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Article: Thionation of quinolizidine alkaloids and their derivatives via Lawesson’s reagent

Koval’skaya, Alena V. / Petrova, Polina R. / Tsypyshev, Dmitry O. / Lobov, Alexander N. / Tsypysheva, Inna P.

Natural product research. 2022 July 15, v. 36, no. 14

2022

Abstract: Direct thionation of quinolizidine alkaloids (-)-cytisine, methylcytisine, thermopsine and some of their carbonyl derivatives was realized. It was established that carrying out of the reaction in the boiling toluene with 0.5 eq. of Lawesson’s reagent (LR) ...

Abstract	Direct thionation of quinolizidine alkaloids (-)-cytisine, methylcytisine, thermopsine and some of their carbonyl derivatives was realized. It was established that carrying out of the reaction in the boiling toluene with 0.5 eq. of Lawesson’s reagent (LR) is most effective for synthesis of thio analogues of methyl-, allyl-, benzylcytisine and thermopsine. It was found, that formation of thioamides is preferable in the case with starting 3-carboxamides of (-)-cytisine or 2-oxo and 4-oxo derivatives of methylcytisine; and an excess of LR is needed for their exhaustive thionation. It was shown, that thionation of ‘cytisine substituted’ urea and thiourea, as well as Diels-Alder adducts of methylcitisine with phenylmaleimide on basis of this approach was not quite successful: only thionation of the 2-pyridone core has occurred. It should be noted that transformation of urea and thiourea is complicated by side reactions leading to low yields of thio products, and the result of LR interaction with mentioned above diastereomeric Diels-Alder adducts depends on their stereochemistry and thermodynamic stability under reaction conditions.
Keywords	cycloaddition reactions ; research ; stereochemistry ; thermodynamics ; thiourea ; toluene ; urea
Language	English
Dates of publication	2022-0715
Size	p. 3538-3543.
Publishing place	Taylor & Francis
Document type	Article
ZDB-ID	2185747-7
ISSN	1478-6427 ; 1478-6419
ISSN (online)	1478-6427
ISSN	1478-6419
DOI	10.1080/14786419.2020.1868460
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Thionation of quinolizidine alkaloids and their derivatives via Lawesson's reagent.

Koval'skaya, Alena V / Petrova, Polina R / Tsypyshev, Dmitry O / Lobov, Alexander N / Tsypysheva, Inna P

Natural product research

2021 Volume 36, Issue 14, Page(s) 3538–3543

Abstract	Direct thionation of quinolizidine alkaloids (-)-cytisine, methylcytisine, thermopsine and some of their carbonyl derivatives was realized. It was established that carrying out of the reaction in the boiling toluene with 0.5 eq. of Lawesson's reagent (LR) is most effective for synthesis of thio analogues of methyl-, allyl-, benzylcytisine and thermopsine. It was found, that formation of thioamides is preferable in the case with starting 3-carboxamides of (-)-cytisine or 2-oxo and 4-oxo derivatives of methylcytisine; and an excess of LR is needed for their exhaustive thionation. It was shown, that thionation of 'cytisine substituted' urea and thiourea, as well as Diels-Alder adducts of methylcitisine with phenylmaleimide on basis of this approach was not quite successful: only thionation of the 2-pyridone core has occurred. It should be noted that transformation of urea and thiourea is complicated by side reactions leading to low yields of thio products, and the result of LR interaction with mentioned above diastereomeric Diels-Alder adducts depends on their stereochemistry and thermodynamic stability under reaction conditions.
MeSH term(s)	Alkaloids ; Organothiophosphorus Compounds ; Quinolizidines ; Thiourea ; Urea
Chemical Substances	Alkaloids ; Organothiophosphorus Compounds ; Quinolizidines ; Urea (8W8T17847W) ; 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (A4125MQ8RX) ; Thiourea (GYV9AM2QAG)
Language	English
Publishing date	2021-01-04
Publishing country	England
Document type	Journal Article
ZDB-ID	2185747-7
ISSN	1478-6427 ; 1478-6419
ISSN (online)	1478-6427
ISSN	1478-6419
DOI	10.1080/14786419.2020.1868460
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Article: Direct formylation of 2-pyridone core of 3-N-methylcytisine via Duff reaction; synthesis of 9-enyl, 9-ynyl and 9-imino derivatives

Petrova, Polina R / Koval’skaya, Alena V / Lobov, Alexander N / Tsypysheva, Inna P

Natural product research. 2019 July 3, v. 33, no. 13

2019

Abstract: The first direct synthesis of 3-N-methyl-9-formylcytisine via electrophylic formylation is described. It is established, that Vilsmeier-Haack and Gatterman variants of this reaction are unsuccessful in the case with 3-substituted (-)-cytisine derivatives, ...

Abstract	The first direct synthesis of 3-N-methyl-9-formylcytisine via electrophylic formylation is described. It is established, that Vilsmeier-Haack and Gatterman variants of this reaction are unsuccessful in the case with 3-substituted (-)-cytisine derivatives, but Duff procedure (with hexamethylenetetramine in trifluoroacetic acid) gives a possibility to obtain the target pseudo aromatic aldehyde with the 69% yield. Convenient precursors for [4 + 2]- or [3 + 2]-cycloaddition reactions are obtained by means of condensation of synthesized 3-N-methyl-9-formylcytisine with acetone, nitromethane and phosphorous ylides with yields from 70 to 87%. Alternative aprroach to alkenyl products and to 9-alkynyl-3-methylcytisine is realized using the Heck and Sonogashira cross-coupling reactions of methyl vinyl ketone, cyclohexenone or trimethylsilylacetylene with 9-bromo-3-methylcytisine (55, 70 and 60% accordingly). It is shown, that interaction of 3-N-methyl-9-formylcytisine with hydroxylamines leads to corresponding nitrone (93%) and oxime (70%). All individual compounds are isolated by column chromatography and completely characterized on the basis of NMR spectroscopy data.
Keywords	acetone ; aldehydes ; chromatography ; cross-coupling reactions ; nuclear magnetic resonance spectroscopy ; phosphorus
Language	English
Dates of publication	2019-0703
Size	p. 1897-1902.
Publishing place	Taylor & Francis
Document type	Article
ZDB-ID	2185747-7
ISSN	1478-6427 ; 1478-6419
ISSN (online)	1478-6427
ISSN	1478-6419
DOI	10.1080/14786419.2018.1478832
Database	NAL-Catalogue (AGRICOLA)

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Article: Synthesis of new 1,3-thiazol derivatives of maleopimaric acid as anticancer, antibacterial and antifungal agents

Sultanova, Rimma M. / Lobov, Alexander N. / Shumadalova, Alina V. / Meshcheryakova, Svetlana A. / Zileeva, Zulfia R. / Khusnutdinova, Nailya S. / Vakhitov, Vener A. / Vakhitova, Yulia V.

Natural product research. 2021 Apr. 3, v. 35, no. 8

2021

Abstract: A series of new 1,3-thiazole derivatives of maleopimaric acid 6a–f, 7a–f were synthesized and evaluated for anticancer, antibacterial and antifungal activities. Evaluation of cytotoxic activity against human embryonic kidney 293 cells (HEK293), human ... ...

Abstract	A series of new 1,3-thiazole derivatives of maleopimaric acid 6a–f, 7a–f were synthesized and evaluated for anticancer, antibacterial and antifungal activities. Evaluation of cytotoxic activity against human embryonic kidney 293 cells (HEK293), human neuroblastoma cell line (SH-SY5Y), hepatocellular carcinoma cell line (HepG2) and human T-cell lymphoblast-like line (Jurkat), showed that introduction of the aminothiazole fragment at position 6 of the diterpenoid molecule leads to decrease of cell viability. Substance 3 was found to be the most active against all tested cell lines, inhibiting cell viability with IC₅₀ values in the range of 2–24 μM. The structure–activity relationship of these compounds was studied and the results show that the compounds 6c and 7e exhibited in vitro antifungal activity against Candida albicans and also possessed antibacterial profile against Enterobacter aerogenes, Klebsiella pneumoniae, Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Proteus vulgaris.
Keywords	Candida albicans ; Enterobacter aerogenes ; Escherichia coli ; Klebsiella pneumoniae ; Proteus vulgaris ; Staphylococcus aureus ; Streptococcus pyogenes ; T-lymphocytes ; antifungal properties ; cell viability ; cytotoxicity ; diterpenoids ; hepatoma ; humans ; kidneys ; neoplasm cells ; research ; structure-activity relationships
Language	English
Dates of publication	2021-0403
Size	p. 1340-1348.
Publishing place	Taylor & Francis
Document type	Article
ZDB-ID	2185747-7
ISSN	1478-6427 ; 1478-6419
ISSN (online)	1478-6427
ISSN	1478-6419
DOI	10.1080/14786419.2019.1648459
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Ortho-Cyclization in Asymmetrically Substituted Arylnitroso Oxides.

Chainikova, Ekaterina M / Khursan, Sergey L / Yusupova, Alfia R / Teregulova, Aigul N / Abdullin, Marat F / Lobov, Alexander N / Safiullin, Rustam L

The Journal of organic chemistry

2020 Volume 85, Issue 16, Page(s) 10813–10822

Abstract: The mechanism of the photooxidation of a number of asymmetrically substituted phenyl azides in acetonitrile was studied. The key intermediates of this reaction are the corresponding nitroso oxides, the unimolecular consumption of which occurs via the cis ...

Abstract	The mechanism of the photooxidation of a number of asymmetrically substituted phenyl azides in acetonitrile was studied. The key intermediates of this reaction are the corresponding nitroso oxides, the unimolecular consumption of which occurs via the cis form when the terminal oxygen atom of the NOO moiety reacts with the ortho position of the aromatic ring. As a result, it is opened to form a nitrile oxide. In the case of 3-methylphenyl azide, the reaction proceeds via the cis/syn form of nitroso oxide with a regioselectivity of 91%. The methoxy substituent at the para position changes the direction of the ortho-cyclization so that it occurs via the cis/anti form of nitroso oxide independently on the nature of a meta substituent. Nitrile oxides, which are formed as a result of these transformations of nitroso oxides, are stabilized by [3 + 2] cycloaddition with acetonitrile to give 1,2,4-oxadiazoles. The observed regioselectivity of the ortho-cyclization of nitroso oxides was explained using theoretical methods. Its cause consists in the extra-stabilization of the transition state of the reaction of the cis/anti form due to a stereoelectronic effect of the
Language	English
Publishing date	2020-07-30
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.0c01314
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Direct formylation of 2-pyridone core of 3-

Petrova, Polina R / Koval'skaya, Alena V / Lobov, Alexander N / Tsypysheva, Inna P

Natural product research

2018 Volume 33, Issue 13, Page(s) 1897–1902

Abstract: The first direct synthesis of 3- ...

Abstract	The first direct synthesis of 3-
MeSH term(s)	Aldehydes ; Alkaloids/chemistry ; Azocines ; Formates/chemistry ; Hydroxylamines/chemistry ; Magnetic Resonance Spectroscopy ; Nitrogen Oxides/chemical synthesis ; Oximes/chemical synthesis ; Pyridones/chemistry ; Quinolizines/chemistry
Chemical Substances	Aldehydes ; Alkaloids ; Azocines ; Formates ; Hydroxylamines ; Nitrogen Oxides ; Oximes ; Pyridones ; Quinolizines ; nitrones ; formic acid (0YIW783RG1) ; cytisine (53S5U404NU) ; 2-hydroxypyridine (6770O3A2I5) ; N-methylcytisine (TT0MW69NCI)
Language	English
Publishing date	2018-05-24
Publishing country	England
Document type	Journal Article
ZDB-ID	2185747-7
ISSN	1478-6427 ; 1478-6419
ISSN (online)	1478-6427
ISSN	1478-6419
DOI	10.1080/14786419.2018.1478832
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: Ortho-Cyclization in Asymmetrically Substituted Arylnitroso Oxides

Chainikova, Ekaterina M. / Khursan, Sergey L. / Yusupova, Alfia R. / Teregulova, Aigul N. / Abdullin, Marat F. / Lobov, Alexander N. / Safiullin, Rustam L.

Journal of organic chemistry. 2020 July 21, v. 85, no. 16

2020

Abstract	The mechanism of the photooxidation of a number of asymmetrically substituted phenyl azides in acetonitrile was studied. The key intermediates of this reaction are the corresponding nitroso oxides, the unimolecular consumption of which occurs via the cis form when the terminal oxygen atom of the NOO moiety reacts with the ortho position of the aromatic ring. As a result, it is opened to form a nitrile oxide. In the case of 3-methylphenyl azide, the reaction proceeds via the cis/syn form of nitroso oxide with a regioselectivity of 91%. The methoxy substituent at the para position changes the direction of the ortho-cyclization so that it occurs via the cis/anti form of nitroso oxide independently on the nature of a meta substituent. Nitrile oxides, which are formed as a result of these transformations of nitroso oxides, are stabilized by [3 + 2] cycloaddition with acetonitrile to give 1,2,4-oxadiazoles. The observed regioselectivity of the ortho-cyclization of nitroso oxides was explained using theoretical methods. Its cause consists in the extra-stabilization of the transition state of the reaction of the cis/anti form due to a stereoelectronic effect of the para-methoxy substituent.
Keywords	acetonitrile ; aromatic compounds ; azides ; cycloaddition reactions ; moieties ; organic chemistry ; oxygen ; photooxidation ; regioselectivity
Language	English
Dates of publication	2020-0721
Size	p. 10813-10822.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.0c01314
Database	NAL-Catalogue (AGRICOLA)

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Article: Synthesis of conjugates of (−)-cytisine derivatives with ferrocene-1-carbaldehyde and their cytotoxicity against HEK293, Jurkat, A549, MCF-7 and SH-SY5Y cells

Tsypysheva, Inna P / Erastov, Alexey S / Koval’skaya, Alena V / Lobov, Alexander N / Petrova, Polina R / Vakhitov, Vener А / Vakhitova, Yulia V / Zileeva, Zulfia R

Tetrahedron. 2020 Feb. 14, v. 76, no. 7

2020

Abstract: First example of conjugation of quinolizidine alkaloids with ferrocene was presented. The cytotoxic properties of the obtained conjugates against cell lines НЕК293, Jurkat, A549, MCF-7 and SH-SY5Y were studied. It was found, that conjugate 17 (having ... ...

Abstract	First example of conjugation of quinolizidine alkaloids with ferrocene was presented. The cytotoxic properties of the obtained conjugates against cell lines НЕК293, Jurkat, A549, MCF-7 and SH-SY5Y were studied. It was found, that conjugate 17 (having ferrocenyl methylene fragment and phenyl carboxamide moiety) produced a relatively higher cytotoxicity towards cancer Jurkat and SH-SY5Y cells with weak activity against non-cancerous HEK293 cells, suggesting the selectivity of this substance to inhibit certain tumor cells. The effect of leading compound 17 on cell cycle progression of HEK293, Jurkat, A549, MCF-7 and SH-SY5Y lines in a time-dependent fashion was studied. It was shown that hit-compound 17 caused a prominent arrest of MCF-7, Jurkat and A-549 cells in S phase along with a decrease of cells in G1 and a nearly total decline of cells in G2/M; the induction of apoptosis in HEK293 and SH-SY5Y cells was cell-cycle independent.
Keywords	apoptosis ; carboxamides ; chemical reactions ; cytotoxicity ; ferrocenes ; human cell lines ; interphase ; moieties ; neoplasm cells ; neoplasms ; quinolizidine alkaloids
Language	English
Dates of publication	2020-0214
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204285-x
ISSN	1464-5416 ; 0040-4020 ; 0563-2064
ISSN (online)	1464-5416
ISSN	0040-4020 ; 0563-2064
DOI	10.1016/j.tet.2019.130902
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Synthesis of new 1,3-thiazol derivatives of maleopimaric acid as anticancer, antibacterial and antifungal agents.

Sultanova, Rimma M / Lobov, Alexander N / Shumadalova, Alina V / Meshcheryakova, Svetlana A / Zileeva, Zulfia R / Khusnutdinova, Nailya S / Vakhitov, Vener A / Vakhitova, Yulia V

Natural product research

2019 Volume 35, Issue 8, Page(s) 1340–1348

Abstract: A series of new 1,3-thiazole derivatives of maleopimaric ... ...

Abstract	A series of new 1,3-thiazole derivatives of maleopimaric acid
MeSH term(s)	Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Antifungal Agents/chemistry ; Antifungal Agents/pharmacology ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Bacteria/drug effects ; Candida albicans/drug effects ; Cell Death/drug effects ; Cell Line ; Humans ; Microbial Sensitivity Tests ; Structure-Activity Relationship ; Thiazoles/chemical synthesis ; Thiazoles/chemistry ; Thiazoles/pharmacology ; Triterpenes/chemical synthesis ; Triterpenes/chemistry ; Triterpenes/pharmacology
Chemical Substances	Anti-Bacterial Agents ; Antifungal Agents ; Antineoplastic Agents ; Thiazoles ; Triterpenes ; maleopimaric acid (2HQ08S46WF)
Language	English
Publishing date	2019-08-20
Publishing country	England
Document type	Journal Article
ZDB-ID	2185747-7
ISSN	1478-6427 ; 1478-6419
ISSN (online)	1478-6427
ISSN	1478-6419
DOI	10.1080/14786419.2019.1648459
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Diastereoselective Synthesis of Triterpenoid 1,2,4-Trioxolanes by Griesbaum Co-ozonolysis.

Kazakova, Oxana B / Khusnutdinova, Elmira F / Petrova, Anastasiya V / Yamansarov, Emil Yu / Lobov, Alexander N / Fedorova, Alexandra A / Suponitsky, Kyrill Yu

Journal of natural products

2019 Volume 82, Issue 9, Page(s) 2550–2558

Abstract: Diastereoselective synthesis of triterpenoid 1,2,4-trioxolanes by Griesbaum co-ozonolysis was shown for the first time. Ozonolysis of 2-methoxyoximes ( ...

Abstract	Diastereoselective synthesis of triterpenoid 1,2,4-trioxolanes by Griesbaum co-ozonolysis was shown for the first time. Ozonolysis of 2-methoxyoximes (
MeSH term(s)	Crystallography, X-Ray ; Heterocyclic Compounds/chemical synthesis ; Heterocyclic Compounds/chemistry ; Molecular Structure ; Oxidation-Reduction ; Ozone/chemistry ; Spectrum Analysis/methods ; Stereoisomerism ; Triterpenes/chemistry
Chemical Substances	1,2,4-trioxane ; Heterocyclic Compounds ; Triterpenes ; Ozone (66H7ZZK23N)
Language	English
Publishing date	2019-09-06
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.9b00393
Database	MEDical Literature Analysis and Retrieval System OnLINE

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