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
-
Recent Advances in Gene Therapy of Endometriosis
Recent Patents on DNA & Gene Sequences Death Receptor Signaling in Cancer Therapy
Current Medicinal Chemistry - Anti-Cancer Agents Gene Therapy for Bone Regeneration
Current Pharmaceutical Design Strategies to Convert PACAP from a Hypophysiotropic Neurohormone Into a Neuroprotective Drug
Current Pharmaceutical Design Subject Index Volume 2
Current Pediatric Reviews Application of Selenium Nanoparticles in Localized Drug Targeting for Cancer Therapy
Anti-Cancer Agents in Medicinal Chemistry Profiling of Autophagy-Associated microRNAs in the Osteosarcoma Cell Line of U2OS
Anti-Cancer Agents in Medicinal Chemistry Protective Effect of α-ketobutyrate on Survival of Hippocampal Neurons Challenged with Hydrogen Peroxide Chemistry Mimicking Brain Ischemia
Current Pharmaceutical Analysis 4-Methylumbelliferones Analogues as Anticancer Agents: Synthesis and in Cell Pharmacological Studies
Anti-Cancer Agents in Medicinal Chemistry WT1 Peptide Vaccine as a Paradigm for “Cancer Antigen-Derived Peptide”-Based Immunotherapy for Malignancies: Successful Induction of Anti-Cancer Effect by Vaccination with a Single Kind of WT1 Peptide
Anti-Cancer Agents in Medicinal Chemistry Heat Shock Proteins as Prognostic Markers of Cancer
Current Cancer Drug Targets Advances in Interleukin-12 Gene Therapy for Acquired Liver Diseases
Current Gene Therapy CXCL12-CXCR4 Axis in Angiogenesis, Metastasis and Stem Cell Mobilization
Current Pharmaceutical Design Nanocarriers to Solid Tumors: Considerations on Tumor Penetration and Exposure of Tumor Cells to Therapeutic Agents
Current Pharmaceutical Biotechnology Nanotechnology and Animal Health
Pharmaceutical Nanotechnology Cellular Toxicity and Apoptosis Studies in Osteocarcinoma Cells, a Comparison of 177Lu-EDTMP and Lu-EDTMP
Current Radiopharmaceuticals Rapid Assays for Quantitating Cytokine Gene Expression Without Target Amplification
Combinatorial Chemistry & High Throughput Screening Targeting Telomerase by Antisense-Based Approaches: Perspectives for New Anti-Cancer Therapies
Current Pharmaceutical Design Multi-Modal Imaging and Cancer Therapy Using Lanthanide Oxide Nanoparticles: Current Status and Perspectives
Current Medicinal Chemistry Double-Faced Role of Human Mesenchymal Stem Cells and their Role/Challenges in Cancer Therapy
Current Stem Cell Research & Therapy