New Synthesis of Isoindolo[2,1–b]isoquinolines. Preparation and Aqueous Bioavailability of its Silica Nanoparticles Hybrid System

Title:New Synthesis of Isoindolo[2,1–b]isoquinolines. Preparation and Aqueous Bioavailability of its Silica Nanoparticles Hybrid System

Volume: 19 Issue: 13

Author(s): Amelia Diaz, J. Manuel Lopez–Romero, Rafael Contreras-Caceres, Manuel Algarra, Rodrigo Rico and Maria Valpuesta

Affiliation:

Keywords: Alkaloid, aza-heterocyclic, cascade reaction, conformational analysis, drug delivery, isoquinolone, oxalyl chloride, toposiomerase- 1.

Abstract: In this paper we report a new strategy for the synthesis of isoindolo[2,1-b]isoquinolines. N-(1,2- Diphenylethyl)acetamides prepared from the corresponding deoxybenzoins were used as starting material. Double cascade cyclization of the amides promoted by oxalyl chloride and stannyl chloride afforded the oxidized isoindolo[ 2,1-b]isoquinolinone derivatives, which by reduction with a BH3·THF complex gave the 5,7,11b,12- tetrahydroisoindolo[2,1-b]isoquinolines 1b and 1d. Cyclization and reduction were also carried out in one-pot reaction improving the overall yield. DFT structural analysis of the tetrahydro derivatives showed a constrained and planar structure similar to that of camptothecin. SiO2 nanoparticles of 1b (1b-SiNP) were also prepared. This hybrid material provides a very good bioavailability for these compounds in aqueous systems.

Cite this article as:

Diaz Amelia, Lopez–Romero J. Manuel, Contreras-Caceres Rafael, Algarra Manuel, Rico Rodrigo and Valpuesta Maria, New Synthesis of Isoindolo[2,1–b]isoquinolines. Preparation and Aqueous Bioavailability of its Silica Nanoparticles Hybrid System, Current Organic Chemistry 2015; 19 (13) . https://dx.doi.org/10.2174/1385272819666150410004957