Claudio santi, stefano santoro and benedetta battistelli affiliation. The authors give an overview of synthesis strategies, introduce bioactive and environmentally friendly organoselenium compounds and discuss their applications from organic synthesis to the clinic. A naturally occurring amino acid in both eukaryotic and prokaryotic organisms. An abstract of the dissertation of hui nian for the doctor of philosophy in biochemistry and biophysics presented on february 26, 2010. The most promising compounds will be evaluated in the in vitro model of oxidative stress induced by a radical generator on vascular smooth muscle cells 11. Organotellurium and organoselenium compounds attenuate mn. Organoselenium chemistry is the corresponding science exploring their properties and reactivity. Organoselenium compound an overview sciencedirect topics. The chemistry chapters are organized according to the different reactivities of various selenium compounds and reagents, with each chapter dealing with a special reaction type. Developments in the chemistry of selenaheterocyclic.
A chiral electrophilic selenium catalyst for highly. Chemistry of biologically important synthetic organoselenium compounds. Organoselenium compounds as the oxidants and oxidation catalysts. Redox cycling of methylselenide and other selenides rse. Pdf chemistry of biologically important synthetic organoselenium.
There are a number of methods for per forming this the most important of which is the abrominationdehydrobromination method. Such compounds were conveniently accessed by treatment of bis. The reaction of 22phenyl5,6dihydro4h1,3oxazinyllithium, containing a sixmembered oxazine ring, with elemental selenium gave lithium aryldiselenolate 14 as the major reaction intermediate along with other polyselenolates 15 and 16, whereas 24,4dimethyl2phenyloxazolinyllithium 21, containing a fivemembered oxazoline ring, on reaction with selenium gave only lithium. Xray crystallographic files cif of crystal data collection and refinement parameters, atomic coordinates, bond lengths and angles. Organoselenium compounds are powerful antioxidants with potent antiinflammatory and analgesic effects as assessed by several animal studies. Main organoselenium compounds in biology and medicine synthesis.
Contributions to the chemistry of organoselenium compounds. An organic compound that contains both selenium and carbon, and frequently other elements, such as the halogens, oxygen, sulfur, or nitrogen explanation of organoselenium chemistry. This book contains five chapters that particularly consider oxidations that involve organoselenium intermediates. Claudio santi, stefano santoro and benedetta battistelli. Reagents, catalysts and intermediates in synthesis of nonselenium compounds during last thirty years the longstanding but modest use of selenium reagents by organic synthetic chemists received a new impetus. Organoselenium compounds in cancer chemoprevention. Selenium is naturally present in soils but it is also produced by pollution from human activities into the environment. Among the topics are the stem cell paradigm and its application to prostate cancer, interactions between the androgen receptor and other signaling pathways implicated in prostate cancer growth and development, organoselenium compounds as a prospect for therapy, molecular genetic alterations in the prostate cancer microenvironment, implication of lysophosphatidic acid signaling and receptor. Organoselenium compounds in biology and medicine rsc. Organoselenium shows incredible promise in medicine, particularly cancer therapy. Regioselective synthesis of selenide ethers through a. Experimental and theoretical investigations reveal that the.
This book discusses organoselenium chemistry and biology in the context of its therapeutic potential, taking the reader through synthetic techniques, bioactivity and therapeutic applications. Mcculla, ryan david, photochemistry and internal eliminations of organosulfur and organoselenium compounds 2005. Organoselenium compounds are chemical compounds containing carbontoselenium chemical bonds. In mtt assay, xylitolse and sucrosese showed cytostatic effects on human hepatocellular carcinoma cells smmc7221 in a dosedependent manner, whereas they had no negative influences on the proliferation. This is why we provide the book compilations in this website. Organoselenium compounds are chemical compounds containing carbon to selenium chemical bonds. Oxidation in organic chemistry covers the preparative use and the mechanistic aspects of the various oxidation reactions. Functional group manipulation usin organoselenium reagents. Organoselenium compounds as catalysts in nature and laboratory. Find out information about organoselenium chemistry.
Photochemistry and internal eliminations of organosulfur and. Organotellurium chemistry in chemistry describes the synthesis and properties of chemical compounds containing a carbon to tellurium chemical bond. Organosulfur compounds occur in the bodies of all living creatures in the form of certain essential amino acids, enzymes, coenzymes, vitamins, and hormones. Organoselenium compounds as catalysts in nature and laboratory volume. File type pdf organoselenium compounds biology medicine synthesis biological organoselenium compounds biology medicine synthesis biological when somebody should go to the books stores, search inauguration by shop, shelf by shelf, it is really problematic. Organoselenium compounds containing pyrazole or phenylthiazole groups. However, despite the interest in the synthesis of organoselenium compounds, to the best of our knowledge, no reports are available on the metalation of selenyl derivatives. This class of compounds possesses antiinflammatory. Photochemistry and internal eliminations of organosulfur. Organoselenium compounds biology medicine synthesis biological.
Molecules free fulltext organoselenium compounds as. After the discovery of the toxic properties of selenium 515 mg kg. Popa centre of supramolecular organic and organometallic chemistry, department of chemistry, faculty of chemistry and chemical engineering, babes. The scope and limitation of the transformation ketones to enones by selenenylation followed selenoxide elimi. Synthesis, structure, tiniv complexes and antiproliferative activity roxana a. This book discusses organoselenium chemistry and biology in the context of its therapeutic potential, taking the reader through synthetic techniques, bioactivity and. Organoselenium compounds as mimics of selenoproteins and. Interest in organochalcogen compounds has been growing since the 1970s, when many reports described the identification of various selenoproteins, which are involved in a widely number of mammals biochemistry mechanisms. Selenaheterocyclic compounds of practical importance 3. Synthesis, characterization, structures and antioxidant activity of nicotinoyl based organoselenium compounds.
New organoselenium methodology dennis liotta department of chemistry, emory university, atlanta, georgia 30322 received january 15, 1982 revised manuscript received july 22, 1983 although the field of organoselenium chemistry dates back to the 19th century, it did not become a part of the mainstream of organic chemistry until the early 1970s. Organoselenium compounds as reagents and catalysts to develop new green protocols. Dipartimento di chimica e tecnologia del farmaco, via del liceo 1 06123perugiaitaly. Chelate ring size effect on the reactivity of 22phenyl5. Also includes a table with 77se nmr shifts to aid in practical problems. His research has been particularly concerned with metal methylation, reactions and transport in the environment and with the roles of mercury, tin, lead, arsenic and antimony in the natural environment. Organoselenium compounds as novel adjuvants of chemotherapy. Organoselenium compounds as phytochemicals from the natural. Selenium influences a number of endocrine processes. Organoselenium compounds in biology and medicine rsc publishing. Indirect detection of selenium77 in nuclear magnetic. Organoselenium compounds in biology and medicine synthesis.
In fact, treatment of selenides with an alkyllithium generally leads to an easy metallithium exchange, thus hampering the formation of carbanions. The book organoselenium chemistry between synthesis and biochemistry edited by prof claudio santi is a useful tool for chemists and biochemists who are interested in delving in the green side of the moon, as prof santi has been calling the new, green aspects of organoselenium chemistry in his lectures around the world. The most straightforward method is the dehydrogenation of car bonyl compounds. Studies on the properties of organoseleniumiv fluorides and. Dietary organosulfur and organoselenium compounds as hdac inhibitors abstract approved. Organoselenium compounds as phytochemicals from the.
Gpxlike activity of each organoselenium compound synthesized in the presence of various oxidants and thiols. Nutritional modulators of pain in the aging population, 2017. Organosulfur compound, a subclass of organic substances that contain sulfur and that are known for their varied occurrence and unusual properties. In other studies, the organoselenium metabolites can inhibit hdac in the cases of prostate cancer 11. Divided into three sections, the first section describes synthetic advances in bioactive selenium compounds, revealing. Glass department of chemistry, university of arizona, tucson, arizona 85721, usa. Name organoselenium compounds accession number dbcat001476 description. Selenium, catalysis, organocatalysis, selenoenzyme, asymmetric synthesis, gluthathione peroxidase, iodothyronine. Enantioselective catalysis for the preparation of organoselenium compounds and applications pp. Organic compounds which contain selenium as an integral part of the molecule.
The reactivity of organoselenium and organotellurium compounds 1, 2 and 3, characterized by high nucleophilicity and antioxidant potential, provides the basis for their pharmacological activities in mammalian models. The chemistry of organoselenium compounds has undergone rapid growth during the past three. Organotellurium chemistry was developed in the wake of organoselenium chemistry and, sharing the same group in the periodic table, both chemistries have much in common. Recent advances of structural chemistry of organoselenium and organotellurium compounds. The chemical structures of selenomethionine a and methylselenocysteine b. Organic chemistry, a series of monographs, volume 5c. Divided into three sections, the first section describes synthetic advances in bioactive selenium compounds, revealing how. Medium acidification assays performed with s2 yeast cells revealed that compounds 4 and 6, but not compounds 2, 3, or 5, exerted an inhibitory activity comparable to eb ic50. Between synthesis and biochemistry the use of organoselenium reagents as catalysts is a common thread that runs through the chapters of this book, introducing important aspects of the modern organoselenium chemistry. Studies on the properties of organoseleniumiv fluorides. Pdf biological importance of organoselenium compounds.
Introduction and general aspects electrophilic selenium, selenocyclizations nucleophilic selenium radical reactions using selenium precursors. The chemistry of sulfur and selenium is very closely related. Antimicrobial activity of some organoselenium compounds. Thomas wirth published by springer berlin heidelberg isbn. This example demonstrates the increase of quantity and quality of chemical diversity by coupling of monomeric units. Due to the fact that organoselenium compounds show better antioxidative effect than classical selenium made a new era of preparing novel synthetic selenium compounds selamoglu talas 2015. All structured data from the file and property namespaces is available under the. Pages in category organoselenium compounds the following 20 pages are in this category, out of 20 total. Organoselenium chemistry article about organoselenium.
Glutathione peroxidase gpxlike antioxidant activity of. Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected selenium can exist with oxidation state. Reich contribution from the department of chemistry, university of wisconsin, madison, wisconsin 53706. Chemoprevention of carcinogenesis by organoselenium compounds. The advance in the area of synthesis and reactivity of organoselenium, as well as the discovery that selenium was the cause of severe intoxication episodes of livestock in the 1930s and the subsequent determination that selenium was an essential trace element in the diet for mammals, has motivated intense studies of the biological properties of both organic and inorganic selenium compounds. Achibat h, alomari na, messina f, sancineto l, khouili m, santi c. The greater expense of selenium and the hazard resulting from its toxicity3 are justifiable only 1 for a comprehensive account of synthetic organoselenium chemistry, see h. Even compounds with a longer or shorter spacer length, such as sfn 6, sfn 9, 6erucin, and phenethyl isothiocyanate, display a similar effect 37. Please read our short guide how to send a book to kindle. Similarly, other natural organoselenium compounds found in yeasts methylselenocysteine and selenomethionine also act as hdac inhibitors with potential anticancer properties 38. Pdf synthesis of new organoselenium compounds containing.
Pdf selenium, a nonmetallic element, has structural and enzymatic roles. The 20th international electronic conference on synthetic organic chemistry november 2016 organoselenium compounds, an overview on the biological activities beyond antioxidant properties iris di leo1, luca sancineto1, federica messina2, claudio santi1 1 department of pharmaceutical sciences university of perugiaitaly. The use of organoselenium reagents as catalysts is a common thread that runs through the chapters of this book, introducing important aspects of the modern organoselenium chemistry. A naphthalene moiety is coupled to different sites of a chroman or an open. Pdf selenium containing nucleosides derived from some heterocyclic moieties such as pyridineselenol, and pyridazineselenol is described. Organoselenium compounds as the oxidants and oxidation. This class of compounds possesses antiinflammatory, antiulcer, anticancer, hepato and neuroprotective properties 1, 47. Organoselenium compound article about organoselenium. It is found in trnas and in the catalytic site of some enzymes. This pdf is available for free download from a site hosted by medknow publications.
Antifungal organoselenium compound loaded nanoemulsions. Organoselenium compounds in biology and medicine synthesis, biological and therapeutic treatments jain, vimal kumar. The compounds were obtained by the reaction of 2chloroselenobenzoyl chloride with an appropriate terpene amine, first synthesized by a multistep methodology starting from the corresponding alcohol pmenthane system. Download pdf organoseleniumchemistry free online new. Wilka a department of organic and pharmaceutical technology, faculty of chemistry, wroclaw university of science and technology, wybrzeze wyspianskiego 29, 50370 wroclaw. Review of organoselenium chemistry between synthesis and. The results obtained can be divided in three main subchapters according to the approached class of compounds. Organometallic compounds in the environment wiley online books. Antioxidantprooxidant properties of a new organoselenium. Organoselenium compounds as catalysts in nature and.
Selenium, a nonmetallic element, has structural and enzymatic roles. The reactivity of organoselenium and organotelurium compounds, characterized by high nucleophilicity and antioxidant potential, provides the basis for their pharmacological activities in mammalian models. Organoselenium compounds biology medicine synthesis. Media in category organoselenium compounds the following 22 files are in this category, out of 22 total. Organoseleium in the form of compounds of selenometionin and metilselenosistein are proven to be therapeutic compounds on colon cancer cases 11. Organoselenium compounds accession number dbcat001476 description.
Organoselenium compounds as phytochemicals from the natural kingdom. This dissertation focuses on two specific aspects of the chemistry of organosulfur and organoselnium compounds. Reich in oxidation in organic chemistry, part c, w. Organoselenium compounds, an overview on the biological. This chapter gives general aspects of organoselenium chemistry and includes synthetic. Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected. The first is the internal elimination of the sulfinate esters, sulfonic esters, and the effects of silylsubstitution on the internal elimination of sulfoxidesthe internal elimination of sulfinate esters proceeds through a 5membered transition state whereas sulfonate esters. Free radical induced selenoxide formation in isomeric organoselenium compounds. Free radical induced selenoxide formation in isomeric.
Phosphorus, sulfur, and silicon and the related elements. Interestingly, the monomeric parts or closely related compounds were also isolated. Organoselenium compounds an overview sciencedirect topics. Synthesis, structure, tiniv complexes and antiproliferative activity. Number in parentheses rep resents the uncertainties of the last digits as reported in the literature. In 1929, the first patent on the use of selenium dioxide in oxidation reactions appeared, 3 but most organic chemists were not interested in selenium chemistry due to the properties of organoselenium compounds. In the last few years, a number of novel synthetic organoselenium compounds have been synthesized for their use as antioxidants in medicinal chemistry. Conversion of ketones to enones by selenoxide syn elimination hans j. Article pdf available in journal of health science 466 december 2000 with 80 reads how we measure reads.