molecular target of this series. The position of the Cl atom does not significantly affect the electronic delocalization. Nevertheless, the position of the Cl atom produces a local variation of bond lengths inducing different dipole moments for these isomers. Variations in dipole moments are consistent with the different melting points and crystal packings. Differences in aqueous solubilities are best explained by subtle changes in H-bonds resulting from different accessibilities of the indole NH's due to steric effects of the Cl substituent. The non-coplanarity plays an important role in the crystalline packing of the molecules in contrast to the position of the Cl. This study leads to a better understanding of the structural and electronic characteristics of this chemical series and can potentially help to better understand their inhibitory activity.

N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential

A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.

DUAL-INHIBITORS OF CELLULAR NECROPTOSIS AND FERROPTOSIS FOR USE IN THE TREATMENT OF ORGAN TRANSPLANT PATIENTS

The invention relates to chemical compounds for use as a medicament in the prevention of organ transplant rejection and/or transplant organ damage. In embodiments of the invention, the compound inhibits and/or reduces ferroptosis and necroptosis of cells of the transplanted organ. In further embodiments, the patient is at risk of transplant rejection and/or is at risk of or shows signs of ischemia-reperfusion injury and/or necroinflammation.

Discovery and synthesis of novel indole derivatives-containing 3-methylenedihydrofuran-2(3H)-one as irreversible LSD1 inhibitors

Lysine-specific demethylase 1 (LSD1), demethylase against mono- and di - methylated histone3 lysine 4, has emerged as a promising target in oncology. More specifically, it has been demonstrated as a key promoter in acute myeloid leukemia (AML), and several LSD1 inhibitors have already entered into clinical trials for the treatment of AML. In this paper, a series of new indole derivatives were designed and synthesized based on a lead compound obtained by a high-throughput screening with our in-house compound library. Among the synthetic compounds, 9e was characterized as a potent LSD1 inhibitor with an IC50 of 1.230 μM and can inhibit the proliferation of THP-1 cells effectively. And most importantly, this is the first irreversible LSD1 inhibitor that is not derived from monoamine oxidase inhibitors. Hence, the discovery of 9e may serve as a proof of concept work for AML treatment.

BICYCLIC HETEROAROMATIC UREA OR CARBAMATE COMPOUNDS FOR USE IN THERAPY

The present invention relates to bicyclic heteroaromatic urea or carbamate compounds of formula I where the variables are as defined in the claims and the description. The invention moreover relates to a pharmaceutical composition containing these compounds I, and to these compounds for use in therapy, especially for use in the treatment or prevention of a disease or disorder selected from the group consisting of an inflammatory disease, a hyperproliferative disease or disorder, a hypoxia-related pathology and a disease characterized by excessive vascularization.

Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides

A highly efficient N,N′-dioxide-NiII catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C-C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98 % yield with up to 91 % enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). A promising approach: Catalytic de-aromatic [3+2] cycloaddition of indoles with epoxides by C-C cleavage of oxiranes is accomplished by using a highly efficient N,N′-dioxide-NiII catalyst system. A range of chiral furo[3,4-b]indoles is obtained with high enantiomeric excesses and diastereomeric ratios.

An efficient one-step synthesis of heterobiaryl pyrazolo[3,4-u] pyridines via indole ring opening

A mild one-step synthetic method to access privileged heterobiaryl pyrazolo[3,4-b]pyridines from indole-3-carboxaldehyde derivatives and a variety of aminopyrazoles has been developed. This novel method constructs heterobiaryls with the wide scope of substrate generality and excellent regioselectivity via indole ring opening.

COMPOUNDS, SCREENS, AND METHODS OF TREATMENT

The present invention features compounds, pharmaceutical compositions, and methods for treating trauma, ischemia, stroke, degenerative diseases associated with cellular necrosis, and other conditions. Screening assays for identifying compounds useful for treating these conditions are also described.

Inhibitors of cellular necrosis

The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.