Selenium-Containing Polymers: Synthesis and Applications
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Recent Advances in the Synthesis of Five- and Six-Membered Selena
290 RECENT ADVANCES IN THE SYNT HESIS OF FIVE - AND SIX - MEMBERED SELENA - HETEROCYCLES DOI: http://dx.medra.org/ 10.17374/targets.2021.24.290 D amiano Tanini * , Antonella Capperucci Department of Chemistry “Ugo Schiff ”, Università di Firenze , Via della Lastruccia 3 - 13, 50019 Sesto Fiorentino (Firenze ) , Italy (e - mail: [email protected] ) Abstract. Organoselenium compounds play an increasingly important role in chemistry and biochemistry. Amongst the wide variety of selenium - containing systems, selena - heterocycles are versatile derivatives with broad applications in organic synthesis, catalysis, medicinal chemistry, and biology. In this context, taking into account the poor stability of most selenylating reagents or intermediates , the developm ent of simple, mild and ver satile synthetic methodologies towards functionalised selena - heterocycles remains an attractive yet challenging topic . This chapter will be focusing on recent advances on the synthesis of different classes of selenium - containing five - and six - member ed ring systems. Contents 1. I ntroduction 2. S ynthesis of heterocyc lic systems containing selenium 3. S ynthesis of heterocyclic systems containing selenium and nitrogen 4. S ynthesis of heterocyclic systems containing selenium and other heteroatoms (O, S, P) 5. C onclusion s and future outlook Acknowledgement s References 1. I ntroduction Selenium - containing small molecules occupy a central position in chemical science , with different application s in organic synthesis, material sciences and polymer chemistry . 1,2,3 Organoselenides are often employed as synthetic intermediates, ligands, and catalysts. 4,5,6,7 Furthermore, owing to their antioxidant, enzyme modulator, and anticancer properties, selenium - containing organic molecules play an increasingly important role in medicinal chemistry and biology. -
Diffraction of Selenium with Sulfide Solution and of Sulfur With
LFIDE SOL UTI01 UTIONS 1- known that selenium dissolves in solutions of alkali and alkaline-earth sulfides to form com- \yith niixed anions [I]. The solubility of seleniunl in sodium sulfide solutions is utilized in tech- -, . or example, sodium sulfide is used for extraction of selenium from sludge by-products in the . acid and pulp and paper industries (21. Several variants have been devised for smelting of dusts .~d-nianufacturingplants with formation of polysulfide slags containing selenium, which are then cd to further hydrometallurgical treatment [8, 41. There are also other possibiIities for effective ion of the properties of solutions of sodium selenosulfides. This makes it all the more necessary %, v.2,!y the interaction of selenium with sodium sulfides and of sulfur with solutions of sodium selenides, .kc. Information on the subject in the literature is very limited. abl le 1 contains data on the solubility of selenium in solutions of sodium mono- and polysulfides, ts! n the niain reactions occurring in the dissolution process. selenium and sulfur were dissolved in the various solutions in closed flasks, agitated by magnetic ,'.~:,.I*s.In order to avoid oxidation of the sulfides and selenides, the samples were withdrawn with the s c ! rubber bulb in a mechanical sampling device through an inverted Schott funnel contained in the reac- ;l.isk. Control experiments were conducted in an atmosphere of technical nitrogen additionally treated pyrogallol to remove oxygen. Sodium sulfide of analytical grade, sulfur containing 99.9% S, and selenium containing 99.99% Se were :W i in the experiments. The potentials were measured with an R-300 potentiometer with the aid of a platinum electrode, 11 .t 0.001 Q. -
Selenophene Transition Metal Complexes Carter James White Iowa State University
Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1994 Selenophene transition metal complexes Carter James White Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Inorganic Chemistry Commons Recommended Citation White, Carter James, "Selenophene transition metal complexes " (1994). Retrospective Theses and Dissertations. 10521. https://lib.dr.iastate.edu/rtd/10521 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if imauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overlaps. -
1/2 Toxic Compound Data Sheet Name: Indene CAS Number: 00095
1/2 Toxic Compound Data Sheet Name: Indene CAS Number: 00095-13-6 Justification: This compound is listed in Ohio Administrative Code 3745 - 114 - 01 because it fulfills one or more of the following criteria: substances that are known to be, or may reasonably be anticipated to be, carcinogenic, mutagenic, teratogenic, or neurotoxic, causes reproductive dysfunction, is acutely or chronically toxic, or causes the threat of adverse environmental effects through ambient concentrations, bioaccumulation, or atmospheric deposition. lndene is acutely toxic with effects on the upper respiratory system (mucous membranes), pulmonary irritation, liver and kidney effects. Molecular Weight (g/mol): 116.15 Synonyms: Indonaphthene U.S. EPA Carcinogenic Classification (IRIS): Not listed on IRIS. PBT: Not listed as persistent, bioaccumulative and toxic. NTP: Not listed by the National Toxicology Program. HAP: Not listed as a hazardous air pollutant (HAP) by U.S. EPA. 112r: Not listed under Section 112(r) of the Clean Air Act. ACGIH: TLV: 10 ppm or 47,505 µg/m3. Critical effects include upper respiratory irritation or damage, pulmonary irritation, and liver and kidney effects. HSDB: Listed in the Hazardous Substances Data Bank. Inhalation of indene vapors is expected to cause irritation of mucous membranes. International IARC: Not listed by International Agency for Research on Cancer (IARC). ATSDR (MRL): Not listed by ATSDR. DataSheet Indene.wpd 2/2 Reference Material 1. American Conference of Governmental Industrial Hygienists (ACGIH) 2006. TLVs and BEIs: -
Biological Chemistry of Hydrogen Selenide
antioxidants Review Biological Chemistry of Hydrogen Selenide Kellye A. Cupp-Sutton † and Michael T. Ashby *,† Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA; [email protected] * Correspondence: [email protected]; Tel.: +1-405-325-2924 † These authors contributed equally to this work. Academic Editors: Claus Jacob and Gregory Ian Giles Received: 18 October 2016; Accepted: 8 November 2016; Published: 22 November 2016 Abstract: There are no two main-group elements that exhibit more similar physical and chemical properties than sulfur and selenium. Nonetheless, Nature has deemed both essential for life and has found a way to exploit the subtle unique properties of selenium to include it in biochemistry despite its congener sulfur being 10,000 times more abundant. Selenium is more easily oxidized and it is kinetically more labile, so all selenium compounds could be considered to be “Reactive Selenium Compounds” relative to their sulfur analogues. What is furthermore remarkable is that one of the most reactive forms of selenium, hydrogen selenide (HSe− at physiologic pH), is proposed to be the starting point for the biosynthesis of selenium-containing molecules. This review contrasts the chemical properties of sulfur and selenium and critically assesses the role of hydrogen selenide in biological chemistry. Keywords: biological reactive selenium species; hydrogen selenide; selenocysteine; selenomethionine; selenosugars; selenophosphate; selenocyanate; selenophosphate synthetase thioredoxin reductase 1. Overview of Chalcogens in Biology Chalcogens are the chemical elements in group 16 of the periodic table. This group, which is also known as the oxygen family, consists of the elements oxygen (O), sulfur (S), selenium (Se), tellurium (Te), and the radioactive element polonium (Po). -
United States Patent Office Patented Jan
2,729,676 United States Patent Office Patented Jan. 3, 1956 1. In order that those skilled in the art may better under stand how the present invention may be carried into 2,729,676 effect, the following methods are provided by way of illustration.To prepare g,6'-diselenodipropionic acid, an alkali PREPARATION OF fSELENODIPROPIONICCD s Selenide such as sodium, potassium, or ammonium selen Donald L. MacPeek, Charleston, W. Va., and William H. ide and the like is slowly reacted with beta propiono Rauscher, Brunswick, N. Y., assignors to the United lactone in aqueous solution to form the addition product. States of America as represented by the Secretary of The product is acidified with a suitable acid such as hydro the Army 0. chloric acid, etc. and the desired product is obtained by No Drawing. Application April 29, 1953, a suitable method such as extraction. The following Serial No. 352,053 examples are illustrative of preferred embodiments of the foregoing method. 1 Claim. (C. 260-537) EXAMPLE This invention relates to fungicidal compounds and 5 A quantity of 38 grams (0.25 mole) of sodium selenide more particularly to new compositions of matter having is dissolved as completely as possible in 50 ml. of water pronounced fungicidal activity. contained in a 500 ml. 3 necked flask having standard Electronic equipment in use may be exposed in many . taper joints. The flask is fitted with a dropping funnel instances to a combination of severe climatic conditions and motor stirrer. The mixture is stirred for about 10 Such as extremes of heat, cold, and humidity. -
Chemical Names and CAS Numbers Final
Chemical Abstract Chemical Formula Chemical Name Service (CAS) Number C3H8O 1‐propanol C4H7BrO2 2‐bromobutyric acid 80‐58‐0 GeH3COOH 2‐germaacetic acid C4H10 2‐methylpropane 75‐28‐5 C3H8O 2‐propanol 67‐63‐0 C6H10O3 4‐acetylbutyric acid 448671 C4H7BrO2 4‐bromobutyric acid 2623‐87‐2 CH3CHO acetaldehyde CH3CONH2 acetamide C8H9NO2 acetaminophen 103‐90‐2 − C2H3O2 acetate ion − CH3COO acetate ion C2H4O2 acetic acid 64‐19‐7 CH3COOH acetic acid (CH3)2CO acetone CH3COCl acetyl chloride C2H2 acetylene 74‐86‐2 HCCH acetylene C9H8O4 acetylsalicylic acid 50‐78‐2 H2C(CH)CN acrylonitrile C3H7NO2 Ala C3H7NO2 alanine 56‐41‐7 NaAlSi3O3 albite AlSb aluminium antimonide 25152‐52‐7 AlAs aluminium arsenide 22831‐42‐1 AlBO2 aluminium borate 61279‐70‐7 AlBO aluminium boron oxide 12041‐48‐4 AlBr3 aluminium bromide 7727‐15‐3 AlBr3•6H2O aluminium bromide hexahydrate 2149397 AlCl4Cs aluminium caesium tetrachloride 17992‐03‐9 AlCl3 aluminium chloride (anhydrous) 7446‐70‐0 AlCl3•6H2O aluminium chloride hexahydrate 7784‐13‐6 AlClO aluminium chloride oxide 13596‐11‐7 AlB2 aluminium diboride 12041‐50‐8 AlF2 aluminium difluoride 13569‐23‐8 AlF2O aluminium difluoride oxide 38344‐66‐0 AlB12 aluminium dodecaboride 12041‐54‐2 Al2F6 aluminium fluoride 17949‐86‐9 AlF3 aluminium fluoride 7784‐18‐1 Al(CHO2)3 aluminium formate 7360‐53‐4 1 of 75 Chemical Abstract Chemical Formula Chemical Name Service (CAS) Number Al(OH)3 aluminium hydroxide 21645‐51‐2 Al2I6 aluminium iodide 18898‐35‐6 AlI3 aluminium iodide 7784‐23‐8 AlBr aluminium monobromide 22359‐97‐3 AlCl aluminium monochloride -
(12) United States Patent (10) Patent No.: US 8,846,032 B2 Liu Et Al
USOO8846032B2 (12) United States Patent (10) Patent No.: US 8,846,032 B2 Liu et al. (45) Date of Patent: *Sep. 30, 2014 (54) MDCK CELL LINES SUPPORTINGVIRAL 2760/16051; C12N 2760/16164; C12N GROWTH TO HIGHTTERS AND 2760/16111; C12N 2760/16211; C12N BOREACTOR PROCESS USING THE SAME 2760/16221; C12N 2760/16351; C12N 2830/85; C12N5/00; C12N 5/0043; C12N (75) Inventors: Jonathan Liu, Milpitas, CA (US); 5/005; C12N5/0075; C07K 14/11; C12O Richard Schwartz, Bethesda, MD (US); 1/70; G01N 2333/11 Mark Thompson, Morgan Hill, CA See application file for complete search history. (US); Luis Maranga, Santa Clara, CA (US); Mridul Ghosh, San Jose, CA (US); Ajit Subramanian, Berkeley, CA (56) References Cited (US); Simon Sheng-Tsiung Hsu, Palo U.S. PATENT DOCUMENTS Alto, CA (US) 5,824,536 A 10, 1998 Webster et al. (73) Assignee: MedImmune, LLC, Gaithersburg, MD 5.948,410 A 9/1999 Van Scharrenburg et al. 6,194,191 B1 2/2001 Zhang et al. (US) 6,245,549 B1 6/2001 Ewasyshyn et al. 6,455,298 B1 9, 2002 Groner et al. (*) Notice: Subject to any disclaimer, the term of this 6,656,720 B2 12/2003 Groner patent is extended or adjusted under 35 6,726,907 B1 4/2004 Zhang et al. U.S.C. 154(b) by 0 days. 6.825,036 B2 11/2004 Makizumi et al. 6.951,752 B2 10/2005 Reiter et al. This patent is Subject to a terminal dis 7,553,665 B2 6/2009 Aloni et al. -
STATES PATENT of FICE 2,414,438 Electrodeposition of SELENIUM Mortimer C
Patented Jan. 21, 1947. 2,414,438 UNITED STATES PATENT of FICE 2,414,438 ELECTRoDEPoSITION OF SELENIUM Mortimer C. Bloom, Newton Highlands, Mass, as signor, by mesne assignments, to Federal Tele phone and Radio Corporation, New York, N.Y., a corporation of Delaware No Drawing. Application December 1, 1942, Serial No. 467,562 4. Claims. (C. 204-56) 2 This invention relates to the electro-deposition Another way of preparing the solution is to of Selenium and has for its object to provide a, dissolve powdered selenium in a solution of SO method of depositing metallic selenium evenly in dium hydroxide. This will form the desired so a pure form and without the use of corrosive SO dium selenide (Na2Se2). It will form, in addi lutionS. tion, sodium selenite (Na2Set4O3) which is use Another object is to attain an even and fine less for the purpose of anodic plating as the --4 grained selenium deposit on a base element which ions will pass to the cathode rather than the will be useful for a rectifier or photocell. anode. Consequently, it is preferred to use a so Selenium has heretofore been electro-deposited lution containing only the desired selenide and cathodically by the use of solutions producing O not the selenite; and the selenide free from the quadrivalent selenium cations (Se). Such a selenite can be had by the method of treating Condition is had in a selenious acid solution Con with the gas H2Se, taining an excess of acid as disclosed and claimed For the anode almost any conducting plate or in copending application Ser. -
Nomenclature Notes
Rules of Nomenclature for Binary Compounds There are three types of binary compounds: Type I. A metal of fixed charge and a nonmetal; Type II. A metal of variable charge and a nonmetal; and Type III. Two nonmetals Metals of ‘variable charge’ tend to be transition elements with some exceptions; metals of fixed charge tend to be the alkali metals and the alkaline earths, along with zinc, cadmium and silver. Nonmetals are those compounds to the right of the bold zig-zag line (see Periodic Table attached) The rules for naming binary compounds are then as follows: • Rule 1. When writing a formula or naming a compound: a). For Type I and Type II compounds, first list the metal then the nonmetal; b) For Type III compounds always list the electropositive species first (the element furthest left in the periodic table) and then the electronegative species. Type III species tend to be exclusively covalently bound compounds. NOTE: It becomes very important that you KNOW YOUR IONS AND THEIR CHARGES (especially the anions, since any given element anion does not have varying charges)!!! • Rule 2. All compound must be neutral UNLESS indicated otherwise. • Rule 3. When naming binary compounds: a). For compounds of Type I and Type II, always use the FULL name of the metal and add the suffix -ide to the root name of the nonmetal (i.e. Metal Nonmetide); b). Type II compounds are handled the same as Type I except the charge on the metal is indicated by using a roman numeral in parentheses immediately following the metal (i.e. -
(Z,Z)-Selanediylbis(2-Propenamides): Novel Class of Organoselenium Compounds with High Glutathione Peroxidase-Like Activity
molecules Article (Z,Z)-Selanediylbis(2-propenamides): Novel Class of Organoselenium Compounds with High Glutathione Peroxidase-Like Activity. Regio- and Stereoselective Reaction of Sodium Selenide with 3-Trimethylsilyl-2-propynamides Mikhail V. Andreev, Vladimir A. Potapov * , Maxim V. Musalov and Svetlana V. Amosova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia; [email protected] (M.V.A.); [email protected] (M.V.M.); [email protected] (S.V.A.) * Correspondence: [email protected] Academic Editor: Derek J. McPhee Received: 3 December 2020; Accepted: 14 December 2020; Published: 15 December 2020 Abstract: The efficient regio- and stereoselective synthesis of (Z,Z)-3,30-selanediylbis(2-propenamides) in 76–93% yields was developed based on the reaction of sodium selenide with 3-trimethylsilyl-2- propynamides. (Z,Z)-3,30-Selanediylbis(2-propenamides) are a novel class of organoselenium compounds. To date, not a single representative of 3,30-selanediylbis(2-propenamides) has been described in the literature. Studying glutathione peroxidase-like properties by a model reaction showed that the activity of the obtained products significantly varies depending on the organic moieties in the amide group. Divinyl selenide, which contains two lipophilic cyclohexyl substituents in the amide group, exhibits very high glutathione peroxidase-like activity and this compound is considerably superior to other products in this respect. Keywords: (Z,Z)-3,30-selanediylbis(2-propenamides); 3-trimethylsilyl-2-propynamides; sodium selenide; glutathione peroxidase-like activity; regioselective reactions; stereoselective reactions; desilylation 1. Introduction Vinyl selenides are important intermediates for organic synthesis [1–9]. -
Fused Five-Membered Aromatic Heterocycles Built on the Α-Pyrone Moiety
molecules Review Synthetic Routes to Coumarin(Benzopyrone)-Fused Five-Membered Aromatic Heterocycles Built on the α-Pyrone Moiety. Part 1: Five-Membered Aromatic Rings with One Heteroatom Eslam Reda El-Sawy 1 , Ahmed Bakr Abdelwahab 2 and Gilbert Kirsch 3,* 1 National Research Centre, Chemistry of Natural Compounds Department, Dokki-Cairo 12622, Egypt; [email protected] 2 Plant Advanced Technologies (PAT), 54500 Vandoeuvre-les-Nancy, France; [email protected] 3 Laboratoire Lorrain de Chimie Moléculaire (L.2.C.M.), Université de Lorraine, 57050 Metz, France * Correspondence: [email protected]; Tel.: +33-03-72-74-92-00; Fax: +33-03-72-74-91-87 Abstract: This review gives an up-to-date overview of the different ways (routes) to the synthesis of coumarin(benzopyrone)-fused, five-membered aromatic heterocycles with one heteroatom, built on the pyrone moiety. Covering 1966 to 2020. Keywords: coumarins; benzopyrones; five-membered aromatic heterocycles; furan; pyrrole; thio- phene; selenophen Citation: El-Sawy, E.R.; Abdelwahab, A.B.; Kirsch, G. Synthetic Routes to 1. Introduction Coumarin(Benzopyrone)-Fused Five-Membered Aromatic Coumarins are a family of benzopyrones (1,2-benzopyrones or 2H-[1]benzopyran- Heterocycles Built on the α-Pyrone 2-ones), which represent an important family of oxygen-containing heterocycles, widely Moiety. Part 1: Five-Membered distributed in nature [1–4]. Coumarins display a broad range of biological and pharma- Aromatic Rings with One cological activities, [5,6] such as antiviral [7–10], anticancer [11–13], antimicrobial [14,15], Heteroatom. Molecules 2021, 26, 483. and antioxidant [16–18] activities. On the other hand, coumarin represents an ingredi- https://doi.org/10.3390/molecules26 ent in perfumes [19], cosmetics [20], and as industrial additives [21,22].