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Usage

Uses

Used in Organic Synthesis:
6-Chloroindole-3-carboxaldehyde is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity allows it to participate in a range of chemical reactions, facilitating the creation of diverse chemical entities.
Used in Pharmaceutical and Medicinal Chemistry:
In the pharmaceutical industry, 6-Chloroindole-3-carboxaldehyde is used as a building block for the development of novel drug candidates. Its structural features can be exploited to design and synthesize new compounds with potential therapeutic applications.
Used in Chemical Research:
6-Chloroindole-3-carboxaldehyde serves as a valuable research tool in academic and industrial laboratories. It is utilized in the study of reaction mechanisms, the development of new synthetic methodologies, and the exploration of structure-activity relationships in chemical biology.
Specific Application:
6-Chloroindole-3-carboxaldehyde can be reacted with dimethyldisulfane to yield 6-chloro-(3-thiomethyl)-indole. This transformation highlights its utility in the synthesis of sulfur-containing indole derivatives, which may have unique properties and applications in various fields, such as materials science, agrochemistry, or as potential pharmaceutical agents.

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

Upstream product

• 17422-33-2 6-chloroindole 
• 68-12-2 N,N-dimethyl-formamide 
• 100-61-8 N-methylaniline 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 2565-30-2 formyl chloride 
• 50517-12-9 1-(6-chloro-1H-indol-3-yl)-N,N-dimethylmethanamine 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 1067653-57-9 6-chloro-3-[3-(4-chlorobenzyl)-5-phenyl-3H-imidazol-4-yl]-1H-indole 
• 1073315-47-5 6-chloro-3-[3-cyclopropylmethyl-5-(3,4-dichlorophenyl)-3H-imidazol-4-yl]-1H-indole 
• 1283706-88-6 C₁₉H₁₄ClN₃O₂ 
• 1283706-74-0 1-benzyl-6-chloro-1H-indole-3-carbaldehyde 
• 158905-35-2 6-chloro-3-methyl-1H-indole 
• 1428236-54-7 C₂₀H₁₈ClNO₃ 
• 1423754-12-4 C₁₇H₁₃ClN₂O₄S 
• 1423754-18-0 (S)-2-((R)-1-(6-chloro-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-pentanal 

Relevant academic research and scientific papers

Synthesis and optimization of new 3,6-disubstitutedindole derivatives and their evaluation as anticancer agents targeting the MDM2/MDMx complex

Twelve derivatives of the general formula 3-substituted-6-chloroindoles were synthesized and tested for their growth inhibitory effects versus p53+/+ colorectal cancer HCT116 and its p53 knockout isogenic cells; colorectal cancer cell p53-

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

Structural Rigidification of N-Aryl-pyrroles into Indoles Active against Intracellular and Drug-Resistant Mycobacteria

A series of indolyl-3-methyleneamines incorporating lipophilic side chains were designed through a structural rigidification approach and synthesized for investigation as new chemical entities against Mycobacterium tuberculosis (Mtb). The screening led to the identification of a 6-chloroindole analogue 7j bearing an N-octyl chain and a cycloheptyl moiety, which displayed potent in vitro activity against laboratory and clinical Mtb strains, including a pre-extensively drug-resistant (pre-XDR) isolate. 7j also demonstrated a marked ability to restrict the intracellular growth of Mtb in murine macrophages. Further assays geared toward mechanism of action elucidation have thus far ruled out the involvement of various known promiscuous targets, thereby suggesting that the new indole 7j may inhibit Mtb via a unique mechanism.

Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles

A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.

Novel chalcone-conjugated, multi-flexible end-group coumarin thiazole hybrids as potential antibacterial repressors against methicillin-resistant Staphylococcus aureus

The increasing resistance of methicillin-resistant Staphylococcus aureus (MRSA) to antibiotics has led to a growing effort to design and synthesize novel structural candidates of chalcone-conjugated, multi-flexible end-group coumarin thiazole hybrids with

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.

Access to Polycyclic Thienoindolines via Formal [2+2+1] Cyclization of Alkynyl Indoles with S8and K2S

The syntheses of polycyclic thienoindolines bearing a dihydrothiophene or tetrahydrothiophene subunit have not been reported, despite the fact that such compounds may have interesting medicinal properties. Herein, we report a protocol for accessing polycyclic dihydrothiophenes by means of formal [2+2+1] intramolecular dearomatizing cyclization of alkynyl indoles with K2S and S8 as the sources of sulfide. In addition, tetrahydrothienoindolines were stereoselectively synthesized via a one-pot, two-step protocol involving AgNO3-catalyzed alkenyl dearomatization followed by two nucleophilic addition reactions involving K2S.

Molecular iodine mediated oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes

The oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups is achieved by employing molecular iodine as a mild oxidizing agent under ambient conditions in the presence of a mild base. The important reaction of C3 formylation of free NH and substituted indoles containing various substituents is accomplished from the corresponding Mannich bases. This methodology can also be extended for the synthesis of aryl and other heteroaryl aldehydes and ketones. Furthermore, the usefulness of the method is successfully demonstrated on a gram scale.

PEPTIDOMIMETIC MACROCYCLES AND USES THEREOF

The present disclosure describes the synthesis of peptidomimetic macrocycles and methods of using peptidomimetic macrocycles to treat a condition. The present disclosure also describes methods of using peptidomimetic macrocycles in combination with at least one additional pharmaceutically-active agent for the treatment of a condition, for example, cancer.

PEPTIDOMIMETIC MACROCYCLES AND USES THEREOF

The present disclosure describes methods of using peptidomimetic macrocycles in combination with an additional therapy to treat a condition, for example, cancer. In some embodiments, the peptidomimetic macrocycle can mitigate a side effect (e.g., mucositis, neutropenia, or thrombocytopenia) of the additional therapy.