Stereoselective synthesis and antiproliferative activity of the isomeric sphinganine analogues

Čonková, Miroslava; Martinková, Miroslava; Gonda, Jozef; Jacková, Dominika; Pilátová, Martina; Kupka, Daniel; Jáger, Dávid

doi:10.1016/j.carres.2018.09.008

Cited by 9 publications

(5 citation statements)

References 61 publications

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“…Instruments and Reagents 1 H-and 13 C-NMR spectra were recorded on a Bruker Avance DRX 500 spectrometer [δ = 0 (TMS)] in the solvents indicated. Chemical shifts are expressed in ppm (δ) relative to TMS as internal reference.…”

Section: Methodsmentioning

confidence: 99%

“…[63] This is probably the steric effect of pinane ring makes 10d and 4-aminobenzotrifluoride like bulky substituent unable to establish desired interactions. Following the procedure as mentioned above, pyrazole pyrimidines 14a -d were obtained by coupling reactions between 10a -d with 4-amino-1-methylpyrazole (13) in good (14a -c) or moderate yields (14d) (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

“…All the physical and chemical properties, detailed antiproliferative and antimicrobial test results, and the spectral data and images of 1 H-NMR, 13 C-NMR and HR-MS of the new, prepared compounds are provided in the Supporting Information.…”

Section: Supporting Informationmentioning

confidence: 99%

“…In recent decades, considerable attention has been paid to 1,2‐aminoalcohols, [1–5] 1,3‐aminoalcohols, [6–8] and 3‐amino‐1,2‐diols, [9–14] with the latter combining the chemical properties of 1,2‐ and 1,3‐aminoalcohols. These compounds play a crucial role in numerous branches of human life sciences.…”

Section: Introductionmentioning

confidence: 99%

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Divergent Synthesis, Antiproliferative and Antimicrobial Studies of 1,3‐Aminoalcohol and 3‐Amino‐1,2‐Diol Based Diaminopyrimidines

Raji

Huỳnh

et al. 2022

Chemistry & Biodiversity

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A series of novel diaminopyrimidines containing pinane moieties were synthesized via an efficient methodology starting from pinane‐based aminoalcohols, aminodiols and 2,4‐dichloropyrimidines. Bioassay tests demonstrated that compound 18a displayed much stronger antiproliferative activities against four human cancer cell lines (HeLa, Siha, MDA‐MB‐231, MCF‐7 and A2780) than positive control cisplatin. In particular, compound 22a was found to be selective in inhibiting HeLa cell proliferation with cancer cell growth inhibition values higher than 95 %. Moreover, the in vitro screening of prepared compounds against different bacterial and fungal strains is reported. The results revealed that 12b and 17a, the most promising compounds, displayed selective inhibition for the Gram‐positive bacteria (B. subtilis and S. aureus) with percent inhibition values ranging from 75 to 95 % at 10 μg/mL concentration. Both selective inhibition and the in vitro activity values demonstrated that these compounds have the potential to be developed into clinically important therapeutic choices for the treatment of infections caused by B. subtilis and S. aureus.

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Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Supporting Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Divergent Synthesis, Antiproliferative and Antimicrobial Studies of 1,3‐Aminoalcohol and 3‐Amino‐1,2‐Diol Based Diaminopyrimidines

Raji

Huỳnh

et al. 2022

Chemistry & Biodiversity

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“…Examples where sphingolipid analogs with non-natural configurations are metabolized by the target enzymes have been precedented. [26][27][28] In addition, previous results from our group on differently configured 2-vinyl S1P analogs, proved the ability of the hS1PL active site to discriminate between the different stereoisomers of the amino diol phosphate framework. 29 Figure 2.…”

Section: Inhibition Of Recombinant Hs1pl By Compounds Rbm10mentioning

confidence: 97%

A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor

et al. 2019

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The synthesis of a series of vinylated analogs of sphingosine-1-phosphate, together with their unambiguous configurational assignment by VCD methods is reported. Among them, compound RBM10-8 can irreversibly inhibit human sphingosine-1-phosphate lyase (hS1PL), while behaving also as an enzyme substrate. These findings, together with the postulated mechanism for S1PL activity, reinforce the role of RBM10-8 as a new mechanism-based hS1PL inhibitor.

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Synthesis and anticancer profile of novel sphingoid base-like compounds with a quaternary stereocentre

Jacková

Brunderová

Fábian

et al. 2020

Carbohydrate Research

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Stereoselective synthesis and antiproliferative activity of the isomeric sphinganine analogues

Cited by 9 publications

References 61 publications

Divergent Synthesis, Antiproliferative and Antimicrobial Studies of 1,3‐Aminoalcohol and 3‐Amino‐1,2‐Diol Based Diaminopyrimidines

Divergent Synthesis, Antiproliferative and Antimicrobial Studies of 1,3‐Aminoalcohol and 3‐Amino‐1,2‐Diol Based Diaminopyrimidines

A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor

Synthesis and anticancer profile of novel sphingoid base-like compounds with a quaternary stereocentre

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