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Hypersphere and Antiviral Activity of Three Alkyl Chain Iminocyclitols with D and L Ribitol Stereochemistry

Received: 16 March 2023    Accepted: 6 April 2023    Published: 20 April 2023
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Abstract

N-Alkyl-C1-dialkyl chains iminocyclitols with D or L-ribitol stereochemistry are synthesized with high diastereoselectivity after Grignard reagents addition to N-quaternary pyrrolines salts, and tested for antiviral activity in bovine viral diarrhea virus (BVDV), surrogate for hepatitis C virus (HCV). Dihedral angles are calculated from carbon chemical shift (δCn[ppm]) with 3-sphere method without building units. 3-Sphere, a hypersphere in 4D, under Hopf fibration and Lie algebra mathematics theories enable calculation of the dihedral angles from the NMR data (vicinal coupling constant 3JHnHn+1[Hz], chemical shift δCn[ppm]). Instead of 3D manifold equations on seven sets unit or six sets units are proposed equations between 4D – 2D, in function of the curvature. The relationship between the antiviral activity and the iminocyclitol structure reveals that monoalkyl chain, N-n-C1-dodecyl β-L-ribitol trifloroacetate salt 30 (IC50 1.5 uM) has higher antiviral activity in tangential space, relative to three alkyl chain, N-Methyl-C1-butil, nonyl-L-ribitol. HCl 26 (IC50 < 2 uM) with torus and Dupin cyclide coordinate, both with coordinates in 2D. Three alkyl chain isopropylidene protected pyrrolidine 25 has in 4D with all equations for calculation of the dihedral angles, and in protected pyrroline 19b double bond moves the coordinates in 2D.

Published in American Journal of Heterocyclic Chemistry (Volume 9, Issue 1)
DOI 10.11648/j.ajhc.20230901.12
Page(s) 9-24
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Grignard Addition, Pyrroline, N-quaternary Pyrrolines Salts, Pyrrolidine, N-Alkyl-C1-dialkyl Chains Iminocyclitols, Hypersphere, Dihedral Angles, Vicinal Coupling Constants 3JHH [Hz]

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    Robert Michael Moriarty, Carmen-Irena Mitan, Baohua Gu, Timothy Block. (2023). Hypersphere and Antiviral Activity of Three Alkyl Chain Iminocyclitols with D and L Ribitol Stereochemistry. American Journal of Heterocyclic Chemistry, 9(1), 9-24. https://doi.org/10.11648/j.ajhc.20230901.12

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    ACS Style

    Robert Michael Moriarty; Carmen-Irena Mitan; Baohua Gu; Timothy Block. Hypersphere and Antiviral Activity of Three Alkyl Chain Iminocyclitols with D and L Ribitol Stereochemistry. Am. J. Heterocycl. Chem. 2023, 9(1), 9-24. doi: 10.11648/j.ajhc.20230901.12

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    AMA Style

    Robert Michael Moriarty, Carmen-Irena Mitan, Baohua Gu, Timothy Block. Hypersphere and Antiviral Activity of Three Alkyl Chain Iminocyclitols with D and L Ribitol Stereochemistry. Am J Heterocycl Chem. 2023;9(1):9-24. doi: 10.11648/j.ajhc.20230901.12

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  • @article{10.11648/j.ajhc.20230901.12,
      author = {Robert Michael Moriarty and Carmen-Irena Mitan and Baohua Gu and Timothy Block},
      title = {Hypersphere and Antiviral Activity of Three Alkyl Chain Iminocyclitols with D and L Ribitol Stereochemistry},
      journal = {American Journal of Heterocyclic Chemistry},
      volume = {9},
      number = {1},
      pages = {9-24},
      doi = {10.11648/j.ajhc.20230901.12},
      url = {https://doi.org/10.11648/j.ajhc.20230901.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20230901.12},
      abstract = {N-Alkyl-C1-dialkyl chains iminocyclitols with D or L-ribitol stereochemistry are synthesized with high diastereoselectivity after Grignard reagents addition to N-quaternary pyrrolines salts, and tested for antiviral activity in bovine viral diarrhea virus (BVDV), surrogate for hepatitis C virus (HCV). Dihedral angles are calculated from carbon chemical shift (δCn[ppm]) with 3-sphere method without building units. 3-Sphere, a hypersphere in 4D, under Hopf fibration and Lie algebra mathematics theories enable calculation of the dihedral angles from the NMR data (vicinal coupling constant 3JHnHn+1[Hz], chemical shift δCn[ppm]). Instead of 3D manifold equations on seven sets unit or six sets units are proposed equations between 4D – 2D, in function of the curvature. The relationship between the antiviral activity and the iminocyclitol structure reveals that monoalkyl chain, N-n-C1-dodecyl β-L-ribitol trifloroacetate salt 30 (IC50 1.5 uM) has higher antiviral activity in tangential space, relative to three alkyl chain, N-Methyl-C1-butil, nonyl-L-ribitol. HCl 26 (IC50 < 2 uM) with torus and Dupin cyclide coordinate, both with coordinates in 2D. Three alkyl chain isopropylidene protected pyrrolidine 25 has in 4D with all equations for calculation of the dihedral angles, and in protected pyrroline 19b double bond moves the coordinates in 2D.},
     year = {2023}
    }
    

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  • TY  - JOUR
    T1  - Hypersphere and Antiviral Activity of Three Alkyl Chain Iminocyclitols with D and L Ribitol Stereochemistry
    AU  - Robert Michael Moriarty
    AU  - Carmen-Irena Mitan
    AU  - Baohua Gu
    AU  - Timothy Block
    Y1  - 2023/04/20
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    N1  - https://doi.org/10.11648/j.ajhc.20230901.12
    DO  - 10.11648/j.ajhc.20230901.12
    T2  - American Journal of Heterocyclic Chemistry
    JF  - American Journal of Heterocyclic Chemistry
    JO  - American Journal of Heterocyclic Chemistry
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    EP  - 24
    PB  - Science Publishing Group
    SN  - 2575-5722
    UR  - https://doi.org/10.11648/j.ajhc.20230901.12
    AB  - N-Alkyl-C1-dialkyl chains iminocyclitols with D or L-ribitol stereochemistry are synthesized with high diastereoselectivity after Grignard reagents addition to N-quaternary pyrrolines salts, and tested for antiviral activity in bovine viral diarrhea virus (BVDV), surrogate for hepatitis C virus (HCV). Dihedral angles are calculated from carbon chemical shift (δCn[ppm]) with 3-sphere method without building units. 3-Sphere, a hypersphere in 4D, under Hopf fibration and Lie algebra mathematics theories enable calculation of the dihedral angles from the NMR data (vicinal coupling constant 3JHnHn+1[Hz], chemical shift δCn[ppm]). Instead of 3D manifold equations on seven sets unit or six sets units are proposed equations between 4D – 2D, in function of the curvature. The relationship between the antiviral activity and the iminocyclitol structure reveals that monoalkyl chain, N-n-C1-dodecyl β-L-ribitol trifloroacetate salt 30 (IC50 1.5 uM) has higher antiviral activity in tangential space, relative to three alkyl chain, N-Methyl-C1-butil, nonyl-L-ribitol. HCl 26 (IC50 < 2 uM) with torus and Dupin cyclide coordinate, both with coordinates in 2D. Three alkyl chain isopropylidene protected pyrrolidine 25 has in 4D with all equations for calculation of the dihedral angles, and in protected pyrroline 19b double bond moves the coordinates in 2D.
    VL  - 9
    IS  - 1
    ER  - 

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Author Information
  • Department of Chemistry, University of Illinois at Chicago, Chicago, USA

  • Department of Chemistry, University of Illinois at Chicago, Chicago, USA; Department of Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Bucharest, Romania

  • Drexel Institute for Biotechnology and Virology Research, College of Medicine, Drexel University, Doylestown, USA

  • Drexel Institute for Biotechnology and Virology Research, College of Medicine, Drexel University, Doylestown, USA

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