Abstract
Novel compounds containing both benzothiazole and azelayl scaffolds were synthesized through Schotten Baumann type reaction between azelayl chloride methyl ester and a series of 2-aminobenzothiazole derivatives bearing different substituents on the aromatic carbocyclic ring. The design of the new hybrids was inspired by their analogy with the structure of some HDAC inhibitors, such as Vorinostat and 9-hydroxystearic acid. Molecular docking on some compounds predicted an activity as inhibitors of HDAC, and this prediction was confirmed by in vitro essays on a human colon cancer cells line (HT 29). The antimicrobial activity against some representative human pathogens and several Lactobacillus and Bifidobacterium strains isolated from human microbiotas was also evaluated. The new hybrids showed antiproliferative activity on cancer cells while no antimicrobial activity was observed in the range of concentrations used for cancer cells and this finding might represent an important tool in the fight against cancer minimizing some side effects on the microbiotas typical of an anticancer treatment.
Keywords: 2-Aminobenzothiazole, azelaic acid, schotten baumann, colon cancer, histone deacetylase inhibitors, 9-hydroxystearic acid, vorinostat.
Current Organic Chemistry
Title:New Hybrids with 2-aminobenzothiazole and Azelayl Scaffolds: Synthesis, Molecular Docking and Biological Evaluation
Volume: 22 Issue: 16
Author(s): Carla Boga*, Gabriele Micheletti*, Isabel Orlando, Elena Strocchi, Beatrice Vitali, Laura Verardi, Giorgio Sartor and Natalia Calonghi
Affiliation:
- Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Bologna,Italy
- Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Bologna,Italy
Keywords: 2-Aminobenzothiazole, azelaic acid, schotten baumann, colon cancer, histone deacetylase inhibitors, 9-hydroxystearic acid, vorinostat.
Abstract: Novel compounds containing both benzothiazole and azelayl scaffolds were synthesized through Schotten Baumann type reaction between azelayl chloride methyl ester and a series of 2-aminobenzothiazole derivatives bearing different substituents on the aromatic carbocyclic ring. The design of the new hybrids was inspired by their analogy with the structure of some HDAC inhibitors, such as Vorinostat and 9-hydroxystearic acid. Molecular docking on some compounds predicted an activity as inhibitors of HDAC, and this prediction was confirmed by in vitro essays on a human colon cancer cells line (HT 29). The antimicrobial activity against some representative human pathogens and several Lactobacillus and Bifidobacterium strains isolated from human microbiotas was also evaluated. The new hybrids showed antiproliferative activity on cancer cells while no antimicrobial activity was observed in the range of concentrations used for cancer cells and this finding might represent an important tool in the fight against cancer minimizing some side effects on the microbiotas typical of an anticancer treatment.
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Cite this article as:
Boga Carla *, Micheletti Gabriele *, Orlando Isabel , Strocchi Elena , Vitali Beatrice , Verardi Laura , Sartor Giorgio and Calonghi Natalia , New Hybrids with 2-aminobenzothiazole and Azelayl Scaffolds: Synthesis, Molecular Docking and Biological Evaluation, Current Organic Chemistry 2018; 22 (16) . https://dx.doi.org/10.2174/1385272822666180803122010
DOI https://dx.doi.org/10.2174/1385272822666180803122010 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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