43142-81-0

Usage

Ester compound

1-methyl-6-chloro-1H-indole-2-carboxylic acid ethyl ester The compound is an ester derived from the carboxylic acid 1-methyl-6-chloro-1H-indole-2-carboxylic acid, indicating the presence of an ester functional group (-COO-) in its structure.

Usage in research

chemical and pharmaceutical The compound is commonly used in both chemical and pharmaceutical research, suggesting its versatility and importance in these fields.

Potential applications

pharmaceutical drug development 1-Methyl-6-chloro-1H-indole-2-carboxylic acid ethyl ester has potential applications in the development of pharmaceutical drugs, highlighting its significance in creating new medications.

Focus area

neuroscience and psychiatric medication The compound is particularly relevant in the fields of neuroscience and psychiatric medication, indicating its potential use in treating neurological and psychiatric disorders.

Molecular structure

chloroindole ring The presence of a chloroindole ring in the compound's molecular structure makes it a common building block in the synthesis of various pharmaceutical compounds, emphasizing its importance in medicinal chemistry and drug development.

Upstream product

• 27034-51-1 ethyl 6-chloro-1H-indole-2-carboxylate 
• 80-48-8 methyl p-toluene sulfonate 
• 74-88-4 methyl iodide 
• 616-38-6 carbonic acid dimethyl ester 
• 540523-98-6 3-(4-chloro-2-nitro-phenyl)-2-oxo-propionic acid ethyl ester 
• 16732-75-5 6-chloro-1H-indole-2-carboxylic acid 
• 89-59-8 4-chloro-2-nitrotoluene 
• 71300-08-8 (4-chloro-2-nitro-phenyl)-pyruvic acid 
• 128672-31-1 Ethyl Pyruvate 2-(2-Chlorophenyl)methylhydrazone 

Downstream Products

• 287099-18-7 1-[[7-Chloro-3-(3-chlorophenyl)-5-methyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indol-1-yl]carbonyl]pyrrolidine 
• 287099-15-4 7-Chloro-N,N-diethyl-3-(3-methoxyphenyl)-5-methyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxamide 
• 287099-27-8 7-Chloro-3-(3-fluorophenyl)-N,N,5-trimethyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxamide 
• 287099-30-3 ethyl 7-chloro-3-(3-chlorophenyl)-5-methyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate 
• 287099-16-5 7-Chloro-3-(3-chlorophenyl)-N,N,5-trimethyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxamide 
• 287099-20-1 7-Chloro-N,N,5-trimethyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxamide 
• 220448-62-4 Ethyl 7-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino [4,5-b]indole-1-carboxylate 

Relevant academic research and scientific papers

PYRIDAZINOINDOLE COMPOUNDS AND METHODS FOR PET IMAGING

Embodiments of the invention include a novel synthesis of the translocator protein (TSPO) ligands, and methods of imaging a molecular events. Also disclosed are compounds for treatment of diseases, including cancer.

Synthesis and in vitro characterization of novel fluorinated derivatives of the TSPO 18 kDa ligand SSR180575

Abstract SSR180575 (1) is a high-affinity (0.83 nM) TSPO 18 kDa ligand belonging to the pyridazino[4,5-b]indole-1-acetamides family. Herein we describe the synthesis and in vitro characterization of two series of new fluorinated analogues. Eleven compounds (out of fifteen) displayed nanomolar to subnamolar affinities (0.30-8.1 nM) and high selectivities (Ki(CBR)/Ki(TSPO) > 103). Two derivatives stand out as promising candidates for drug development or use as PET probes for in vivo neuroinflammation imaging, once fluorine-18-labelled.

Facile synthesis of SSR180575 and discovery of 7-chloro-N,N,5-trimethyl-4-oxo-3(6-[18F]fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide, a potent pyridazinoindole ligand for PET imaging of TSPO in cancer

A novel synthesis of the translocator protein (TSPO) ligand 7-chloro-N,N,5-trimethyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide (SSR180575, 3) was achieved in four steps from commercially available starting materials. Focused structure-activity relationship development about the pyridazinoindole ring at the N3 position led to the discovery of 7-chloro-N,N,5-trimethyl-4-oxo-3(6-fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide (14), a novel ligand of comparable affinity. Radiolabeling with fluorine-18 (18F) yielded 7-chloro-N,N,5-trimethyl-4-oxo-3(6-[18F]fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide ([18F]-14) in high radiochemical yield and specific activity. In vivo studies of [18F]-14 revealed this agent as a promising probe for molecular imaging of glioma.

Targeted, NIR imaging agents for therapy efficacy monitoring, deep tissue disease demarcation and deep tissue imaging

Compounds and methods related to NIR molecular imaging, in-vitro and in-vivo functional imaging, therapy/efficacy monitoring, and cancer and metastatic activity imaging. Compounds and methods demonstrated pertain to the field of peripheral benzodiazepine

4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxamide derivatives, preparation and therapeutic use

4-Oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxamide derivatives having affinity for the peripheral benzodiazepine receptors are useful for the prevention or treatment of peripheral neuropathies and for the treatment of central neurogenerative disea

Use of pyridazino[4,5-b]indole-1-acetamide derivatives for preparing medicines for treating diseases related to the dysfunction of peripheral benzodiazepin receptors

Pyridazino[4,5-b]indole-1-acetamide derivatives for the prevention or treatment of diseases linked to the dysfunctioning of peripheral-type benzodiazepine receptors.

4-Oxo-3,5-dihydro-4H-pyridazino[4,5-b]-indole-1-acetamide derivatives, their preparation and their application in therapy

Compounds of general formula (I) in which X represents a hydrogen or halogen atom or a methyl, methoxy or phenylmethoxy group, Y represents a hydrogen atom, 1 or 2 halogen atoms or a hydroxyl, methoxy, nitro or methyl group, R1represents a hydr

Synthesis, biological evaluation, and structure-activity relationships of 3-acylindole-2-carboxylic acids as inhibitors of the cytosolic phospholipase A2

3-Acylindole-2-carboxylic acid derivatives were prepared and evaluated for their ability to inhibit the cytosolic phospholipase A2 of intact bovine platelets. To define the structural requirements for enzyme inhibition, the carboxylic acid group, the acyl residue, and the moiety in position 1 were systematically modified. Furthermore, different substituents were introduced into the phenyl part of the indole. Replacement of the carboxylic acid group in position 2 of the indole with an acetic or propionic acid substituent led to a decrease of inhibitory potency. Enzyme inhibition was optimal when the acyl residue in position 3 had a length of 12 or more carbons. Conformational restriction of the acyl residue did not influence activity. Introduction of alkyl chains at position 1 of the indole with 8 or more carbons resulted in a loss of activity. However, replacing the Ω-methyl group of such compounds with a carboxylic acid moiety was found to increase inhibitory potency significantly. Among the tested indole derivatives, 1-[2-(4- carboxyphenoxy)ethyl]-3-dodecanoylindole-2-carboxylic acid (29b) had the highest potency. With an IC50 of 0.5 μM it was about 20-fold more active than the standard cPLA2 inhibitor arachidonyl trifiuoromethyl ketane (IC50: 11μM).

Abnormal Fischer indolization and its related compounds. XXII. Fischer indolization of ethyl pyruvate 2-(2-chloro- and 2,6-dichlorophenyl)methylhydrazones

The Fischer indolization of ethyl pyruvate 2-(2-chlorophenyl)methylhydrazone (17) with HCI/EtOH proceeded rapidly to give six 1-methylindoles, ethyl 7-chloro (19), 6-chloro (22), and unsubstituted (24)-1-methylindole-2-carboxylates, and dichloro derivativ

Indoline Analogues of Idazoxan: Potent α2-Antagonists and α1-Agonists

The synthesis and α-adrenergic activity of a series of substituted 2-imidazolinylindolines are described.Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent.Many of the derivatives possess greater presynaptic antagonist potency that the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this α2-antagonism is often accompanied by α1-agonist activity.It was not possible to separate α2-antagonist from α1-agonist properties in this series.Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18 and 5-chloro-N-ethyl 23 derivatives, all being potent α2-antagonists and α1-agonists.Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.