120607-72-9Relevant academic research and scientific papers
Unconventional Knoevenagel-type indoles: Synthesis and cell-based studies for the identification of pro-apoptotic agents
Spallarossa, Andrea,Caneva, Chiara,Caviglia, Matteo,Alfei, Silvana,Butini, Stefania,Campiani, Giuseppe,Gemma, Sandra,Brindisi, Margherita,Zisterer, Daniela M.,Bright, Sandra A.,Williams, Clive D.,Crespan, Emmanuele,Maga, Giovanni,Sanna, Giuseppina,Delogu, Ilenia,Collu, Gabriella,Loddo, Roberta
, p. 648 - 660 (2015/09/07)
A new series of indole-based analogues were recently identified as potential anticancer agents. The Knoevenagel-type indoles herein presented were prepared via a one-pot condensation of iminium salts with active methylene reagents and were isolated as single geometric isomers. Biological evaluation in different cell-based assays revealed an antiproliferative activity for some analogues already in the nanomolar range against leukaemia, breast and renal cancer cell lines. To explain these effects, the most promising analogues of the series were engaged in further cell-based studies. Compounds 5e, l, p and 6a, b highlighted a pro-apoptotic potential being able to induce apoptosis in HL60, K562 and MCF-7 cell lines in a dose and time-dependent manner. The ability of these compounds to arrest cell cycle at the G2/M phase inspired the immunofluorescence studies which allowed us to identify tubulin as a potential target for compounds 5l and 6b.
Scandium-catalyzed intramolecular friedel-crafts reactions of 2-[(2-Alkyl-1 H -indol-3-yl)methylene]malonates
Oh, Chang Ho,Park, Hyo Seung,Park, Nari,Kim, So Young,Piao, Lanhua
, p. 579 - 585 (2014/03/21)
We have synthesized a variety of 2-[(2-alkyl-1H-indol-3-yl)methylene] malonates and studied their scandium-catalyzed intramolecular Friedel-Crafts reactions leading to the corresponding polycyclic compounds such as indeno[1,2-b]indoles and benzo[1,2-b]carbazoles. Georg Thieme Verlag Stuttgart New York.
Unconventional stereoselective one-pot synthesis of Knoevenagel-type indoles via in situ condensation of iminium salts with active methylene reagents in memory of Professor Angelo Ranise
Ranise, Angelo,Lucchesini, Francesco,Caviglia, Matteo,Alfei, Silvana,Spallarossa, Andrea,Caneva, Chiara
, p. 10858 - 10868 (2014/01/06)
A simple one-pot procedure for the stereoselective synthesis of Knoevenagel-type indoles is described. The method is based on the in situ reaction of indole iminium salts (four of them are fully characterized) with acyclic symmetrical and unsymmetrical active methylene reagents in the presence of triethylamine. In general, the overall yields are moderate to good. Some of relevant reaction parameters and steric effects affecting stereoselectivity are discussed.
Synthesis of Various Pyrazole-1-carbonylindoles
Hiremath, Shivayogi P.,Ullagaddi, Ashok,Sekhar, K. Raja,Purohit, Muralidhar G.
, p. 758 - 762 (2007/10/02)
Indole-2-carbohydrazides (1a-n) when heated with acetylacetone and ethyl acetoacetate in methanol afford the substituted 2-(3',5'-dimethylpyrazole-1'-carbonyl)indoles (2a-n) and 3-methyl-1(2'-indolyl)-5(4H)-pyrazolones (3e-a), respectively in good yields.The schiff's bases (4a-h) from hydrazides (1a-h) and acetophenone on reaction with POCl3 and DMF produce the substituted 2-(4'-formyl-3'-phenylpyrazole-1'-carbonyl)indoles (5a-h).Indole-3-carboxaldehydes (6a-f) undergo condensation with ethyl cyanoacetate and malononitrile to give the acrylonitriles 7a-f and 9a-e which on reaction with hydrazine hydrate yield 3-amino-5-hydroxy-4-(3'-indolylmethylene)pyrazoles (8a-f) and 3,5-diamino-4-(3'-indolylmethylene)pyrazoles (10a-e), respectively.Similarly indole-2-carboxaldehydes (11a-d) react with ethyl cyanoacetate and hydrazine hydrate to furnish the respective pyrazoles (13a-d).
