Low temperature calorimetry of 3-fluoro-5-(3-pyridinyloxy) benzenamine and N-[3-fluoro-5-(3-pyridinyloxy)phenyl]-N’-3-pyridinyl urea
Abstract
The investigation on thermodynamic properties of drug intermediates plays a crucial role in the design and synthesis of new drugs as well as understanding their biological activities in vivo. In this work, the thermodynamic properties of two drug intermediates of 3-fluoro-5-(3-pyridinyloxy) benzenamine and N-[3-fluoro-5-(3-pyridinyloxy)phenyl]-N’-3-pyridinyl urea were studied by means of low temperature calorimety performed in a Physical Property Measurement System calorimeter. The heat capacities of these two compounds were measured over the temperature region from (1.9 to 300) K, and the corresponding thermodynamic functions were consequently calculated on the basis of the heat capacity curve fitting. Additionally, a group additivity method were employed for estimating the heat capacity values of these two compounds at 298.15 K, which are in good agreement with the values measured in this work.
Keywords
References
- 1. Ghodsi R, Zarghi A, Daraei B, et al. Design, synthesis and biological evaluation of new 2,3-diarylquinoline derivatives as selective cyclooxygenase-2 inhibitors. Bioorg Med Chem. 2010; 18: 1029-1033.
- 2. Cornall LM, Mathai ML, Hryciw DH, McAinch AJ. GPR120 agonism as a countermeasure against metabolic deseases. Drug Discovery Today. 2014; 19: 670-679.
- 3. Hara T, Kimura I, Inoue D, et al. Free fatty acid receptors and their role in regulation of energy metabolism. Rev Physiol Biochem Pharmacol. 2013; 164: 77-116.
- 4. Teerlink JR. A novel approach to improve cardiac performance: cardiac myosin activators. Heart Failure Rev. 2009; 14: 289-298.
- 5. Offermanns S. Free fatty acid (FFA) and hydroxyl carboxylic acid (HCA) receptors. Annu Rev Pharmacol Toxicol. 2014; 54: 407-434.
- 6. Azevedo CMG, Watterson KR, Wargent ET, et al. Non-acidic free fatty acid receptor 4 agonists with antidiabetic activity. J Med Chem. 2016; 59: 8868-8878.
- 7. Morgan BP, Muci A, Lu PP, et al. Discovery of omecamtiv mecarbil the first, selective, small molecule activator of cardiac myosin. ACS Med Chem Lett. 2010; 1: 472-477.
- 8. Schwaller MA, Dodin G, Aubard J. Thermodynamics of drug-DNA interactions: entropy-driven intercalation and enthalpy-driven outside binding in the ellipticine series. Biopolymers. 1991; 31: 519-527.
Details
Primary Language
English
Subjects
Engineering
Journal Section
Short Communication
Authors
Rongchun Li
This is me
Key Laboratory of Coordination Chemistry and Functional Materials, College of Chemistry and Chemical Engineering, Dezhou University, Dezhou, Shandong 253023, China
China
Keyan Sun
This is me
Thermochemistry Laboratory, Liaoning Province Key Laboratory of Thermochemistry for Energy and Materials, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
China
Yushan Hua
This is me
Key Laboratory of Coordination Chemistry and Functional Materials, College of Chemistry and Chemical Engineering, Dezhou University, Dezhou, Shandong 253023, China
China
Zhicheng Tan
This is me
Thermochemistry Laboratory, Liaoning Province Key Laboratory of Thermochemistry for Energy and Materials, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
China
Quan Shi
This is me
Thermochemistry Laboratory, Liaoning Province Key Laboratory of Thermochemistry for Energy and Materials, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
China
Publication Date
September 1, 2017
Submission Date
February 13, 2017
Acceptance Date
August 1, 2017
Published in Issue
Year 2017 Volume: 20 Number: 3
Cited By
Power and efficiency optimization for an energy selective electron heat engine with double-resonance energy filter
Energy
https://doi.org/10.1016/j.energy.2016.04.006Calculation of the Isobaric Heat Capacities of the Liquid and Solid Phase of Organic Compounds at 298.15K by Means of the Group-Additivity Method
Molecules
https://doi.org/10.3390/molecules25051147Standard methods for heat capacity measurements on a Quantum Design Physical Property Measurement System
The Journal of Chemical Thermodynamics
https://doi.org/10.1016/j.jct.2019.105974