Sulfonation of Betulinic Acid by Sulfamic Acid

Levdanskii, V. A.; Левданский, А.В.; Кузнецов, Б. Н.

doi:10.1007/s10600-015-1442-1

Cited by 4 publications

(5 citation statements)

References 5 publications

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“…White solid powder. 1 H and 13 C NMR spectra match those reported in literature [ 69 ]. Table 3 contains the trivial name and structural formula of BI.…”

Section: Methodssupporting

confidence: 85%

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Comparison of In Vitro Antimelanoma and Antimicrobial Activity of 2,3-Indolo-betulinic Acid and Its Glycine Conjugates

Lombrea

Scurtu

Magyari-Pavel

et al. 2023

Plants

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Malignant melanoma is one of the most pressing problems in the developing world. New therapeutic agents that might be effective in treating malignancies that have developed resistance to conventional medications are urgently required. Semisynthesis is an essential method for improving the biological activity and the therapeutic efficacy of natural product precursors. Semisynthetic derivatives of natural compounds are valuable sources of new drug candidates with a variety of pharmacological actions, including anticancer ones. Two novel semisynthetic derivatives of betulinic acid—N-(2,3-indolo-betulinoyl)diglycylglycine (BA1) and N-(2,3-indolo-betulinoyl)glycylglycine (BA2)—were designed and their antiproliferative, cytotoxic, and anti-migratory activity against A375 human melanoma cells was determined in comparison with known N-(2,3-indolo-betulinoyl)glycine (BA3), 2,3-indolo-betulinic acid (BA4) and naturally occurring betulinic acid (BI). A dose-dependent antiproliferative effect with IC50 values that ranged from 5.7 to 19.6 µM was observed in the series of all five compounds including betulinic acid. The novel compounds BA1 (IC50 = 5.7 µM) and BA2 (IC50 = 10.0 µM) were three times and two times more active than the parent cyclic structure B4 and natural BI. Additionally, compounds BA2, BA3, and BA4 possess antibacterial activity against Streptococcus pyogenes ATCC 19615 and Staphylococcus aureus ATCC 25923 with MIC values in the range of 13–16 µg/mL and 26–32 µg/mL, respectively. On the other hand, antifungal activity toward Candida albicans ATCC 10231 and Candida parapsilosis ATCC 22019 was found for compound BA3 with MIC 29 µg/mL. This is the first report of antibacterial and antifungal activity of 2,3-indolo-betulinic acid derivatives and also the first extended report on their anti-melanoma activity, which among others includes data on anti-migratory activity and shows the significance of amino acid side chain on the observed activity. The obtained data justify further research on the anti-melanoma and antimicrobial activity of 2,3-indolo-betulinic acid derivatives.

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“…White solid powder. 1 H and 13 C NMR spectra match those reported in literature [ 69 ]. Table 3 contains the trivial name and structural formula of BI.…”

Section: Methodssupporting

confidence: 85%

“…Using 1 H and 13 C NMR spectroscopy, the structures of all produced compounds were confirmed. The NMR spectra of betulonic acid, BI, BA3, and BA4 matched those previously described in the literature [ 50 , 68 , 69 , 70 , 71 ]. All NMR spectral data are provided in the Supplementary Figures S1–S12 attached to the current publication.…”

Section: Resultssupporting

confidence: 74%

Comparison of In Vitro Antimelanoma and Antimicrobial Activity of 2,3-Indolo-betulinic Acid and Its Glycine Conjugates

Lombrea

Scurtu

Magyari-Pavel

et al. 2023

Plants

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“…The composition and structure of the betulin disulfate sodium salt was confirmed by 13 C NMR spectroscopy. According to the literature data [59], the chemical shift of the secondary C3 carbon atom bonded to the hydroxyl group is observed at 78-79 ppm and the chemical shift of the primary C28 carbon atom, at 59-60 ppm. An analysis of the 13 C NMR spectra of the initial betulin and the betulin disulfate sodium salt showed that the chemical shift of the C3 carbon atom in the initial betulin is observed at 78.25 ppm and the chemical shift of the C28 carbon atom, at 58.96 ppm.…”

Section: Nuclear Magnetic Resonance Studymentioning

confidence: 82%

Catalytic Sulfation of Betulin with Sulfamic Acid: Experiment and DFT Calculation

Akman

Vasilieva

Issaoui

et al. 2022

IJMS

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Betulin is an important triterpenoid substance isolated from birch bark, which, together with its sulfates, exhibits important bioactive properties. We report on a newly developed method of betulin sulfation with sulfamic acid in pyridine in the presence of an Amberlyst®15 solid acid catalyst. It has been shown that this catalyst remains stable when being repeatedly (up to four cycles) used and ensures obtaining of sulfated betulin with a sulfur content of ~10%. The introduction of the sulfate group into the betulin molecule has been proven by Fourier-transform infrared, ultraviolet-visible, and nuclear magnetic resonance spectroscopy. The Fourier-transform infrared (FTIR) spectra contain absorption bands at 1249 and 835‒841 cm‒1; in the UV spectra, the peak intensity decreases; and, in the nuclear magnetic resonance (NMR) spectra, of betulin disulfate, carbons С3 and С28 are completely shifted to the weak-field region (to 88.21 and 67.32 ppm, respectively) with respect to betulin. Using the potentiometric titration method, the product of acidity constants K1 and K2 of a solution of the betulin disulfate H+ form has been found to be 3.86 × 10‒6 ± 0.004. It has been demonstrated by the thermal analysis that betulin and the betulin disulfate sodium salt are stable at temperatures of up to 240 and 220 °C, respectively. The density functional theory method has been used to obtain data on the most stable conformations, molecular electrostatic potential, frontier molecular orbitals, and mulliken atomic charges of betulin and betulin disulfate and to calculate the spectral characteristics of initial and sulfated betulin, which agree well with the experimental data.

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“…[142][143][144][145][146] In a recent study, betulinic acid prepared from betulin was sulfonated by SA in the presence of urea in homogeneous 1,4-dioxane or DMF solution at 65-75°C in 2.5-3.5 h to give betulinic acid 3-sulfate with 96 % yield (Scheme 80). [147] Naturally occurring β-Amino alcohols, which are intermediates for the synthesis of a number of important bioactive natural and synthetic compounds, are normally prepared by opening the epoxide ring with amines. Several methodologies were adopted for the preparation of amino alcohols, but the drawbacks of the classical methods promoted Kamal et.…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

“…In a recent study, betulinic acid prepared from betulin was sulfonated by SA in the presence of urea in homogeneous 1,4‐dioxane or DMF solution at 65–75 °C in 2.5–3.5 h to give betulinic acid 3‐sulfate with 96 % yield (Scheme 80). [147] …”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Chopra

Lambat²,

Mahmood

et al. 2021

ChemistrySelect

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In recent times, synthetic organic reactions have gained significant attention as they are becoming a versatile tool in the synthesis of pharmaceuticals, agrochemicals and their intermediates. Sulfamic acid (SA) is an acid catalyst that demonstrated high efficiency in various organic transformations that will be highlighted in this review. These include efforts to develop green approaches using SA catalyst for the CÀ C bond formation reactions and functional group trans-formations, as well as the synthesis of various OÀ and Nheterocyclic compounds and other miscellaneous reactions including multicomponent reactions. The easy recovery (for subsequent reuse) of the catalyst by filtration without the need for solvents is an important advantage of SA catalyst. In this review, SA promoted greener methodologies that were developed and the applicability of these methodologies are addressed.

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Sulfonation of Betulinic Acid by Sulfamic Acid

Cited by 4 publications

References 5 publications

Comparison of In Vitro Antimelanoma and Antimicrobial Activity of 2,3-Indolo-betulinic Acid and Its Glycine Conjugates

Comparison of In Vitro Antimelanoma and Antimicrobial Activity of 2,3-Indolo-betulinic Acid and Its Glycine Conjugates

Catalytic Sulfation of Betulin with Sulfamic Acid: Experiment and DFT Calculation

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

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