28 results on '"Sergey G. Klochkov"'
Search Results
2. EUDESMANE SESQUITERPENE LACTONES OF THE GENUS INULA AND THEIR BIOLOGICAL ACTIVITY
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S. V. Afanasyeva, Sergey G. Klochkov, and S. A. Pukhov
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chemistry.chemical_classification ,Phytochemistry ,Inula ,biology ,Stereochemistry ,fungi ,Organic Chemistry ,Farnesyl pyrophosphate ,biological activity ,Plant Science ,Pharmacognosy ,Sesquiterpene ,biology.organism_classification ,Terpenoid ,Biomaterials ,chemistry.chemical_compound ,chemistry ,Chemotaxonomy ,Sesquiterpene lactones ,eudesmanes ,Lactone - Abstract
Sesquiterpene lactones (SL) are widely distributed in nature (formed biosynthetically in plants from farnesyl pyrophosphate) and are a structurally diverse class of terpenoids with 15 carbon atoms in the skeleton and, in addition to the lactone cycle, can contain various functional groups. Some of them exhibit biological activity both in a rather wide range and in relation to a specific target. An increase in the number of undescribed natural plant compounds of this class, as well as detection in various plant species, opens up new possibilities for their use for the purposes of medical chemistry, phytochemistry, pharmacognosy, chemotaxonomy, and related fields. Using the example of SL of the eudesmane structural type found in plants of the genus Inula, this review attempts to show the relevance of studies of such compounds that investigate the mechanism of action on various biological models, including the goal of developing new effective antitumor agents.
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- 2021
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3. Synthesis and Cytotoxic Activity of the Products of Addition of Thiophenol to Sesquiterpene Lactones
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A. V. Semakov, Lada V. Anikina, and Sergey G. Klochkov
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chemistry.chemical_classification ,Stereochemistry ,Thiophenol ,Organic Chemistry ,Prodrug ,Sesquiterpene ,Biochemistry ,chemistry.chemical_compound ,Residue (chemistry) ,chemistry ,Bioorganic chemistry ,Cytotoxicity ,Lactone ,Conjugate - Abstract
Abstract— Derivatives of sesquiterpene lactones modified at the lactone ring with a thiophenol residue have been synthesized. The resulting conjugates with thiophenol have capacity for the oxidation–elimination reaction by the action of ROS of a tumor cell with the release of initial cytotoxic lactones. It has been proposed to use the resulting sulfur-containing conjugates as ROS-activated prodrugs of sesquiterpene lactones. The antiproliferative properties of the conjugates have been examined on tumor and pseudonormal cell lines. The cytotoxicity of the conjugates is lower than that of parent lactones; however, in some cases, as with the conjugates of alantolactone with artemisiten, it remains moderate in all tumor cell lines tested.
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- 2021
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4. Regioselective Synthesis, Structure, and Chemosensitizing Antitumor Activity of Cyclic Hydroxamic Acid Based on DL-Valine
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Alexander V. Chernyak, T. E. Sashenkova, E. N. Klimanova, D. V. Mishchenko, Yu. R. Aleksandrova, Margarita E. Neganova, I. V. Vystorop, Gennady V. Shilov, U. Yu. Allayarova, and Sergey G. Klochkov
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Hydroxamic acid ,Cyclophosphamide ,Organic Chemistry ,Regioselectivity ,Alkylation ,Pharmacology ,medicine.disease ,Biochemistry ,Metastasis ,chemistry.chemical_compound ,chemistry ,In vivo ,Valine ,medicine ,Bioorganic chemistry ,medicine.drug - Abstract
The reaction of DL-valine hydroxamic acid with triacetonamine proceeds as the N,N'-regioselective condensation to form (±)-1-hydroxy-3-isopropyl-7,7,9,9-tetramethyl-1,4,8-triazaspiro[4,5]decan-2-one. A study of the antimetastatic and antitumor activities of the resulting hydroxamic acid in vivo by the combined therapy with a cytostatic of the alkylation type on a model of experimental transplanted mouse melanoma B16 showed that the compound is capable of increasing the sensitivity of the tumor to the known antitumor drug cyclophosphamide applied at a subtherapeutic dose. The chemosensitizing activity of hydroxamic acid combined with cyclophosphamide led to an almost twofold increase in the antitumor effect of the cytostatic and a marked decrease in the number of metastases, which showed up as an increase in the metastasis inhibition index (MII) to 74%.
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- 2021
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5. Promising Molecular Targets for Design of Antitumor Drugs Based on Ras Protein Signaling Cascades
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Sergey G. Klochkov, Yu. R. Aleksandrova, and M. E. Neganova
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0301 basic medicine ,MAPK/ERK pathway ,chemistry.chemical_classification ,010405 organic chemistry ,Kinase ,Cell growth ,Organic Chemistry ,Biology ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,03 medical and health sciences ,030104 developmental biology ,Enzyme ,chemistry ,Apoptosis ,Cancer research ,Signal transduction ,Receptor ,PI3K/AKT/mTOR pathway - Abstract
Oncological diseases have always been among the most significant pathologies. Therefore, development of effective antitumor drugs is considered one of the priorities of modern healthcare. Inhibitors of proteins, enzymes, and receptors that regulate the signaling pathways of tumor cells, as well as apoptosis inductors, are used for tumor chemotherapy. The most significant and studied signaling pathways are the Raf/MEK/ERK and phosphoinositide-3 kinase (PI3K). Changes in the cascades of these pathways lead to the modulation of many cellular functions, such as cell growth and survival, proliferation, differentiation, and adhesion. These signaling cascades are closely related to Ras proteins. Oncogenic forms of Ras proteins are detected in a large number of tumor diseases—more than 30% of all forms of neoplasms. The literature data of the last 30 years on the study of the key stages of signaling cascades initiated by oncogenic Ras proteins are considered in this review. The processing features of Ras proteins, which are currently considered as promising molecular targets for the development of antitumor drugs, are analyzed separately. Literature data on new strategies to search for effective antineoplastic agents, which are based on Ras proteins signaling pathways, and bipharmacophore compounds are presented and discussed.
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- 2020
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6. The Hydroxamic Acids as Potential Anticancer and Neuroprotective Agents
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Gjumrakch Aliev, Margarita E. Neganova, Sergey G. Klochkov, and Yulia R. Aleksandrova
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Antineoplastic Agents ,Mitochondrion ,Hydroxamic Acids ,01 natural sciences ,Biochemistry ,Neuroprotection ,Epigenesis, Genetic ,Pathogenesis ,03 medical and health sciences ,Drug Discovery ,Humans ,Epigenetics ,0101 mathematics ,030304 developmental biology ,Pharmacology ,chemistry.chemical_classification ,0303 health sciences ,biology ,Organic Chemistry ,Biological activity ,010101 applied mathematics ,Histone Deacetylase Inhibitors ,Enzyme ,Histone ,Neuroprotective Agents ,chemistry ,biology.protein ,Molecular Medicine ,Histone deacetylase - Abstract
Hydroxamic acids are a promising class of chemical compounds with proven antitumor potential, primarily due to their ability to inhibit the activity of histone deacetylase enzymes. The analysis of modern experimental data shows a wide range of biological activities of hydroxamic acids, which make them equally worthy candidates for the fight against neuropathologies. A characteristic feature of hydroxamic acids is their ability to act simultaneously on several promising molecular targets for the correction of both neuropathologies and oncological diseases, thereby exhibiting multifunctionality. This review discusses the effect of hydroxamic acids on key parts of cancer and neurodegenerative disorders' pathogenesis. Pathological changes in the processes associated with oxidative stress, the functioning of mitochondria, and the activity of metal enzymes of the class of histone deacetylases, as the main links in the epigenetic regulation of pathological conditions, are such molecular targets.
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- 2020
7. Amino Derivatives of Natural Epoxyalantolactone: Synthesis and Cytotoxicity toward Tumor Cells
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S. A. Pukhov, Lada V. Anikina, Sergey G. Klochkov, E. S. Dubrovskaya, S. V. Afanasyeva, and A. V. Semakov
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010405 organic chemistry ,Chemistry ,Organic Chemistry ,medicine.disease_cause ,01 natural sciences ,Biochemistry ,In vitro ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Apoptosis ,medicine ,Bioorganic chemistry ,Cytotoxic T cell ,Signal transduction ,Cytotoxicity ,Oxidative stress ,Conjugate - Abstract
Reactions of natural epoxyalantolactone with primary and secondary amines, which lead to hydrated benzo[g]furo[4,3,2-cd]indolones and eudesmane-type amino derivatives, respectively, have been studied. Epoxyalantolactone conjugates have been synthesized with the involvement of pharmacophoric amines, and their cytotoxic activity toward some tumor cell lines has been tested. The involvement of the signaling pathway of protein p53 in the death of tumor cells, the contribution of oxidative stress, and the induction of apoptosis have been investigated in experiments in vitro.
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- 2018
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8. Synthesis and Antiproliferative Activity of Conjugates of Anthracycline Antibiotics with Sesquiterpene Lactones of the Elecampane
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S. V. Afanasyeva, S. A. Pukhov, Sergey G. Klochkov, A. V. Semakov, and Lada V. Anikina
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Daunorubicin ,Sesquiterpene ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,hemic and lymphatic diseases ,polycyclic compounds ,medicine ,Cytotoxic T cell ,Doxorubicin ,Elecampane ,neoplasms ,Inula ,biology ,010405 organic chemistry ,organic chemicals ,Organic Chemistry ,biology.organism_classification ,0104 chemical sciences ,carbohydrates (lipids) ,010404 medicinal & biomolecular chemistry ,chemistry ,Cell culture ,Conjugate ,medicine.drug - Abstract
The daunorubicin and doxorubicin anthracycline antibiotics were modified with the Inula helenium L. sesquiterpene lactones (alantolactone, isoalantolactone, and alloalantolactone) and with their epoxy derivatives. Antiproliferative properties of these conjugates were studied on tumor and normal cell lines. The daunorubicin conjugates with the sesquiterpene lactones (isoalantolactone, allantolactone, and alloalantolactone) and with their epoxy derivatives were found to exhibit the higher activity against human tumor cell lines than the corresponding doxorubicin conjugates. The daunorubicin conjugate with epoxyisoalantolactone proved to be the most effective compound, because it was more cytotoxic than daunorubicin towards a number of cell lines, including those daunorubicin-resistant, and did not affect normal human cells.
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- 2018
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9. Synthesis, structural characterization and cytotoxic activity of heterocyclic compounds containing the furoxan ring
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Ivan V. Ananyev, Alexander S. Kulikov, Lada V. Anikina, Leonid L. Fershtat, Sergey G. Klochkov, Jacques Royer, Marina I. Struchkova, S. A. Pukhov, Alexander A. Larin, Anna A. Romanova, and Nina N. Makhova
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lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Furoxan ,Cytotoxic T cell ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Combinatorial chemistry ,0104 chemical sciences - Published
- 2017
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10. Synthesis and Structure of (3R,3aR,4S,4aR,5S,9aR)-4-Hydroxy-4a,5-Dimethyl-3-{[4-(4-Fluorophenyl)-Piperazino]Methyl}-3a,4,4a,5,6,7,9,9a-Octahydronaphtho [2,3-b]Furan-2(3H)-One
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S. V. Afanas′eva, Anna A. Romanova, I. V. Anan‘ev, Sergey G. Klochkov, and S. A. Pukhov
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010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,chemistry ,010405 organic chemistry ,Furan ,Organic chemistry ,Plant Science ,General Chemistry ,01 natural sciences ,General Biochemistry, Genetics and Molecular Biology ,0104 chemical sciences - Published
- 2018
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11. A Novel Heterocyclic System Based on Natural Epoxyalantolactone
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Sergey G. Klochkov, Sergey A. Pukhov, Svetlana V. Afanasieva, Margarita E. Neganova, Ivan V. Ananiev, Marco Avila-Rodriguez, Vadim V. Tarasov, and Gjumrakch Aliev
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Reaction mechanism ,synthesis ,02 engineering and technology ,010402 general chemistry ,Ring (chemistry) ,Sesquiterpene ,01 natural sciences ,lcsh:Chemistry ,chemistry.chemical_compound ,new heterocyclic system ,sesquiterpene lactones ,Organic chemistry ,Methylene ,epoxyalantolactone ,Spectral data ,Original Research ,chemistry.chemical_classification ,Primary (chemistry) ,Chemistry ,General Chemistry ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,lcsh:QD1-999 ,Michael reaction ,0210 nano-technology ,Lactone - Abstract
Natural sesquiterpene lactones which contain an exocyclic methylene group in the β-position of the lactone ring react readily with N-nucleophiles. When studying the reaction of the natural epoxyalantolactone with the primary amines we demonstrate the formation of a new heterocyclic system - the hydrogenated benzo[g]furo[4,3,2-cd]indol-3(1H)-one. Spectral data on the characteristics of the synthesized compounds are presented. The data on the reaction mechanisms and its applicability for the preparation are discussed.
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- 2019
12. Application of Acyzol in the Context of Zinc Deficiency and Perspectives
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Vladimir N. Chubarev, Vadim V. Tarasov, Svetlana A. Lebedeva, Boris A. Trofimov, Susanna S Sologova, Pavel A. Galenko-Yaroshevsky, Sergey G. Klochkov, Lidiya N. Parshina, Gjumrakch Aliev, Alfiya Makhmutova, Yi Li, and Marco Avila-Rodriguez
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0301 basic medicine ,medicine.medical_treatment ,Drug Evaluation, Preclinical ,Zinc Acetate ,Disease ,Review ,Bioinformatics ,lcsh:Chemistry ,Mice ,Antidote ,lcsh:QH301-705.5 ,Spectroscopy ,media_common ,Clinical Studies as Topic ,zinc ,Imidazoles ,Acyzol ,General Medicine ,Computer Science Applications ,Nutrition Disorders ,Treatment Outcome ,Drug ,media_common.quotation_subject ,chemistry.chemical_element ,Context (language use) ,Zinc ,Catalysis ,carbon monoxide ,Inorganic Chemistry ,03 medical and health sciences ,Immune system ,Psoriasis ,medicine ,Animals ,Humans ,Physical and Theoretical Chemistry ,zinc deficiency conditions ,Molecular Biology ,030109 nutrition & dietetics ,business.industry ,Organic Chemistry ,medicine.disease ,Trace Elements ,030104 developmental biology ,lcsh:Biology (General) ,lcsh:QD1-999 ,chemistry ,Zinc deficiency ,pharmacological activity ,business - Abstract
Zinc is one of the most important essential trace elements. It is involved in more than 300 enzyme systems and is an indispensable participant in many biochemical processes. Zinc deficiency causes a number of disorders in the human body, the main ones being the delay of growth and puberty, immune disorders, and cognitive dysfunctions. There are over two billion people in the world suffering from zinc deficiency conditions. Acyzol, a zinc-containing medicine, developed as an antidote against carbon monoxide poisoning, demonstrates a wide range of pharmacological activities: Anti-inflammatory, reparative, detoxifying, immunomodulatory, bacteriostatic, hepatoprotective, adaptogenic, antioxidant, antihypoxic, and cardioprotective. The presence of zinc in the composition of Acyzol suggests the potential of the drug in the treatment and prevention of zinc deficiency conditions, such as Prasad’s disease, immune system pathology, alopecia, allergodermatoses, prostate dysfunction, psoriasis, stomatitis, periodontitis, and delayed mental and physical development in children. Currently, the efficiency of Acyzol in the cases of zinc deficiency is shown in a large number of experimental studies. So, Acyzol can be used as a highly effective drug for pharmacologic therapy of a wide range of diseases and conditions and it opens up new perspectives in the treatment and prevention of zinc deficiency conditions.
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- 2019
13. 1,5-Diaryl-3-oxo-1,4-pentadienes based on (4-oxopiperidin-1-yl)(aryl)methyl phosphonate scaffold: synthesis and antitumor properties
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Margarita E. Neganova, Lada V. Anikina, Mikhail V. Makarov, Sergey G. Klochkov, Denis V. Mischenko, S. A. Pukhov, Ekaterina Yu. Rybalkina, Valery K. Brel, Victor N. Khrustalev, and Zinaida S. Klemenkova
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010405 organic chemistry ,Stereochemistry ,Aryl ,Organic Chemistry ,01 natural sciences ,Medicinal chemistry ,Phosphonate ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,chemistry ,Bromide ,Ic50 values ,Moiety ,General Pharmacology, Toxicology and Pharmaceutics ,Acetonitrile ,Human cancer ,Boron trifluoride - Abstract
Novel 3,5-bis(arylidene)-4-piperidones modified with diethyl[(aryl)methyl]phosphonate moiety attached to the piperidone nitrogen atom have been synthesized by crotonic condensation of aromatic aldehydes with diethyl[(4-oxopiperidin-1-yl)(aryl)methyl]phosphonates in the presence of LiClO4/Et3N system or acetonitrile solution of boron trifluoride etherate. The synthesized phosphonate derivatives of 3,5-bis(arylidene)-4-piperidone series displayed inhibitory properties toward RD, PC3, HCT116, and MCF7 human cancer cell lines with IC50 values in the range of 2.5–8.5 μM, as assessed by an in vitro 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.
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- 2016
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14. Amination Products of Inula britannica Lactones and Their Antitumor Activity
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S. V. Afanas’eva, Lada V. Anikina, S. A. Pukhov, Sergey G. Klochkov, and A. B. Ermatova
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Antitumor activity ,Addition reaction ,biology ,Stereochemistry ,Plant Science ,General Chemistry ,Sesquiterpene ,biology.organism_classification ,General Biochemistry, Genetics and Molecular Biology ,Solvent ,chemistry.chemical_compound ,chemistry ,Inula britannica ,Michael reaction ,Organic chemistry ,Amine gas treating ,Amination - Abstract
The reactions with amines of the sesquiterpene lactones britanin and inuchinenolide C isolated from Inula britannica were studied. Migration of the acetyl group during the addition reaction was observed and depended on the nature of the amine and solvent. Compounds with antitumor activity were found among the new amine derivatives.
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- 2015
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15. Study of Distribution and Biological Effects of Fullerene C60after Single and Multiple Intragastrical Administrations to Rats
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Alexander I. Yaropolov, Olga D. Hendrickson, Boris B. Dzantiev, Sergey O. Bachurin, Olga Morozova, Sergey G. Klochkov, and Anatoly V. Zherdev
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Gastrointestinal tract ,Biodistribution ,Materials science ,Stomach ,Organic Chemistry ,Spleen ,Pharmacology ,Atomic and Molecular Physics, and Optics ,Small intestine ,Excretion ,Toxicology ,medicine.anatomical_structure ,In vivo ,medicine ,Distribution (pharmacology) ,General Materials Science ,Physical and Theoretical Chemistry - Abstract
In this study, male rats were intragastrically exposed to fullerene C60 for 1-day and 30-day periods at daily doses of 2000 and 250 mg/kg of body weight, respectively. Fullerene was detected in organs and tissues by HPLC after the extraction from biosamples with toluene. No statistically significant differences in hematological and biochemical parameters of control and treated rats were found after single and multiple administrations. Throughout the observation periods no lethality was observed. At necropsy, no pathomorphological changes in internal organs were recorded. Fullerene was found in stomach, small intestine, liver, lungs, spleen, kidneys, and blood. The amounts of the detected fullerene in comparison to the administered doses are far smaller which is the evidence of its efficient excretion. Hence, it can be assumed that fullerene nanoparticles penetrate from the gastrointestinal tract of rats into the bloodstream and translocate into secondary organs with no pronounced toxic effect in experimen...
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- 2014
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16. Stereochemistry of the aza-Michael reaction with natural alantolactones
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S. A. Pukhov, I. V. Anan’ev, S. V. Afanas'eva, and Sergey G. Klochkov
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Stereochemistry ,Chemistry ,Organic Chemistry ,Michael reaction ,Nmr data - Abstract
Hydrogenated 3-aminomethylnaphtho[2,3-b]furan-2-ones were synthesized by the reaction of natural alantolactones with pharmacophoric amines. Determination of the newly formed asymmetric center configuration by two-dimensional NMR data is presented. The structure of the obtained compounds was proved by X-ray structural analysis.
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- 2012
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17. Synthesis and biological activity of isoalantolactone—tryptamine conjugates
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Yu. N. Bulychev, S. V. Afanas’eva, Sergey G. Klochkov, Elena F. Shevtsova, and Margarita E. Neganova
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Tryptamine ,chemistry.chemical_compound ,Chemistry ,Michael reaction ,Organic chemistry ,Biological activity ,General Chemistry ,Sesquiterpene ,human activities ,Derivative (chemistry) ,Tryptamines ,Conjugate ,Adduct - Abstract
Previously unknown adducts of substituted tryptamines with sesquiterpene lactones, viz., isoalantolactone and its epoxy derivative, were synthesized by the Michael reaction. The compounds obtained were tested for various types of biological activity.
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- 2012
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18. Modified cinnamic acid derivatives as effective mito- and neuroprotective substances
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O. M. Redkozubova, Sergey G. Klochkov, Elena F. Shevtsova, M. Semenova, Margarita E. Neganova, V. Semenov, and D. Mischenko
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Pharmacology ,Psychiatry and Mental health ,chemistry.chemical_compound ,Neurology ,chemistry ,Organic chemistry ,Pharmacology (medical) ,Neurology (clinical) ,Neuroprotection ,Biological Psychiatry ,Cinnamic acid - Published
- 2017
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19. Modification of alantolactones by natural alkaloids
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A. V. Chudinov, A. B. Ermatova, S. V. Afanasˈeva, and Sergey G. Klochkov
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chemistry.chemical_classification ,Chemistry ,Alkaloid ,Michael reaction ,Organic chemistry ,Plant Science ,General Chemistry ,Sesquiterpene lactone ,General Biochemistry, Genetics and Molecular Biology - Abstract
Previously unknown compounds combining fragments of a sesquiterpene lactone and a natural alkaloid were synthesized. Derivatives of alantolactone were modified using a Michael reaction with alkaloids of various structural types.
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- 2011
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20. Synthesis and Antioxidant Activity of Securinine Derivatives
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Margarita E. Neganova, Elena F. Shevtsova, Sergey G. Klochkov, and S. V. Afanas’eva
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Pharmacology ,Tryptamine ,Antioxidant ,Chemistry ,Stereochemistry ,medicine.medical_treatment ,Alkaloid ,Biological activity ,Tryptamines ,Adduct ,chemistry.chemical_compound ,Drug Discovery ,Michael reaction ,medicine ,Organic chemistry ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
A series of 9-amino-14-oxa-7-azatetracyclo[6.6.1.01.11.02,7]pentadeca-11-en-13-ones were synthesized. The starting material was the natural alkaloid securinine, which underwent a Michael reaction with pharmacophoric tryptamines and substituted piperazines. The structure and stereochemistry of the previously unknown adduct with 5-methoxytryptamine were established using two-dimensional NMR experiments (COSY and NOESY). The biological activity of the synthesized securinine amino-derivatives was investigated. It was shown that several of the synthesized securinine conjugates exhibited antioxidant and iron-chelating activity and were interesting for further studies as potential pharmacologically active compounds.
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- 2014
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21. Synthesis and cytotoxic activity of α-santonin amino-derivatives
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G. K. Gerasimova, Sergey G. Klochkov, S. V. Afanas’eva, Yu. N. Bulychev, A. N. Pushin, and N. K. Vlasenkova
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chemistry.chemical_classification ,Stereochemistry ,Amino derivatives ,macromolecular substances ,Plant Science ,General Chemistry ,Sesquiterpene lactone ,General Biochemistry, Genetics and Molecular Biology ,chemistry.chemical_compound ,chemistry ,Michael reaction ,Cytotoxic T cell ,Organic chemistry ,Santonin - Abstract
Previously unknown amino-derivatives of the natural sesquiterpene lactone α-santonin were synthesized. The activity of the products against several human tumor-cell lines was studied.
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- 2009
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22. Synthesis and biological activity of amination products of the alkaloid securinine
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Sergey G. Klochkov, S. V. Afanas’eva, and V. V. Grigor’ev
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chemistry.chemical_classification ,Nucleophilic addition ,Double bond ,Plant Science ,General Chemistry ,General Biochemistry, Genetics and Molecular Biology ,Stereospecificity ,chemistry ,Moiety ,Organic chemistry ,Stereoselectivity ,Amine gas treating ,Trifluoromethanesulfonate ,Amination - Abstract
A method for stereospecific synthesis of allomargaritarin and other amination products of the natural alkaloid securinine was developed. Stereoselective nucleophilic addition of an amine at the double bond of the azobicyclooctane moiety of securinin was achieved by using ytterbium triflate as the catalyst. The biological activity of securining caused by adding pharmacophores to the molecule was shown to change experimentally.
- Published
- 2008
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23. Acidic isomerization of alantolactone derivatives
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S. V. Afanas’eva, Sergey G. Klochkov, and A. N. Pushin
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chemistry.chemical_classification ,chemistry.chemical_compound ,Double bond ,chemistry ,Decalin ,Moiety ,Organic chemistry ,Plant Science ,General Chemistry ,Ring (chemistry) ,Sesquiterpene ,Isomerization ,General Biochemistry, Genetics and Molecular Biology - Abstract
A series of derivatives of the natural sesquiterpene lactones alantolactone (1) and isoalantolactone (2) was prepared. The α-methylene-γ-lactone moiety was retained in the structures of these for further modifications using reactions that affected exclusively the nonconjugated double bonds of the decalin ring.
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- 2006
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24. New Synthesis of Eremophilanes from Alantolactone
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A. V. Semakov, S. V. Afanas′eva, and Sergey G. Klochkov
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0301 basic medicine ,03 medical and health sciences ,030104 developmental biology ,Chemistry ,Organic chemistry ,Plant Science ,General Chemistry ,General Biochemistry, Genetics and Molecular Biology - Published
- 2016
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25. Mechanisms of antioxidant effect of natural sesquiterpene lactone and alkaloid derivatives
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Elena F. Shevtsova, S. V. Afanas’eva, Sergey G. Klochkov, and Margarita E. Neganova
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Tryptamine ,Antioxidant ,Free Radicals ,Stereochemistry ,medicine.medical_treatment ,Sesquiterpene lactone ,Antioxidants ,General Biochemistry, Genetics and Molecular Biology ,Lipid peroxidation ,Structure-Activity Relationship ,chemistry.chemical_compound ,Alkaloids ,Animals, Outbred Strains ,medicine ,Animals ,Organic chemistry ,Chelating Agents ,chemistry.chemical_classification ,Tissue Extracts ,Chemistry ,Alkaloid ,Brain ,General Medicine ,Thiobarbiturates ,Rats ,Neuroprotective Agents ,Lipid Peroxidation ,Sesquiterpenes ,Lactone - Abstract
We performed screening of potential antioxidants among natural lactone and alkaloid derivatives and characterized their antioxidant effects. The substances exhibiting antioxidant and metal-chelating potential, in particular, tryptamine derivatives, are promising neuroprotector agents.
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- 2012
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26. Molecular Structure of Epoxyalloalantolactone
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Sergey G. Klochkov, I. V. Anan’ev, S. A. Pukhov, and S. V. Afanas’eva
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Chemistry ,Organic chemistry ,Molecule ,Plant Science ,General Chemistry ,General Biochemistry, Genetics and Molecular Biology - Published
- 2013
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27. Formation of a novel heterocyclic system based on natural alantolactone
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S. V. Afanasˈeva, S. A. Pukhov, and Sergey G. Klochkov
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chemistry.chemical_classification ,Tryptamine ,Inula ,biology ,Stereochemistry ,Organic Chemistry ,Secondary metabolite ,Sesquiterpene ,biology.organism_classification ,Ring (chemistry) ,chemistry.chemical_compound ,chemistry ,Michael reaction ,medicine ,Methylene ,Lactone ,medicine.drug - Abstract
Natural sesquiterpene lactones which contain an exocyclic methylene group in the -position of the lactone ring react readily with N-nucleophiles to give compounds having novel forms of biological activity when compared with the starting compounds [1]. When the reaction was carried out with 5-epoxyalantolactone (1) (a secondary metabolite of the plant genus Inula L. [2]) and the tryptamine derivatives 2a,b we were able to show the formation of the novel heterocyclic system, namely the hydrogenated benzo[g]furo[4,3,2-cd]indolones 3a,b.
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- 2012
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28. Lavandoside from Lavandula spica flowers
- Author
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M. Lamrini, V. A. Kurkin, and Sergey G. Klochkov
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Silica gel ,Natural compound ,Lavandula ,Chemical structure ,Plant Science ,General Chemistry ,Spica ,General Biochemistry, Genetics and Molecular Biology ,Ferulic acid ,chemistry.chemical_compound ,Column chromatography ,chemistry ,Polyamide ,Organic chemistry ,Nuclear chemistry - Abstract
The new natural compound lavandoside with the structure ferulic acid 4-O-β-D-glucopyranoside was isolated by column chromatography over silica gel and polyamide from the extract of Lavandula spica flowers. The chemical structure of lavandoside was established using UV, NMR, and mass spectra and chemical transformations.
- Published
- 2008
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