Anna S. Komendantova

N.D. Zelinsky Institute of Organic Chemistry

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Trends

Author Order

Document Type

Co-Authors

ИВ

И. В. Заварзин

N.D. Zelinsky Institute of Organic Chemistry

Yulia A. Volkova

N.D. Zelinsky Institute of Organic Chemistry

A. V. Komkov

N.D. Zelinsky Institute of Organic Chemistry

KА

Konstantin А. Lyssenko

National Research University Higher School of Economics

Leonid G. Menchikov

N.D. Zelinsky Institute of Organic Chemistry

E. I. Chernoburova

N.D. Zelinsky Institute of Organic Chemistry

ВЗ

Валерий З. Ширинян

N.D. Zelinsky Institute of Organic Chemistry

Alexander M. Scherbakov

N. I. Lobachevsky State University of Nizhny Novgorod

Olga E. Andreeva

Ministry of Health of the Russian Federation

Yu. A. Volkova

A. N. Nesmeyanov Institute of Organoelement Compounds

Cooperative Institutions

Russian Academy of Sciences

N.D. Zelinsky Institute of Organic Chemistry

Lomonosov Moscow State University

A. N. Nesmeyanov Institute of Organoelement Compounds

Ministry of Health of the Russian Federation

Russian Cancer Research Center NN Blokhin

National Medical Research Center of Cardiology

Endocrinology Research Center

Moscow State University

Plekhanov Russian University of Economics

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Field

A Straightforward Approach toward Multifunctionalized Pyridazines via Imination/Electrocyclization

Organic Letters (2015)

A. V. Komkov Anna S. Komendantova Leonid G. Menchikov E. I. Chernoburova Yulia A. Volkova

A facile synthesis of functionalized 3-carbamide pyridazines starting from readily available chlorovinyl aldehydes and oxamic acid thiohydrazides via cascade imination/electrocyclization is reported. In the presence of p-toluenesulfuric acid, various ketones have been efficiently incorporated into the pyridazine derivatives through a two-step sequence involving a Vilsmeier-Haack reaction and imination. The synthetic value of this method has been demonstrated by efficient synthesis of steroidal pyridazines.

Pyridazine

Sequence (biology)

10.1021/acs.orglett.5b01718

Cite

Citations (28)

Iodine-promoted synthesis of pyrazoles from 1,3-dicarbonyl compounds and oxamic acid thiohydrazides

Organic Chemistry Frontiers (2020)

Anna S. Komendantova Konstantin А. Lyssenko И. В. Заварзин Yulia A. Volkova

A novel approach to 3,4-dicarbonyl-substituted pyrazoles from 1,3-dicarbonyl compounds and oxamic acid thiohydrazides was developed via iodine-promoted cascade imination/halogenation/cyclization/ring contraction reaction.

10.1039/d0qo00476f

Cite

Citations (22)

CCDC 1402494: Experimental Crystal Structure Determination

The Cambridge Structural Database (2016)

A. V. Komkov Anna S. Komendantova Leonid G. Menchikov E. I. Chernoburova Yu. A. Volkova

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1j2drr

Cite

Citations (0)

Facile Synthesis of Carboxamide-Substituted 1,3,4-Thiadiazines and 5,6-Dihydro-4H-1,3,4-Thiadiazin-5-Ols

Chemistry of Heterocyclic Compounds (2019)

Anna S. Komendantova Ksenya A. Ivanova Konstantin V. Lyssenko Yulia A. Volkova И. В. Заварзин

Carboxamide

Substitution (logic)

Phenacyl

Reaction conditions

10.1007/s10593-019-02514-5

Cite

Citations (4)

CCDC 1990863: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Anna S. Komendantova Konstantin А. Lyssenko И. В. Заварзин Yulia A. Volkova

10.5517/ccdc.csd.cc24tnd1

Cite

Citations (0)

Steroidal Pyrimidines and Dihydrotriazines as Novel Classes of Anticancer Agents against Hormone-Dependent Breast Cancer Cells

Frontiers in Pharmacology (2018)

Alexander M. Scherbakov A. V. Komkov Anna S. Komendantova Margarita A. Yastrebova Olga E. Andreeva

Most breast and prostate tumors are hormone-dependent, making it possible to use hormone therapy in patients with these tumors. The design of effective endocrine drugs that block the growth of tumors and have no severe side effects is a challenge. Thereupon, synthetic steroids are promising therapeutic drugs for the treatment of diseases such as hormone-dependent breast and prostate cancers. Here, we describe novel series of steroidal pyrimidines and dihydrotriazines with anticancer activities. A flexible approach to unknown pyrimidine and dihydrotriazine derivatives of steroids with selective control of the heterocyclization pattern is disclosed. A number of 18-nor-5α-androsta-2,13-diene[3,2-d]pyrimidine, androsta-2-ene[3,2-d]pyrimidine, Δ1, 3, 5(10)-estratrieno[16,17-d]pyrimidine, and 17-chloro-16-dihydrotriazine steroids were synthesized by condensations of amidines with β-chlorovinyl aldehydes derived from natural hormones. The synthesized compounds were screened for cytotoxicity against breast cancer cells and showed IC50 values of 7.4 μM and higher. Compounds were tested against prostate cancer cells and exhibited antiproliferative activity with IC50 values of 9.4 μM and higher comparable to that of cisplatin. Lead compound 4a displayed selectivity in ERα-positive breast cancer cells. At 10 μM concentration, this heterosteroid inhibited 50% of the E2-mediated ERα activity and led to partial ERα down-regulation. The ERα reporter assay and immunoblotting were supported by the docking study, which showed the probable binding mode of compound 4a to the estrogen receptor pocket. Thus, heterosteroid 4a proved to be a selective ERα modulator with the highest antiproliferative activity against hormone-dependent breast cancer and can be considered as a candidate for further anticancer drug development. In total, the synthesized heterosteroids may be considered as new promising classes of active anticancer agents.

Docking (animal)

IC50

10.3389/fphar.2017.00979

Cite

Citations (55)

Cyclization of β‐Chlorovinyl Thiohydrazones into Pyridazines: A Mechanistic Study

European Journal of Organic Chemistry (2018)

Anna S. Komendantova Артем Н. Фахрутдинов Leonid G. Menchikov Alexey Yu. Sukhorukov И. В. Заварзин

Extensive experimental and theoretical investigations on the isomerization and heterocyclizations of β‐chlorovinyl thiohydrazones derived from oxamic acid thiohydrazides and β‐chlorovinyl aldehydes were performed to elucidate the reaction mechanism of pyridazine formation. We showed that model β‐chlorovinyl thiohydrazone undergoes multiple isomerization reactions in solution induced by thione–thiol tautomerism and Z/E ‐isomerization at the C=N bond. Mechanistic rationalization along with computational studies demonstrated that pyridazine is predominantly generated from the Z ‐thiol isomers by 6 π‐electrocyclization of the thiohydrazone‐derived 2,3‐diazatriene intermediate. The autocatalytic character of cyclization accelerated by the formation of acid was demonstrated by means of 1 H NMR monitoring.

Pyridazine

Thiol

Autocatalysis

10.1002/ejoc.201801118

Cite

Citations (7)

CCDC 1990862: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Anna S. Komendantova Konstantin А. Lyssenko И. В. Заварзин Yulia A. Volkova

10.5517/ccdc.csd.cc24tnc0

Cite

Citations (0)

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

Bioorganic Chemistry (2019)

Anna S. Komendantova Alexander M. Scherbakov A. V. Komkov V. V. Chertkova Alexey O. Gudovanniy

10.1016/j.bioorg.2019.103142

Cite

Citations (31)

Efficient Synthesis of 4‐ and 5‐Substituted 2‐Aminopyrimidines by Coupling of β‐Chlorovinyl Aldehydes and Guanidines

European Journal of Organic Chemistry (2017)

Anna S. Komendantova A. V. Komkov Yulia A. Volkova И. В. Заварзин

A general, practical, and simple synthesis of functionalized 2‐aminopyrimidines starting from β‐chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently transformed into the pyrimidine derivatives by a two‐step sequence involving the Vilsmeier–Haack reaction followed by a condensation reaction with guanidines. The protocol is distinguished by operational simplicity, inexpensive reagents, and functional‐group tolerance. In many cases, pure solid products can be obtained in high to excellent yields without using column chromatography. The synthetic value of the method was demonstrated by the efficient synthesis of steroidal pyrimidines and a precursor of the antitumor agents Imatinib and Mocetinostat.

Functional group

Potassium carbonate

Coupling reaction

10.1002/ejoc.201700737

Cite

Citations (12)