S 98 Synthesis and tuberculostatic activity of fluoridized 3-Z-hydrazine-2-benzoyl acrylates and their cyclization products / M. A. Kravchenko, E. V. Nosova, G. N. Lipunova, O. M. Chasovskikh, V. A. Sokolov, V. N. Charushin // Problemy tuberkuleza . - 2003. - №7. - С. 49-52 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ACRYLIC ACID DERIVATIVE -- PYRAZOLE -- TUBERCULOSTATIC AGENT Аннотация: A rapid development of the resistance of drugs and their toxic and adverse reactions suggest that new antituberculous drugs should be designed. Of the greatest importance is isoniazid resistance. Testing new compounds (IIa, b) has established that the minimum inhibitory concentration of the drug (IIa), 0.39 microgram/ml suppresses the growth of Mycobacterium tuberculosis (MBT) in the macrophages up to 50%, that of the drug (IIb), 1.56 micrograms/ml, causes death in 25% of cases, which is indicative of the high activity of compounds (IIa, b) against MBT |
S 98 Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions [Electronic resource] / M. A. Kravchenko, E. V. Verbitskiy, I. D. Medvinskiy, G. L. Rusinov, V. N. Charushin // Bioorganic and Medicinal Chemistry Letters. - 2014. - Vol. 24, №14. - С. 3118-3120 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINE -- ANTIMICOBACTERIAL -- TUBERCULOSIS Аннотация: Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions proved to be a convenient method for the synthesis of 5-styryl-4-(hetero)aryl substituted pyrimidines from commercially available 5-bromopyrimidine. All intermediate 5-bromo-4-(hetero)aryl substituted pyrimidines and also the targeted 5-styryl-4-(hetero)arylpyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H37Rv, avium, terrae, and multi-drug-resistant strain isolated from tuberculosis patients in Ural region (Russia). It has been found that some of these compounds possess a low toxicity and have a bacteriostatic effect, comparable and even higher with that of first-line antituberculosis drugs \\\\expert2\\nbo\\Bioorganic and Medicinal Chemistry Letters\\2014, v. 24, p. 3118.pdf |
S 98 Synthesis, antimycobacterial and antifungal evaluation of some new 1-ethyl-5-(hetero)aryl-6-styryl-1,6-dihydropyrazine-2,3-dicarbonitriles [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, M. A. Kravchenko, S. N. Skornyakov, N. P. Evstigneeva, N. V. Kungurov, N. V. Zil'berberg, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Bioorganic and Medicinal Chemistry Letters. - 2015. - Vol. 25, № 3. - С. 524-528. - Bibliogr. : p. 528 (16 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINES -- ANTITUBERCULOSIS ACTIVITY -- PETASIS REACTION Аннотация: The Petasis reaction of 6-hydroxy adducts of 1-alkyl-2,3-dicyano-5-arylpyrazinium salts with trans-styrylboronic acids proved to proceed smoothly at room temperature to give the corresponding 5-(hetero)aryl-6-styryl substituted 1,6-dihydropyrazine derivatives. Also it has been found that C(6) unsubstituted 1,6-dihydro- or 1,4,5,6-tetrahydropyrazine derivatives can be easy prepared in high yields from the corresponding pyrazinium salts by reduction with triethylsilane. All synthesized compounds were screened in vitro for their antifungal activities against seven pathogenic fungal strains and antimycobacterial activities against Mycobacterium tuberculosis H(37)Rv, avium, terrae and multi-drug-resistant strains isolated from tuberculosis patients in the Ural region (Russia) \\\\expert2\\nbo\\Bioorganic and Medicinal Chemistry Letters\\2015, v. 25, p. 524.pdf |
S 98 Synthesis and evaluation of antitubercular activity of fluorinated 5-aryl-4-(hetero)aryl substituted pyrimidines [Электронный ресурс] / E. V. Verbitskiy, S. A. Baskakova, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Bioorganic and Medicinal Chemistry. - 2016. - Vol. 24, № 16. - С. 3771-3780 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINE -- ANTIMYCOBACTERIAL ACTIVITY -- TUBERCULOSIS Аннотация: Various 5-(fluoroaryl)-4-(hetero)aryl substituted pyrimidines have been synthesized based on the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (S-N(H)) reactions starting from commercially available 5-bromopyrimidine and their antitubercular activity against Mycobacterium tuberculosis H(37)Rv has been explored. The outcome of the study disclose that, some of the compounds have showed promising activity in micromolar concentration against Mycobacterium tuberculosis H(37)Rv, Mycobacterium avium, Mycobacterium terrae, and multidrug-resistant strains isolated from tuberculosis patients in Ural region (Russia). The data concerning the 'structure-activity' relationship for fluorinated compounds have been discussed \\\\expert2\\NBO\\Bioorganic and Medicinal Chemistry\\2016, V.24, N 16, p.3771-3780.pdf |
S 98 Synthesis and antimycobacterial activity of N-(2-aminopurin-6-yl) and N-(purin-6-yl) amino acids and dipeptides [Electronic resource] / V. P. Krasnov, A. Yu. Vigorov, V. V. Musiyak, I. A. Nizova, D. A. Gruzdev, T. V. Matveeva, G. L. Levit, V. N. Charushin // Bioorganic and Medicinal Chemistry Letters. - 2016. - Vol. 26, № 11. - С. 2645-2648 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PURINE -- GLUTAMIC ACID -- AMINO ACIDS Аннотация: Synthetic routes to novel N-(purin-6-yl)- and N-(2-aminopurin-6-yl) conjugates with amino acids and glycine-containing dipeptides were developed. In vitro testing of 42 new and known compounds made it possible to reveal a series of N-(purin-6-yl)- and N-(2-aminopurin-6-yl) conjugates exhibiting significant antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium avium, Mycobacterium terrae, and multidrug-resistant M. tuberculosis strain isolated from tuberculosis patients in the Ural region (Russia). N-(2-Aminopurin-6-yl)- and N-(purin-6-yl)-glycyl-(S)-glutamic acids were the most active compounds. (C) 2016 Elsevier Ltd. All rights reserved \\\\expert2\\NBO\\Bioorganic and Medicinal Chemistry Letters\\2016, v. 26, p. 2645.pdf |
S 98 Synthesis and Antitubercular Evaluation on Novel 1-Ethyl-5-(hetero)aryl- 1,6-dihydropyrazine-2,3-dicarbonitriles and 3-Cyano-1-ethyl-5-(hetero) aryl-2(1H)-pyrazinones / M. A. Kravchenko, E. V. Verbitskiy, S. N. Skornyakov, P. A. Slepukhin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Anti-Infective Agents. - 2016. - Vol. 14, № 2. - С. 139-144 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINES -- ANTITUBERCULOSIS ACTIVITY -- 2(1H)-PYRAZINONE Аннотация: A simple method based on hydrolysis of 2,3-dicyanopyrazinium salts has been used for the synthesis of the corresponding 5-(hetero)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones. Also, the series of novel 1-ethyl-5-(hetero)aryl-1,6-dihydropyrazine-2,3-dicarbonitriles have been obtained through reduction of the same pyrazinium salts with triethylsilane. The obtained compounds proved to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H37Rv, Mycobacterium avium, Mycobacterium terrae, as well as against rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis. The data for acute in vivo toxicity in mice have been obtained for these compounds which appear to be promising antitubercular agents |
Т 81 Туберкулостатическая активность производных 2-амино-6-хлорпурина / В. П. Краснов, А. Ю. Вигоров, В. А. Груздев, Г. Л. Левит, М. А. Кравченко, С. Н. Скорняков, О. Б. Беккер, Д. А. Маслов, В. Н. Даниленко, В. Н. Чарушин // Химико-фармацевтический журнал. - 2017. - Т. 51, № 9. - С. 20-23 Рубрики: ЗДРАВООХРАНЕНИЕ. МЕДИЦИНСКИЕ НАУКИ Кл.слова (ненормированные): ПУРИНЫ -- ТУБЕРКУЛОСТАТИЧЕСКАЯ АКТИВНОСТЬ -- ПРОТЕИНКИНАЗЫ -- PURINES -- SERINE-THREONINE PROTEIN KINASES -- TUBERCULOSTATIC ACTIVITY Аннотация: В результате изучения антимикобактериальной активности 2-амино-6-хлорпурина и его N-ацилпроизводных в отношении лабораторных (Mycobacterium tuberculosis H37Rv, M. avium, M. terrae) и клинических штаммов микобактерий туберкулеза (МЛУ-ТБ) выявлены соединения, проявляющие высокую туберкулостатическую активность (МИК от 0,35 до 1,5 мкг/мл). Изучена цитотоксическая активность соединений, проявивших антимикобактериальную активность, в отношении фибробластов эмбриона человека в МТТ-тесте и установлено, что изученные соединения являются практически нетоксичными (IC50 > 50 мкМ). Их дальнейшая химическая модификация может привести к получению соединений, перспективных для создания лекарственных средств лечения туберкулеза. С целью выяснения возможного механизма туберкулостатической активности проверена способность тестируемых соединений ингибировать микобактериальные серин-треониновые протеинкиназы (СТПК). Установлено, что туберкулостатическая активность производных 2-амино-6-хлорпурина не связана с ингибированием ими СТПК. \\\\Expert2\\NBO\\Электрон. библиотека (Отеч.периодика)\\Химико-фармацевтический журнал\\2017 Т. 51 № 9 С.20-24.pdf |
М 90 Мультикомпонентные реакции в синтезе дигидропиримидинсодержащих подандов, обладающих туберкулостатической активностью / О. В. Федорова, Е. С. Филатова, Ю. А. Титова, М. А. Кравченко, И. Г. Медвинский, Г. Л. Русинов, В. Н. Чарушин // Известия Академии наук. Серия химическая. - 2018. - № 4. - С. 743-746 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ДИГИДРОПИРИМИДИНСОДЕРЖАЩИЕ ПОДАНДЫ -- ТИПИЧНЫЕ И АТИПИЧНЫЕ ШТАММЫ МИКОБАКТЕРИЙ -- РЕАКЦИЯ БИДЖИНЕЛЛИ -- ТУБЕРКУЛОСТАТИЧЕСКАЯ АКТИВНОСТЬ Аннотация: В условиях мультикомпонентной реакции Биджинелли синтезированы дигидропиримидинтионовые поданды, а также поданды с 2-тиенильными заместителями. Туберкулостатическая активность новых подандов зависит от длины полиэфирного фрагмента. В частности, активность дигидропиримидинтионовых подандов в отношении лабораторных штаммов Mycobacterium tuberculosis H37Rv, M. avium, M. terrae и клинического штамма M. tuberculosis с множественной лекарственной устойчивостью увеличивается при уменьшении длины полиэфирного фрагмента. |
R 43 Renaissance of 4-(5-nitrofuran-2-yl)-5-arylamino substituted pyrimidines: microwave-assisted synthesis and antitubercular activity / E. V. Verbitskiy, S. A. Baskakova, D. V. Belyaev [et al.] // Mendeleev Communications. - 2021. - Vol. 31, № 2. - P210-212 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The Buchwald–Hartwig cross-coupling of 5-bromo-4-(furan-2-yl)pyrimidine with various anilines afforded the corresponding new 5-(arylamino)pyrimidines, the reaction being accelerated by microwave irradiation. Most of the obtained compounds proved to possess a high bacteriostatic in vitro effect against Mycobacterium tuberculosis H37Rv, Neisseria gonorrhoeae, and Staphylococcus aureus including Methicillin-resistant strain, which is stronger than that of the commercial drug Spectinomycin. |
New approach to biologically active indolo[2,3-b]quinoxaline derivatives through intramolecular oxidative cyclodehydrogenation / G. Sadykhov, D. V. Belyaev, M. G. Pervova [et al.] // ChemistrySelect. - 2022. - Vol. 7, № 18. - Pe202200497 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient synthetic protocol to antiviral agent B-220 and a series of similar indolo[2,3-b]quinoxaline derivatives has been developed. This synthetic approach is based on Buchwald-Hartwig cross-coupling and subsequent annulation by intramolecular oxidative cyclodehydrogenation. For the first time, 6H-indolo[2,3-b]quinoxaline amine derivatives were evaluated for antimycobacterial activity. The moderate bacteriostatic effect against Mycobacterium tuberculosis H37Rv was found. A plausible mechanism of antibacterial action was elucidated by the molecular docking. |