149685-64-3Relevant academic research and scientific papers
Synthesis of heteroarylogous 1H-indole-3-carboxamidines via a three-component interrupted Ugi reaction
La Spisa, Fabio,Meneghetti, Fiorella,Pozzi, Beatrice,Tron, Gian Cesare
, p. 489 - 496 (2015)
A novel one-pot multicomponent synthesis of heteroarylogous 1H-indole-3-carboxamidines starting from readily available N-alkyl-N-(1H-indol-2-ylmethyl)amines, isocyanides, and carbonyl compounds is reported. The strategy exploits the ability of the indole nucleus to interrupt the classical Ugi reaction, by intercepting the nascent nitrilium ion.
Synthesis and biological evaluation of potential inhibitors of the cysteine proteases cruzain and rhodesain designed by molecular simplification
Braga, Saulo Fehelberg Pinto,Martins, Luan Carvalho,da Silva, Elany Barbosa,Sales Júnior, Policarpo Ademar,Murta, Silvane Maria Fonseca,Romanha, Alvaro José,Soh, Wai Tuck,Brandstetter, Hans,Ferreira, Rafaela Salgado,de Oliveira, Renata Barbosa
, p. 1889 - 1900 (2017/03/08)
Analogues of 8-chloro-N-(3-morpholinopropyl)-5H-pyrimido[5,4-b]indol-4-amine 1, a known cruzain inhibitor, were synthesized using a molecular simplification strategy. Five series of analogues were obtained: indole, pyrimidine, quinoline, aniline and pyrrole derivatives. The activity of the compounds was evaluated against the enzymes cruzain and rhodesain as well as against Trypanosoma cruzi amastigote and trypomastigote forms. The 4-aminoquinoline derivatives showed promising activity against both enzymes, with IC50values ranging from 15 to 125?μM. These derivatives were selective inhibitors for the parasitic proteases, being unable to inhibit mammalian cathepsins B and S. The most active compound against cruzain (compound 5a; IC50?=?15?μM) is considerably more synthetically accessible than 1, while retaining its ligand efficiency. As observed for the original lead, compound 5a was shown to be a competitive enzyme inhibitor. In addition, it was also active against T. cruzi (IC50?=?67.7?μM). Interestingly, the pyrimidine derivative 4b, although inactive in enzymatic assays, was highly active against T. cruzi (IC50?=?3.1?μM) with remarkable selectivity index (SI?=?128) compared to uninfected fibroblasts. Both 5a and 4b exhibit drug-like physicochemical properties and are predicted to have a favorable ADME profile, therefore having great potential as candidates for lead optimization in the search for new drugs to treat Chagas disease.
Synthesis of free NH 2-(aminomethyl)indoles through copper-catalyzed reaction of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols with amines and palladium/copper- cocatalyzed domino three-component Sonogashira cross-coupling/cyclization/substitu
Cacchi, Sandro,Fabrizi, Giancarlo,Iazzetti, Antonia,Molinaro, Carmela,Verdiglione, Rosanna,Goggiamani, Antonella
, p. 1053 - 1059 (2015/03/30)
Free NH 2-(aminomethyl)indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficie
Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from 3-(o -trifluoroacetamidoaryl)-1-propargylic alcohols and amines
Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Molinaro, Carmela,Verdiglione, Rosanna
, p. 401 - 407 (2014/01/17)
A novel palladium-catalyzed approach to 2-(aminomethyl)indoles from 3-(o-trifluoroacetamidoaryl)-1-propargylic alcohols and amines has been developed.
Highly enantioselective synthesis of tetrahydro-β-carbolines and tetrahydro-γ-carbolines via Pd-catalyzed intramolecular allylic alkylation
Bandini, Marco,Melloni, Alfonso,Piccinelli, Fabio,Sinisi, Riccardo,Tommasi, Simona,Umani-Ronchi, Achille
, p. 1424 - 1425 (2007/10/03)
A novel Pd-catalyzed intramolecular allylic alkylation of indoles allows THBCs and THGCs to be effectively synthesized in high yields and excellent enantiomeric excesses (ee up to 97%). Copyright
New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: Controlling the regioselectivity
Bandini, Marco,Melloni, Alfonso,Umani-Ronchi, Achille
, p. 3199 - 3202 (2007/10/03)
(Chemical Equation Presented) A systematic study addressed toward the optimization of the Pd-catalyzed alkylation of indoles by allylic carbonates is presented. The protocol uses a catalytic amount of [PdCl(π-allyl)] 2/phosphine as a promoting
