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
-
Prediction of Disease-Related Genes Based on Hybrid Features
Current Proteomics MicroRNA-183 Functions As an Oncogene by Regulating PDCD4 in Gastric Cancer
Anti-Cancer Agents in Medicinal Chemistry Targeting the Lung: Preclinical and Comparative Evaluation of Anticancer Aerosols in Dogs with Naturally Occurring Cancers
Current Cancer Drug Targets ICE Regimen for Relapsed/Refractory Bone and Soft Tissue Sarcomas in Children
Reviews on Recent Clinical Trials Selective Thyroid Hormone Receptor Modulators
Current Topics in Medicinal Chemistry Cancer Gene Therapy through Autonomous Parvovirus - Mediated Gene Transfer
Current Gene Therapy Estrogen Receptor Neurobiology and its Potential for Translation into Broad Spectrum Therapeutics for CNS Disorders
Current Molecular Pharmacology Diverse Roles of GADD45α in Stress Signaling
Current Protein & Peptide Science To Cardiovascular Disease and Beyond: New Therapeutic Perspectives of Statins in Autoimmune Diseases and Cancer
Current Drug Targets Alpha-Particle Microdosimetry
Current Radiopharmaceuticals The PAX8 / PPARγ Fusion Oncogene as a Potential Therapeutic Target in Follicular Thyroid Carcinoma
Current Drug Targets - Immune, Endocrine & Metabolic Disorders MicroRNA-212-3p Attenuates Neuropathic Pain via Targeting Sodium Voltage-gated Channel Alpha Subunit 3 (NaV 1.3)
Current Neurovascular Research Role of Nitric Oxide in Motor Control: Implications for Parkinsons Disease Pathophysiology and Treatment
Current Pharmaceutical Design Development and Uses of Offline and Web-Searchable Metabolism Databases - The Case of Benzo[a]pyrene
Current Drug Metabolism Targeting Tumor Suppressor p53 for Cancer Therapy: Strategies, Challenges and Opportunities
Current Drug Targets Galanthus nivalis Agglutinin (GNA)-Related Lectins: Traditional Proteins, Burgeoning Drugs?
Current Chemical Biology Development and Clinical Application of Peptide-Based Radiopharmaceuticals
Current Pharmaceutical Design Bioactive Triterpenic Acids: From Agroforestry Biomass Residues to Promising Therapeutic Tools
Mini-Reviews in Organic Chemistry Fluoride Effects: The Two Faces of Janus
Current Medicinal Chemistry HtrA Protease Family as Therapeutic Targets
Current Pharmaceutical Design