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. Mcculla, ryan david, photochemistry and internal eliminations of organosulfur and organoselenium compounds 2005. Selenaheterocyclic compounds of practical importance 3. Oxidation in organic chemistry covers the preparative use and the mechanistic aspects of the various oxidation reactions. This book contains five chapters that particularly consider oxidations that involve organoselenium intermediates. Redox cycling of methylselenide and other selenides rse.
Synthesis, characterization, structures and antioxidant activity of nicotinoyl based organoselenium compounds. Download pdf organoseleniumchemistry free online new. 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. Popa centre of supramolecular organic and organometallic chemistry, department of chemistry, faculty of chemistry and chemical engineering, babes. Selenium is naturally present in soils but it is also produced by pollution from human activities into the environment. This class of compounds possesses antiinflammatory, antiulcer, anticancer, hepato and neuroprotective properties 1, 47. Organosulfur compound, a subclass of organic substances that contain sulfur and that are known for their varied occurrence and unusual properties. Chelate ring size effect on the reactivity of 22phenyl5. Studies on the properties of organoseleniumiv fluorides. 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. Conversion of ketones to enones by selenoxide syn elimination hans j. Antimicrobial activity of some organoselenium compounds.
Review of organoselenium chemistry between synthesis and. 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. Such compounds were conveniently accessed by treatment of bis. Achibat h, alomari na, messina f, sancineto l, khouili m, santi c. Divided into three sections, the first section describes synthetic advances in bioactive selenium compounds, revealing how. Organoselenium compounds are chemical compounds containing carbontoselenium chemical bonds. An abstract of the dissertation of hui nian for the doctor of philosophy in biochemistry and biophysics presented on february 26, 2010. Find out information about organoselenium chemistry. Number in parentheses rep resents the uncertainties of the last digits as reported in the literature. Organoselenium compounds biology medicine synthesis. Free radical induced selenoxide formation in isomeric organoselenium compounds.
Organoselenium compounds biology medicine synthesis biological. Wilka a department of organic and pharmaceutical technology, faculty of chemistry, wroclaw university of science and technology, wybrzeze wyspianskiego 29, 50370 wroclaw. Chemistry of biologically important synthetic organoselenium compounds. After the discovery of the toxic properties of selenium 515 mg kg.
Organoselenium compounds in biology and medicine rsc publishing. Organoselenium compounds in biology and medicine synthesis. Dietary organosulfur and organoselenium compounds as hdac inhibitors abstract approved. 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. Divided into three sections, the first section describes synthetic advances in bioactive selenium compounds, revealing.
Organoselenium compounds as the oxidants and oxidation. Pdf selenium containing nucleosides derived from some heterocyclic moieties such as pyridineselenol, and pyridazineselenol is described. This dissertation focuses on two specific aspects of the chemistry of organosulfur and organoselnium compounds. Organoselenium compounds as reagents and catalysts to develop new green protocols. Antifungal organoselenium compound loaded nanoemulsions. Organoselenium compounds as phytochemicals from the natural kingdom. Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected. Organoselenium compounds as mimics of selenoproteins and. This pdf is available for free download from a site hosted by medknow publications. 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. Organoselenium chemistry is a unique resource in this branch of organicorganometallic chemistry. In fact, treatment of selenides with an alkyllithium generally leads to an easy metallithium exchange, thus hampering the formation of carbanions.
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. The chemistry of sulfur and selenium is very closely related. 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. Dipartimento di chimica e tecnologia del farmaco, via del liceo 1 06123perugiaitaly. Organoselenium chemistry is the corresponding science exploring their properties and reactivity. 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 in biology and medicine rsc. Organoselenium shows incredible promise in medicine, particularly cancer therapy. Similarly, other natural organoselenium compounds found in yeasts methylselenocysteine and selenomethionine also act as hdac inhibitors with potential anticancer properties 38. Photochemistry and internal eliminations of organosulfur and. In the last few years, a number of novel synthetic organoselenium compounds have been synthesized for their use as antioxidants in medicinal chemistry. In addition to work at wisconsin, research groups headed by. Claudio santi, stefano santoro and benedetta battistelli. Indirect detection of selenium77 in nuclear magnetic.
Organic chemistry, a series of monographs, volume 5c. This is why we provide the book compilations in this website. Organoselenium compounds, an overview on the biological. Selenium influences a number of endocrine processes. Pdf selenium, a nonmetallic element, has structural and enzymatic roles. Synthesis, structure, tiniv complexes and antiproliferative activity. 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.
Organoselenium compounds accession number dbcat001476 description. Chemoprevention of carcinogenesis by organoselenium compounds. The reactivity of organoselenium and organotelurium compounds, characterized by high nucleophilicity and antioxidant potential, provides the basis for their pharmacological activities in mammalian models. Enantioselective catalysis for the preparation of organoselenium compounds and applications pp. Also includes a table with 77se nmr shifts to aid in practical problems. The results obtained can be divided in three main subchapters according to the approached class of compounds. It is found in trnas and in the catalytic site of some enzymes. 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. Organoselenium compounds in cancer chemoprevention. Reich contribution from the department of chemistry, university of wisconsin, madison, wisconsin 53706. This class of compounds possesses antiinflammatory.
Glass department of chemistry, university of arizona, tucson, arizona 85721, usa. Pdf chemistry of biologically important synthetic organoselenium. Glutathione peroxidase gpxlike antioxidant activity of. The most straightforward method is the dehydrogenation of car bonyl compounds. All structured data from the file and property namespaces is available under the. 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. Please read our short guide how to send a book to kindle. There are a number of methods for per forming this the most important of which is the abrominationdehydrobromination method. Main organoselenium compounds in biology and medicine synthesis. 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. Diorgano diseleniumi compounds compounds from this class have attracted considerable interest in the last decade. The scope and limitation of the transformation ketones to enones by selenenylation followed selenoxide elimi. Organoselenium chemistry article about organoselenium. Xray crystallographic files cif of crystal data collection and refinement parameters, atomic coordinates, bond lengths and angles.
Organoselenium compounds containing pyrazole or phenylthiazole groups. 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. Media in category organoselenium compounds the following 22 files are in this category, out of 22 total. Organotellurium chemistry in chemistry describes the synthesis and properties of chemical compounds containing a carbon to tellurium chemical bond. Introduction and general aspects electrophilic selenium, selenocyclizations nucleophilic selenium radical reactions using selenium precursors. 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. Article pdf available in journal of health science 466 december 2000 with 80 reads how we measure reads. A chiral electrophilic selenium catalyst for highly. Organotellurium and organoselenium compounds attenuate mn. 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. This book discusses organoselenium chemistry and biology in the context of its therapeutic potential, taking the reader through synthetic techniques, bioactivity and therapeutic applications. 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. Organoselenium compounds as catalysts in nature and laboratory.
Regioselective synthesis of selenide ethers through a. Recent advances of structural chemistry of organoselenium and organotellurium compounds. A naphthalene moiety is coupled to different sites of a chroman or an open. 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. Organoselenium compounds in biology and medicine synthesis, biological and therapeutic treatments jain, vimal kumar. Organoselenium compounds as the oxidants and oxidation catalysts. Feihu cui, jing chen, shixia su, yanli xu, hengshan wang, yingming pan.
Experimental and theoretical investigations reveal that the. This example demonstrates the increase of quantity and quality of chemical diversity by coupling of monomeric units. 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. 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 chapter gives general aspects of organoselenium chemistry and includes synthetic. The factors that are responsible for the relatively low glutathione peroxidase gpxlike antioxidant activity of organoselenium compounds such as ebselen 1, 2phenyl1,2benzisoselenazol32hone in the reduction of hydroperoxides with aromatic thiols such as benzenethiol and 4methylbenzenethiol as cosubstrates are described.
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. 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. Thomas wirth published by springer berlin heidelberg isbn. Nutritional modulators of pain in the aging population, 2017. 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. Selenium, catalysis, organocatalysis, selenoenzyme, asymmetric synthesis, gluthathione peroxidase, iodothyronine. Reich in oxidation in organic chemistry, part c, w. Claudio santi, stefano santoro and benedetta battistelli affiliation. Organoselenium compounds are chemical compounds containing carbon to selenium chemical bonds.
This book discusses organoselenium chemistry and biology in the context of its therapeutic potential, taking the reader through synthetic techniques, bioactivity and. The chemical structures of selenomethionine a and methylselenocysteine b. A naturally occurring amino acid in both eukaryotic and prokaryotic organisms. Antioxidantprooxidant properties of a new organoselenium. 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. Name organoselenium compounds accession number dbcat001476 description. View the article pdf and any associated supplements and figures for a period of 48 hours. Organoselenium compounds as novel adjuvants of chemotherapy. Organoselenium compounds as catalysts in nature and. Organometallic compounds in the environment wiley online books.
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. Interestingly, the monomeric parts or closely related compounds were also isolated. Synthesis, structure, tiniv complexes and antiproliferative activity roxana a. Free radical induced selenoxide formation in isomeric. Organoselenium compounds are powerful antioxidants with potent antiinflammatory and analgesic effects as assessed by several animal studies. Pages in category organoselenium compounds the following 20 pages are in this category, out of 20 total. Molecules free fulltext organoselenium compounds as. 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. Organoselenium compound an overview sciencedirect topics.
Photochemistry and internal eliminations of organosulfur. Pdf synthesis of new organoselenium compounds containing. Selenium, a nonmetallic element, has structural and enzymatic roles. Malignant diseases present a serious public health burden and their treatment with traditional chemotherapy cannot be considered an allround solution, due to toxic side effects. The chemistry of organoselenium compounds has undergone rapid growth during the past three. Catalytic application of selenium and tellurium compounds. Gpxlike activity of each organoselenium compound synthesized in the presence of various oxidants and thiols. Developments in the chemistry of selenaheterocyclic. Click download or read online button to organoseleniumchemistry book pdf for free now. Studies on the properties of organoseleniumiv fluorides and.
Organoselenium compounds as phytochemicals from the. Functional group manipulation usin organoselenium reagents. Phosphorus, sulfur, and silicon and the related elements. Organoselenium compounds an overview sciencedirect topics. Organoseleium in the form of compounds of selenometionin and metilselenosistein are proven to be therapeutic compounds on colon cancer cases 11. In other studies, the organoselenium metabolites can inhibit hdac in the cases of prostate cancer 11. Organoselenium compounds as catalysts in nature and laboratory volume.
Organosulfur compounds occur in the bodies of all living creatures in the form of certain essential amino acids, enzymes, coenzymes, vitamins, and hormones. 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. Even compounds with a longer or shorter spacer length, such as sfn 6, sfn 9, 6erucin, and phenethyl isothiocyanate, display a similar effect 37. Contributions to the chemistry of organoselenium compounds.
1020 461 410 1025 1166 605 391 1299 824 61 167 987 491 782 1547 1239 251 1403 24 787 237 763 389 377 395 246 1225 1129 647 1207 77