Abstract
A series of 2-phenylbenzothiazoles has been synthesized either by i) condensation of different aromatic aldehydes with 2-aminothiophenol or ii) condensation of N-(2-chlorophenyl)benzothioamides in KOH catalyzed by potassium fericyanide. The structures of synthesized compounds were confirmed by IR, MS, and 1H-NMR. The results of biological activity screening showed that six compounds including 2-phenylbenzothiazol (1a), 2-(2-chlorophenyl)benzothiazole (1b), 2- (3-chlorophenyl)benzothiazole (1c), 2-(4-hydroxyphenyl)benzothiazole (1e), 2-(4-dimethylaminophenyl)benzothiazole (1h) and 2-(2,3,4-trimethoxyphenyl)benzothiazole (1i) exhibited significant antibacterial activities; two compounds (1a, 1e) exhibited antifungal activities. Especially, 1e showed considerable antimicrobial activity against both A. niger and F. oxysporum. The brominated derivative of 1e displayed extended spectrum against all four bacterial strains tested with lower MIC values. In vitro cytotoxicity of the synthesized compounds was evaluated on three cancer cell lines (A549, HT1080, MCF7-MDR). The results indicated that three compounds (1e, 1g, 1i) exhibited significant cytotoxic activity on A549 and MCF7-ADR cells (IC50, 10.07-13.21μg/ml). Brominated and nitrated derivatives (1k, 1l, respectively) of 1e exhibited even more potent cytotoxicity.
Keywords: 2-Phenylbenzothiazole, synthesis, cytotoxicity, antibacterial, antifungal, condensation, aromatic aldehydes, antimicrobial, IR, MS, 1H-NMR
Medicinal Chemistry
Title: Synthesis and Biological Evaluation of a Series of 2-(Substitutedphenyl) benzothiazoles
Volume: 7 Issue: 2
Author(s): Nguyen Hai Nam, Phan Thi Phuong Dung and Phuong Thien Thuong
Affiliation:
Keywords: 2-Phenylbenzothiazole, synthesis, cytotoxicity, antibacterial, antifungal, condensation, aromatic aldehydes, antimicrobial, IR, MS, 1H-NMR
Abstract: A series of 2-phenylbenzothiazoles has been synthesized either by i) condensation of different aromatic aldehydes with 2-aminothiophenol or ii) condensation of N-(2-chlorophenyl)benzothioamides in KOH catalyzed by potassium fericyanide. The structures of synthesized compounds were confirmed by IR, MS, and 1H-NMR. The results of biological activity screening showed that six compounds including 2-phenylbenzothiazol (1a), 2-(2-chlorophenyl)benzothiazole (1b), 2- (3-chlorophenyl)benzothiazole (1c), 2-(4-hydroxyphenyl)benzothiazole (1e), 2-(4-dimethylaminophenyl)benzothiazole (1h) and 2-(2,3,4-trimethoxyphenyl)benzothiazole (1i) exhibited significant antibacterial activities; two compounds (1a, 1e) exhibited antifungal activities. Especially, 1e showed considerable antimicrobial activity against both A. niger and F. oxysporum. The brominated derivative of 1e displayed extended spectrum against all four bacterial strains tested with lower MIC values. In vitro cytotoxicity of the synthesized compounds was evaluated on three cancer cell lines (A549, HT1080, MCF7-MDR). The results indicated that three compounds (1e, 1g, 1i) exhibited significant cytotoxic activity on A549 and MCF7-ADR cells (IC50, 10.07-13.21μg/ml). Brominated and nitrated derivatives (1k, 1l, respectively) of 1e exhibited even more potent cytotoxicity.
Export Options
About this article
Cite this article as:
Hai Nam Nguyen, Thi Phuong Dung Phan and Thien Thuong Phuong, Synthesis and Biological Evaluation of a Series of 2-(Substitutedphenyl) benzothiazoles, Medicinal Chemistry 2011; 7 (2) . https://dx.doi.org/10.2174/157340611794859361
DOI https://dx.doi.org/10.2174/157340611794859361 |
Print ISSN 1573-4064 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6638 |

- Author Guidelines
- Bentham Author Support Services (BASS)
- 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
Related Articles
-
A Comprehensive Review of Dysregulated miRNAs Involved in Cervical Cancer
Current Genomics Genetically Engineered Bacteriocins and their Potential as the Next Generation of Antimicrobials
Current Pharmaceutical Design Epigenetic Mechanism Involved in the HBV/HCV-Related Hepatocellular Carcinoma Tumorigenesis
Current Pharmaceutical Design Betulinic Acid and Brosimine B Hybrid Derivatives as Potential Agents against Female Cancers
Anti-Cancer Agents in Medicinal Chemistry AIDS in African Nonhuman Primate Hosts of SIVs: A New Paradigm of SIV Infection
Current HIV Research Azacitidine, as a DNMT Inhibitor Decreases hTERT Gene Expression and Telomerase Activity More Effective Compared with HDAC Inhibitor in Human Head and Neck Squamous Cell Carcinoma Cell Lines
Current Molecular Pharmacology Radiopharmaceuticals for Oncology Drug Development: A Pharmaceutical Industry Perspective
Current Pharmaceutical Design Current Clinical Applications of Botulinum Toxin
Current Pharmaceutical Design Pleiotropic Effect of Mahanine and Girinimbine Analogs: Anticancer Mechanism and its Therapeutic Versatility
Anti-Cancer Agents in Medicinal Chemistry Advancement of Targeted Ultrasound Contrast Agents and their Applications in Molecular Imaging and Targeted Therapy
Current Pharmaceutical Design Drug-Loaded Nanocarriers in Tumor Targeted Drug Delivery
Current Biotechnology Oncogenic Properties of HIV-Tat in Colorectal Cancer Cells
Current HIV Research Anti-Cancerous Effect of Rutin Against HPV-C33A Cervical Cancer Cells via G0/G1 Cell Cycle Arrest and Apoptotic Induction
Endocrine, Metabolic & Immune Disorders - Drug Targets Small Heat Shock Proteins and the Endoplasmic Reticulum: Potential Attractive Therapeutic Targets?
Current Molecular Medicine P-Selectin Glycoprotein Ligand-1 as a Potential Target for Humoral Immunotherapy of Multiple Myeloma (Supplementry Material)
Current Cancer Drug Targets Image-Guided Photonic Energy Deposition for Cancer Ablation and Drug Delivery
Current Medical Imaging Cell Arrest and Apoptosis Induced by the Next Generation of Vanadium Based Drugs: Action Mechanism to Structure Relation and Future Perspectives
Anti-Cancer Agents in Medicinal Chemistry Microarray Analysis of Human Epithelial Cell Responses to Bacterial Interaction
Infectious Disorders - Drug Targets Sleep Duration as a Risk Factor for Cardiovascular Disease- a Review of the Recent Literature
Current Cardiology Reviews Zinc Dependent Histone Deacetylase Inhibitors in Cancer Therapeutics: Recent Update
Current Medicinal Chemistry