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.
Export Options
About this article
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 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Development of Patents and Clinical Trials on Regenerative Therapy: Gene Therapy
Recent Patents on Regenerative Medicine Novel Agents Targeting Bioactive Sphingolipids for the Treatment of Cancer
Current Medicinal Chemistry The Roles of Parathyroid Hormone and Calcitonin in Bone Remodeling: Prospects for Novel Therapeutics
Endocrine, Metabolic & Immune Disorders - Drug Targets Potential of Modulating Wnt Signaling Pathway Toward the Development of Bone Anabolic Agent
Current Molecular Pharmacology Modified Polysaccharides as Carriers for Biomolecules
Pharmaceutical Nanotechnology Effect of Proteasome Inhibitors on the AAV-Mediated Transduction Efficiency in Retinal Bipolar Cells
Current Gene Therapy Recent Nanocarrier Approaches for Targeted Drug Delivery in Cancer Therapy
Current Molecular Pharmacology FAK and p53 Protein Interactions
Anti-Cancer Agents in Medicinal Chemistry APE1/Ref-1Role in Redox Signaling: Translational Applications of Targeting the Redox Function of the DNA Repair/Redox Protein APE1/Ref-1
Current Molecular Pharmacology Iontophoretic Mediated Intraarticular Delivery of Deformable Liposomes of Diclofenac Sodium
Current Drug Delivery Cellular Changes, Molecular Pathways and the Immune System Following Photodynamic Treatment
Current Medicinal Chemistry Renal and Hepatic Kinetics of Tc-99m-labelled Hexakis-methoxy-isobutyl Isonitrile
Drug Metabolism Letters Perspective of Cyclin-dependent kinase 9 (CDK9) as a Drug Target
Current Pharmaceutical Design Epigenetic Regulation of Osteogenic Differentiation of Mesenchymal Stem Cells
Current Stem Cell Research & Therapy Gene Delivery by Functional Inorganic Nanocarriers
Recent Patents on DNA & Gene Sequences A Natural Membrane Vesicle Exosome-based Sinomenine Delivery Platform for Hepatic Carcinoma Therapy
Current Topics in Medicinal Chemistry Liposomes: An Emerging Approach for the Treatment of Cancer
Current Pharmaceutical Design The Problem of Amino Acid Complementarity and Antisense Peptides
Current Protein & Peptide Science Emerging Anabolic Treatments in Osteoporosis
Current Drug Safety Cancer Stem Cells: The ‘Achilles Heel’ of Chemo-Resistant Tumors
Recent Patents on Anti-Cancer Drug Discovery