Image Pyrimidin.svg thumb right Pyrimidine Pyrimidinediones are a class of chemical compounds characterized by a pyrimidine ring substituted with two carbonyl groups. Examples include naturally occurring metabolite s class wikitable Trivial name IUPAC name Structure Pathway Uracil Pyrimidine 2,4 1 H ,3 H dione Image Uracil.svg Pyrimidine biosynthesis Thymine 5 Methylpyrimidine 2,4 1 H ,3 H dione File Thymine chemical structure.png 150px Pyrimidine biosynthesis 5,6 Diaminopyrimidine 2,4 1 H ,3 H dione Riboflavin biosynthesis and drugs Image Primidone.png thumb right Primidone Fluorouracil Idoxuridine Primidone Trifluridine References http www.biam2.org www Cla20291.html Classe PYRIMIDINEDIONE heterocyclic stub Category Pyrimidinediones fr Pyrimidinedione ja sr Pirimidindion zh ... more details
chembox verifiedrevid 443354280 ImageFile 5 Bromouracil structure.png ImageSize 150px IUPACName 5 Bromo 1H pyrimidine 2,4 dione OtherNames 5 Bromo 2,4 dihydroxypyrimidine Section1 Chembox Identifiers Abbreviations 5 BrU br 5 BU ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 5597 InChIKey LQLQRFGHAALLLE UHFFFAOYAN ChEMBL Ref ebicite correct EBI ChEMBL 144730 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C4H3BrN2O2 c5 2 1 6 4 9 7 3 2 8 h1H, H2,6,7,8,9 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey LQLQRFGHAALLLE UHFFFAOYSA N CASNo Ref cascite correct CAS CASNo 51 20 7 EINECS PubChem 5802 SMILES Br C1 C NC O NC1 O InChI 1 C4H3BrN2O2 c5 2 1 6 4 9 7 3 2 8 h1H, H2,6,7,8,9 RTECS MeSHName ChEBI Ref ebicite correct EBI ChEBI 20552 KEGG Ref keggcite correct kegg KEGG ATCCode prefix ATCCode suffix ATC Supplemental Section2 Chembox Properties Formula C sub 4 sub H sub 3 sub BrN sub 2 sub O sub 2 sub MolarMass 190.983 g mol Appearance Density MeltingPt Melting notes BoilingPt Boiling notes Solubility SolubleOther Solvent pKa pKb Section7 Chembox Hazards EUClass EUIndex MainHazards NFPA H NFPA F NFPA R NFPA O RPhrases SPhrases RSPhrases FlashPt Autoignition ExploLimits PEL 5 Bromouracil or 5 bromo 2,4 1H,3H pyrimidinedione or 5 BrU or 5 BU is a brominated derivative of uracil that acts as an antimetabolite or base analog , substituting for thymine in DNA , and can induce DNA mutation in the same way as 2 aminopurine . It is used mainly as an experimental mutagen , but its deoxyriboside derivative 5 bromo 2 deoxy uridine is used to treat neoplasm s. 5 BrU exists in three tautomer ic forms that have different base pairing properties. The Ketone keto form shown in the infobox is complementary to adenine , so it can be incorporated into DNA by aligning opposite adenine residues during DNA replication see below left . Alternatively, the enol below right and ion forms are complementary to guanine . This means that 5 BrU can be present in DNA eit ... more details
Drugbox IUPAC name 5 ethyl 5 3 hexanyl 2 thioxodihydro 4,6 1 H ,5 H pyrimidinedione image Thiotetrabarbital structure.png CAS number 467 38 9 CAS supplemental br ATC prefix None ATC suffix PubChem 3083570 ChemSpiderID 2340756 chemical formula C sub 12 sub H sub 20 sub N sub 2 sub O sub 2 sub S molecular weight 256.364 g mol smiles O C1NC S NC O C1 C CC CCC CC synonyms JL 1014 InChI 1 C12H20N2O2S c1 4 7 8 5 2 12 6 3 9 15 13 11 17 14 10 12 16 h8H,4 7H2,1 3H3, H2,13,14,15,16,17 InChIKey SSWATJQIZBUQQZ UHFFFAOYAC StdInChI 1S C12H20N2O2S c1 4 7 8 5 2 12 6 3 9 15 13 11 17 14 10 12 16 h8H,4 7H2,1 3H3, H2,13,14,15,16,17 StdInChIKey SSWATJQIZBUQQZ UHFFFAOYSA N bioavailability protein bound metabolism elimination half life excretion pregnancy category legal status routes of administration Thiotetrabarbital International Nonproprietary Name INN Thionarcex is a drug which is a short acting barbiturate derivative that is used as an anesthetic . ref name Macdonald1997 cite book author Macdonald, F. title Dictionary of Pharmacological Agents url http books.google.com books?id DeX7jgInYFMC&pg PA955 accessdate 22 April 2012 year 1997 publisher CRC Press isbn 978 0 412 46630 4 page 1964 ref ref name Westhorpe2002 cite journal author RN Westhorpe, C Ball title The intravenous barbiturates journal International Congress Series volume 1242 pages 57 69 year 2002 month December pmid doi 10.1016 S0531 5131 02 00758 6 url http dx.doi.org 10.1016 S0531 5131 02 00758 6 ref ref name BJA1955 cite journal title Newer barbiturates journal British Journal of Anaesthesia volume 27 issue 8 pages 418 419 year 1955 pmid doi 10.1093 bja 27.8.418 url http bja.oxfordjournals.org content 27 8 418.extract ref ref name Hewer1963 cite book author Christopher Langton Hewer title Recent advances in an sthesia and analgesia url http books.google.com books?id sAtVAAAAYAAJ accessdate 27 April 2012 year 1963 publisher Little, Brown page 31 ref ref name DundeeWyant1974 cite book author1 John Wharry Dundee author2 Gordon ... more details
Chembox verifiedrevid 446035918 ImageFileL1 Divicine.svg ImageSizeL1 110px ImageCaptionL1 pyrimidine tautomer ImageFileR1 Divicine2.svg ImageSizeR1 95px ImageCaptionR1 pyrimidinone tautomer IUPACName 2,6 diamino 4,5 dihydroxypyrimidine OtherNames 2,6 diamino 4,5 pyrimidinediol 2,6 diamine 5 hydroxy 4 3 H pyrimidinone 2,4 diamino 5,6 dihydroxypyrimidine Section1 Chembox Identifiers CASNo 32267 39 3 CASNo Comment ref name ChemboxRef http www.druglead.com cds divicine.html ref PubChem 91606 SMILES OC1 C O C N NC N N1 SMILES Comment pyrimidine tautomer SMILES1 O C1C O C N NC N N1 SMILES1 Comment pyrimidinone tautomer ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 2971290 InChI 1 C4H6N4O2 c5 2 1 9 3 10 8 4 6 7 2 h9H, H5,5,6,7,8,10 InChIKey ZMWZGZSARWJATP UHFFFAOYAO StdInChI Ref stdinchicite correct chemspider StdInChI 1S C4H6N4O2 c5 2 1 9 3 10 8 4 6 7 2 h9H, H5,5,6,7,8,10 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey ZMWZGZSARWJATP UHFFFAOYSA N Section2 Chembox Properties C 4 H 6 N 4 O 2 Appearance Brownish needles Density MeltingPt BoilingPt Solubility Soluble in 10 KOH Section3 Chembox Hazards MainHazards FlashPt Autoignition Divicine 2,6 diamino 4,5 dihydroxypyrimidine is an oxidant and a base with alkaloidal properties found in fava beans and Lathyrus sativus . It is an aglycone of vicine . A common derivative is the diacetate form 2,6 diamino 1,6 dihydro 4,5 pyrimidinedione . ref name Structure cite journal author Bendich, C. year 1953 journal Biochim. Biophys. volume 12 page 462 ref Occurrence Divicine is found in fava beans and in the legume Lathyrus sativus , also known as khesari, which is a cheap and robust food source commonly grown in Asia and East Africa. Synthesis In plants, reduced divicine is formed from the hydrolysis of the inactive glucoside, vicine . ref name Baker cite journal author Baker, M. Bosia, A. year 1984 title Mechanism of Action of Divicine in a Cell free System and in Glucose 6 phosphate Dehydrogenase defic ... more details
chembox Verifiedfields changed verifiedrevid 418274850 Name Uracil ImageFile Uracil.svg ImageSize 120px ImageName Structural formula of uracil ImageFileL1 Uracil 3D balls.png ImageSizeL1 120px ImageNameL1 Ball and stick model of uracil ImageFileR1 Uracil 3D vdW.png ImageSizeR1 120px ImageNameR1 Space filling model of uracil IUPACName Pyrimidine 2,4 1 H ,3 H dione OtherNames 2 oxy 4 oxy pyrimidine, br 2,4 1H,3H pyrimidinedione, br 2,4 dihydroxypyrimidine, br 2,4 pyrimidinediol Section1 Chembox Identifiers UNII Ref fdacite changed FDA UNII 56HH86ZVCT SMILES O C1NC CC O N1 CASNo 66 22 8 CASNo Ref cascite correct CAS ChEMBL Ref ebicite changed EBI ChEMBL 566 RTECS YQ8650000 Section2 Chembox Properties Formula C sub 4 sub H sub 4 sub N sub 2 sub O sub 2 sub MolarMass 112.08676 g mol Appearance Solid Density 1.32 g cm Solubility Soluble MeltingPt 335 C ref Richard L. Myers, Rusty L. Myers The 100 most important chemical compounds, 92 93 http books.google.com books?id a4DuGVwyN6cC&pg PA92&lpg PA92&dq Uracil boiling point&source bl&ots hn9HyffT W&sig uFAWcfhiBiFfpbctZgEWYQUnRf8&hl en&ei Ei8TSp bEYGQjAfV 7WwBA&sa X&oi book result&ct result&resnum 7 PPA92,M1 link ref BoilingPt N A decomposes Section7 Chembox Hazards MainHazards carcinogen & teratogen with chronic exposure NFPA H 1 NFPA F 1 NFPA R FlashPt non flammable Section8 Chembox Related OtherCpds Thymine br Cytosine Uracil IPAc en icon y r s l one of the four nucleobase s in the nucleic acid of RNA that are represented by the letters A, G, C and U. The others are adenine , cytosine , and guanine . In RNA, uracil U binds to adenine A via two hydrogen bonds. In DNA , the uracil nucleobase is replaced by thymine . Uracil is a common and naturally occurring pyrimidine derivative. ref name Garrett1 Garrett, Reginald H. Grisham, Charles M. Principals of Biochemistry with a Human Focus. United States Brooks Cole Thomson Learning, 1997. ref Originally discovered in 1900, it was isolated by hydrolysis of yeast nuclein th ... more details
with a pyrimidinedione, the metabolic stability was increased and the result was a potent ... when quinazolinone was replaced with a pyrimidinedione . Alogliptin has shown excellent ... more details
oral Primidone is an anticonvulsant of the pyrimidinedione ref name biam2 cite web author Biam year 2001 title PRIMIDONE French work PYRIMIDINEDIONE url http www.biam2.org www Sub2339.html accessdate ... more details
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