BIOMAT Database Logo BIOMAT Database Logo

1,5-Benzothiazepine Derivatives: Green Synthesis, In Silico and In Vitro Evaluation as Anticancer Agents. 2022

Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Hofuf 31982, Al-Ahsa, Saudi Arabia.

Considering the importance of benzothiazepine pharmacophore, an attempt was carried out to synthesize novel 1,5-benzothiazepine derivatives using polyethylene glycol-400 (PEG-400)-mediated pathways. Initially, different chalcones were synthesized and then subjected to a cyclization step with benzothiazepine in the presence of bleaching clay and PEG-400. PEG-400-mediated synthesis resulted in a yield of more than 95% in less than an hour of reaction time. Synthesized compounds 2a-2j were investigated for their in vitro cytotoxic activity. Moreover, the same compounds were subjected to systematic in silico screening for the identification of target proteins such as human adenosine kinase, glycogen synthase kinase-3β, and human mitogen-activated protein kinase 1. The compounds showed promising results in cytotoxicity assays; among the tested compounds, 2c showed the most potent cytotoxic activity in the liver cancer cell line Hep G-2, with an IC50 of 3.29 ± 0.15 µM, whereas the standard drug IC50 was 4.68 ± 0.17 µM. In the prostate cancer cell line DU-145, the compounds displayed IC50 ranges of 15.42 ± 0.16 to 41.34 ± 0.12 µM, while the standard drug had an IC50 of 21.96 ± 0.15 µM. In terms of structural insights, the halogenated phenyl substitution on the second position of benzothiazepine was found to significantly improve the biological activity. This characteristic feature is supported by the binding patterns on the selected target proteins in docking simulations. In this study, 1,5-benzothiazepines have been identified as potential anticancer agents which can be further exploited for the development of more potent derivatives.

UI MeSH Term Description Entries
D008297 Male Males
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D004354 Drug Screening Assays, Antitumor Methods of investigating the effectiveness of anticancer cytotoxic drugs and biologic inhibitors. These include in vitro cell-kill models and cytostatic dye exclusion tests as well as in vivo measurement of tumor growth parameters in laboratory animals. Anticancer Drug Sensitivity Tests,Antitumor Drug Screens,Cancer Drug Tests,Drug Screening Tests, Tumor-Specific,Dye Exclusion Assays, Antitumor,Anti-Cancer Drug Screens,Antitumor Drug Screening Assays,Tumor-Specific Drug Screening Tests,Anti Cancer Drug Screens,Anti-Cancer Drug Screen,Antitumor Drug Screen,Cancer Drug Test,Drug Screen, Anti-Cancer,Drug Screen, Antitumor,Drug Screening Tests, Tumor Specific,Drug Screens, Anti-Cancer,Drug Screens, Antitumor,Drug Test, Cancer,Drug Tests, Cancer,Screen, Anti-Cancer Drug,Screen, Antitumor Drug,Screens, Anti-Cancer Drug,Screens, Antitumor Drug,Test, Cancer Drug,Tests, Cancer Drug,Tumor Specific Drug Screening Tests
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013841 Thiazepines Compounds that are derivatives of THIEPINS, with a nitrogen replacing a carbon in the seven-membered heterocyclic compound. Thiazepine
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D045744 Cell Line, Tumor A cell line derived from cultured tumor cells. Tumor Cell Line,Cell Lines, Tumor,Line, Tumor Cell,Lines, Tumor Cell,Tumor Cell Lines

Related Publications

Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Evaluation of 2,3-Dihydro-1,5-benzothiazepine Derivatives as Potential Tyrosinase Inhibitors: In Vitro and In Silico Studies.
May 2023, ACS omega,
Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Diacylphloroglucinol derivatives as antioxidant agents: green synthesis, optimisation, in vitro, and in silico evaluation.
March 2022, Natural product research,
Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Synthesis and biological evaluation of a novel series of 1,5-benzothiazepine derivatives as potential antimicrobial agents.
July 2009, European journal of medicinal chemistry,
Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Uridine Derivatives: Synthesis, Biological Evaluation, and In Silico Studies as Antimicrobial and Anticancer Agents.
June 2023, Medicina (Kaunas, Lithuania),
Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Synthesis, Biological and Computational Evaluation of Novel 2,3-dihydro-2-aryl-4-(4- isobutylphenyl)-1,5-benzothiazepine Derivatives as Anticancer and Anti-EGFR Tyrosine Kinase Agents.
January 2020, Anti-cancer agents in medicinal chemistry,
Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Novel lycorine derivatives as anticancer agents: synthesis and in vitro biological evaluation.
February 2014, Molecules (Basel, Switzerland),
Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation.
July 2021, Molecules (Basel, Switzerland),
Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Design, synthesis and in vitro evaluation of fangchinoline derivatives as potential anticancer agents.
January 2020, Bioorganic chemistry,
Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Green synthesis and biological evaluation of novel 5-fluorouracil derivatives as potent anticancer agents.
December 2019, Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society,
Michelyne Haroun, and Santosh S Chobe, and Rajasekhar Reddy Alavala, and Savita M Mathure, and Risy Namratha Jamullamudi, and Charushila K Nerkar, and Vijay Kumar Gugulothu, and Christophe Tratrat, and Mohammed Monirul Islam, and Katharigatta N Venugopala, and Mohammed Habeebuddin, and Mallikarjun Telsang, and Nagaraja Sreeharsha, and Md Khalid Anwer
Biological Evaluation in Vitro and in Silico of Azetidin-2-one Derivatives as Potential Anticancer Agents.
January 2017, ACS medicinal chemistry letters,
Copied contents to your clipboard!