Svetlana B Tsogoeva

Svetlana B Tsogoeva
Friedrich-Alexander-University Erlangen-Nürnberg | FAU · Department of Chemistry and Pharmacy

Prof. Dr.
organocatalysis • domino & one-pot processes • deracemization • medicinal chemistry

About

216
Publications
24,229
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Introduction
Svetlana B Tsogoeva currently works at the Department of Chemistry and Pharmacy, Friedrich-Alexander-University of Erlangen-Nürnberg. Svetlana does research in Organic Synthesis, Catalysis and Medicinal Chemistry. Their current projects are (i) 'Development of Efficient Organocatalyzed Domino Reactions and One-Pot Processes; (ii) 'CORE - European Training Network on Continuous Resolution and Deracemization of Chiral Compounds by Crystallization' and (iii) 'Design and Synthesis of Natural Product Hybrids for Medicinal Chemistry'.
Additional affiliations
February 2007 - present
Friedrich-Alexander-University Erlangen-Nürnberg
Position
  • Professor of Organic Chemistry
January 2002 - January 2007
University of Göttingen

Publications

Publications (216)
Article
Full-text available
Electrochemical transformations are considered a green alternative to classical redox chemistry as it eliminates the necessity for toxic and waste producing redox reagents. Typical electrochemical reactions require the addition of a supporting electrolyte – an ionic compound to facilitate reaction medium conductivity. However, this is often accompa...
Article
Quinazolines, particularly fluoro-quinazolines, represent important structural motifs in bioactive molecules and pharmaceuticals. Despite several known synthetic routes, the efficient synthesis of fluorine-containing quinazolines remains a challenge. Herein, the straightforward and sustainable synthesis of fluorine-substituted quinazolines using do...
Article
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Photocatalysis using transition‐metal complexes is widely considered the future of effective and affordable clean‐air technology. In particular, redox‐stable, easily accessible ligands are decisive. Here, we report a straightforward and facile synthesis of a new highly stable 2,6‐bis(triazolyl)pyridine ligand, containing a nitrile moiety as a maske...
Preprint
The selective formation of ortho-fluoroanilines, representing versatile intermediates for the pharmaceutical and fine chemical industries, relies to date on, e.g., transition-metal-catalyzed fluorination of azobenzenes, which must be pre-formed from aniline derivatives. While few efficient methods for aniline synthesis were reported, sustainable, s...
Article
Full-text available
In response to the spread of artemisinin (ART) resistance, ART-based hybrid drugs were developed, and their activity profile was characterized against drug-sensitive and drug-resistant Plasmodium falciparum parasites. Two hybrids were found to display parasite growth reduction, stage-specificity, speed of activity, additivity of activity in drug co...
Article
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Malaria is one of the most widespread diseases worldwide. Besides a growing number of people potentially threatened by malaria, the consistent emergence of resistance against established antimalarial pharmaceuticals leads to an urge toward new antimalarial drugs. Hybridization of two chemically diverse compounds into a new bioactive product is a su...
Preprint
Full-text available
In response to the spread of artemisinin (ART) resistance, ART-based hybrid drugs were developed and their activity profile was characterized against drug-sensitive and drug-resistant Plasmodium falciparum parasites. Two hybrids were found to display parasite growth reduction, stage-specificity, speed of activity, additivity of activity in drug com...
Article
We report the development of a straightforward, waste-reducing, environmentally friendly, FeIII-catalyzed domino aza-Michael/aldol/aromatization reaction in the presence of water to access high-value functionalized quinolines by using 2-aminobenzophenones and ethyl buta-2,3-dienoate as starting compounds. The tangible advantages, that is, the utili...
Article
Full-text available
The selective formation of ortho-fluoroanilines, representing versatile intermediates for the pharmaceutical and fine chemical industries, relies to date on, e.g., transition-metal-catalyzed fluorination of azobenzenes, which must be pre-formed from aniline...
Article
Full-text available
Malaria is one of our planet's most widespread and deadliest diseases, and there is an ever-consistent need for new and improved pharmaceuticals. Natural products have been an essential source of hit and lead compounds for drug discovery. Antimalarial drug artemisinin (ART), a highly effective natural product, is an enantiopure sesquiterpene lacton...
Article
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Drug modification by a fluorescent label is a common tool for studying its mechanism of action with fluorescence microscopy techniques. However, the attachment of a fluorescent label can significantly alter the polarity, solubility, and biological activity of the investigated drug, and, as a result, the studied mechanism of action can be misreprese...
Preprint
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Heterocyclic compounds play a central role in drug development research and are contained in most pharmaceuticals on the market. Quinazoline and thiohydantoin are heterocycles and hold very prominent positions due to their diverse pharmacological profiles. While quinazolines fused with other heterocyclic units are already found in various clinicall...
Article
The Front Cover shows a light‐induced enolization of o‐methyl benzophenones/Diels–Alder reaction, combined with deprotection/aromatization steps in one pot toward new antiviral phthalazines. The Temple of Jupiter in the background is a colossal Roman temple in sunny Baalbek (Lebanon), that was dedicated to Jupiter Heliopolitanus, known as a SUN God...
Article
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Starting in 2019, the spread of respiratory syndrome coronavirus 2 (SARS-CoV-2) and the associated pandemic of the corona virus disease (COVID-19) has led to enormous efforts in the development of medical countermeasures. Although innovative vaccines have scaled back the number of severe COVID cases, the emergence of the omicron variant (B.1.1.529)...
Article
Full-text available
We report the development of a metal‐free four‐step one‐pot synthetic strategy to access high‐value functionalized phthalazines using o‐methyl benzophenones as starting compounds. Combining a light‐mediated enolization of o‐methyl benzophenones/Diels‐Alder reaction domino process with a subsequent deprotection/aromatization domino reaction in one‐p...
Article
Olefin metathesis gives access to important petrochemicals, polymers, and pharmaceuticals. The catalysts for these transformations are often based on high‐valent metal ions e.g., Ru(IV), which have been improved through ligand modifications. An attractive, but challenging goal is to catalyze olefin metathesis with a non‐toxic, bio‐compatible, and a...
Article
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The “metathesis reaction” is a straightforward and often metal‐catalyzed chemical reaction that transforms two hydrocarbon molecules to two new hydrocarbons by exchange of molecular fragments. Alkane, alkene and alkyne metathesis have become an important tool in synthetic chemistry and have provided access to complex organic structures. Since the d...
Article
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“We report a first example of a metal‐free, visible‐light‐induced atom economical and sustainable two‐step domino process, employing an organic dye (fluorescein) as a photosensitizer to obtain tetrahydroisoquinoline‐butenolides with good to high yields (up to 97 %). Furthermore, we show that a simple thiourea additive can significantly improve the...
Article
The Front Cover illustrates a new efficient metal‐free visible‐light‐driven two‐step (aerobic amine oxidation/vinylogous Mannich) domino reaction. The combination of fluorescein as a cheap organic photosensitizer and thiourea as a simple additive allows a cost‐effective, straightforward, and waste reducing access to a broad scope of bioactive tetra...
Article
Full-text available
An efficient metal‐free visible‐light‐driven two‐step domino reaction towards new bioactive tetrahydroisoquinoline‐butenolide hybrid compounds was developed for the first time. The combination of fluorescein as photosensitizer and thiourea as an additive was found to be the most effective way to promote an aerobic amine oxidation/vinylogous Mannich...
Article
Full-text available
Organic peroxides are an important class of compounds for organic synthesis, pharmacological chemistry, materials science, and the polymer industry. Here, for the first time, we summarize the main achievements in the synthesis of organic peroxides by the action of Lewis acids and heteropoly acids. This review consists of three parts: (1) metal-base...
Article
Full-text available
The newly emerged severe acute respiratory syndrome coronavirus 2 (SARS‐CoV‐2) cause life‐threatening diseases in millions of people worldwide, in particular, in patients with cancer, and there is an urgent need for antiviral agents against this infection. While in vitro activities of artemisinins against SARS‐CoV‐2 and cancer have recently been de...
Preprint
Full-text available
The transamination reaction, which involves the conversion of one amine to another, traditionally relies on biological enzyme catalysts. Although chemists have recently developed few catalytic methods, mimicking these enzymes to interconvert amine groups in acyclic substrates via transamination metathesis of a single C(sp2)–N bond, transamination o...
Article
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Invited for the cover of this issue are Manfred Marschall, Svetlana B. Tsogoeva and co‐workers at Friedrich‐Alexander University of Erlangen–Nürnberg. The image depicts a new anti‐SARS‐CoV‐2 compound in front of SARS‐CoV‐2 viruses. Read the full text of the article at 10.1002/chem.202103861.
Preprint
Full-text available
We report the development of an unprecedented metal-free four-step one-pot synthetic strategy to access high-value functionalized phthalazines using o-methyl benzophenones as starting compounds. Combination of a light-mediated enolization of o-methyl benzophenones/Diels-Alder reaction domino process with a subsequent deprotection/aromatization domi...
Article
A new anti‐SARS‐CoV‐2 compound, developed in this joint study, is shown in front of SARS‐CoV‐2 viruses. The ongoing pandemic of human SARS‐CoV‐2 infections (COVID‐19) creates a high demand for antiviral drug development. The shown quinoline–morpholine hybrid and other new quinoline‐based compounds were synthesized and investigated for their in vitr...
Article
Full-text available
New quinoline‐based compounds were synthesized via conventional synthetic methods, including copper‐catalyzed azide‐alkyne cycloaddition reactions (CuAAC) and were studied for their activity against SARS‐CoV‐2. These quinoline derivatives showed pronounced cell culture‐based inhibitory profiles against the virus (EC50 down to 1.5±1.0 μM), thus pres...
Preprint
Full-text available
An efficient metal-free visible light-driven two-step domino reaction towards new bioactive tetrahydroisoquinoline-butenolide hybrid compounds was developed for the first time. Combination of fluorescein as photosensitizer and thiourea as an additive was found to be the most effective way to promote an aerobic amine oxidation/vinylogous Mannich dom...
Article
Full-text available
Human cytomegalovirus (HCMV) is a major pathogenic herpesvirus that is prevalent worldwide and it is associated with a variety of clinical symptoms. Current antiviral therapy options do not fully satisfy the medical needs; thus, improved drug classes and drug-targeting strategies are required. In particular, host-directed antivirals, including phar...
Article
Full-text available
This year’s Nobel Prize in Chemistry was awarded to Benjamin List and David MacMillan in recognition of their contributions to the efficient synthesis of enantiomers. Their discoveries have affected pharmacology and alleviated environmental pollution.
Article
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A recently developed artemisinin-quinoline hybrid, named 163A, has been shown to display potent activity against the asexual blood stage of Plasmodium, the malaria parasite. In this study, we determined its in vitro cytotoxicity to mammalian cells, its potency to suppress P. berghei hepatic infection and to decrease the viability of P. falciparum g...
Article
The cover image is based on the Review Article Artemisinin‐derived dimers from a chemical perspective by Aysun Çapcı et al., https://doi.org/10.1002/med.21814.
Article
Full-text available
Gliomas are primary brain tumors with still poor prognosis for the patients despite a combination of cytoreduction via surgery followed by a radio-chemotherapy. One strategy to find effective treatment is to combine two different compounds in one hybrid molecule via linker to add to or at best potentiate their impact on malignant cells. Here, we re...
Article
Full-text available
In 1966, Zimmerman proposed a type of Möbius aromaticity that involves through‐space electron delocalization; it has since been widely applied to explain reactivity in pericyclic reactions, but is considered to be limited to transition‐state structures. Although the easily accessible hexahelicene radical anion has been known for more than half a ce...
Article
Hexaarylbenzene (HAB) scaffolds, containing six different aromatic rings around central benzene core, are a synthetic challenge. In their Research Article (DOI: 10.1002/anie.202104437), Svetlana B. Tsogoeva and co-workers report a process which allows to generate such HAB simply and straightforwardly. In an efficient, two-component four-step domino...
Article
Hexaarylbenzol(HAB)-Grundgerüste, die sechs verschiedene aromatische Ringe um einen zentralen Benzolkern enthalten, sind eine synthetische Herausforderung. In ihrem Forschungsartikel (DOI: 10.1002/ange.202104437) stellen Svetlana B. Tsogoeva und Mitarbeiter ein Verfahren vor, mit dem sich solche HABs einfach und unkompliziert herstellen lassen. In...
Article
Full-text available
Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular‐scale devices, organic light‐emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or Diels–Alder...
Preprint
Full-text available
The newly emerged severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) cause life-threatening diseases in millions of people worldwide and there is an urgent need for antiviral agents against this infection. While in vitro activities of artemisinins (containing endoperoxide moiety) and chloroquine (containing quinoline subunit) against SARS...
Preprint
Full-text available
The newly emerged severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) cause life-threatening diseases in millions of people worldwide and there is an urgent need for antiviral agents against this infection. While in vitro activities of artemisinins (containing endoperoxide moiety) and chloroquine (containing quinoline subunit) against SARS...
Article
Full-text available
Considerable progress has been made with the rather recently developed dimer approach, which has already found applications in the development of new effective artemisinin-derived antimalarial, anticancer, and antiviral agents. One observation common to these potential applications is the significant (i.e., much more than double) improvement in act...
Article
Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular-scale devices, organic light-emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via low-yielding cyclotrimerization o...
Article
Full-text available
Ring synthesis via catalysis has emerged as a transformative platform. This Special Collection of articles on “The Catalysis of Ring Synthesis” covers the most recent strategies of ring syntheses, including catalytic domino reactions and one‐pot processes, and presents the current progress in this exciting field. The contributions include transitio...
Article
Substituted 2,6-dicyanoanilines are versatile electron donor-acceptor compounds, which have recently received considerable attention, since they exhibit strong fluorescence and may have utility in the synthesis of fluorescent materials, non-natural photosynthetic systems, and materials with nonlinear optical properties. The majority of known synthe...
Preprint
Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, redox materials, organic light-emitting diodes and photochemical switches. Statistical synthesis of simple symmetrical HABs is known via low-yielding cyclotrimerization or Diels-Alder reacti...
Article
Full-text available
Human cytomegalovirus (HCMV) is a human pathogenic herpesvirus associated with a variety of clinical symptoms. Current antiviral therapy is not always effective, so that improved drug classes and drug-targeting strategies are needed. Particularly host-directed antivirals, including pharmaceutical kinase inhibitors (PKIs), may help to overcome probl...
Preprint
Full-text available
Gliomas are primary brain tumors with still poor prognosis for the patients despite a combination of cytoreduction via surgery followed by a radio-chemotherapy. One strategy to find effective treatment is to combine two different compounds to add or at best potentiate their impact on malignant cells. Here, we report on the effects of a newly synthe...
Article
Full-text available
Construction of carbon–carbon bonds is one of the most important tools for the synthesis of complex organic molecules. Among multiple possibilities are the carbonyl–alkyne and carbonyl–olefin metathesis reactions, which are used to form new carbon–carbon bonds between carbonyl derivatives and unsaturated organic compounds. As many different approac...
Article
Full-text available
Viedma deracemization is based on solution phase racemization, dissolution of racemic or scalemic conglomerates and crystal growth through autocatalytic cluster formation. With rate limiting racemization, its acceleration by appropriate catalysts may result in speeding up deracemization. A conglomerate‐forming chiral compound may principally racemi...
Article
Full-text available
Viral infections cause life‐threatening diseases in millions of people worldwide every year and there is an urgent need for new, effective antiviral drugs. Hybridization of two chemically diverse compounds into a new bioactive effector product is a successful concept to improve the properties of a hybrid drug relative to the parent compounds. In th...
Article
Full-text available
Human cytomegalovirus (HCMV) is a major human pathogen associated with severe pathology. Current options of antiviral therapy only partly satisfy the needs of a well-tolerated long-term treatment/prophylaxis free from drug-induced viral resistance. Recently, we reported the strong antiviral properties in vitro and in vivo of the broad-spectrum anti...
Article
Structural hybridization of bioactive heterocycles is a promising tool to develop new efficient therapeutics for the treatment of various diseases including viral infections. The merging of two differently acting heterocycles—artemisinin and isoquinoline—in one hybrid molecule results in the discovery of a new and potent antiviral agent, which exce...
Article
The Cover Feature summarizes the results of a joint computational and experimental study demonstrating that faster racemization through water‐catalyzed enolization could result in faster deracemization of a scalemic slurry of a chiral hydrazine derivative. More information can be found in the Article by Michael Mauksch, Svetlana B. Tsogoeva and co‐...
Article
Structural hybridization of preclinically and clinically validated pharmacologically active molecules has emerged as a promising tool to develop new generations of safe and highly efficient drug candidates against various diseases including microbial infections, virus infections and cancer. Strategies of drug-drug combinations have been adopted to...
Article
Full-text available
In the search for new and effective treatments of breast and prostate cancer, a series of hybrid compounds based on tamoxifen, estrogens, and artemisinin were successfully synthesized and analyzed for their in vitro activities against human prostate (PC‐3) and breast cancer (MCF‐7) cell lines. Most of the hybrid compounds exhibit a strong anticance...
Article
Human cytomegalovirus (HCMV) infection is associated with serious pathology such as transplant rejection or embryonic developmental defects. Antiviral treatment with currently available drugs targeting viral enzymes is often accompanied with severe side effects and the occurrence of drug-resistant viruses. For this reason, novel ways of anti-HCMV t...
Article
Human cytomegalovirus (HCMV) causes serious and even life-threatening diseases, particularly upon congenital or post-transplant infection. Treatment of HCMV infections with currently available drugs targeting viral enzymes is often limited by severe side effects and the emergence of drug-resistant viruses. To avoid this problem, novel therapeutic o...
Article
Full-text available
Viedma ripening is a deracemization process that has been used to deracemize a range of chiral molecules. The method has two major requirements: the compound needs to crystallize as a conglomerate and it needs to be racemizable under the crystallization conditions. Although conglomerate formation can be induced in different ways, the number of race...
Cover Page
Full-text available
The picture displays a population of racemic conglomerate crystals of a BINOL derivative undergoing deracemization through Viedma ripening, leading to the formation of enantiopure crystals. The combined use of UV light and an organic base is an essential prerequisite to allow the compound to continuously racemize in solution via an ESPT (excited st...
Article
Full-text available
Catalysis mediated by iron complexes is emerging as an eco-friendly and inexpensive option in comparison to traditional metal catalysis. The epoxidation of alkenes constitutes an attractive application of iron(III) catalysis, in which terminal olefins are challenging substrates. Herein, we describe our study on the design of biomimetic non-heme lig...
Article
Die Überwindung der Wirkstoffresistenz von Malariaparasiten gegen verfügbare Medikamente kann durch den Einsatz von Wirkstoffhybriden gelingen, wie S. B. Tsogoeva, L. Ackermann, J. Wang et al. in ihrem Forschungsartikel (DOI: 10.1002/ange.201907224) berichten. Die Kombination zweier unterschiedlich wirkender Medikamente (z. B. Artemisinin und Chlor...
Article
Overcoming drug resistance in malaria parasites against available drugs is now possible by using drug hybrids, as reported by S. B. Tsogoeva, L. Ackermann, J. Wang, and co‐workers in their Research Article (DOI: 10.1002/anie.201907224). The merging of two differently acting drugs (e.g., artemisinin and chloroquine) in one hybrid compound enables th...
Article
Full-text available
A substantial challenge worldwide is emergent drug resistance in malaria parasites against approved drugs, such as chloroquine (CQ). To address these unsolved CQ resistance issues, only rare examples of artemisinin (ART)‐based hybrids have been reported. Moreover, protein targets of such hybrids have not been identified yet, and the reason for the...
Article
Full-text available
ortho‐Terphenyls are of high interest for medicinal chemistry and materials science, but they are difficult to access. Herein, we demonstrate a straightforward and sustainable synthesis of highly functionalized ortho‐terphenyls via joining an organocatalyzed two‐step domino reaction (Knoevenagel/vinylogous Michael) with a DABCO/CuBr2 co‐catalyzed t...
Article
Full-text available
Hybride auf Artemisinin‐Basis, die wirksam gegen CQ‐ und multiresistente Parasiten sind und eine starke Wirksamkeit bei experimenteller Malaria aufweisen, wurden synthetisiert. Durch chemische Proteomik wurden neue, möglicherweise hybridbindende Proteine zusätzlich zu den bekannten Zielproteinen von Chinolin und Artemisinin identifiziert, was darau...