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Upstream product

• 942-24-5 3-methoxycarbonylindole 
• 67-56-1 methanol 
• 16066-91-4 5-iodo-1H-indole 
• 76-02-8 trifluoroacetyl chloride 
• 14454-14-9 N-(4-iodophenyl)hydroxylamine 
• 922-67-8 propynoic acid methyl ester 
• 636-98-6 p-nitrobenzene iodide 

Relevant academic research and scientific papers

[Carboxyl-11C]Labelling of Four High-Affinity cPLA2α Inhibitors and Their Evaluation as Radioligands in Mice by Positron Emission Tomography

Cytosolic phospholipase A2α (cPLA2α) may play a critical role in neuropsychiatric and neurodegenerative disorders associated with oxidative stress and neuroinflammation. An effective PET radioligand for imaging cPLA2α in living brain might prove useful for biomedical research, especially on neuroinflammation. We selected four high-affinity (IC50 2.1–12 nm) indole-5-carboxylic acid-based inhibitors of cPLA2α, namely 3-isobutyryl-1-(2-oxo-3-(4-phenoxyphenoxy)propyl)-1H-indole-5-carboxylic acid (1); 3-acetyl-1-(2-oxo-3-(4-(4-(trifluoromethyl)phenoxy)phenoxy)propyl)-1H-indole-5-carboxylic acid (2); 3-(3-methyl-1,2,4-oxadiazol-5-yl)-1-(2-oxo-3-(4-phenoxyphenoxy)propyl)-1H-indole-5-carboxylic acid (3); and 3-(3-methyl-1,2,4-oxadiazol-5-yl)-1-(3-(4-octylphenoxy)-2-oxopropyl)-1H-indole-5-carboxylic acid (4), for labelling in carboxyl position with carbon-11 (t1/2=20.4 min) to provide candidate PET radioligands for imaging brain cPLA2α. Compounds [11C]1–4 were obtained for intravenous injection in adequate overall yields (1.1–5.5 %) from cyclotron-produced [11C]carbon dioxide and with moderate molar activities (70–141 GBq μmol?1) through the use of Pd0-mediated [11C]carbon monoxide insertion on iodo precursors. Measured logD7.4 values were within a narrow moderate range (1.9–2.4). After intravenous injection of [11C]1–4 in mice, radioactivity uptakes in brain peaked at low values (≤0.8 SUV) and decreased by about 90 % over 15 min. Pretreatments of the mice with high doses of the corresponding non-radioactive ligands did not alter brain time–activity curves. Brain uptakes of radioactivity after administration of [11C]1 to wild-type and P-gp/BCRP dual knock-out mice were similar (peak 0.4 vs. 0.5 SUV), indicating that [11C]1 and others in this structural class, are not substrates for efflux transporters.

Synthesis method of 5-iodoindole compound

The invention discloses a synthesis method of a 5-iodo indole compound, and the method comprises the following steps: by using an indole compound as a starting raw material and Niodo succinimide or iodine as an iodine source, carrying out free radical reaction in a halogenated organic solvent at normal temperature and normal pressure in the presence of Lewis acid to synthesize the 5-iodo indole compound. The synthesis method is mild in condition, wide in substrate application range, good in functional group tolerance and free of metal participation, and has the advantages of being easy to operate, environmentally friendly, high in specific regioselectivity and the like.

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.

Synthesis of analogs of wasabi phytoalexin (methyl 1-methoxyindole-3-carboxylate)

Syntheses of wasabi phytoalexin analogs, such as 6-bromo-5-iodo, 2-bromo-5-iodo, 6-nitro, 5-chloroacetyl, and 6-chloroacetyl congeners, are reported. An interesting effect of the 1-methoxy group on the regioselectivity of electrophilic substitution reactions on indole nucleus is observed.

Syntheses of wasabi phytoalexin (methyl 1-methoxyindole-3-carboxylate) and its 5-iodo derivative, and their nucleophilic substitution reactions

A simple synthetic method for methyl 1-methoxyindole-3-carboxylate, a phytoalexin isolated from Wasabia japonica, syn. Eutrema wasabi, and its 5-iodo derivative is reported. They underwent nucleophilic substitution reactions selectively at the 2-position.