Article
Chemistry, Organic
Yury A. Vasev, Ekaterina R. Nasibullina, Anton S. Makarov, Maxim G. Uchuskin
Summary: The key carbenoid intermediate in the transition-metal-catalyzed furan-yne cyclization of Hashmi phenol synthesis can be efficiently reacted with water under improved reaction conditions to provide functionalized unsaturated dicarbonyl compounds, which can serve as convenient precursors for the straightforward synthesis of annulated pyridazines.
Article
Biochemistry & Molecular Biology
Haider N. Sultani, Ibrahim Morgan, Hidayat Hussain, Andreas H. Roos, Haleh H. Haeri, Goran N. Kaluderovic, Dariush Hinderberger, Bernhard Westermann
Summary: Multicomponent reactions, especially the Ugi-four component reaction, provide efficient access to compounds with potent biological and pharmacological effects, such as betulinic acid, fusidic acid, and cholic acid conjugates with TEMPO. The application of these compounds in electron paramagnetic resonance spectroscopy and the study of their cytotoxic effects were highlighted.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Organic
Cheng Yuan, Jiatong Wang, Gangqiang Wang, Shaofa Sun, Jian Wang
Summary: This article describes an unprecedented example of synthesizing multi-substituted pyridazines via the [4+2] cycloaddition of azoalkenes generated in situ. The protocol has a wide range of substrate compatibility and allows for the rapid assembly of pyridazines. Importantly, this process provides an alternative method for in situ generation of azoalkenes.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zheng Fang, Yun Teng, Huilin Yang, Rongxing Li, Qiuhong Li, Yi You, Zhiqiang Weng
Summary: A base-promoted annulation method for synthesizing highly functionalized 4-trifluoromethyl pyridazines without heavy metal catalysts has been developed. The reaction is compatible with various functional groups and the mechanism involves trifluoroacetylated hydrazone as an active intermediate. The versatility of the method has been demonstrated through aminolysis and condensation towards amide and pyridazino[4,5-c]pyridazine derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qiu-Hong Huang, Qian-Yi Zhou, Chen Yang, Li Chen, Jin-Pei Cheng, Xin Li
Summary: An efficient desymmetrizing asymmetric ortho-selective mono-bromination of bisphenol phosphine oxides under chiral squaramide catalysis was reported, leading to a variety of chiral products with high yields and enantioselectivities. The reaction could be scaled up for practical use, demonstrating the synthetic utility of the P-stereogenic compounds in asymmetric reactions.
Article
Biochemistry & Molecular Biology
Beatrice-Cristina Ivan, Stefania-Felicia Barbuceanu, Camelia Mia Hotnog, Octavian Tudorel Olaru, Adriana Iuliana Anghel, Robert Viorel Ancuceanu, Mirela Antonela Mihaila, Lorelei Irina Brasoveanu, Sergiu Shova, Constantin Draghici, George Mihai Nitulescu, Florea Dumitrascu
Summary: New pyrrolo[1,2-b]pyridazines were synthesized by cycloaddition reaction and evaluated for their cytotoxicity on plant cells, crustacean animal cells, and human adenocarcinoma-derived adherent cell lines. The compounds exhibited low toxicity on plant cells and showed toxic effects on crustacean animal cells to varying degrees. In vitro compound-mediated cytotoxicity assays demonstrated dose- and time-dependent cytotoxic activity for several compounds, with the highest anti-tumor activity observed against colon cancer cells.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Sebastien G. Guillet, Aleksei A. Logvinov, Vladislav A. Voloshkin, Ekaterina A. Martynova, Steven P. Nolan
Summary: Researchers report a simple method for the synthesis of azetidines from 2-isoxasoline-3-carboxylates and alkenes, using [Au(cbz)(NHC)] complexes as photocatalysts. The reaction is applicable to a wide range of substrates. Mechanistic studies confirm the energy transfer pathway. This study further expands the potential application of gold catalysts in energy transfer chemistry and catalysis.
Article
Chemistry, Organic
Uros Todorovic, Immo Klose, Nuno Maulide
Summary: Thiocyanates, a versatile building block in organic synthesis, can be easily accessed through an interrupted Pummerer reaction of sulfoxides. This dealkylative functionalization can proceed under mild conditions by electrophilic activation of the sulfoxide partner, and the resulting thiocyanate can be used as a handle for diversification in a straightforward one-pot procedure.
Article
Chemistry, Physical
Beata Zdun, Piotr Ciesla, Jan Kutner, Pawel Borowiecki
Summary: This study explores the enzymatic kinetic resolution (EKR) of 2-arylpropanoic acids and successfully obtains optically active products with moderate-to-good enantioselectivity through the optimization of reaction conditions.
Review
Psychology, Multidisciplinary
Hansen Li, Xing Zhang, Hongying Wang, Zongqian Yang, Haowei Liu, Yang Cao, Guodong Zhang
Summary: Research shows that virtual nature exposure can promote psychological and physiological relaxation, improve attentional resources, cognitive performance, and pain experience. However, there is insufficient evidence regarding the advantages of VR over traditional two-dimensional media in simulated nature exposure, requiring further study.
FRONTIERS IN PSYCHOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Shibaram Panda, Prasanta Ghorai
Summary: Leveraging unexplored regions of chemical space, the integration of spirocyclic cyclobutane in a molecular scaffold offers a new approach in modern drug discovery. However, the strategies for asymmetric construction of these motifs remain a formidable challenge. In this study, a chiral Bronsted acid-catalyzed enantioselective synthesis of 1-azaspiro cyclobutanone was demonstrated for the first time, providing access to a wide range of cyclobutanone containing spiroindoline and spiropyrrolidine derivatives with excellent stereoselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Qianrui Liu, Jiaming Jiang, Xuanzeng Ye, Jiawen Sun, Yao Wu, Yinlin Shao, Chao Deng, Fangjun Zhang
Summary: Simple and commercially available iodine was used as a highly efficient and chemoselective catalyst for the oxidative annulation of β,γ-unsaturated hydrazones to produce 1,6-dihydropyridazines under mild conditions. Interestingly, when β,γ-unsaturated hydrazone compounds containing electron-donating groups such as furyl, thienyl, and cycloalkyl were used, pyrroles were obtained. The gram-scale preparation experiment and derivatization of pyridazines demonstrated the potential applicability of this synthesis method. Experimental studies and density functional theory calculations revealed the origin of the chemoselectivity determining the formation of different products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Engineering, Chemical
Xiao Tang, Liangliang Song
Summary: Ugi reactions have been extensively studied due to their mild reaction conditions, high structural variability, and wide applications. By carefully choosing the starting four components, Ugi adducts have proven to be highly efficient for various post-transformations. Various post-Ugi transformations have been employed for the synthesis of structurally novel polycyclic N-heterocycles. This minireview summarizes the recent developments of post-Ugi reactions for the synthesis of polycycles after the year 2019, utilizing transition metal catalysis and transition metal-free approaches.
Article
Chemistry, Organic
Xuefeng Wang, Yulian Tang, Shengqing Ye, Jun Zhang, Yunyan Kuang, Jie Wu
Summary: A photocatalyzed transformation from sulfinic acids to sulfoxides under visible-light irradiation in the presence of N-heterocyclic carbene has been developed. Various alkyl groups from four-substituted Hantzsch esters or Meyer nitriles are smoothly converted to the corresponding sulfoxides through a radical coupling pathway in the presence of 1,1-carbonyldiimidazole. This method provides an alternative route for sulfoxide synthesis without relying on the oxidation of sulfides.
Article
Polymer Science
Qiankun Li, Hongliang Mu, Zhongbao Jian
Summary: A new family of neutral salicylaldiminato nickel(II) catalysts (Ni1-Ni5) with well designed ortho substituents to the phenoxy moiety is developed, showing moderate to high activity for ethylene polymerization. By using these catalysts, polyethylene materials with lower molecular weight and significantly higher branching degree can be obtained, facilitating the synthesis of various polyethylene products ranging from solid plastic to wax and oil. The upgraded catalysts Ni6 and Ni7 produce polymers with high molecular weight and high branching degree, resulting in polyethylenes with excellent elastic properties.
Article
Chemistry, Multidisciplinary
Svetlana K. Vorontsova, Igor Zavarzin, Valerii Z. Shirinian, Eugene Bozhenko, Olga E. Andreeva, Danila Sorokin, Alexander M. Scherbakov, Mikhail E. Minyaev
Summary: Carbocyclic steroids with D-annulation at the 16 alpha and 17 alpha positions, along with a 5-membered ring E, can be easily synthesized through the interrupted Nazarov cyclization. These steroids exhibit geometries that perfectly match the active site of the human androgen receptor. Experimental results also demonstrate the antiproliferative activity and inhibition of the AR pathway in prostate cancer cells, providing insights for the development of novel drugs targeting nuclear receptors in cancer cells.
Article
Chemistry, Medicinal
Stepan K. Krymov, Alexander M. Scherbakov, Diana I. Salnikova, Danila V. Sorokin, Lyubov G. Dezhenkova, Ivan V. Ivanov, Daniela Vullo, Viviana De Luca, Clemente Capasso, Claudiu T. Supuran, Andrey E. Shchekotikhin
Summary: Carbonic anhydrase IX is a potential target for the development of new antitumor compounds. A series of 1-substituted isatin-5sulfonamides were designed and synthesized, and the trifluoromethylthio derivative 5r was found to inhibit tumor cell growth and induce apoptosis.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Natalia Moiseeva, Lidia A. Laletina, Timur Fetisov, Leyla F. Makhmudova, Angelika E. Manikaylo, Liliya Y. Fomina, Denis A. Burov, Ekaterina A. Lesovaya, Beniamin Y. Bokhyan, Victoria Y. Zinovieva, Alice S. Vilkova, Larisa Mekheda, Nikolay A. Kozlov, Alexander M. Scherbakov, Evgeny M. Kirilin, Gennady A. Belitsky, Marianna G. Yakubovskaya, Kirill Kirsanov
Summary: The aim of this study was to analyze the mechanism of multidrug resistance (MDR) in different types of soft tissue sarcomas (STS). The expression of ABC-transporters, MVP, and YB-1 were assessed, and their correlation with chemosensitivity of cancer cells was analyzed. Pgp expression was found in some STS samples and was strongly correlated with the sensitivity to certain chemotherapy drugs. Overall, STS demonstrated high heterogeneity in chemosensitivity, highlighting the importance of in vitro testing for personalized therapy.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Wilmer H. Perera, Alexander M. Scherbakov, Galina Buravchenko, Ekaterina Mikhaevich, Suzana Guimaraes Leitao, Paul Cos, Andrey E. Shchekotikhin, Lianet Monzote, William N. Setzer
Summary: This study explored the in vitro antimicrobial, antiparasitic, antiproliferative, and cytotoxic activities of essential oils from Baccharis parvidentata and Lippia origanoides. The results showed that both essential oils exhibited significant effects against parasitic protozoans and malignant cells, with selectivity towards non-malignant cells.
Review
Chemistry, Organic
Alexander V. Komkov, Anna A. Sukhanova, Leonid G. Menchikov, Igor V. Zavarzin
Summary: The review summarizes the methods of synthesizing o-aminopyrimidine aldehydes and o-aminopyrimidine ketones, and their application in constructing fused pyrimidines. Various fused pyrimidine compounds, including pyrido[2,3-d]pyrimidines, pyrimido[4,5-d]pyrimidines, pyrazolo[3,4-d]pyrimidines, quinazolines, pyrimido[4,5,6-de]quinazolines, thieno[2,3-d]pyrimidines, pyrrolo[2,3-d]pyrimidines, cyclopenta[d]-pyrimidines, pyrimido[4,5-b]azepines, and pyrimido[4,5-b]quinolines, are discussed.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2022)
Article
Oncology
Alexander M. Scherbakov, Svetlana K. Vorontsova, Alvina Khamidullina, Jasminka Mrdjanovic, Olga E. Andreeva, Fedor B. Bogdanov, Diana I. Salnikova, Vladimir Jurisic, Igor V. Zavarzin, Valerii Z. Shirinian
Summary: The antiproliferative and (anti)estrogenic activities of novel pentacyclic derivatives and benzylidenes of the progesterone series were investigated. Benzylidenes demonstrated stronger inhibitory effects, possibly due to their increased affinity for the receptor. Compound 1d showed the most active antiproliferative and anti-estrogenic effects, inducing apoptosis and exhibiting high inhibitory potency against resistant breast cancer cells. Further research on these novel derivatives is of great importance for medicinal chemistry, drug design, and oncology.
INVESTIGATIONAL NEW DRUGS
(2023)
Review
Biochemistry & Molecular Biology
Yulia Volkova, Igor Zavarzin
Summary: Heterocycles functionalized with pentavalent phosphorus are of great importance in various fields. This review focuses on the synthetic strategies towards aromatic monocyclic six-membered N-heterocycles bearing phosphonates and phosphine oxides, which have been reported from 2012 to 2022.
Review
Biochemistry & Molecular Biology
Leonid G. Menchikov, Anatoliy V. Popov
Summary: The paper reviews the research on the anticancer activity of germanium compounds in the past decade, analyzes their actual toxicity, corrects misconceptions, and proposes a putative mechanism of germanium-mediated protection from oxidative stress. Furthermore, it clarifies the distorted and suppressed discovery history of water-soluble organic germanium compounds.
Article
Biochemistry & Molecular Biology
Valentina Birukova, Alexander Scherbakov, Anastasia Ilina, Diana Salnikova, Olga Andreeva, Yaraslau Dzichenka, Igor Zavarzin, Yulia Volkova
Summary: In this study, a novel series of androstenes modified with imidazole-annulated pendants were synthesized and evaluated for their anticancer activity against prostate and breast cancer cell lines, as well as cytochromes P450. Compound 3h, an imidazo[1,2-a]pyridine derivative, was identified as a promising candidate for future anticancer drug design, particularly for ER alpha-positive breast cancer.
JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY
(2023)
Article
Pharmacology & Pharmacy
Yuri Yu. Shchegolev, Danila V. Sorokin, Alexander M. Scherbakov, Olga E. Andreeva, Diana I. Salnikova, Ekaterina I. Mikhaevich, Margarita V. Gudkova, Mikhail A. Krasil'nikov
Summary: In this study, the mechanism of breast cancer cell resistance to target drugs, including mTOR blockers, was investigated. The role of exosomes in intercellular resistance transfer was particularly studied. It was found that DNMT3A suppression is one of the necessary elements for the development of acquired rapamycin resistance. The study suggests that DNA demethylation and increased expression of key genes may contribute to the progression and maintenance of resistant cell phenotype, including exosome-induced resistance.
Article
Chemistry, Multidisciplinary
T. A. Bogush, K. S. Spiridonova, E. A. Bogush, A. N. Grishanina, A. M. Scherbakov, M. I. Volkova, Z. M. Safarov, V. B. Matveev, V. S. Kosorukov
Summary: The expression of PD-L1 protein was measured in urothelial bladder cancer samples, with higher levels found in non-muscle-invasive bladder cancer compared to muscle-invasive bladder cancer. High expression of PD-L1 was more frequently observed in non-muscle-invasive bladder cancer, suggesting potential for early use of immune checkpoint inhibitors.
MOSCOW UNIVERSITY CHEMISTRY BULLETIN
(2023)
Article
Oncology
Alexander M. Scherbakov, Anna A. Basharina, Danila V. Sorokin, Ekaterina I. Mikhaevich, Iman E. Mizaeva, Alexandra L. Mikhaylova, Tatiana A. Bogush, Mikhail A. Krasil'nikov
Summary: This study aimed to analyze the effect of long-term incubation of ER alpha-positive MCF7 breast cancer cells with 4-hydroxytamoxifen (HT) on their sensitivity to tubulin polymerization inhibitor docetaxel. The results showed that long-term incubation led to decreased sensitivity of MCF7/HT cells to 4-hydroxytamoxifen, but increased sensitivity to docetaxel. In addition, MCF7/HT cells exhibited decreased ER alpha expression and increased Akt activity, while TUBB3 expression was found to be the lowest in these cells.
CANCER DRUG RESISTANCE
(2023)
Article
Pharmacology & Pharmacy
Alexander M. Scherbakov, Yury Kuznetsov, Margarita A. Yastrebova, Alvina I. Khamidullina, Danila V. Sorokin, Maria O. Tserfas, Inna S. Levina
Summary: This study investigated the antiproliferative activities of natural 13-beta and epimeric 13-alpha series steroids (kuz7 and kuz8b) against triple-negative MDA-MB-231 breast cancer cells. Both synthesized compounds showed high antiproliferative activity, with kuz7 being more active than kuz8b. Both compounds induced apoptosis and decreased the expression of GLUT1 glucose transporter. The combination of kuz7 with metformin demonstrated synergistic effects on cell growth and expression of anti-apoptotic protein Bcl-2.
BRAZILIAN JOURNAL OF PHARMACEUTICAL SCIENCES
(2023)
Review
Biochemistry & Molecular Biology
Leonid G. Menchikov, Alexander A. Shestov, Anatoliy V. Popov
Summary: The Nobel Prize Winner (1931) Dr. Otto H. Warburg established that the primary energy source of cancer cells is aerobic glycolysis (the Warburg effect), which is still debated nowadays. Despite the debate, his discovery was widely recognized but overshadowed by the argument about the prime cause of cancer. Understanding the prime cause of cancer is important for prevention and diagnosis, but influencing tumor growth and restoring normal cell function are more crucial for cancer treatment.
BIOCHEMISTRY-MOSCOW
(2023)
Review
Chemistry, Multidisciplinary
Leonid G. Menchikov, Mamed Kh Dzhafarov, Igor Zavarzin
Summary: This article is the first review of the chemical research on avermectins, discussing the total synthesis and chemical modification methods, as well as the structure-biological activity relationships. The review also considers the optimal strategies for chemical modification of avermectins.
RUSSIAN CHEMICAL REVIEWS
(2022)
