Novel Thiazole Derivatives of Medicinal Potential: Synthesis and Modeling
TL;DR: In this article, the synthesis of new thiazole derivatives that could be profitably exploited in medical treatment of tumors was discussed and correlated with the molecular structure using density function theory (DFT) framework.
Abstract: This paper reports on the synthesis of new thiazole derivatives that could be profitably exploited in medical treatment of tumors. Molecular electronic structures have been modeled within density function theory (DFT) framework. Reactivity indices obtained from the frontier orbital energies as well as electrostatic potential energy maps are discussed and correlated with the molecular structure. X-ray crystallographic data of one of the new compounds is measured and used to support and verify the theoretical results.
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TL;DR: Novel heterocyclic compounds containing pyrazole, thiazole and pyridine moieties were designed and prepared based on the condensation reaction between 1,3-thiazole or aminopyridine derivatives and 1,2,4-triazole, revealing a good agreement between the experimental and the theoretical findings.
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TL;DR: The effectiveness of potent PTP1B inhibitors as pharmaceutical agents to treat type 2 diabetes is described and it is suggested that it is possible to get small-molecule PTP 1B inhibitors with the required potency and selectivity.
Abstract: Introduction: Protein tyrosine phosphatase 1B (PTP1B) inhibition has been recommended as a crucial strategy to enhance insulin sensitivity in various cells and this fact is supported by human genetic data. PTP1B inhibitors improve the sensitivity of the insulin receptor and have the ability to cure insulin resistance-related diseases. In the latter years, targeting PTP1B inhibitors is being considered an attractive target to treat T2DM and therefore libraries of PTP1B inhibitors are being suggested as potent antidiabetic drugs. Areas covered: This review provides an overview of published patents from January 2015 to December 2018. The review describes the effectiveness of potent PTP1B inhibitors as pharmaceutical agents to treat type 2 diabetes. Expert opinion: Enormous developments have been made in PTP1B drug discovery which describes progress in natural products, synthetic heterocyclic scaffolds or heterocyclic hybrid compounds. Various protocols are being followed to boost the pharmacological effects of PTP1B inhibitors. Moreover these new advancements suggest that it is possible to get small-molecule PTP1B inhibitors with the required potency and selectivity. Furthermore, future endevours via an integrated strategy of using medicinal chemistry and structural biology will hopefully result in potent and selective PTP1B inhibitors as well as safer and more effective orally available drugs.
50 citations
Additional excerpts
...(antifungal), and tiazofurin (anticancer) [73,74]....
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TL;DR: In this article, a benzenesulfonamide-based benzoxazine compound (BSB) was synthesized from sulfamethizole, salicylaldehyde, and paraformaldehyde in a series of reaction steps.
Abstract: A benzenesulfonamide-based benzoxazine compound (BSB) was synthesized from sulfamethizole, salicylaldehyde, and paraformaldehyde in a series of reaction steps. The novel phenolic compound was structurally identified by spectroscopic techniques such as nuclear magnetic resonance (1H & 13C-NMR) and Fourier transform infrared spectroscopy. This novel benzoxazine compound possesses some highly electronegative atoms that are responsible for its corrosion inhibition behavior. The corrosion inhibition performance of BSB against X60 steel corrosion in 15% HCl at 25, 40, and 60 °C, which mimics an oil-well acidizing environment, was investigated by weight loss (WL) measurements and electrochemical techniques. The surface chemical compositions of the inhibitor and substrate (before and after corrosion) were examined using energy dispersive X-ray (EDX), and Fourier transform infrared spectroscopy (FTIR) techniques, respectively. Structural analysis was performed on the corroded steel samples, by scanning electron microscopy (SEM), and atomic force microscopy (AFM) measurements. The WL study of BSB at room temperature revealed over 88% inhibition efficiency for its 600 ppm concentration at room temperature and the efficiency slightly increased to 91% at 60 °C. Furthermore, the study suggested adsorption of BSB at a concentration of 600 ppm could involve the chemisorption adsorption mechanism. However, the PDP results at all the studied concentrations revealed BSB to act as a mixed-type inhibitor with a cathodic predominance. The EDS and FTIR analyses confirmed the BSB adsorption to the steel surface to have occurred via interactions between the BSB heteroatoms and the carbon steel surface. Hence, BSB adsorption follows the Langmuir adsorption isotherm.
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References
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01 Jan 2012
139,059 citations
"Novel Thiazole Derivatives of Medic..." refers background in this paper
...3-(Thiazole-2-ylamino) Benzo[e][1,4]oxazepin-5(1H)-one (3a)....
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...The formed precipitate was filtered off and recrystallized from the suitable solvent to afford compounds 3a–e. 3-(Thiazole-2-ylamino) Benzo[e][1,4]oxazepin-5(1H)-one (3a)....
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...N-(Thiazole-2-yl)-4H-benzo[b][1,4]thiazine-2-amine (3d)....
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...The thiazole has an important component effect of the pharmacophores of a large number of medicinal significance molecules and the evaluation of their biological activity, such as antibacterial [1], antiprotozoal [2], antitubercular [3], antifungal [4, 5], and anthelmintic [6], with emphasis on their potential medicinal applications, is desirable....
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Book•
01 Apr 1993
4,394 citations
"Novel Thiazole Derivatives of Medic..." refers methods in this paper
...The bold values corresponded to values calculated from DFT. 2.1.1....
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...The structure produced (Figure 1 and Table 2) is in excellent match with the optimized structure obtained by quantum chemical calculations within the density functional theory (DFT) [33, 34] using WB97XD/6-31G(d) model....
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...In the present study, quantum chemical computations will be performed within DFT using WB97XD/6-31G(d) model to investigate the molecular structure, IR, and NMR of the newly synthetized molecules [32–38]....
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...(4) Nucleophilicity (N): while the electrophilicity of the molecules accounts for the reactivity towards nucleophiles, it has been shown by Domingo and his coworkers [36–39] that a simple index chosen for the nucleophilicity, 𝑁, based on the HOMO energy, within DFT, is useful to explain the reactivity of these new compounds towards electrophiles....
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...The most relevant indices defined within the conceptual DFT [33] for the study of the organic reactivity are discussed elsewhere [35–39]....
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TL;DR: This chapter discusses the development of DFT as a tool for Calculating Atomic andMolecular Properties and its applications, as well as some of the fundamental and Computational aspects.
Abstract: I. Introduction: Conceptual vs Fundamental andComputational Aspects of DFT1793II. Fundamental and Computational Aspects of DFT 1795A. The Basics of DFT: The Hohenberg−KohnTheorems1795B. DFT as a Tool for Calculating Atomic andMolecular Properties: The Kohn−ShamEquations1796C. Electronic Chemical Potential andElectronegativity: Bridging Computational andConceptual DFT1797III. DFT-Based Concepts and Principles 1798A. General Scheme: Nalewajski’s ChargeSensitivity Analysis1798B. Concepts and Their Calculation 18001. Electronegativity and the ElectronicChemical Potential18002. Global Hardness and Softness 18023. The Electronic Fukui Function, LocalSoftness, and Softness Kernel18074. Local Hardness and Hardness Kernel 18135. The Molecular Shape FunctionsSimilarity 18146. The Nuclear Fukui Function and ItsDerivatives18167. Spin-Polarized Generalizations 18198. Solvent Effects 18209. Time Evolution of Reactivity Indices 1821C. Principles 18221. Sanderson’s Electronegativity EqualizationPrinciple18222. Pearson’s Hard and Soft Acids andBases Principle18253. The Maximum Hardness Principle 1829IV. Applications 1833A. Atoms and Functional Groups 1833B. Molecular Properties 18381. Dipole Moment, Hardness, Softness, andRelated Properties18382. Conformation 18403. Aromaticity 1840C. Reactivity 18421. Introduction 18422. Comparison of Intramolecular ReactivitySequences18443. Comparison of Intermolecular ReactivitySequences18494. Excited States 1857D. Clusters and Catalysis 1858V. Conclusions 1860VI. Glossary of Most Important Symbols andAcronyms1860VII. Acknowledgments 1861VIII. Note Added in Proof 1862IX. References 1865
3,890 citations
Book•
01 Jan 1977
TL;DR: Molecular Orbitals and Frontier Orbitals.
Abstract: Molecular Orbitals and Frontier Orbitals. Ionic Reactions. Thermal Pericyclic Reactions. Radical Reactions. Photochemical Reactions. Exceptions.
2,548 citations
TL;DR: The electrostatic potential of a system of nuclei and electrons is formulated directly from Coulomb's law and is a physical observable, which can be determined both experimentally and computationally.
Abstract: The electrostatic potential V(r) that is created by a system of nuclei and electrons is formulated directly from Coulomb's law and is a physical observable, which can be determined both experimentally and computationally. When V(r) is evaluated in the outer regions of a molecule, it shows how the latter is ‘seen’ by an approaching reactant, and thus is a useful guide to the molecule's reactive behavior, especially in noncovalent interactions. However, V(r) is a fundamental property of a system, the significance of which goes beyond its role in reactivity. For example, the energy of an atom or molecule can be expressed rigorously in terms of the electrostatic potentials at its nuclei. These and other features of V(r) are discussed in this overview. © 2011 John Wiley & Sons, Ltd. WIREs Comput Mol Sci 2011 1 153-163 DOI: 10.1002/wcms.19
977 citations