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Structure and Conformational Study of Drug Compounds using NMR and Ab-initio Calculations

Chashmniam, Saeed | 2018

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  1. Type of Document: Ph.D. Dissertation
  2. Language: Farsi
  3. Document No: 51070 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Tafazzoli, Mohsen
  7. Abstract:
  8. NMR spectroscopy as a powerful technique is often used to investigate on structural and conformational studies on proteins and drug compounds. In this work, conformations and structural properties of drug compounds and some nucleoside derivations have been studied using advanced NMR techniques including H-H COSY, HMQC, HMBC and NOESY and quantum based calculations.Experimental analysis on Valsartan show that there are two simultaneous conformers (M and m) with unequal population in M-m type solvents and two stable conformers (N and n) in the N-n type solvents. As the results show, different intramolecular hydrogen bond is the reason for stability af all available conformers. In the calculation section, potential energy scanning using DFT/B3LYP/6-311++G** on single bonds predicted four stable conformers (V1-V4).NMR analysis of repaglinide show that repaglinide structure has strong dependence on environment condition. In chloroform solution, there are several strong barrier energies on single bonds and it can be claimed repaglinide has so rigis structure and there is no rotational motion.In the next section, structural properties of gemcitabine as a anti cancer drug have been investigated. As the result show, there is a strong barrier energy due to intramolecular hydrogen bond. Also, strong intermolecular interaction between gemcitabine and solvent (water) have been observed experimentally
  9. Keywords:
  10. Conformation ; Nuclear Magnetic Resonance ; Ab Initio Calculation ; Valsartan Comound ; Repaglinide Compound ; Gemcitabine Compound

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