Institute of Physiologically Active Compounds

Chernogolovka, Russia

Institute of Physiologically Active Compounds

Chernogolovka, Russia
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Luzina E.L.,Institute of Physiologically Active Compounds | Popov A.V.,University of Pennsylvania
European Journal of Medicinal Chemistry | Year: 2010

A number of N-bis(trifluoromethyl)alkyl-N′-substituted ureas have been synthesized and evaluated for their in vitro anticancer activity against the human cancer cell lines at the National Cancer Institute (NCI, USA). Marked activity was shown for compounds 4a and 5a. The most sensitive cell lines relative to the tested compounds were: 4a UO-31 (renal cancer, log GI 50 -5.62), HS 578T (breast cancer, log GI50 -5.50), 5a HCC-2998 (colon cancer, log GI50 -5.94), NCI-H322M (lung cancer, log GI50 -5.75) and PC-3 (prostate cancer, log GI50 -5.66). © 2010 Elsevier Masson SAS. All rights reserved.


Dmitriev M.E.,Institute of Physiologically Active Compounds | Ragulin V.V.,Institute of Physiologically Active Compounds
Tetrahedron Letters | Year: 2012

A mild procedure for the synthesis of N-protected α- aminoalkylphosphinic acids by the reaction of N,N′-benzylidene- or N,N′-alkylidenebiscarbamates, trifluoroacetic anhydride and the corresponding alkylphosphonous acids in methylene chloride or toluene is described. The results obtained confirm the earlier proposed mechanism for amidoalkylation of hydrophosphorylic compounds involving an Arbuzov-type reaction step. © 2011 Elsevier Ltd. All rights reserved.


Luzina E.L.,Institute of Physiologically Active Compounds | Popov A.V.,University of Pennsylvania
Journal of Fluorine Chemistry | Year: 2014

Novel trifluoromethylated mono- and bicyclic succinimides derived from trifluoromethylmaleic anhydride were synthesized using cyclopentadiene or 2,3-dimethylbutadiene and (het)arylamines. The biological activity of these compounds was evaluated using prediction methods and experimental studies. This series of new trifluoromethyl succinimides (3a,b and 6a-c) were tested by the National Cancer Institute (NCI, Bethesda, USA) by Program NCI-60 DTP Human Tumor Cell Line Screen at a single high dose (10-5 M). Imides revealed activity on Leukemia cell lines (RPMI-8226 - myeloma cell line), Non-Small Cell Lung Cancer cell lines (A549/ATCC - lung carcinoma epithelial cells) and Renal cancer cell lines (A498 and SN12 C). © 2014 Elsevier B.V. All rights reserved.


Trashin S.A.,Institute of Physiologically Active Compounds | Dubinina T.V.,Moscow State University | Fionov A.V.,Moscow State University | Tomilova L.G.,Moscow State University
Journal of Porphyrins and Phthalocyanines | Year: 2011

The electrochemical and spectroelectrochemical behavior of two planar binuclear naphthalocyanines containing benzene and naphthalene π-conjugated bridges was investigated for the first time. Their intense absorption in the near infrared region was observed even in a low polar solvent such as o-dichlorobenzene after electrochemical reduction at a potential of -0.4 V vs. SCE, which was not enough to reduce the complexes into their first reduction state. These data and EPR studies allow us to conclude that the electrochemically generated form is the true neutral form of the synthesized compounds whereas the suppression of the near-infrared bands is a result of the presence of their cation radicals as one-electron oxidized forms. © 2011 World Scientific Publishing Company.


Luzina E.L.,Institute of Physiologically Active Compounds | Popov A.V.,University of Pennsylvania
Journal of Fluorine Chemistry | Year: 2015

A new method is described for producing 3,3,3-trifluoroethyl isocyanate from perfluoroisobutene (PFIB). Isocyanate was used for synthesis of carbamates and ureas. A series of trifluoroethyl-substituted ureas has been tested in the National Cancer Institute (NCI, Bethesda, USA) by the NCI-60 DTP Human Tumor Cell Line Screening Program at a single high dose (10-5 M). The moderate anticancer activity was shown against some types of cancer on the individual human cell lines for leukemia, non-small cell lung cancer and renal cancer. © 2015 Published by Elsevier B.V.


Luzina E.L.,Institute of Physiologically Active Compounds | Popov A.V.,University of Pennsylvania
Journal of Fluorine Chemistry | Year: 2013

1,1-Bis(trifluoromethyl)alkyl isocyanates obtained from perfluoroisobutene (PFIB) react with aroyl(arylsulfonyl)hydrazines. Twenty eight prospective biologically active polyfluorinated 1,4-substituted semicarbazides were synthesized. The structure of each new product was confirmed by analytical and spectroscopic methods. The Lipinski's and Gelovani's parameters were then calculated. Two adjustments to the Lipinski rules of five are suggested for fluorinated drug candidates. © 2013 Elsevier B.V.


Aksinenko A.Y.,Institute of Physiologically Active Compounds | Goreva T.V.,Institute of Physiologically Active Compounds | Epishina T.A.,Institute of Physiologically Active Compounds | Sokolov V.B.,Institute of Physiologically Active Compounds
Journal of Fluorine Chemistry | Year: 2012

The first representative of 3-fluoro-2-(dialkoxyphosphoryl)imidazo[1,2-a] pyridines has been synthesized by the reaction of N-(pyridin-2-yl)-2,2,2- trifluoroacetimidoyl chloride with triethyl phosphite. © 2012 Elsevier B.V.


Gakh A.A.,Oak Ridge National Laboratory | Gakh A.A.,University of Virginia | Sosnov A.V.,Institute of Physiologically Active Compounds | Krasavin M.,Griffith University | And 2 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2013

The combination of experimental (inhibition of colchicine binding) and computational (COMPARE, docking studies) data unequivocally identified diaryl 5-amino-1,2,4-oxadiazoles as potent tubulin inhibitors. Good correlation was observed between tubulin binding and cytostatic properties for all tested compounds with the notable exception of the lead candidate, 3-(3-methoxyphenyl)- 5-(4-methoxyphenyl)amino-1,2,4-oxadiazole (DCP 10500078). This compound was found to be substantially more active in our in vitro experiments than the monofluorinated title compound, 3-(2-fluorophenyl)-5-(4-methoxyphenyl)amino-1,2, 4-oxadiazole (DCP 10500067/NSC 757486), which in turn demonstrated slightly better tubulin binding activity. Comparative SAR analysis of 25 diaryl 5-amino-1,2,4-oxadiazoles with other known tubulin inhibitors, such as combretastatin A-4 (CA-4) and colchicine, provides further insight into the specifics of their binding as well as a plausible mechanism of action. © 2012 Elsevier Ltd. All rights reserved.


Dmitriev M.E.,Institute of Physiologically Active Compounds | Ragulin V.V.,Institute of Physiologically Active Compounds
Tetrahedron Letters | Year: 2010

A new and milder version of the procedure for the synthesis of N-protected α-aminoalkylphosphorylic compounds by reaction of alkyl carbamates, aldehydes and hydrophosphorylic compounds in acetic anhydride/acetyl chloride and a new mechanism for this type of reaction are described. The isolation, for the first time, of N,N′-benzylidene- and N,N′-alkylidenebiscarbamates as intermediates from the reaction medium and studies of the direct reaction of pre-obtained biscarbamates and hydrophosphorylic compounds in acetic anhydride are reported. A new version of the mechanism for this reaction which includes an Arbuzov-type reaction is proposed. © 2010 Elsevier Ltd. All rights reserved.


Luzina E.L.,Institute of Physiologically Active Compounds | Popov A.V.,University of Pennsylvania
European Journal of Medicinal Chemistry | Year: 2012

A series of new synthesized N-bis(trifluoromethyl)alkyl-N'-substituted ureas have been tested in the National Cancer Institute (NCI, Bethesda, USA) by Program NCI-60 DTP Human Tumor Cell Line Screen at a single high dose (10 -5 M). COMPARE analysis has been carried out for all tested compounds. The tested compounds showed antitumor activity against individual cell lines. The most sensitive cell lines relative to the tested compounds are: 5g Leukemia RPMI-8226 (GI% 52.7), Non-Small Cell Lung cancer HOP-92 (GI % 88.53), NCI-H522 (GI % 64.41), Melanoma UACC-62 (GI% 53.08), SK-MEL-5 (GI % 74.63), Breast cancer MDA-MB-468 (GI% 51.29), T-47D (GI % 65.1), 5b Leukemia K-562 (GI % 55.55), 7m Leukemia HL-60(TB) (GI % 51.76). © 2012 Elsevier Masson SAS. All rights reserved.

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