Abstract
Six new arylpiperazinylbenzofurane derivatives as potential hybrid antihypertensive agents were designed and synthesized. The discussed compounds were prepared as free bases and subsequently they were transformed into hydrochloride salts. The position of preferential protonation of nitrogen in piperazine ring in hydrochloride salts was determined by means of IR spectra, 13C CP/MAS NMR spectra and 15N CP/MAS NMR spectra. These results were supported by ab initio/DFT calculations of partial charges and proton affinities. Physico-chemical properties of free bases and hydrochloride salts are discussed; especially partition and distributive coefficients log P and log D7.4, dissociation constants pKa, molecular surfaces and volumes. The experimental results were also subsequently correlated with ab initio/DFT calculations.
Keywords: Antihypertensive Agents, Synthesis, arylpiperazinylbenzofurane derivatives, hydrochloride salts, Physico-chemical properties, Hypertension, cardiovascular system
Current Organic Chemistry
Title: Synthesis, Characterization and Physico-chemical Properties of New 2-(4- Arylpiperazine-1-yl)-1-(3-methylbenzofuran-2-yl)ethanoles as Potential Antihypertensive Agents
Volume: 13 Issue: 10
Author(s): Radka Opatrilova, Josef Jampilek, Ivan Raich, Sandra Kacerova, Jaroslav Havlicek, Tomas Pekarek, Jiri Dohnal and Jozef Csollei
Affiliation:
Keywords: Antihypertensive Agents, Synthesis, arylpiperazinylbenzofurane derivatives, hydrochloride salts, Physico-chemical properties, Hypertension, cardiovascular system
Abstract: Six new arylpiperazinylbenzofurane derivatives as potential hybrid antihypertensive agents were designed and synthesized. The discussed compounds were prepared as free bases and subsequently they were transformed into hydrochloride salts. The position of preferential protonation of nitrogen in piperazine ring in hydrochloride salts was determined by means of IR spectra, 13C CP/MAS NMR spectra and 15N CP/MAS NMR spectra. These results were supported by ab initio/DFT calculations of partial charges and proton affinities. Physico-chemical properties of free bases and hydrochloride salts are discussed; especially partition and distributive coefficients log P and log D7.4, dissociation constants pKa, molecular surfaces and volumes. The experimental results were also subsequently correlated with ab initio/DFT calculations.
Export Options
About this article
Cite this article as:
Opatrilova Radka, Jampilek Josef, Raich Ivan, Kacerova Sandra, Havlicek Jaroslav, Pekarek Tomas, Dohnal Jiri and Csollei Jozef, Synthesis, Characterization and Physico-chemical Properties of New 2-(4- Arylpiperazine-1-yl)-1-(3-methylbenzofuran-2-yl)ethanoles as Potential Antihypertensive Agents, Current Organic Chemistry 2009; 13 (10) . https://dx.doi.org/10.2174/138527209788680808
DOI https://dx.doi.org/10.2174/138527209788680808 |
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
-
Emerging Molecular Targets for Imaging of Atherosclerotic Plaque using Positron Emission Tomography
Current Radiopharmaceuticals Effects of Lipid-Lowering Agents on Inflammation, Haemostasis and Blood Pressure
Current Pharmaceutical Design Cognitive Function and Heart Failure: The Role of the Adrenergic System
Recent Patents on Endocrine, Metabolic & Immune Drug Discovery A Novel Potential Reproductive Effects of Pterocarpus marsupium Methanolic Extract on Testosterone Propionate Induced Polycystic Ovary Syndrome in Female Albino Rats
Endocrine, Metabolic & Immune Disorders - Drug Targets How does Chronic Atrial Fibrillation Influence Mortality in the Modern Treatment Era?
Current Cardiology Reviews Effects of Biologic Agents and Other Disease-Modifying Antirheumatic Drugs on Cardiovascular Outcomes in Psoriasis and Psoriatic Arthritis: A Systematic Review
Current Pharmaceutical Design Obstructive Sleep Apnea Syndrome: Implications in Cardiovascular Disease
Current Respiratory Medicine Reviews Effect of Various Bulk Sweeteners on the Survivability of <i>Lactobacillus casei</i> 431 in Milk Chocolate: Rheological and Sensory Properties Analysis
Current Pharmaceutical Biotechnology Risk-Benefit Perspectives in COX-2 Blockade
Current Drug Safety Drug and Medical Device Interactions: Stent Thrombosis and Personalizing Clopidogrel Therapy
Current Pharmacogenomics and Personalized Medicine Oxidative Stress, Inflammation and Endothelial Biomarkers in Arterial Hypertension
Current Hypertension Reviews CREG: A Possible Candidate for Both Prevention and Treatment of Proliferative Vascular Disease
Current Molecular Medicine Novel Aspects in the Pathogenesis of Nonalcoholic Steatohepatitis
Current Molecular Medicine Therapeutic Potential of Natural Compounds that Regulate the Activity of Protein Kinase C
Current Medicinal Chemistry Glutathione Peroxidase: A Potential Marker for the Most Common Diseases and Disorders
Recent Patents on Biomarkers Novel Therapeutic Strategies for the Homozygous Familial Hypercholesterolemia
Recent Patents on Cardiovascular Drug Discovery Herbal Medicines for Diabetes Management and its Secondary Complications
Current Diabetes Reviews Correlation between Serum 25 hydroxy vitamin D level and plasminogen activator inhibitor 1 in type 2 diabetic patients
Endocrine, Metabolic & Immune Disorders - Drug Targets Fatty Acids - Induced Lipotoxicity and Inflammation
Current Drug Metabolism Advances in Clinical Study of Curcumin
Current Pharmaceutical Design