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2 article(s) from Poštová Slavětínská, Lenka

Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives

Martin Pošta,
Václav Zima,
Lenka Poštová Slavětínská,
Marika Matoušová and
Petr Beier

Beilstein J. Org. Chem. 2022, 18, 549–554, doi:10.3762/bjoc.18.57

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Figure 1: Structures of naturally occurring karrikins.

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Scheme 1: i) P₄S₁₀, THF; ii) 2-chloropropionyl chloride, Et₃N; iii) Ph₃P, NaOAc, Ac₂O.

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Figure 2: Target compounds with highlighted positions of oxygen to sulfur exchange.

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Scheme 2: i) Lawesson’s reagent, HMDO, toluene, MW irradiation, 120 °C, 60 min.

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Scheme 3: i) P₄S₁₀ or Lawesson’s reagent, see table for conditions; ii) 2-chloropropionyl chloride, Et₃N, DCM...

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Scheme 4: i) LiHMDS, MeI, THF, −78 °C.

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Scheme 5: i) a) NaOH, MeOH/H₂O, rt, Amberlyst 15 [H⁺], b) AcOH 70% aq, reflux, 2 h; ii) a) EtOCOCl, pyridine,...

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Scheme 6: i) Lawesson’s reagent, HMDO, toluene, MW irradiation (120 °C), 60 min.

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Published 16 May 2022

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Pyrrolidine nucleotide analogs with a tunable conformation

Lenka Poštová Slavětínská,
Dominik Rejman and
Radek Pohl

Beilstein J. Org. Chem. 2014, 10, 1967–1980, doi:10.3762/bjoc.10.205

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Figure 1: Examples of biologically active acyclic and cyclic nucleotide analogs.

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Figure 2: The pyrrolidine nucleotide analogs investigated in this study.

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Scheme 1: The synthesis of pyrrolidine nucleotides 7–14.

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Figure 3: The numbering of the pyrrolidine ring, the nucleobase and the endocyclic phase angles for the purpo...

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Figure 4: The aliphatic part (pyrrolidine protons) of the ¹H NMR spectra of 9 measured in D₂O at different pD...

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Figure 5: Changes of selected ¹H and ¹³C chemical shifts of 9 upon pD change.

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Figure 6: The deuteration equilibria of phosphonomethyl derivatives 7–10.

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Figure 7: The aliphatic part (pyrrolidine protons) of the ¹H NMR spectra of 13 measured in D₂O at different p...

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Figure 8: Amide rotamers of phosphonoformyl derivatives 11–14.

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Figure 9: The ³¹P NMR spectra (202.3 MHz) of 14 measured (the black curve) and simulated (the red curve) at v...

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Figure 10: A part of the H,C-HSQC spectrum of derivative 13, showing the assignment of rotamers A and B.

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Figure 11: The pseudorotation pathway of the pyrrolidine ring in the compounds studied. The sign B stands for ...

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Figure 12: An example of the stereospecific assignment of pyrrolidine-ring protons of 14 in the H,H-ROESY spec...

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Figure 13: The energy profile of the five-membered pyrrolidine ring pseudorotation for adenine derivatives 9 a...

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Figure 14: The most stable conformations of adenine derivatives 9 and 13A calculated by the B3LYP/6-31++G* met...

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Published 22 Aug 2014

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