Review
Chemistry, Medicinal
Monika Shukla, Komal Rathi, Mohammad Hassam, Dinesh Kumar Yadav, Manvika Karnatak, Varun Rawat, Ved Prakash Verma
Summary: The demand for novel, fast-acting, and effective antimalarial medications is rapidly increasing due to the spread of multidrug resistant forms of malaria parasites. Various strategies have been employed to address drug resistance, including targeted therapies, the hybrid drug idea, and the development of advanced analogues of existing drugs. The 1,2,4-trioxane ring system in artemisinin (ART) has been identified as a key pharmacophoric moiety for the potential of endoperoxide-based antimalarials.
MEDICINAL RESEARCH REVIEWS
(2023)
Article
Chemistry, Medicinal
Andreia Mendes, Ana Armada, Lilia I. L. Cabral, Patricia S. M. Amado, Lenea Campino, Maria L. S. Cristiano, Sofia Cortes
Summary: Leishmaniasis, a neglected tropical disease, is difficult to treat. A study found that certain synthetic endoperoxides have anti-proliferative activity against Leishmania parasites responsible for the disease.
Review
Chemistry, Medicinal
Junman Fang, Feng Song, Fawei Wang
Summary: This review article emphasizes the current status of 1,2,4-trioxolane/trioxane hybrids and dimers with potential antimalarial activity from January 2012 to January 2022. The structure-activity relationships are also discussed to facilitate the rational design of more effective candidates.
ARCHIV DER PHARMAZIE
(2022)
Article
Biochemistry & Molecular Biology
Somruedee Jansongsaeng, Nitipol Srimongkolpithak, Jutharat Pengon, Sumalee Kamchonwongpaisan, Tanatorn Khotavivattana
Summary: A series of 5-phenoxy primaquine analogs were synthesized and one hybrid compound showed significantly increased antimalarial activity with low toxicity against mammalian cells. These compounds also exhibited heme polymerization inhibition, which could contribute to their improved antimalarial activity and make them promising candidates for further development of antimalarial agents.
Article
Chemistry, Medicinal
Dickson Mambwe, Constance M. Korkor, Amanda Mabhula, Zama Ngqumba, Cleavon Cloete, Malkeet Kumar, Paula Ladeia Barros, Meta Leshabane, Dina Coertzen, Dale Taylor, Liezl Gibhard, Mathew Njoroge, Nina Lawrence, Janette Reader, Diogo Rodrigo Moreira, Lyn-Marie Birkholtz, Sergio Wittlin, Timothy J. Egan, Kelly Chibale
Summary: Iterative medicinal chemistry optimization led to the discovery of a highly potent compound 23 with metabolic stability and selectivity, displaying activity against multiple stages of malaria and showing in vivo efficacy in mice.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Aisha Y. Hassan, Sara N. Shabaan, Samiha A. El-Sebaey, Eman S. Abou-Amra
Summary: In this study, various novel nitrogen-rich heterocycles were designed in one molecule. Green, simple, and efficient aza-annulations were developed under solvent-free conditions using a versatile building block, resulting in the synthesis of bridgehead tetrazines and azepines. The protocol allows for the synthesis of essential biological derivatives without the need for catalysis, with high yields and functional group tolerance.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Medicinal
Daniel L. Priebbenow, Mitch Mathiew, Da-Hua Shi, Jitendra R. Harjani, Julia G. Beveridge, Marina Chavchich, Michael D. Edstein, Sandra Duffy, Vicky M. Avery, Robert T. Jacobs, Stephen Brand, David M. Shackleford, Wen Wang, Longjin Zhong, Given Lee, Erin Tay, Helena Barker, Elly Crighton, Karen L. White, Susan A. Charman, Amanda De Paoli, Darren J. Creek, Jonathan B. Baell
Summary: A series of novel 3,3'-disubstituted-5,5'-bi(1,2,4-triazine) compounds with potent in vitro activity against Plasmodium falciparum parasites were recently discovered. The new structure-activity relationship investigation led to the identification of second-generation highly potent antimalarial bis-triazines, with improved in vitro metabolic stability and a fast-killing profile. This new class of orally available antimalarial compounds is of considerable interest.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Mohit K. Tiwari, Paolo Coghi, Prakhar Agrawal, Dharmendra K. Yadav, Li Jun Yang, Qiu Congling, Dinkar Sahal, Vincent Kam Wai Wong, Sandeep Chaudhary
Summary: A series of lipophilic, halogenated-arylvinyl-1,2,4-trioxanes were synthesized and evaluated for their in vitro anti-plasmodial activity, with ten analogues showing potent activity and selective potential against Plasmodium cells. The most active compound, arylvinyl-1,2,4-trioxane 8f(2), exhibited significant cytotoxic potential in comparison to standard drugs against lung cancer cell lines. Furthermore, in-silico docking studies demonstrated strong virtual interaction of the potent halogenated 1,2,4-trioxanes with the epidermal growth factor receptor.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Anna Korotina, Svetlana G. Tolshchina, Rashida I. Ishmetova, Natalya P. Evstigneeva, Natalya A. Gerasimova, Natalya Zilberberg, Nikolay Kungurov, Gennady L. Rusinov, Oleg N. Chupakhin, Valery N. Charushin
Summary: A series of novel triazolo[1,5-b][1,2,4,5]tetrazines have been synthesized through oxidation reaction, and they can be easily modified at C(3) position. The reactivity of these compounds has been studied, and they exhibit significant antifungal activity against pathogenic fungi.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Energy & Fuels
Luhao Liu, Xinghui Jin, Jianhua Zhou, Bingcheng Hu
Summary: In this study, a series of high energy compounds based on [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine were designed and their electronic structures, thermodynamic properties, and explosive characteristics were calculated. Seven compounds were identified as potential candidates for high energy materials based on their detonation properties and thermal stabilities. The study also proposed a new research direction for high energy materials by presenting the electronic structures.
INTERNATIONAL JOURNAL OF ENERGY RESEARCH
(2021)
Article
Chemistry, Organic
Patricia S. M. Amado, Luis M. T. Frija, Jaime A. S. Coelho, Paul M. O'Neill, Maria L. S. Cristiano
Summary: A novel protocol for the synthesis of nonsymmetrical 1,2,4,5-tetraoxanes and 1,2,4-trioxanes using heterogeneous silica sulfuric acid (SSA) catalyst has been reported. The method involves different ketones reacting under mild conditions to generate corresponding endoperoxides in good yields, with the assistance of molecular orbital calculations. This approach provides a valid alternative for the synthesis of new biologically active endoperoxides using readily available and inexpensive reagents with recyclable properties.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Tianyun Pei, Xuanhe Zhang, Zhenzhen Yang, Zhonglu Ke, Qingsong Shi, Qingqing Mao, Shunze Gong, Hanwei Zeng, Feng Xu, Defeng Xu
Summary: A series of triazole-tetrazine derivatives were synthesized and screened for their anticancer activity, with compound 4g exhibiting good activity against human colon carcinoma.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2022)
Article
Engineering, Environmental
Gennady F. Rudakov, Valery P. Sinditskii, I. A. Andreeva, Anastasya Botnikova, Polina R. Veselkina, Shirak K. Kostanyan, Nikolay Yudin, Valery V. Serushkin, Georgij Cherkaev, Olga Dorofeeva
Summary: A thermal cyclization method has been developed for the preparation of fused tricyclic tetrazines, resulting in a new high-energy heterocyclic compound with high thermal stability and detonation characteristics.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Physical
M. V. Polyakov, M. D. Vedenyapina, A. M. Skundin, I. A. Yaremenko, P. S. Radulov, V. V. Kuznetsov
Summary: The behavior of a smooth gold electrode in aqueous solutions of the potassium salt of bridging 1,2,4,5-tetraoxane containing a biperoxide cyclic fragment was studied using cyclic voltammetry. The cathode process involving four electrons was analyzed in detail. The products of electrolysis of the potassium salt were studied, and a reaction mechanism was proposed.
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Chemistry, Physical
Yuan-Yuan Feng, Chang-E Dong, Rui Li, Xiao-Qing Zhang, Wei Wang, Xing-Rui Zhang, Wei -Wei Liu, Da-Hua Shi
Summary: A series of new hybrids of 1,2,4-triazine-quinoline were designed, synthesized, and evaluated as antimalarial agents. The structures of these hybrids were confirmed, and compound 5c exhibited the best inhibitory activity.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Medicinal
Oxana B. Kazakova, Natalya Medvedeva, Irina E. Smirnova, Tatyana Lopatina, Alexander V. Veselovsky
Summary: A series of nitrogen derivatives based on lupane, oleanane, and ursane triterpenoids were synthesized and evaluated for their high antitubercular activities. Some compounds showed promising inhibitory effects against Mycobacterium tuberculosis, indicating the potential for development into new anti-tubercular agents.
MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
V. A. Vydrina, R. R. Sayakhov, M. P. Yakovleva, Z. R. Zileeva, R. F. Talipov, G. Yu Ishmuratov
Summary: A new synthesis method was developed to produce 3-oxo-28-hydroxylup-20(29)-ene from the natural triterpenoid betulin. Alpha, omega-diketodiesters were successfully prepared for the first time by different methods, with the highest yields obtained under Steglich reaction conditions. One of the synthesized alpha, omega-diketodiesters exhibited moderate in vitro activity against A-549 lung carcinoma cells.
CHEMISTRY OF NATURAL COMPOUNDS
(2021)
Article
Infectious Diseases
Elmira F. Khusnutdinova, Veronique Sinou, Denis A. Babkov, Oxana Kazakova, Jean Michel Brunel
Summary: A series of oleanolic acid derivatives with different long chain polyamines were synthesized and evaluated for their antimicrobial activities. These derivatives showed good to moderate activity against Gram-positive and Gram-negative bacteria, including the disruption of the outer bacterial membrane. Computational ADMET profiling suggested that one of the derivatives is a suitable starting point for pharmacokinetic optimization.
Article
Chemistry, Multidisciplinary
Yuliya Myasoedova, Liliya R. Garifullina, Evelina R. Belyaeva, Gumer Yu Ishmuratov
Summary: Ozonolytic transformations of (R)-(-)-carvone were conducted in aprotic and proton-donor solvents in the presence of pyridine, leading to the formation of various compounds, including pentadioic acids and cyclohexenones.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2022)
Article
Chemistry, Medicinal
M. P. Yakovleva, R. R. Sayakhov, K. M. Saitov, N. Medvedeva, V. A. Vydrina, G. A. Yunusova, R. Gorshunova, G. Yu Ishmuratov
Summary: Syntheses of mono- and diester derivatives of betulin, allobetulin, and betulinic acid with ibuprofen using Steglich condensation or acid-chloride coupling are reported.
CHEMISTRY OF NATURAL COMPOUNDS
(2022)
Editorial Material
Chemistry, Medicinal
M. P. Yakovleva, R. R. Sayakhov, N. Medvedeva, G. Yu Ishmuratov
CHEMISTRY OF NATURAL COMPOUNDS
(2022)
Article
Chemistry, Inorganic & Nuclear
R. R. Sayakhov, N. I. Medvedeva, M. P. Yakovleva, E. S. Meshcheryakova, L. M. Khalilov, G. Yu. Ishmuratov
Summary: This article presents the preparation of 2,17 beta-Dicyano-3,4-seco-4(23),20(29)-lupadien and the study of its crystal structure using X-ray diffraction.
JOURNAL OF STRUCTURAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
E. R. Belyaeva, Yu. V. Myasoedova, N. M. Ishmuratova, G. Yu. Ishmuratov
Summary: Synthesis of hybrid molecules incorporating fragments of natural compounds and pharmacophore groups allows for the development of a wide range of biologically active compounds. These compounds possess diverse pharmacological activities, including antibacterial, antituberculosis, antifungal, antitumor, anti-inflammatory, anticonvulsant, antiviral, and antiprotozoal properties.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Marina P. Yakovleva, Valentina A. Vydrina, Kseniya S. Denisova, Aleksandr G. Tolstikov, Gumer Y. Ishmuratov
Summary: Two potentially useful macrolides with diethylene glycol and dihydrazide fragments were synthesized based on 7-oxooctanoic acid. The obtained compounds were characterized using IR and NMR spectroscopy, as well as chromatography-mass spectrometry.
Article
Chemistry, Multidisciplinary
Yu Myasoedova, G. N. Sakhabutdinova, E. R. Belyaeva, G. Z. Raskil'dina, G. Yu Ishmuratov, S. S. Zlotsky
Summary: The paper proposes a new one-pot ozonolytic synthesis of acylhydrazones from phenylacrolein acetals, using ozonolytic cleavage and treatment with various hydrazides.
Article
Chemistry, Applied
N. I. Petukhova, V. V. Zorin, A. R. Sakaeva, A. V. Mityagina, E. R. Nurieva, V. A. Vydrina, M. P. Yakovleva, G. Yu. Ishmuratov
Summary: This article reports a method for synthesizing (2S)-tridecyl acetate and two (S)-1-methylbutyl esters from the commercially available compound 5-hexen-2-one. In this process, enantioselective bioreduction and chemoselective reactions were used to achieve the desired products.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY
(2022)
Article
Chemistry, Organic
Yu Myasoedova, E. R. Belyaeva, L. R. Garifullina, D. A. Prosvirnina, G. Yu Ishmuratov
Summary: In this study, five novel 20-(N'-acylhydrazinylidene)betulin derivatives were synthesized, and an efficient procedure for the synthesis of messagenin was proposed using low-temperature ozonolysis and glacial acetic acid treatment.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yu Myasoedova, K. S. Denisova, M. P. Yakovleva, G. Yu Ishmuratov
Summary: A new approach for the synthesis of keto acids has been proposed, which involves the ozonolytic cleavage of 1-alkylcycloalkenes in a mixture of methylene chloride and acetic acid, followed by the oxidation of peroxide ozonolysis products using 30% H2O2-SeO2.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Olexander M. Semenenko, Victoria V. Lipson, Alina O. Sadchenko, Olga V. Vashchenko, Natalia A. Kasian, Liliia Sviechnikova, Longin M. Lisetski, Mykola L. Babak, Volodymyr M. Vakula, Oleksandr Borysov, Yuliia Holota, Sergey O. Zozulya, Petro O. Borysko, Olexander Mazepa
Summary: An efficient protocol for the synthesis of novel methotrexate-betulonic acid hybrids has been developed and their structures and properties have been fully established. The hybrids showed inferior interactions with artificial lipid membranes, possibly due to their increasing lipophilicity.
Article
Biochemistry & Molecular Biology
Mohadese Yaghoobi Anzabi, Piotr Cmoch, Roman Luboradzki, Zbigniew Pakulski
Summary: Friedelin and 3-acetoxyfriedel-3-en-2-one, known as friedelane triterpenoids, have been isolated from cork smoker wash solids and used as starting materials for the synthesis of new friedelane derivatives. Reduction reactions result in the formation of friedelinol and epi-cerin derivatives.
Article
Biochemistry & Molecular Biology
Detlef Thieme, Aniko Krumbholz, Martin Bidlingmaier, Christoph Geffert, Annika Hameder, Andreas Stoever, Matthias Graw, Annekathrin M. Keiler
Summary: Ethanol can affect testosterone metabolism and potentially influence steroid biosynthesis and blood steroid profiles. The study emphasizes the importance of sufficient time interval from food and ethanol intake during blood sampling, particularly for diagnostics in doping control.
Article
Biochemistry & Molecular Biology
Masanobu Murao, Tetsuo Imano, Yoshinobu Sato, Masaaki Nakajima
Article
Biochemistry & Molecular Biology
Jingyuan Wang, Ye Feng, Brian Liu, Wen Xie
Summary: Sulfation and desulfation of steroids are opposing processes that regulate steroid homeostasis and are involved in steroid-related diseases. Cytosolic sulfotransferase and steroid sulfatase modify and regulate steroids to affect hormonal dysregulation, metabolic diseases, and cancer.
Article
Biochemistry & Molecular Biology
Noah K. Babel, Brian J. Feldman
Summary: Our research identified a previously unrecognized ADAMTS1-PTN-Wnt pathway in regulating adipose precursor cell behavior. The non-muscle myosin protein MYH9 was found to be a key target of this pathway for modulating adipogenesis. These findings offer potential for developing novel therapeutics for obesity and related metabolic disorders.
Article
Biochemistry & Molecular Biology
Martiniano Bello
Summary: This study explores the structural and thermodynamic basis of molecular recognition between ERβ and DPN and its derivatives using molecular dynamics simulations and end-point methods. The results show that the MMGBSA approach is able to reproduce experimental trends and identify eight residues that strongly interact with the ligands.