94004-61-2Relevant academic research and scientific papers
Nenitzescu Synthesis of 5-Hydroxyindoles with Zinc, Iron and Magnesium Salts in Cyclopentyl Methyl Ether
Azzena, Ugo,Beccu, Andrea,Carboni, Silvia,Carraro, Massimo,De Luca, Lidia,Gaspa, Silvia,Livesi, Marco,Pira, Giovanni Michele,Pisano, Luisa,R?mer, Melina,Satta, Giuseppe,Solinas, Angelo,Usala, Elena
, p. 5835 - 5842 (2021/11/17)
In this work, mild Lewis acids and low environmental impact solvents were investigated for Nenitzescu synthesis. Cyclopentyl methyl ether can be used at room temperature in substitution of halogenated solvents with zinc, iron and magnesium salts as homogeneous catalysts to give 5-hydroxyindoles in fair to good yields. The reaction features a straightforward workup and excellent solvent recycle.
Structural comparison of Mtb-DHFR and h-DHFR for design, synthesis and evaluation of selective non-pteridine analogues as antitubercular agents
Sharma, Kalicharan,Tanwar, Omprakash,Sharma, Shweta,Ali, Shakir,Alam,Zaman,Akhter, Mymoona
, p. 319 - 333 (2018/07/25)
Tuberculosis is an infectious disease that affects millions of population every year. Mtb-DHFR is a validated target that is vital for nucleic acids biosynthesis and therefore DNA formation and cell replication. This paper report identification and synthesis of novel compounds for selective inhibition of Mtb-DHFR and unleash the selective structural features necessary to inhibit the same. Virtual screening of databases was carried out to identify novel compounds on the basis of difference between the binding pockets of the two proteins. Consensus docking was performed to improve upon the results and best ten hits were selected. Hit 1 was subjected to analogues design and the analogues were docked against Mtb-DHFR. From the docking results 11 compounds were selected for synthesis and biological assay against H37Rv. Most potent compound (IND-07) was tested for selectivity using enzymatic assay against Mtb-DHFR and h-DHFR. The compounds were found to have good inhibitory activity (25–200 μM) against H37Rv and in enzyme assay against Mtb-DHFR and h-DHFR the compound was found selective towards Mtb-DHFR with selectivity index of 6.53. This work helped to identify indole moiety as novel scaffold for development of novel selective Mtb-DHFR inhibitors as antimycobacterial agents.
Lewis acid catalyzed Nenitzescu indole synthesis
Velezheva, Valeriya S.,Kornienko, Albert G.,Topilin, Sergey V.,Turashev, Ascar D.,Peregudov, Alexander S.,Brennan, Patrick J.
, p. 873 - 879 (2007/10/03)
A novel method for Lewis acid catalyzed Nenitzescu indole syntheses of 5-hydroxyindoles bearing different substituents in positions 1 (Alk, Bn, Ar), 2 (Me, Et, Ph), and 3 (COOEt, COMe, CONHPh) as well as tricyclic derivatives are reported. The method is simple, rapid, efficient, and allows preparation of hydroxyindoles from 1,4-benzoquinone and enamines in good to excellent yields with the use of low-polar solvents in the presence of weak Lewis acids catalysts. The formation of 5-hydroxyindoles under such mild conditions is explained in terms of a non-redox mechanism.
