Novel steroidal 1,3,4-thiadiazines: Synthesis and biological evaluation in androgen receptor-positive prostate cancer 22Rv1 cells

Komendantova, Anna S.; Scherbakov, Alexander M.; Komkov, A. V.; Chertkova, V. V.; Gudovanniy, Alexey O.; Chernoburova, E. I.; Sorokin, Danila V.; Dzichenka, Yaraslau; Ширинян, Валерий З.; Volkova, Yu. A.; Заварзин, И. В.

doi:10.1016/j.bioorg.2019.103142

Cited by 28 publications

(20 citation statements)

References 54 publications

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“…The growth inhibitory activities of EO, carvacrol, and reference compounds were assessed using the 3-[4,5-dimethylthiazol-2-yl]−2 ,5-diphenyltetrazolium bromide (MTT; AppliChem GmbH, Darmstadt, Germany) assay. 93,94…”

Section: Tumor Cell Antiproliferative Assaysmentioning

confidence: 99%

Pharmacological Assessment of the Carvacrol Chemotype Essential Oil From Plectranthus amboinicus Growing in Cuba

Monzote

Scherbakov

Scull

et al. 2020

Natural Product Communications

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Plant-derived products are employed in various public health practices and have been considered as a major source of medicines. The genus Plectranthus (Lamiaceae) has been widely respected for its nutritional properties, its essential oil, and its therapeutic values. In the present work, the chemical characterization, antimicrobial, antiparasitic, and cytotoxic properties of the essential oil from Plectranthus amboinicus (Lour.) Spreng and its main compound carvacrol were studied. Twenty-one components were identified in the oil by gas chromatography coupled with a mass spectrometric detector. In this oil, carvacrol constitutes the major compound (71%), which represented the more abundant chemotype. The essential oil did not inhibit growth of Escherichia coli, Staphylococcus aureus, Candida albicans, Trypanosoma cruzi, or Leishmania infantum, but displayed activity against Plasmodium falciparum (half-maximal inhibitory concentration [IC50] = 5.9 µg/mL), Trypanosoma brucei (IC50 = 34.9 µg/mL), and Leishmania amazonensis (IC50 = 58.2 µg/mL), and the human tumor-derived cell lines MCF-7 (IC50 = 29.1 µg/mL), MDA-MB-231 (IC50 = 41.5 µg/mL), and 22Rv1 (IC50 = 29.6 µg/mL), but no cytotoxicity was observed against nonmalignant macrophages. The antiproliferative activity of the oil could be attributed to carvacrol. However, this compound showed certain level of cytotoxicity, which suggests unspecific activity. This study provides evidence about antimicrobial and anticancer potential of the essential oil from P. amboinicus against protozoa and neoplastic diseases, particularly as an antimalarial natural product.

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Section: Tumor Cell Antiproliferative Assaysmentioning

confidence: 99%

Pharmacological Assessment of the Carvacrol Chemotype Essential Oil From Plectranthus amboinicus Growing in Cuba

Monzote

Scherbakov

Scull

et al. 2020

Natural Product Communications

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“…THF was distilled over LiAlH 4 ; other solvents were distilled without drying agents. TAAD, 23 TAAD•HCl, 43 (3β)-21-Bromo-20-oxopregna-5,16-dien-3-yl acetate (2a), 44 quaternary salt 4a, 40 2-bromoacetyl chloride 45 and polymer PS-CH 2 -TAAD 27 were prepared according to previously described protocols. 1,4,7-Triazacyclononane trihydrochloride (TACN•3HCl), 1,8-bis(dimethylamino)naphthalene (proton sponge), glycylglycylglycine, p-thiocresol, n-heptanethiol, glutathione and all inorganic reagents were commercial grade and used as received.…”

Section: General Methods and Instrumentationmentioning

confidence: 99%

Iron(IV) Complexes with Tetraazaadamantane-based Ligands: Synthesis, Structure, Application in Dioxygen Activation and Labeling of Biomolecules

Golovanov

Leonov

Lesnikov

et al. 2021

Preprint

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4,6,10-Trihydroxy-1,4,6,10-tetraazaadamantane (TAAD) has been shown to form a stable Fe(IV) complex having a diamantane cage structure, in which the metal center is coordinated by three oxygen atoms of the deprotonated ligand. The complex was characterized by X-ray, HRMS, NMR, FT-IR, Mössbauer spectroscopy and DFT calculations, which supported d4 configuration of iron. The Fe(IV)-TAAD complex showed excellent performance in dioxygen activation under mild conditions serving as a mimetic of the thiol oxidase enzyme. The nucleophilicity of the bridge-head nitrogen atom in TAAD provides a straightforward way for conjugation of Fe(IV)-TAAD complexes to various functional molecules. Using this approach, steroidal and peptide molecules having an iron(IV) label have been prepared for the first time. Also, the Fe(IV)-TAAD complex was covalently bounded to a polystyrene matrix and the resulting material was shown to serve as a heterogeneous catalyst for aerobic oxidation of thiols to disulfides.

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“…It should be noted that some of these compounds exhibit no significant hormonal activity [28][29][30][31]. Both heterocyclic analogs I [32][33][34][35][36][37][38][39] and carbocyclic analogs II [40,41] of pentacyclic steroids have attracted considerable attention (Scheme 1). Steroids bearing an additional carbocycle annulated at the 16 and 17 positions of the ring D (III) are characterized by unique biological activity [42][43][44][45].…”

Section: Introductionmentioning

confidence: 99%

“…In a continuation of our research on the synthesis of semi-synthetic steroid derivatives and evaluation of their antitumor activity [36,37,52,53], we focused on the development of a convenient method for the synthesis of D-annulated pentacyclic steroid of the progesterone series IV bearing the cyclopentanone moiety as an additional ring. The Nazarov cyclization reaction represents one of the most effective methods for the construction of five-membered carbocyclic rings, and it has been applied in the total synthesis of many useful natural products.…”

Section: Introductionmentioning

confidence: 99%

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Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells

Vorontsova

Yadykov

Scherbakov³

et al. 2020

Molecules

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The acid-catalyzed cyclization of benzylidenes based on 16-dehydropregnenolone acetate (16-DPA) was studied. It was found that these compounds readily undergo regioselective interrupted Nazarov cyclization with trapping chloride ion and an efficient method of the synthesis of d-annulated pentacyclic steroids based on this reaction was proposed. The structures of the synthesized pentacyclic steroids were determined by NMR and X-ray diffraction. It was found that the reaction affords a single diastereomer, but the latter can crystallize as two conformers depending on the structure. Antiproliferative activity of synthesized compounds was evaluated against two breast cancer cell lines: MCF-7 and MDA-MB-231. All tested compounds showed relatively high antiproliferative activity. The synthetic potential of the protocol developed was illustrated by the gram-scale experiment.

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Novel steroidal 1,3,4-thiadiazines: Synthesis and biological evaluation in androgen receptor-positive prostate cancer 22Rv1 cells

Cited by 28 publications

References 54 publications

Pharmacological Assessment of the Carvacrol Chemotype Essential Oil From Plectranthus amboinicus Growing in Cuba

Pharmacological Assessment of the Carvacrol Chemotype Essential Oil From Plectranthus amboinicus Growing in Cuba

Iron(IV) Complexes with Tetraazaadamantane-based Ligands: Synthesis, Structure, Application in Dioxygen Activation and Labeling of Biomolecules

Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells

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