131653-79-7

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 73430-27-0 1-dimethylamino-2-nitroethene 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 75-52-5 nitromethane 

Downstream Products

• 3610-42-2 5-bromotryptamine 
• 1241777-73-0 C₃₆H₃₄BrN₃O₂ 
• 125443-66-5 eudistomidin B 
• 1241777-71-8 C₃₅H₃₂BrN₃O₃ 
• 1241777-72-9 C₃₅H₃₀BrN₃O₂ 
• 61-54-1 tryptamine 
• 1384331-20-7 C₃₅H₃₂BrN₃O₂ 
• 1318767-45-1 eudistomidin I 
• 1554471-74-7 4-(1-(5-bromo-1H-indol-3-yl)-2-nitroethyl)-2-iodoaniline 
• 1007893-75-5 (6-bromo-9H-pyrido[3,4-b]indol-1-yl)(4-hydroxyphenyl)methanone 
• 1007893-77-7 (3-bromo-4-hydroxyphenyl)(6-bromo-9H-pyrido[3,4-b]indol-1-yl)methanone 
• 1007893-79-9 (6-bromo-9H-pyrido[3,4-b]indol-1-yl)(3,5-dibromo-4-hydroxyphenyl)methanone 

Relevant academic research and scientific papers

SYNTHESIS OF N(10)-ACETYLEUDISTOMIN L

The marine indole alkaloid derivative N(10)-acetyleudistomin L has been prepared in a convergent synthesis, starting from 5-bromoindole and L-cysteine.

Marine AChE inhibitors isolated from Geodia barretti: Natural compounds and their synthetic analogs

Barettin, 8,9-dihydrobarettin, bromoconicamin and a novel brominated marine indole were isolated from the boreal sponge Geodia barretti collected off the Norwegian coast. The compounds were evaluated as inhibitors of electric eel acetylcholinesterase. Barettin and 8,9-dihydrobarettin displayed significant inhibition of the enzyme, with inhibition constants (Ki) of 29 and 19 μM respectively towards acetylcholinesterase via a reversible noncompetitive mechanism. These activities are comparable to those of several other natural acetylcholinesterase inhibitors of marine origin. Bromoconicamin was less potent against acetylcholinesterase, and the novel compound was inactive. Based on the inhibitory activity, a library of 22 simplified synthetic analogs was designed and prepared to probe the role of the brominated indole, common to all the isolated compounds. From the structure-activity investigation it was shown that the brominated indole motif is not sufficient to generate a high acetylcholinesterase inhibitory activity, even when combined with natural cationic ligands for the acetylcholinesterase active site. The four natural compounds were also analysed for their butyrylcholinesterase inhibitory activity in addition and shown to display comparable activities. The study illustrates how both barettin and 8,9-dihydrobarettin display additional bioactivities which may help to explain their biological role in the producing organism. The findings also provide new insights into the structure-activity relationship of both natural and synthetic acetylcholinesterase inhibitors.

Metal-Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous-Flow

A metal-free, phosphine-catalyzed intramolecular “umpolung Michael addition” on alkynes to form spiroindol(en)ines is reported. This nucleophilic catalysis enables the formation of a wide scope of five- and six-membered spiroindol(en)ines in moderate to excellent yields in batch as well as under continuous-flow conditions. Triphenylphosphine-catalyzed nucleophilic activation of alkynes allows the exclusive formation of exo-product under mild reaction conditions.

Visible-Light-Induced Trifluoromethylation of Isonitrile-Substituted Indole Derivatives: Access to 1-(Trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indole and β-Carboline Derivatives

A visible-light-induced trifluoromethylation of isonitrile-substituted indole derivatives has been developed from the reaction of isonitrile-substituted indoles with Togni II reagent, affording 1-(trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indoles in mo

Asymmetric dearomatization of indoles through a Michael/Friedel-Crafts-Type cascade to construct polycyclic spiroindolines

A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N-dioxide/MgII catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction.

Enantioselective total synthesis of eudistomidins G, H, and I

Asymmetric first total synthesis of eudistomidins G, H, and I, tetrahydro-β-carboline alkaloids from the Okinawan marine tunicate Eudistoma glaucus, has been accomplished with the Bischler-Napieralski reaction and the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configurations of eudistomidins G, H, and I were confirmed from comparison of the 1H and 13C NMR, and CD spectral data of synthetic and natural eudistomidins G, H, and I, respectively.

Approaches to the tetracyclic eudistomins: the synthesis of N(10)-acetyleudistomin L

The successful synthesis of the tetracyclic ring system present in eudistomins C, E, K, and L involves a convergent approach to N(10)-acetyleudistomin L from 5-bromo-N'-hydroxytryptamine and a suitably protected cysteinal derivate.Ring C in the eudistomin was constructed by a modified Pictet-Spengler reaction and the unique 1,3,7-oxathiazepine ring (ring D) by an unprecedented intramolecular sila-Pummerer reaction.An interesting diastereoselectivity is observed in the former process.The formation of an alternative seven-membered ring cyclization product under certain conditions in the sila-Pummerer reaction is also described.