Abstract
A new series of 9-O-3-(1-piperazinyl/morpholinyl/piperidinyl)pentyl-berberines has been efficiently formulated via coupling 1,5-dibromopentane with berberrubine which was obtained by treating berberine in a vacuum oven at optimum temperature and pressure. Nucleophilic substitution of a variety of substituted piperazines, morpholine, carbazole and piperidine furnished analogues 5a-i. Final compounds were evaluated for their in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6- sulphonic acid) (ABTS) bioassays. Also, cancer cell inhibitory potential of titled compounds was screened for cervical cancer, HeLa and CaSki employing SRB assay in terms of cytotoxicity. A minimum inhibitory concentration of 5a-i towards normal cells was studied using Madin-Darby canine kidney (MDCK) cell line. Final compounds with carbazole and 1-(naphthalen-2-yl)piperazine showed excellent free radical scavenging efficacies in DPPH and ABTS bioassays, respectively. The presence of naphthyl, benzhydryl, benzoyl, furoyl and heterocyclic rings on the piperazine system was essential to exert anticipated cytotoxic effects against cancer cell lines. The structure of the final compounds was adequately confirmed via spectroscopic techniques, elemental analysis analysis and characterization of physical properties.
Keywords: Berberine, piperazine, piperidine, carbazole, morpholine, antioxidant, cytotoxicity, cervical cancer, DPPH assay, ABTS assay.
Anti-Cancer Agents in Medicinal Chemistry
Title:Synthesis of 9-O-3-(1-piperazinyl/morpholinyl/piperidinyl)pentyl-berberines as Potential Antioxidant and Cytotoxic Agents
Volume: 16 Issue: 6
Author(s): Bhupendra M. Mistry, Rahul V. Patel, Young-Soo Keum and Doo Hwan Kim
Affiliation:
Keywords: Berberine, piperazine, piperidine, carbazole, morpholine, antioxidant, cytotoxicity, cervical cancer, DPPH assay, ABTS assay.
Abstract: A new series of 9-O-3-(1-piperazinyl/morpholinyl/piperidinyl)pentyl-berberines has been efficiently formulated via coupling 1,5-dibromopentane with berberrubine which was obtained by treating berberine in a vacuum oven at optimum temperature and pressure. Nucleophilic substitution of a variety of substituted piperazines, morpholine, carbazole and piperidine furnished analogues 5a-i. Final compounds were evaluated for their in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6- sulphonic acid) (ABTS) bioassays. Also, cancer cell inhibitory potential of titled compounds was screened for cervical cancer, HeLa and CaSki employing SRB assay in terms of cytotoxicity. A minimum inhibitory concentration of 5a-i towards normal cells was studied using Madin-Darby canine kidney (MDCK) cell line. Final compounds with carbazole and 1-(naphthalen-2-yl)piperazine showed excellent free radical scavenging efficacies in DPPH and ABTS bioassays, respectively. The presence of naphthyl, benzhydryl, benzoyl, furoyl and heterocyclic rings on the piperazine system was essential to exert anticipated cytotoxic effects against cancer cell lines. The structure of the final compounds was adequately confirmed via spectroscopic techniques, elemental analysis analysis and characterization of physical properties.
Export Options
About this article
Cite this article as:
Mistry M. Bhupendra, Patel V. Rahul, Keum Young-Soo and Kim Hwan Doo, Synthesis of 9-O-3-(1-piperazinyl/morpholinyl/piperidinyl)pentyl-berberines as Potential Antioxidant and Cytotoxic Agents, Anti-Cancer Agents in Medicinal Chemistry 2016; 16 (6) . https://dx.doi.org/10.2174/1871520615666151009114759
DOI https://dx.doi.org/10.2174/1871520615666151009114759 |
Print ISSN 1871-5206 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5992 |
Call for Papers in Thematic Issues
Advances in Nanomedicines and Targeted Therapies for Colorectal Cancer
Colorectal cancer remains a significant global health challenge, with high incidence and mortality rates despite advancements in treatment strategies. Conventional therapies often face limitations such as systemic toxicity, drug resistance, and suboptimal targeting. The advent of nanomedicines and innovative drug delivery systems offers new hope for overcoming these challenges and ...read more
Discovery of Lead compounds targeting transcriptional regulation
Transcriptional regulation plays key physiological functions in body growth and development. Transcriptional dysregulation is one of the important biomarkers of tumor genesis and progression, which is involved in regulating tumor cell processes such as cell proliferation, differentiation, and apoptosis. Additionally, it plays a pivotal role in angiogenesis and promotes tumor ...read more
Induction of cell death in cancer cells by modulating telomerase activity using small molecule drugs
Telomeres are distinctive but short stretches present at the corners of chromosomes that aid in stabilizing chromosomal makeup. The resynthesis of telomeres is supported by the activity of reverse transcriptase ribonucleoprotein complex telomerase. There is no telomerase activity in human somatic cells, but the stem cells and germ cells undergo ...read more
Innovative targets in medicinal chemistry
Medicinal chemistry continuously evolves in response to emerging healthcare needs and advancements in scientific understanding. This special issue explores the current landscape of innovative targets in medicinal chemistry, highlighting the quest for novel therapeutic avenues. From traditional drug targets such as enzymes and receptors to emerging targets like protein-protein interactions ...read more
- 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
Related Articles
-
Therapeutic Applications of Crocus sativus L. (Saffron): A Review
The Natural Products Journal Targeting mTOR Pathways in Human Malignancies
Current Pharmaceutical Design Inhibitors of the Immunoproteasome: Current Status and Future Directions
Current Pharmaceutical Design Computer-Aided Drug Design Applied to Secondary Metabolites as Anticancer Agents
Current Topics in Medicinal Chemistry Burden and Prevention of HPV. Knowledge, Practices and Attitude Assessment Among Pre-Adolescents and their Parents in Italy
Current Pharmaceutical Design Combined Treatment with Laser Ablation and Tyrosine-Kinase Inhibitor as A Novel Multimodality Approach to Locally Advanced Thyroid Cancer: A Case Report
Endocrine, Metabolic & Immune Disorders - Drug Targets Heat Shock Factor 1-Regulated miRNAs Can Target Huntingtin and Suppress Aggregates of Mutant Huntingtin
MicroRNA Oxytocin and Diabetes Mellitus: A Strong Biochemical Relation. Review
Current Diabetes Reviews Fgf10: A Paracrine-Signaling Molecule in Development, Disease, and Regenerative Medicine
Current Molecular Medicine Alpha-Interferon and Its Effects on Signalling Pathways Within Cells
Current Protein & Peptide Science Gamma Secretase Inhibitor: Therapeutic Target via NOTCH Signaling in T Cell Acute Lymphoblastic Leukemia
Current Drug Targets A SAR Study: Evaluation of Bromo Derivatives of 8-Substituted Quinolines as Novel Anticancer Agents
Letters in Drug Design & Discovery Cranberry as Promising Natural Source of Potential Anticancer Agents: Current Evidence and Future Perspectives
Anti-Cancer Agents in Medicinal Chemistry A Review of the Recent Developments in Synthetic Anti-Breast Cancer Agents
Anti-Cancer Agents in Medicinal Chemistry Environmental Risk Assessment of Replication Competent Viral Vectors Applied in Clinical Trials: Potential Effects of Inserted Sequences
Current Gene Therapy Development of Ribonucleotide Reductase Inhibitors: A Review on Structure Activity Relationships
Mini-Reviews in Medicinal Chemistry Heteroaromatization of Coumarin Part I: Design, Synthesis, Reactions, Antitumor Activities of Novel Pyridine and Naphthyridine Derivatives
Current Organic Synthesis Synthesis, Cytotoxicity and Antioxidant Activity of New Analogs of RC-121 Synthetic Derivatives of Somatostatin
Anti-Cancer Agents in Medicinal Chemistry MiRNAs in Human Cancers: The Diagnostic and Therapeutic Implications
Current Pharmaceutical Design Morin Inhibits Ovarian Cancer Growth through the Inhibition of NF-κB Signaling Pathway
Anti-Cancer Agents in Medicinal Chemistry