Projects funded by the NCN

Information on the principal investigator and host institution

Information of the project and the call

Keywords

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Modifications of aglycones of leucomycins via Michael addition and Huisgen dipolar cycloaddition as a new routes of synthesis of ribosomal 50S inhibitors

2012/05/E/ST5/03792

Keywords:

leucomycins ribosomal 50S subunit inhibitors antibacterial activity molecular docking spectroscopy structure-activity relationship Michael addition Huisgen cycloaddition

Descriptors:

  • ST5_16:
  • ST5_11:
  • ST5_20:

Panel:

ST5 - Materials: materials synthesis, structure-properties relations, advanced and functional materials with designed properties, (macro)molecular architecture, material engineering

Host institution :

Uniwersytet im. Adama Mickiewicza w Poznaniu, Wydział Chemii

woj. wielkopolskie

Other projects carried out by the institution 

Principal investigator (from the host institution):

dr hab. Piotr Przybylski 

Number of co-investigators in the project: 4

Call: SONATA BIS 1 - announced on 2012-03-15

Amount awarded: 986 800 PLN

Project start date (Y-m-d): 2013-03-19

Project end date (Y-m-d): 2016-03-18

Project duration:: 36 months (the same as in the proposal)

Project status: Project settled

Equipment purchased [PL]

  1. Wyparka próżniowa z pompą próżniową (Bucchi Rotavapor R-210) (20 000 PLN)
  2. Program do edycji i obróbki widm NMR (Mastre-C) (4 500 PLN)
  3. Aparat FT-IR (kompaktowy i przenośny) wraz z akcesoriami (220 000 PLN)

Information in the final report

  • Publication in academic press/journals (8)
  • Articles in post-conference publications (19)
  1. Impact of metal cation complexation and protonation on tautomeric and resonance forms of the oxaalkyl Schiff bases derived from 5-substituted salicylaldehyde and 2-hydroxy-1- naphthlaldehyde
    Authors:
    K. Pyta, P. Przybylski*, K. Klich, W. Schilf, B. Kamienski, E. Grech, B. Kołodziej, A. Szady-Chełmieniecka, B. Brzezinski
    Academic press:
    Structural Chemistry (rok: 2014, tom: 25, strony: 1733–1746), Wydawca: Springer
    Status:
    Published
    DOI:
    10.1007/s11224-014-0447-x - link to the publication
  2. The mechanism of activation of amidobenzylidene ruthenium chelates – latent catalysts of olefin metathesis
    Authors:
    Szymon Rogalski, Patrycja Żak, Natalia Tadeuszyk, Krystian Pyta, Piotr Przybylski and Cezary Pietraszuk
    Academic press:
    Dalton Trans. (rok: 2017, tom: 46, strony: 1277-1282), Wydawca: Royal Society in Chemistry
    Status:
    Published
    DOI:
    10.1039/c6dt04290b - link to the publication
  3. Impact of metal cation complexation and protonation on tautomeric and resonance forms of the oxaalkyl Schiff bases derived from 5-substituted salicylaldehyde and 2-hydroxy-1- naphthlaldehyde
    Authors:
    K. Pyta, P. Przybylski*, K. Klich, W. Schilf, B. Kamienski, E. Grech, B. Kołodziej, A. Szady-Chełmieniecka, B. Brzezinski
    Academic press:
    Structural Chemistry (rok: 2014, tom: 25, strony: 1733–1746), Wydawca: Springer
    Status:
    Published
    DOI:
    10.1007/s11224-014-0447-x - link to the publication
  4. Synthesis, Antibacterial, and Anticancer Evaluation of Novel Spiramycin-Like Conjugates Containing C(5) Triazole Arm
    Authors:
    Katarzyna Klich, Krystian Pyta, Marcelina M. Kubicka, Piotr Ruszkowski, Lech Celewicz, Marzena Gajecka, Piotr Przybylski
    Academic press:
    Journal of Medicinal Chemistry (rok: 2016, tom: 59, strony: 7963–7973), Wydawca: American Chemical Society
    Status:
    Published
    DOI:
    10.1021/acs.jmedchem.6b00764 - link to the publication
  5. Regio- and Stereoselective Functionalization of 16-Membered Lactone Aglycone of Spiramycin via Cascade Strategy
    Authors:
    K. Klich, K. Pyta, P. Przybylski*
    Academic press:
    Journal of Organic Chemistry (rok: 2015, tom: 80, strony: 7040−7049), Wydawca: American Chemical Society
    Status:
    Published
    DOI:
    10.1021/acs.joc.5b00847 - link to the publication
  6. 16-Membered Macrolide Lactone Derivatives Bearing a Triazole-Functionalized Arm at the Aglycone C13 Position as Antibacterial and Anticancer Agents
    Authors:
    Joanna Domagalska, Anna Janas, Krystian Pyta, Paulina Pecyna, Piotr Ruszkowski, Lech Celewicz, Marzena Gajecka, Franz Bartl, Piotr Przybylski
    Academic press:
    ChemMedChem (rok: 2016, tom: 11, strony: 1886-1891), Wydawca: WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
    Status:
    Published
    DOI:
    10.1002/cmdc.201600250 - link to the publication
  7. Conversion of leucomycin-A3 antibiotic into novel triazole analogues via regio- and diastereoselective SN10 substitution with allylic rearrangement and 1,3-dipolar cycloaddition of CuAAC type
    Authors:
    J. Domagalska, K. Pyta, P. Przybylski*
    Academic press:
    Tetrahedron Letters (rok: 2016, tom: 57, strony: 1661–1666), Wydawca: Elsevier
    Status:
    Published
    DOI:
    10.1016/j.tetlet.2016.02.113 - link to the publication
  8. Synthesis, Antibacterial, and Anticancer Evaluation of Novel Spiramycin-Like Conjugates Containing C(5) Triazole Arm
    Authors:
    Katarzyna Klich, Krystian Pyta, Marcelina M. Kubicka, Piotr Ruszkowski, Lech Celewicz, Marzena Gajecka, Piotr Przybylski
    Academic press:
    Journal of Medicinal Chemistry (rok: 2016, tom: 59, strony: 7963–7973), Wydawca: American Chemical Society
    Status:
    Published
    DOI:
    10.1021/acs.jmedchem.6b00764 - link to the publication
  1. Regio- and Stereospecific functionalization of 16-membered Lactone Aglycone of Macrolide type Antibiotics via Intramolecular cascade reactions
    Authors:
    K. Klich, K. Pyta, P. Przybylski
    Conference:
    XVIth Tetrahedron Symposium Challenges in Bioorganic & Organic Chemistry" (rok: 2015, ), Wydawca: Elsevier
    Data:
    konferencja 16-19 June
    Status:
    Published
    DOI:
    link to the publication
  2. Application of 1D and 2D NMR Spectroscopy to determination of novel Spiramycin derivatives structures
    Authors:
    K. Klich, K. Pyta, P. Przybylski
    Conference:
    VIIIth Symposium on: Nuclear Magnetic Resonance in Chemistry, Physics and Biological Sciences (rok: 2014, ), Wydawca: Instytut Chemii Organicznej PAN, Warszawa
    Data:
    konferencja 24-26 września
    Status:
    Published
  3. The E1cb elimination as an efficient method leading to obtain of novel derivatives of leucomycin A3
    Authors:
    Katarzyna Klich, Krystian Pyta, Piotr Przybylski
    Conference:
    Central European School on Physical Organic Chemistry-"From molecule to material chemistry for the future" (rok: 2013, ), Wydawca: University of Wroclaw, PTCH
    Data:
    konferencja 27.05-31.05
    Status:
    Published
  4. Diastereo- and regioselective functionalization of josamycin aglycone using untypical reaction in dienol system
    Authors:
    J. Domagalska, K. Pyta, P. Przybylski
    Conference:
    XVIth Tetrahedron Symposium Challenges in Bioorganic & Organic Chemistry" (rok: 2015, ), Wydawca: Elsevier
    Data:
    konferencja 16-19 June
    Status:
    Published
  5. Modification of the aglycone Josamycin with using the regioselective nucleophilic substitution SN1' type and dipolar Huisgen cycloaddition
    Authors:
    J. Domagalska, K. Pyta, P. Przybylski
    Conference:
    Euromar 2015, European Congress on Magnetic Resonance (rok: 2015, ), Wydawca: Comittee of European Congress on Magnetic Resonance
    Data:
    konferencja 5 - 10 July
    Status:
    Published
  6. Poster: "Synthesis of new heterocyclic derivatives of josamycin via SN1' and dipolar cycloaddition of CuAAC type"
    Authors:
    K. Pyta, J. Domagalska, P. Przybylski
    Conference:
    Trans Mediterranean Colloquium on Heterocyclic Chemistry TRAMECH VIII (rok: 2015, ), Wydawca: Organizing Comittee of TRAMECH VIII
    Data:
    konferencja 11-15 November
    Status:
    Published
  7. Stereo- and Regioselective modifications of Spiramycin and Josamycin Lactone Aglycones as a source of novel type inhibitors of 50S ribosomal subunit
    Authors:
    P. Przybylski, K. Klich, J. Domagalska, K. Pyta
    Conference:
    Frontiers in Medicinal Chemistry (rok: 2015, ), Wydawca: Comittee of Frontiers in Medicinal Chemistry
    Data:
    konferencja 14-16 September
    Status:
    Published
  8. Application of 1D and 2D NMR Spectroscopy to determination of novel Josamycin derivative structures
    Authors:
    J. Domagalska, K. Pyta, P. Przybylski
    Conference:
    VIIIth Symposium on: Nuclear Magnetic Resonance in Chemistry, Physics and Biological Sciences (rok: 2014, ), Wydawca: Instytut Chemii Organicznej PAN, Warszawa
    Data:
    konferencja 24-26 września
    Status:
    Published
  9. Poster: "Synthesis of new heterocyclic derivatives of josamycin via SN1' and dipolar cycloaddition of CuAAC type"
    Authors:
    K. Pyta, J. Domagalska, P. Przybylski
    Conference:
    Trans Mediterranean Colloquium on Heterocyclic Chemistry TRAMECH VIII (rok: 2015, ), Wydawca: Organizing Comittee of TRAMECH VIII
    Data:
    konferencja 11-15 November
    Status:
    Published
  10. Wystąpienie ustne: "Regio- and stereoselective cascade and click" modifications of macrolide antibiotics as a source of new heterocyclic antibacterial agents"
    Authors:
    P. Przybylski, K. Klich, J. Domagalska, K. Pyta
    Conference:
    Trans Mediterranean Colloquium on Heterocyclic Chemistry TRAMECH VIII (rok: 2015, ), Wydawca: Organizing Comitee of TRAMECH VIII
    Data:
    konferencja 11-15 November
    Status:
    Published
    DOI:
    link to the publication
  11. The E1cb elimination as an efficient method leading to obtain of novel derivatives of leucomycin A3
    Authors:
    Katarzyna Klich, Krystian Pyta, Piotr Przybylski
    Conference:
    Central European School on Physical Organic Chemistry-"From molecule to material chemistry for the future" (rok: 2013, ), Wydawca: University of Wroclaw, PTCH
    Data:
    konferencja 27.05-31.05
    Status:
    Published
  12. Modification of the aglycone Josamycin with using the regioselective nucleophilic substitution SN1' type and dipolar Huisgen cycloaddition
    Authors:
    J. Domagalska, K. Pyta, P. Przybylski
    Conference:
    Euromar 2015, European Congress on Magnetic Resonance (rok: 2015, ), Wydawca: Comittee of European Congress on Magnetic Resonance
    Data:
    konferencja 5 - 10 July
    Status:
    Published
  13. Diastereo- and regioselective functionalization of josamycin aglycone using untypical reaction in dienol system
    Authors:
    J. Domagalska, K. Pyta, P. Przybylski
    Conference:
    XVIth Tetrahedron Symposium Challenges in Bioorganic & Organic Chemistry" (rok: 2015, ), Wydawca: Elsevier
    Data:
    konferencja 16-19 June
    Status:
    Published
  14. Transformation of josamycin in solution – Michael addition or SN2 substitution
    Authors:
    P. Przybylski, K. Pyta, K. Klich
    Conference:
    "Ogólnopolskie sympozjum Chiralność-od cząstki elementarnej do Uniwersum" (rok: 2013, ), Wydawca: Wydział Chemii UAM i PTCH
    Data:
    konferencja 07.06.
    Status:
    Published
  15. Poster "Regio- and stereospecific functionalization of 16-membered lactone aglycone of macrolide type antibiotics via intramolecular cascade reactions"
    Authors:
    K. Klich, K. Pyta, P. Przybylski
    Conference:
    Trans Mediterranean Colloquium on Heterocyclic Chemistry TRAMECH VIII (rok: 2015, ), Wydawca: Organizing Comitee of TRAMECH VIII
    Data:
    konferencja 11-15 November
    Status:
    Published
  16. Wystąpienie ustne: "Regio- and stereoselective cascade and click" modifications of macrolide antibiotics as a source of new heterocyclic antibacterial agents"
    Authors:
    P. Przybylski, K. Klich, J. Domagalska, K. Pyta
    Conference:
    Trans Mediterranean Colloquium on Heterocyclic Chemistry TRAMECH VIII (rok: 2015, ), Wydawca: Organizing Comitee of TRAMECH VIII
    Data:
    konferencja 11-15 November
    Status:
    Published
    DOI:
    link to the publication
  17. Poster "Regio- and stereospecific functionalization of 16-membered lactone aglycone of macrolide type antibiotics via intramolecular cascade reactions"
    Authors:
    K. Klich, K. Pyta, P. Przybylski
    Conference:
    Trans Mediterranean Colloquium on Heterocyclic Chemistry TRAMECH VIII (rok: 2015, ), Wydawca: Organizing Comitee of TRAMECH VIII
    Data:
    konferencja 11-15 November
    Status:
    Published
  18. Transformation of josamycin in solution – Michael addition or SN2 substitution
    Authors:
    P. Przybylski, K. Pyta, K. Klich
    Conference:
    "Ogólnopolskie sympozjum Chiralność-od cząstki elementarnej do Uniwersum" (rok: 2013, ), Wydawca: Wydział Chemii UAM i PTCH
    Data:
    konferencja 07.06.
    Status:
    Published
  19. Regio- and Stereospecific functionalization of 16-membered Lactone Aglycone of Macrolide type Antibiotics via Intramolecular cascade reactions
    Authors:
    K. Klich, K. Pyta, P. Przybylski
    Conference:
    XVIth Tetrahedron Symposium Challenges in Bioorganic & Organic Chemistry" (rok: 2015, ), Wydawca: Elsevier
    Data:
    konferencja 16-19 June
    Status:
    Published
    DOI:
    link to the publication

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